Travel

Your Complete Guide to Exploring the Chesapeake Bay

Your Complete Guide to Exploring the Chesapeake Bay
Photograph by Edwin Remsburg.

The Chesapeake Bay holds more than 18 trillion gallons of water; sprawls across an area larger than Connecticut; harbors 3,600-plus species of fish, plants, and animals; and provides jobs and food for millions of people. You’re forgiven if you sometimes forget it’s there.

For many Washingtonians, the Chesapeake is something to be crossed over or, in the case of the Bay Bridge-Tunnel, driven under. It’s a beautiful distraction on our way to someplace else. But that “great protein factory,” as Baltimore scribe H.L. Mencken dubbed it, is pretty much the reason we’re here, plopped down on a marsh alongside one of its major tributaries.

The Chesapeake—the largest estuary in the nation—stretches 200 miles from Havre de Grace, Maryland, in the north to Norfolk, Virginia, in the south. It has a western shore and an Eastern Shore—the latter a land so distinct we insist on capitalizing its name.

The bay’s communities have a culture all their own. They make up a land of winding rivers and flat country roads, of ramshackle houses and million-dollar mansions, of ospreys and herons and chicken farms and resolute watermen, whose numbers dwindle every year in proportion to the oysters and crabs they catch.

Consider these pages a Chesapeake primer of sorts. We’ve included dozens of ideas on how to explore the area, and once you get to know the bay’s charms, you’ll never again forget it’s there.

In/Near Annapolis

Photograph by Flickr user <a href="https://www.flickr.com/photos/39908901@N06/">m01229</a>.
Photograph by Flickr user m01229.

Annapolis Ice Cream Company

Owners Walter and Nancy Giera create their concoctions at Annapolis Ice Cream Company using cream with a whopping 17 per-cent butterfat. Cream of the crop: Peanut Butter Oreo—peanut butter and chunks of cookie in vanilla ice cream. 196 Main St., Annapolis; 443-482-3895.

Annapolis Yacht Club races

As they say in Maryland’s capital, “the weekend begins on Wednesdays.” That’s when the Annapolis Yacht Club (410-263-9279) holds its Wednesday Night Races, a tradition since 1959. Every Wednesday, May through August, at 6 p.m., more than 125 boats (and many more spectators’ boats) crowd the mouth of Spa Creek awaiting the starting gun. Beyond a race, it’s a full-fledged party. Watch from the Spa Creek Bridge or Carrol’s Creek Cafe (410 Severn Ave., Annapolis; 410-263-8102) in Eastport, then walk over to the Boatyard Bar and Grill (400 Fourth St., Annapolis; 410-216-6206) for the post-race festivities.

Dragonfly boat ride

Trimarans—three-hulled, sail-powered boats—are a more common sight in tropical locales than on the Chesapeake, which is what makes a trip aboard the Dragonfly (410-349-4360) an unusual experience. The 26-foot-long boat is among the fastest crafts on the bay, but its multi-hull design also makes it one of the more stable. On a two- or three-hour daytime or sunset sail along the Magothy River or out in the bay, you’ll whiz past the Baltimore Harbor Light, look for stingrays and jumping fish, and ogle multimillion-dollar homes along Gibson Island. If you don’t mind getting wet, climb onto the netting between hulls and you’ll feel as if you’re skimming over the water. The $250 fee for up to four passengers includes a $20 gift certificate to Deep Creek Restaurant & Marina (1050 Deep Creek Ave., Arnold; 410-757-4045), where the boat is docked.

Jimmy Cantler’s Riverside Inn

Two things to remember at this 42-year-old favorite: corn and crabs. The corn on the cob, steamed in its husk, is local and wonderfully sweet and juicy. The crabs (from the Chesapeake when possible, other times from Louisiana or Texas) are usually full of flavor and can be bashed on an open-air table overlooking breezy Mill Creek. Tax the kitchen with more creative dishes (bacon-wrapped scallops with plum sauce, say) and you risk disappointment. Waits tend to be long, so hang out with a canned beer in the parking lot—or do as the locals do and pull up in your boat. 458 Forest Beach Rd., Annapolis; cantlers.com, 410-757-1311. Open year-round.

Photograph by Scott Suchman.
Watch the Annapolis Yacht Club’s Wednesday Night Races, a tradition since 1959. Photograph by Scott Suchman.

Mike’s Crab House

Watch the boats pull in at this 58-year-old South River institution, a short drive from downtown Annapolis. Crowds on the river-side deck whack away at nicely steamed and spiced hard-shells, in a full spectrum of sizes during the summer peak. The menu runs large and crabhouse-classic, with many steamed, broiled, and fried specialties from the bay and beyond. Don’t miss the soft-shell clams with melted butter for dunking, fried oysters in season, or bacon-capped clams casino anytime. 3030 Riva Rd., Riva; mikescrabhouse.com; 410-956-2784. Open year-round.

The Point

It takes a little work to find this glass-walled hangout—wind your way through a subdivision until you hit the marina, then walk toward the docks—but boy, is it worth it. The Point’s hard-shells were the sweetest we tasted. (Even the mediums were satisfying.) Salads are bountiful and fresh, the delicious crab dip is spiked with a good dose of sherry, juicy wings are perked up with Old Bay, and often standard-issue sides like mayo-bound slaw get unusual twists such as a shower of blue cheese. One caveat: The bar fills early; on many weekends, you can expect a Rose’s Luxury–level wait. 700 Mill Creek Rd., Arnold; 410-544-5448. Open year-round.

Sandy Point State Park

There’s something supremely satisfying about digging your toes into the sand at Sandy Point State Park (1100 E. College Pkwy., Annapolis; 410-974-2149) as you smugly watch ocean-bound traffic pile up along the Bay Bridge. Although Sandy Point’s relatively petite stretch of coarse sand will never be mistaken for the vast, powdery stuff in Ocean City, its shallow, calm waters—reached without crossing the bridge—make swimming easy for little ones. (Just watch out for nettles.) In addition to the beach, the park offers fishing, hiking, picnic pavilions, and boat rentals. Admission: $5 a person for Maryland residents on summer weekends, $7 for nonresidents.

Photograph courtesy of Allison Zaucha and The Point.
Enjoy the sweetest hard-shells on the water at The Point. Photograph courtesy of Allison Zaucha and The Point.

Schooner Woodwind

The schooner Woodwind (410-263-1981), a 74-foot sailing yacht, offers two-hour public cruises daily out of Annapolis throughout the summer and into fall, from $41 a person. For a taste of the live-aboard life—without the pricey boat maintenance and dockage fees—you can even spend the night onboard. You’ll join other passengers for the evening’s traditional sunset sail, then bunk in one of the yacht’s four staterooms. Breakfast comes with crab quiche and coffee the following morning. $305 for two.

Thomas Point Shoal Lighthouse

Built in 1875, the Thomas Point Shoal Lighthouse (410-362-7255) is the last screwpile light (a lighthouse built on piles screwed into the sandy bottom) in its original location on the bay—and perhaps the Chesapeake’s most photographed. For the ultimate close-up, join one of the Annapolis Maritime Museum’s three-hour, docent-led boat tours. There’s room for only 18, so reservations are a must. Tours ($70) run through October.

US Naval Academy

Incredible as it may seem, all 4,400 midshipmen at the US Naval Academy eat every meal at the same time in the same building and, as academy brass (and the super-efficient food servers) like to boast, are served all their meals within five minutes. That tidbit is one of the surprising facts you’ll pick up on the hour-and-15-minute Naval Academy tour, which departs every half hour during summer Mondays through Saturdays 9:30 to 3 and Sundays noon to 3 from the academy’s visitors center (52 King George St., Annapolis; 410-293-8687). While on the grounds, check out the crypt of naval hero John Paul Jones and the academy’s well-done museum, with its sprawling collection of model ships, including ones carved from animal bones by prisoners.

Wild Country Seafood

Father-and-son watermen Pat Mahoney Sr. and Jr. are behind Wild Country Seafood, which has a few picnic tables for digging into fat steamed crabs, crisp rockfish sandwiches, and some of the tastiest soft-shells we’ve encountered. No room to sit? Free steaming and ample equipment (paper, mallets) make for easy crab feasts to go. 124 Bay Shore Ave., Annapolis; 410-267-6711.


Upper Bay/Maryland’s Upper and Mid–Eastern Shore

Crow Farmstay B&B. Photograph by Loblolly.
Crow Farmstay B&B. Photograph by Loblolly.

Academy Art Museum

With a half dozen busy galleries and a respected fine-arts museum, little Easton regularly gets named one of the best small towns for art in America. Ground zero is the Academy Art Museum (106 South St., Easton; 410-822-2787), which features both regional and internationally known artists in its permanent and changing exhibitions. (The work of colorblind printmaker Peter Winslow Milton is on display through July 17.) Don’t miss the Maryland town’s 12th annual Plein Air Festival (July 9 through 17), a juried outdoor art competition.

Adkins Arboretum

All those reed-like phragmites and bright-purple loosestrife that grow along rivers and creeks in the watershed may look pretty, but they don’t belong there. Europeans transported them unknowingly in their ships’ ballast, and for years they’ve been crowding out the natives. But you won’t find them at Adkins Arboretum (12610 Eveland Rd., Ridgely; 410-634-2847), home to the largest collection of native plants in the Mid-Atlantic. Five miles of pathways lead through more than 600 species of native shrubs, trees, wildflowers, grasses, and ferns. Free docent-led walks depart the visitors center the first Saturday of every month at 10 a.m. Best part: You can buy plants from the Adkins nursery to create your own native arboretum.

Bartlett Pear Inn

Jordan Lloyd gets accolades for his French-inspired Chesapeake cuisine. Bonus: Lloyd and his wife, Alice, recently opened a bakery/market across the street from their seven-room inn and restaurant. 28 S. Harrison St., Easton; bartlettpearinn.com; 410-770-3300. From $234.

Bartlett Pear Inn dining room. Photograph by Jenna Walcott Photography via Bartlett Pear Inn.
Bartlett Pear Inn dining room. Photograph by Jenna Walcott Photography via Bartlett Pear Inn.

Bomboy’s Home Made Ice Cream

A northern-bay tradition since the 1970s. After, visit Bomboy’s Home Made Candy shop across the street. Cream of the crop: Duck, Duck, Goose—caramel swirls and peanut-butter chunks in vanilla. 329 Market St., Havre de Grace; 410-939-2924.

The Brampton Inn

Among the cottages, you can find the proper amorous accoutrements—two-person hammocks, porch swings, a wood-burning fireplace, and outdoor Japanese-style soaking tubs. 25227 Chestertown Rd., Chestertown; bramptoninn.com; 410-778-1860. Cottages from $215; rooms from $175.

C&D Canal Museum

For early mariners, the nearly 300-mile trip around the Delmarva Peninsula to reach Baltimore from Philadelphia or vice versa was a real pain in the britches. But a 14-mile trip through a waterway linking the Chesapeake Bay and Delaware River? Much better. Since its construction in 1824, the C&D Canal has been one of the world’s busiest waterways. A visit to Chesapeake City is the best way to see skyscraper-size tankers, cargo ships, and yachts go by. For a historical look at the engineering feat behind the canal, visit the C&D Canal Museum (815 Bethel Rd., Chesapeake City; 410-885-5622), in the original 18th-century pump house that once controlled water levels in the locks.

Chesapeake Bay Environmental Center

With all the development sprouting on Kent Island, parcels of unspoiled nature are harder to find. Just ten minutes off of Route 50, the Chesapeake Bay Environmental Center (600 Discovery La., Grasonville; 410-827-6694) makes for a refreshing respite. Its 500-plus acres have four miles of level trails with observation decks and blinds for viewing ospreys and other waterfowl. If you’ve got a few hours to spare, rent a kayak at the visitors center and paddle along Marshy Creek, looking for otters, muskrats, cownose rays, and terrapins. Guided kayak tours take place on weekends through October.

Photograph courtesy of Chesapeake Bay Maritime Museum.
Photograph courtesy of Chesapeake Bay Maritime Museum.

Chesapeake Bay Maritime Museum

For background on all things Chesapeake, head to the Chesapeake Bay Maritime Museum (213 N. Talbot St., St. Michaels; 410-745-2916). Its artifacts and displays, spread among several buildings, tell the story of 400 years of bay culture, exploration, ecology, and history. You’ll find a retired drawbridge, a lighthouse to explore, and a working boatyard where visitors can apprentice for a day. Definitely take the Miles River cruise aboard the museum’s 1920 buyboat, Winnie Estelle, or rent your own skiff, kayak, or rowboat built in the museum’s boatyard.

Chesapeake Landing Seafood Restaurant & Carry Out

This no-frills joint is a favorite among St. Michaels locals, who are quick to recommend the crabcakes, crispy fried chicken, and steamed crabs. Eat there or order to go through the retail section. Bay Hundred Seafood, a wholesaler that’s steps away, provides much of the fresh, local catch. 23713 St. Michaels Rd., St. Michaels; chesapeakelandingrestaurant.com; 410-745-9600.

RELATED: 11 Charming Small Towns You Need to Explore Around the Chesapeake Bay

Chesapeake Views bike trail

The fact that the Eastern Shore is as flat as a pancake makes for great bicycling. Gear up with the cycler’s guide published by Talbot County, which highlights a half dozen trails, such as the 38-mile Chesapeake Views Trail along waterfront roadways. The guide also lists places to rent bikes. Find it at tourtalbot.org or contact the Talbot County Office of Tourism at 410-770-8000.

Chesapeake Wine Trail

With its fertile soil and temperate bay breezes, the Eastern Shore has exploded with wineries. “Chardonnay and Sauvignon Blanc do extraordinarily well, but we’ve even seen grapes like Malbec rising in popularity,” says Kevin Atticks, executive director of the Maryland Wineries Association. Get a taste along the Chesapeake Wine Trail, which encompasses 16 vineyards from Dove Valley Winery in the north to Wicomico County’s Bordeleau, a perennial winner at wine competitions, in the south.

Photograph courtesy of The Crab Claw.
Photograph courtesy of The Crab Claw.

Chester River Seafood

You can order succulent river crabs by the half or full dozen (or a bushel for a party), live or steamed, from this market, which also offers speedy delivery should you be bound to a boat dock. 4954 Ashley Rd., Rock Hall; chesterriverseafood.com; 410-639-7018.

The Crab Claw

Yes, this St. Michaels crabhouse packs in the tourists, thanks to its central location abutting the Chesapeake Bay Maritime Museum, waterside tables, and half-century history. And yes, we’ve sampled sweeter steamed crabs. Still, the brick-red eatery isn’t without its draws—a prime harbor view from the second-floor dining room, crisp-edged crabcakes and crab balls with sweet-pickle-heavy rémoulade, and towering wedges of Smith Island Cake for dessert. 304 Burns St., St. Michaels; thecrabclaw.com; 410-745-2900. Open March through November.

Crow Farmstay B&B

Crow Farm started with Angus beef and expanded into grapes in 2010. Guests get old-fashioned rooms, but also a pool, farmhouse breakfasts, and a short walk back to their rooms after visiting the winery. A dozen varieties of wine are available for purchase—as are packages of grass-fed beef. 12441 Vansants Corner Rd., Kennedyville; 302-304-0551. From $155.

Delmarva Balloon Rides

For a bird’s-eye view, book a hot-air-balloon trip with Delmarva Balloon Rides (301-814-3297). The hourlong excursions depart year-round from Kent Island and float over the back roads and farmlands of the Eastern Shore; $265 a person.

Photograph by by James Trudeau.
Photograph by by James Trudeau.

Dixon’s Furniture Auction

Looking for an antique pie chest? Or maybe the steering wheel from a 1952 Dodge DeSoto? At Dixon’s Furniture Auction (2017 Dudley Corners Rd., Crumpton; 410-928-3006), a.k.a. the Crumpton Auction, you never know what you might find. The Wednesday auctions have been a destination for antiques and bargain hunters since Norman Dixon laid out some furniture in 1961 and started calling for bids. These days, Dixon’s is a whirlwind of action, as multiple auctions for furniture, small antiques, and jewelry take place at the same time. More than 200 items sell each hour, thousands by the end of the day. Great fun but not for the faint of heart.

Eastern Neck National Wildlife Refuge

The Eastern Shore’s position along the Atlantic flyway makes for spectacular bird-watching. To see regal tundra swans, head to Eastern Neck National Wildlife Refuge (1730 Eastern Neck Rd., Rock Hall; 410-639-7056), where thousands make their temporary winter home. In summer, look for ospreys, herons, blue-winged teals, and lots of songbirds.

RELATED: What the Hell Is a “Chicken-Necker?” And 9 Other Terms You Should Know Before Visiting the Bay

Eastern Shore Food Tours

Food, drinks, history—and a touch of local gossip—are all dished out during Bill and Kathy Bernard’s Eastern Shore Food Tours (443-786-4471). On the three-hour walking tours of St. Michaels (Fridays), Easton (Saturdays), and Cambridge (occasional Sundays), tour-goers sample bite-size crabcakes, tuna tacos, even shots of rum from a micro-distillery. Each stop is accompanied by conversations with the chef or owner of the business, and “no one ever goes away hungry,” claims Kathy Bernard. $59 a person.

Gay’s Seafood

Captain Rennie Gay harvests some of the fattest, sweetest crabs we’ve sampled in the Easton area, and you can pick them up steamed and spiced or live and feisty. A small grocery adjoining the riverfront shack provides extras such as seasoning and fresh crabmeat. 896 Port St., Easton; yelp.com; 410-822-5019.

Chesapeake Bay Museums: The Massey Air Museum. Photograph courtesy of Massey Air Musem.
The Massey Air Museum. Photograph courtesy of Massey Air Musem.

Harris Crab House

Just ten minutes from the Bay Bridge, Harris Crab House makes a good pit stop en route to the beach—and a fine destination in itself. The eatery is enormous, as is the menu. Snag a table on the balcony overlooking Kent Narrows, forgo new dishes like lobster grilled cheese, and stick to what the place knows best: imperial stuffed soft-shells, all-you-can-eat steamed crabs (Monday through Friday), or the lightly fried seafood combo platter. 433 Kent Narrows Way N., Grasonville; 410-827-9500. Open year-round.

Havre de Grace Decoy Museum

In the northern bay, the Havre de Grace Decoy Museum (215 Giles St., Havre de Grace; 410-939-3739) has an impressive flock showcasing the area’s own carving masters.

RELATED: The 11 Best Crab Houses to Eat at Around the Chesapeake Bay

Highland Aerosports

For a dramatic Facebook photo, book a hang-gliding adventure with Highland Aerosports (410-634-2700), which offers introductory flights, from 2,000 feet to a mile high, out of Ridgely, Maryland. Flights start at $165.

Ice Cream Barn at Lockbriar Farms

Several years ago, this pick-your-own farm found another outlet for its strawberries, blackberries, peaches, and other fruit and started whipping up ice cream. Cream of the crop: Blueberry chip, made with fresh berries and chocolate chips. 10051 Worton Rd., Chestertown; lockbriarfarms.com;410-778-9112.

Photograph courtesy of Robert Morris Inn.
Photograph courtesy of Robert Morris Inn.

Inn at Perry Cabin by Belmond

Looking for a resort with enough amenities that you technically never have to leave? Book a room at the Inn at Perry Cabin by Belmond (308 Watkins La., St. Michaels; 410-745-2200), which has restaurants, a spa, and opportunities for getting out on the water. The Inn at Perry Cabin also has a sailing academy with yachts for guests. Alas, eventually, you will have to check out.

Inn at 202 Dover

This posh inn contains the well-regarded Peacock Restaurant as well as some of the more exotically decorated rooms on the shore. Choose from five suites done up in Asian, French, English, Victorian, or safari style. 202 E. Dover St., Easton; innat202dover.com; 866-450-7600. From $289.

Massey Air Museum

This working airfield/museum harks back to a day when rural airfields dotted the Eastern Shore. The property has a grass runway and a couple of hangars full of vintage airplanes, including a DC-3 you can tour. Don’t miss: Biplane rides, $120 for 30 minutes, depart two weekends a month spring through fall (410-535-4136)33541 Maryland Line Rd., Massey; masseyaero.org; 410-928-5270.

Masthead at Pier Street Marina

Come for the gorgeous water views—especially at sunset—at this crabhouse that features a spacious deck along the Tred Avon River and $3 margaritas. We like to round out our order with a bread bowl of creamy crab dip to start and a plate of pickles and cheese for snacking while picking. 104 W. Pier St., Oxford; themastheadatpierstreet.com; 410-226-5171. Open April through October.

ice cream parlors Photograph courtesy of Scottish Highland Creamery.
Photograph courtesy of Scottish Highland Creamery.

Osprey Point

The main house overlooks a 160-slip marina on peaceful Swan Creek. You can get out on the water in one of the inn’s kayaks or paddleboards, or charter a boat from Gratitude Marina nearby. 20786 Rock Hall Ave., Rock Hall; ospreypoint.com; 410-639-2194. From $180.

Oxford-Bellevue Ferry

Oxford has resisted the development and glitz of neighboring Easton and St. Michaels, instead exuding a quiet charm. Take a stroll—with views of the Tred Avon River—or a jaunt aboard the Oxford-Bellevue Ferry, operating since 1683. Local tip: Browse the beautiful boats, and the museum, at Cutts & Case Shipyard (306 Tilghman St.; 410-226-5416), nationally known for restoring vintage vessels.

RELATED: 7 Pieces of Chesapeake Bay Lore Every Washingtonian Should Know

Robert Morris Inn

This historic waterfront inn/restaurant is where James Michener stayed while researching his novel Chesapeake. The author declared the restaurant’s crabcakes the best he’d ever had, but Michener might have enjoyed present-day chef Mark Salter’s version even more. 314 N. Morris St., Oxford; robertmorrisinn.com; 410-226-5111. Rooms from $145.

Schooner’s on the Creek

When the local crabs aren’t biting, Schooner’s isn’t steaming. It’s a sign of the quality of this gem in sleepy Oxford, though there’s plenty to tempt from the menu anytime. Zesty house-made Maryland crab soup and fat peel-and-eat shrimp are delicious ways to start, the latter steamed Chesapeake-style with plenty of spice and onions. The no-frills crabcake is also no-filler. Save room for cones at the Scottish Highland Creamery next door. 314 Tilghman St., Oxford; 410-226-0160. Open April through September.

Turnbridge Point Bed & Breakfast. Photograph by Matt Simpkins Photography , courtesy of Turnbridge Point.
Turnbridge Point Bed & Breakfast. Photograph by Matt Simpkins Photography , courtesy of Turnbridge Point.

Scottish Highland Creamery

Owner Victor Barlow grew up in Scotland above an Italian ice-cream parlor that dates to 1907. He started working there at age 15 and claims he was the only person outside the family to learn its recipes. Cream of the crop: Tiramisu. 314 Tilghman St., Oxford; scottishhighlandcreamery.com; 410-924-6298.

St. Michaels Crab & Steakhouse

You’ll have plenty of opportunities for water views, rain or shine, at this popular eatery adjoining the St. Michaels Marina and boasting a 75-seat dining room that overlooks the harbor plus an outdoor bar and crab deck for 100. We’d suggest focusing on the classic fin fare from chef/owner Eric Rosen, whether sweet steamed clams or local crabs, a lush imperial (both crab and crab-stuffed oyster), or golden rockfish bites. 305 Mulberry St., St. Michaels; stmichaelscrabhouse.com; 410-745-3737. Open April through mid-December.

Tuckahoe Machine Shop Museum

This place boasts some serious heavy metal: vintage tractors, steam-powered machinery, and a machine shop full of antique industrial lathes, drill presses, and mills. Also on the property is the Rural Life Museum, which has a recreated general store and farmhouse kitchen that looks as if it were ripped from the set of The Waltons. Don’t miss: The Tuckahoe Steam & Gas Association Show, held annually the weekend after July 4, brings antique truck and tractor pulls, steam- and gas-engine exhibits, and live music to the grounds. 11472 Ocean Gateway, Easton; 410-822-9868.

Photograph by David Owne Hawxhurst.
Photograph by David Owne Hawxhurst.

Turnbridge Point Bed & Breakfast

Pastry chef Steve Konopelski, a finalist on Food Network’s 2015 Holiday Baking Championship, is part owner of this B&B. You can sample his breads and pastries at the inn’s decadent buffet breakfasts or take one of his pastry-making classes. 119 Gay St., Denton; turnbridgepoint.com; 443-448-4782. From $130.

Vanderwende’s Farm Creamery

A popular stop on the way to the Delaware beaches. You’ll literally see where the ice cream comes from: It’s made with milk from the farm’s cows. Cream of the crop: Annie’s Apple Pie with John Deere Tracks (green and yellow sprinkles). 4003 Seashore Hwy., Bridgeville, Del.; 302- 349-5110.

Watermen Heritage Tours

As crab and oyster stocks have diminished over the years, Chesapeake watermen have gone after a new catch: tourists. More than 20 different Watermen Heritage Tours are designed to introduce landlubbers to the seafarers’ way of life, such as Captain Danny Crabbe’s oyster-tonging tours along Little Wicomico River or Captain Butch and Macy Walters’s Somerset County peeler-crab tours. On several of the tours, you can buy what you catch.

Woody’s Crabhouse

Along with steamed Eastern Shore corn and creamy coleslaw, hushpuppies are a Maryland crabhouse staple. Perhaps no place does them so well as this northern-bay dining room, strung with netting and glass buoys. It’s hard not to fill up on the deep-fried orbs of soft cornbread, especially when they’ve been dunked in honey butter. Still, if you make it to the main event, hard-shell crabs steamed in the kitchen’s own spice blend are worth it. Less work and just as tasty: deftly fried soft-shells and bountiful crabcakes (both better than the bland crab imperial and crab au gratin). 29 S. Main St., North East; woodyscrabhouse.com; 410-287-3541. Open year-round.


Maryland’s Lower Eastern Shore/Virginia’s Eastern Shore

Photograph by Adam Xenides.
Photograph by Adam Xenides.

Adam Xenides’s fishing tours

Unlike many Chesapeake fishing guides, Adam Xenides eschews the wide-open waters of the bay for the back creeks, marshes, and, as he calls them, “unexpected areas” of the watershed, mainly in and around Maryland’s Dorchester County. “Where we go, it’s rare that we’ll even see another boat,” says Xenides, who maneuvers his 18-foot-long skiff into the shallowest of waterways, unreachable by bigger boats, hoping to hook rockfish, speckled trout, catfish, or perch. Xenides also runs custom nature and photography tours for clients, which he says are almost as popular as his fishing trips. “I’ll talk to a client first to see what they’re interested in seeing—blue herons, pelicans, egrets. I usually know where to find them.” Nature tours from $40; fishing trips $50 an hour. 410-330-1242.

Bay Creek Resort & Club

It’s not hard to pretend that the two golf courses at Bay Creek Resort & Club (3335 Stone Rd., Cape Charles, Va.; 757-331-8620)—one designed by Arnold Palmer, the other by Jack Nicklaus—are a poor man’s St. Andrews, with the Chesapeake standing in for the North Sea. Both Virginia courses—particularly the Palmer—feature some of the most beautifully sited holes in the Mid-Atlantic, replete with dunes, bay grasses, water views, and just enough wind blowing off the bay to keep things interesting.

RELATED: Your Guide to Summer Chesapeake Bay Festivals

Blackwater National Wildlife Refuge

Blackwater National Wildlife Refuge (2145 Key Wallace Dr., Cambridge; 410-228-2677) has dozens of species of birds, including the largest population of bald eagles north of Florida.

Brown Dog Ice Cream

The exotic flavors—such as avocado-jalapeño-strawberry-lime—come from the creative mind of owner Miriam Elton, who whips up a changing assortment of ice creams daily—sometimes hourly. Cream of the crop: Caramelized fig and mascarpone cheese swirled with gingersnaps and bittersweet chocolate. 203 Mason Ave., Cape Charles, Va.; browndogicecream.com; 757-695-3868.

Chesapeake Wine Trail

With its fertile soil and temperate bay breezes, the Eastern Shore has exploded with wineries. “Chardonnay and Sauvignon Blanc do extraordinarily well, but we’ve even seen grapes like Malbec rising in popularity,” says Kevin Atticks, executive director of the Maryland Wineries Association. Get a taste along the Chesapeake Wine Trail, which encompasses 16 vineyards from Dove Valley Winery in the north to Wicomico County’s Bordeleau, a perennial winner at wine competitions, in the south.

Photograph by Loblolly.
Photograph by Loblolly.

 Delmarva Discovery Center & Museum

The Delmarva Discovery Center & Museum is a kid-friendly look at the ecology and history of the lower Eastern Shore, with plenty of hands-on activities. Children (and their parents) can try tonging for oysters, taking the wheel of a two-story steamship replica, or crawling through a beaver lodge. Don’t miss: Scorchy the diamondback terrapin is a museum favorite—at least until a pair of river otters, scheduled to arrive this summer, take center stage. 2 Market St., Pocomoke City; 410-957-9933.

Harriet Tubman Underground Railroad Byway

Tubman isn’t just getting her face on the $20 bill in a few years—she’s also receiving a proper museum dedicated to her legacy. When it opens in March 2017, the Harriet Tubman Underground Railroad State Park and Visitor Center will tell the story of her contributions to the Underground Railroad as well as her later years as a civil-rights worker and suffragist. The museum—in Dorchester County, where Tubman was born—will be the highlight of the already existing Harriet Tubman Underground Railroad Byway, a self-guided, scenic driving tour with more than 30 sites related to freedom seekers in the 1800s. Stops along the way include the farm site where Tubman spent her early years, the Tubman Museum and Educational Center in Cambridge, and “depots” along the Underground Railroad that survive. Pick up a map at the Dorchester County Visitors Center (2 Rose Hill Pl., Cambridge; 410-228-1000) or download an audio tour online at harriettubmanbyway.org.

Hotel Cape Charles

This 22-room boutique hotel offers contemporary rooms and lofts, some with kitchens and balconies overlooking the harbor. Bring your dog—some rooms are pet-friendly—for a walk by the sweet bayfront beach, two blocks away. 235 Mason Ave., Cape Charles, Va.; hotelcapecharles.com; 757-695–3854. From $180.

Hyatt Regency Chesapeake Bay

Looking for a resort with enough amenities that you technically never have to leave? Book a room at the Hyatt Regency Chesapeake Bay (100 Heron Blvd., Cambridge; 410-901-1234). You’ll find restaurants, a spa, and opportunities for getting out on the water. The Hyatt also sports 18-hole golf courses.

Island Creamery

TripAdvisor dubbed this family-run creamery, which has been churning out house-made flavors since the 1970s, one of the best in the country. The long lines during summer back up the claim. Cream of the crop: Pony Tracks—vanilla ice cream with peanut-butter cups and a fudge-and-peanut-butter swirl. 6243 Maddox Blvd., Chincoteague, Va.; islandcreamery.net; 757-336-6236.

Photograph courtesy of Ocean Odyssey.
Photograph courtesy of Ocean Odyssey.

 Kiptopeke State Park

Kiptopeke State Park (3540 Kiptopeke Dr., Cape Charles, Va.; 757-331-2267), near the tip of the Delmarva Peninsula, is a mecca for raptors and those who watch them. Its annual “hawk watch” counts in excess of 70,000 birds.

Ocean Odyssey

The picnic tables outside don’t have much of a view (just cars whizzing by on Route 50), but it won’t matter if you’re in the mood for a tasting menu’s worth of crab dishes. Consult the chalkboard for sizes and pricing on the hard-shells (often caught right there in Cambridge) or go for a meaty, light-on-filler crabcake. Don’t ignore a trio of indulgent starters—gloriously gooey crab dip, fried crab nuggets, and crab-flecked tater tots with pink Marie Rose sauce. To go with it all are Maryland and Virginia brews. 316 Sunburst Hwy., Cambridge; toddseafood.com; 410-228-8633. Open April through November.

The Red Roost

If tasty fried chicken, barbecue, and steamed crabs sound like a perfect combination, head to this atmospheric eatery in a former chicken house on the Delmarva Peninsula. The menu panders to big appetites, with four all-you-can-eat options, loaded steam pots, and the ironically named “just enough” meal (fried shrimp and chicken, clam strips, fries, hushpuppies, corn, and a choice of steamed crab or shrimp). Take a break over craft beers—the owners are also behind Salisbury’s Evolution Craft Brewing Co. 2670 Clara Rd., Whitehaven; theredroost.com; 410-546-5443. Open April through October.

Savage Neck Dunes

Savage Neck Dunes on Virginia’s Eastern Shore, just north of Cape Charles off US 13, is a beautiful, almost prehistoric beach and preserve. There’s no Boardwalk Fries or arcade games here, but you can walk a mile-long path through mossy ponds, a hardwood forest, loblolly pines, and high sand dunes. You’ll see lots of birds, odd plants, eroded tree stumps, and the endangered tiger beetle, which makes its home on the preserve. Best of all, it’s free.” -Rona Kobell

SouthEast Expeditions

Fourteen islands around the bay are held under the auspices of the Nature Conservancy. For a firsthand look, SouthEast Expeditions (757-990-2011) offers kayak tours to Mockhorn Island, where you’ll spot herons, egrets, and ospreys as well as the shells of buildings abandoned long ago.

Photograph courtesy of Southeast Expeditions.
Photograph courtesy of Southeast Expeditions.

 University Restaurant

“One of my favorite hidden gems is University Restaurant in the Lewis General Store (1042 Hudson Rd./Rt. 343, Cambridge; 410-228-3924). It’s on a back road outside Cambridge, in a building that dates to 1875. The restaurant takes its name from ‘Lewis University,’ a bit of local shorthand used hereabouts to describe the level of knowledge on display when old-timers show up and swap stories at the store. Chef Youngman Collins likes his ingredients local and traditional, but you will find flavors from places like Morocco and Thailand on his menu as well.” -Jim Duffy, Founder, Secrets of the Eastern Shore website.

Virginia Barrier Island Center

The Chesapeake Bay islands’ communities have been well preserved thanks to the Virginia Barrier Island Center (7295 Young St., Machipongo, Va.; 757-678-5550). The museum houses more than 7,500 artifacts—photographs, musical instruments, spinning wheels—in a two-story almshouse that dates to the 1890s.

Virginia Hang Gliding

On a trip with Virginia Hang Gliding (757-709-0759), you’ll see Tangier Island, Chincoteague, and the uninhabited barrier islands along Virginia’s Eastern Shore. Flights from $189.

Virginia Oyster Trail

Virginia already has wine trails, linking wineries by region across the state. Now it has one of the country’s first trails highlighting oysters. The Virginia Oyster Trail is a clearinghouse of sorts, connecting oyster-related activities around the bay, from growers offering tours to boat trips with watermen to restaurants specializing in the bay’s most famous bivalve. See virginiaoystertrail.com for a list of destinations.

Ward Museum of Waterfowl Art

The Ward Museum of Waterfowl Art (909 S. Schumaker Dr., Salisbury; 410-742-4988) houses the world’s largest collection of antique decoys, including dozens of pricey creations by the men the museum is named for, Lem and Steve Ward, onetime barbers who found they could make more money trimming blocks of wood than heads of hair. You can also visit the brothers’ Crisfield workshop by appointment (410-968-2501).


Maryland’s Western Shore

Cypress Swamp. Photograph by Pat Blackley/Alamy.
Cypress Swamp. Photograph by Pat Blackley/Alamy.

American Chestnut Land Trust

Calvert County’s Parkers Creek is one of the last undeveloped tributaries on the bay’s western shore. The 3,000 acres along the creek have been preserved and protected by the nonprofit American Chestnut Land Trust (410-414-3400). You can walk paths throughout the property, but the best way to see the area is on an ACLT-led canoe tour. The three-hour round trip reveals unspoiled salt marsh and wooded wetlands much the same as they were 400 years ago when explorer John Smith passed by. Paddles depart a few Saturdays a month, spring through fall. Tours are free, but there’s a suggested $15 donation per person.

Battle Creek Cypress Swamp Sanctuary

Swamps don’t get great PR. They’re full of mosquitoes, mucky water, and creatures you wouldn’t want in your living room. But Battle Creek Cypress Swamp Sanctuary (2880 Grays Rd., Prince Frederick; 410-535-5327) is worth any bug bites. It contains one of the northernmost strands of knobby-kneed-cypress trees in North America. Start at the nature center to get the lay of the land, then follow the boardwalk trail through the otherworldly swamp, admiring the prehistoric-looking trees and listening to the bullfrogs and green frogs that sing during the day. Just remember the DEET.

RELATED: 8 Great Chesapeake Bay Restaurants (Beyond Crab Houses)

Bob Evans Seafood

You’ll find perch, oysters, croaker, and live crabs as well as shedding tanks for soft-shells in season. Call ahead—popular items such as large hard-shells can go quickly. 5527 Muddy Creek Rd., Churchton; facebook.com/bobevansseafood; 410-867-3884.

Calvert Cliffs State Park

Ten to 16 million years ago, the entire Chesapeake region was one vast ocean populated by sharks, whales, and prehistoric corals. Those creatures are long gone, but their fossilized remains can be found scattered along bay beaches, particularly in Calvert County. Bring a trowel—and a keen eye—to Calvert Cliffs State Park (10540 HG Trueman Rd., Lusby; 301-743-7613), a hotbed for unearthing Miocene-era sharks’ teeth, including fragments of three-to-seven-inch-long choppers once belonging to the school-bus-size megalodon shark.

Chesapeake Beach Railway Museum

More than 100 years ago, Washingtonians would pay 50 cents for the 28-mile train ride to Chesapeake Beach to relax on the sand. (Trains departed several times daily during summer from a station in Northeast DC’s Deanwood neighborhood, where Minnesota and Nannie Helen Burroughs avenues meet.) The museum captures the era through hundreds of photographs and artifacts from the rail line, defunct since the Great Depression. Don’t miss: The museum itself is housed in the line’s last remaining depot, which dates to 1900. 4155 Mears Ave., Chesapeake Beach; cbrm.org; 410-257-3892.

Photograph courtesy of Historic St. Mary’s City.
Photograph courtesy of Historic St. Mary’s City.

Flag Ponds Nature Park

The beaches of Flag Ponds Nature Park (1525 Flag Ponds Pkwy., Lusby; 410-586-1477) have been known to offer traces of ancient sharks, whales, even crocodiles.

Historic St. Mary’s City

Before there was Annapolis, there was St. Mary’s City. Maryland’s first city—and the fourth permanent English settlement in North America—served as the colony’s capital for 61 years until moving to A-Town in 1695. Historic St. Mary’s City (18559 Hogaboom La.; 240-895-4990) is a mini-Williamsburg of sorts, with costumed interpreters demonstrating antiquated skills such as how to run a printing press or harvest tobacco. Check the calendar at hsmcdigshistory.org for weekly events, including archaeological digs open for public viewing.

St. Clement’s Island-Potomac River Museum

On March 25, 1634, some 150 weary travelers from England dropped anchor by an island in the Potomac. They dubbed it St. Clement’s after Pope St. Clement, the patron saint of mariners, and held the first Roman Catholic Mass in the British colonies. To reach the island today, take a scurvy-free, 20-minute water-taxi ride, departing from the St. Clement’s Island–Potomac River Museum (38370 Point Breeze Rd., Coltons Point; 301-769-2222). There, you can gaze at the 40-foot-tall stone cross erected in 1934 for Maryland’s tricentennial, picnic, hike, or tour a replica of Blackistone Lighthouse, which stood from 1851 through 1956, when it was destroyed by fire.

Watermen Heritage Tours

As crab and oyster stocks have diminished over the years, Chesapeake watermen have gone after a new catch: tourists. More than 20 different Watermen Heritage Tours are designed to introduce landlubbers to the seafarers’ way of life, such as Captain Danny Crabbe’s oyster-tonging tours along Little Wicomico River or Captain Butch and Macy Walters’s Somerset County peeler-crab tours. On several of the tours, you can buy what you catch. See watermenheritagetours.com for a list of trips.

Woodlawn Farm

Part of Maryland’s first estate, the land was deeded in 1634 to Leonard Calvert, Maryland’s first governor. The main manor house, on Calvert Creek, has two period-decorated rooms, but the sweet Magnolia Cottage gets its own private courtyard. 16040 Woodlawn Dr., Ridge; woodlawn-farm.com; 301-872-0555. From $140.


Virginia’s Northern Neck

chesapeake-bay-virginia-oyster-trail

Chesapeake Bay Wine Trail

The Chesapeake Bay Wine Trail includes ten wineries, mainly along the Northern Neck.

Hope and Glory Inn

Whimsy reigns at this Northern Neck inn, a former schoolhouse where guests are invited to drink at a bar called Detention and eat at the Dining Hall restaurant. Don’t miss the secluded garden bath, with its outdoor shower and antique claw-foot tub—perhaps the bay’s most inviting place to bathe. 65 Tavern Rd., Irvington, Va.; hopeandglory.com; 804-438-6053. From $200.

Northern Neck Heritage trail

The Northern Neck Heritage Trail Bicycling Route Network links historic sites, such as George Washington’s birthplace and Robert E. Lee’s Stratford Hall, with small towns along 88 miles of quiet roadway.

Reedville Fishermen’s Museum

The fishing industry created Reedville, Virginia—including opulent Victorian houses that once belonged to prominent boat captains—so the town created this museum to showcase and preserve the heritage of what continues to be the highest-producing commercial fishing port on the East Coast. The museum has myriad indoor and outdoor exhibits on the growth of the menhaden industry—the small, oily fish that’s been used in everything from lubricants to fish-oil capsules—and the waterman’s way of life. Don’t miss: The free cruise on the Elva C., one of the museum’s historic boats docked along Cockrell’s Creek. 504 Main St., Reedville; rfmuseum.org; 804-453-6529.

Tides Inn

Looking for a resort with enough amenities that you technically never have to leave? Book a room at the Tides Inn (480 King Carter Dr., Irvington, Va.; 844-244-9486) which has restaurants, a spa, and opportunities for getting out on the water. The Tides also sports 18-hole golf courses.

Virginia Oyster Trail

Virginia already has wine trails, linking wineries by region across the state. Now it has one of the country’s first trails highlighting oysters. The Virginia Oyster Trail is a clearinghouse of sorts, connecting oyster-related activities around the bay, from growers offering tours to boat trips with watermen to restaurants specializing in the bay’s most famous bivalve.

This article appears in our July 2016 issue of Washingtonian.

Don’t miss a new restaurant again. Subscribe to our weekly newsletters.

Questions or comments? You can reach us on Twitter, via e-mail, or by contacting the author directly:
Ann Limpert
Executive Food Editor/Critic

Ann Limpert joined Washingtonian in late 2003. She was previously an editorial assistant at Entertainment Weekly and a cook in New York restaurant kitchens, and she is a graduate of the Institute of Culinary Education. She lives in Logan Circle.

Anna Spiegel
Food Editor

Anna Spiegel covers the dining and drinking scene in her native DC. Prior to joining Washingtonian in 2010, she attended the French Culinary Institute and Columbia University’s MFA program in New York, and held various cooking and writing positions in NYC and in St. John, US Virgin Islands.