Dream Weekends: Insider's Guide to the Eastern Shore

Forget the touristy spots. Here’s an insider’s guide to the Eastern Shore—from a day sail to a crab feast to other cherished haunts.

By: Andrea Poe

Once you cross the Chesapeake Bay Bridge to the Eastern Shore, the tension in your shoulders relaxes. You breathe easier.

I know. A native New Yorker, I arrived on the Eastern Shore almost nine years ago and fell in love with the pretty historic towns, the open spaces, and all that water. Most of all I fell in love with the kinder, gentler way of life.

The water, the farms, the sailboats, the quaint towns—it’s little wonder shore residents affix bumper stickers that read there’s no life west of the chesapeake bay.

Locals know how to enjoy their summers, but they do in their own way, often invisible to tourists. To tap into the authentic Eastern Shore experience—where you won’t find tourists, T-shirt shops, or taffy—do as the locals do.

These are 12 shore things locals love. Most are within a two-hour drive of the Beltway, for an easy day trip, but we’ve also given suggestions of where to stay overnight if you want to make a weekend of it.

Log-Canoe Races

Log-canoe races are to the Chesapeake Bay what polo is to Hunt Country.

Log canoes—slim wooden boats that are long on sail and short on hull—started as a hybrid of Powhatan tribal canoes and English sailing ingenuity and developed into work boats for watermen. As upkeep of the canoes—handcrafted of loblolly pine and poplar—has become more expensive, log-canoe racing has become a sport for well-funded sailors.

For spectators the fun is in watching crews keep the sail-heavy crafts upright as they accelerate to 15 miles an hour. The only way to see races is from the water, and at docks you can hire a ride out to the action. One of the most knowledgeable sailors is Captain Iris Clarke, who will zip you from St. Michaels to the races aboard the Selina II, a 1920s-era yacht originally owned by her grandparents.

Races take to the Miles, Chester, and Tred Avon rivers every weekend from June through September. For a schedule of races and details on the history of log canoes, see logcanoes.com.

Captain Clarke can be reached at 410-726-9400 or sail-selina.com. She charges $50 a person for a scheduled tour; $285 for a private two-hour sail for up to six people.

Make a weekend of it: Consider a stay at Wades Point Inn on the Bay near St. Michaels, a comfortable bayfront 19th-century manor on 120 acres of fields and woodlands. It has kayaks and a nature trail. Call 888-923-3466 or see wadespoint.com. Rooms start at $145 a night.

Where to eat: Sherwood’s Landing at the Inn at Perry Cabin is all about elegant waterfront dining. A menu that tweaks the traditional includes such entrées as rockfish with corn pudding and Jack Daniels corn sauce. Or enjoy the same chef’s fare, in a more casual (and cheaper) setting, at the inn’s Purser’s Pub. The cozy lounge serves such selections as fish and chips and shepherd’s pie inspired by chef Mark Salter’s English homeland. Call 410-745-2200 or see perrycabin.com.

Food Lover’s Tour

Chef Andrew Evans of the Inn at Easton has put together an insider’s look at the best of Chesapeake Bay cuisine. Weaving along country lanes, Evans brings small groups to the farmers and watermen who deliver the area’s produce, crabs, rockfish, and oysters.

Evans picks different purveyors depending on season. One spring tour included a waterfront farm where black sex links, barred rocks, and New Hampshire reds roost in a Victorian-styled hen house affectionately known as the Egg-mobile. On a different day, the tour visited a snail grower who swears that a diet of classic-rock music along with mangoes, lettuce, and cabbage keeps the snails healthy, mating, and ready for such customers as Alain Ducasse and the Inn at Little Washington.

The tour ends back at the luxury inn where Evans’s restaurant, one of the region’s best, is located. There he prepares lunch using ingredients from that day’s purveyors. The menu might include fried oysters with semolina crust, corn soufflé with lobster roe, and crab cakes with tartar sauce and tomato confit.

Cost: $200 a person for the day, including a three-course lunch. See theinnateaston.com or call 888-800-8091 to reserve a spot.

Make a weekend of it: The Inn at Easton is a sophisticated country inn. The seven-room bed-and-breakfast features bold colors, 400-thread-count Italian linens, and Aveda toiletries. When not serving bounty from local farms, the inn’s restaurant features fare from Evans’s previous life Down Under. Here’s your chance to sample such Australian specialties as roasted kangaroo loin and sticky-fig-and-ginger pudding. Rooms start at $200 a night.

Duck, Duck, Goose

It used to be that every waterman could whittle a decent decoy. Today, thanks to mass-produced synthetic decoys, carving is a dying art—which is what makes it so treasured.

At the Ward Museum of Wildfowl Art in Salisbury you can learn to carve a decoy from such masters as Ernie Muehlmatt and Larry Barth, who keep the tradition alive. One- to three-day workshops run from $60 to $365.

If you’re short on time, you can simply have a look at the museum’s extensive collection of antique decoys and contemporary wildfowl sculptures. The gift shop sells hand-carved decoys. For more information, see wardmuseum.org or call 410-742-4988.

Make a weekend of it: The Atlantic Hotel, a few minutes’ drive from Salisbury, is a recently revived Victorian. It’s in downtown Berlin, an antique-filled town best known for its role in Julia Roberts and Richard Gere’s film Runaway Bride. It’s at 800-814-7672. Rooms start at $85.

Where to eat: Near the Ward Museum is Brew River Restaurant & Bar, a casual waterfront spot known for sweet and savory homemade muffins, classic crab dip, and fried oysters. It’s at 502 West Main Street; 410-677-6757.

Everyone Loves a Parade

Just about every community has a Fourth of July parade, and the waterfront towns on the Eastern Shore are no different—except their parades take place on the water.

In Cambridge the boat parade is led by the Nathan of Dorchester, a wooden skipjack. Join spectators on the lawn of Sailwinds Park or sip mai tais at the tiki bar at Snappers Waterfront Café (112 Commerce St.; 410-228-0112) while you cheer on the red-white-and-blue-bedecked boats as they pass.

The parade begins at 4 pm on July 4. Boats assemble at the channel of the Frederick C. Malkus Bridge.

Make a weekend of it: Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina has bright rooms overlooking the Choptank River. Multiple pools—including an indoor/outdoor pool and hot tub, an infinity pool, and one with a water slide—not to mention a spa, golf course, and boat rentals make this a destination in itself. Rooms start at $199. Call 410-901-1234 or see chesapeakebay.hyatt.com.

Where to eat: Blue Point Provision Company is part of the Hyatt, but it’s not just for tourists. Locals come for fresh seafood and sunsets over the water. It’s at 410-901-4610.

Go Antiquing

The Eastern Shore is an antique hunter’s dream. You can’t drive far without stumbling on an auction, barn sale, or antique shop.

For high-quality antiques, head to Queenstown, where two of the region’s best dealers sit side by side. DHS Designs features things you may have dreamt of—from 17th-century marble fireplace mantels salvaged from French chateaux to carved limestone fountains. Next door at Chesapeake Antique Center, 50 to 60 dealers sell Sotheby’s-worthy antiques, from Hepplewhite to Chippendale.

Both are at the intersection of Routes 50 and 301, behind Chesapeake Outlet Village. For DHS Designs, call 410-827-8167 or see dhsdesigns.com. J.R.’s Antique Center is at 410-810-1006; jrsantiques.com.

Make a weekend of it: Queenstown Inn Bed & Breakfast, in the quiet town of Queenstown, has airy country-style rooms. It’s at 888-744-3407; queenstowninn.com. Rooms start at $140 a night.

Where to eat: Chesapeake Chicken & Rockin’ Ribs, a casual local hangout (with a Bethesda outpost), cooks up the juiciest roasted chicken you may ever taste. Pair it with homemade sides like sweet slaw, mashed potatoes, and melt-in-your-mouth honey-drop biscuits, and you’ll become a convert. It’s at 101 Hissey Road, Grasonville; 410-827-0030.

Sail on a Skipjack

One of the great traditions of the shore is its lore. No one dishes more than Captain Wade Murphy, a fifth-generation waterman.

He also happens to own the country’s oldest working skipjack, built in 1886. When you book passage on his oystering vessel, Rebecca T. Ruark, you’ll sail the Choptank River and be rewarded with history of the bay. If you ask nicely you’ll get the best oyster-shucking lesson of your life.

Captain Wade can be reached at 410-829-3976. Rebecca T. Ruark is docked in Dogwood Harbor on Tilghman Island; skipjack.org. A two-hour sail costs $30 a person.

Make a weekend of it: Relaxing in Adirondack chairs while watching snow-white egrets in the marsh make it hard to resist the Tilghman Island Inn. Dogs and cats are welcome, too. Call 800-866-2141 or see tilghmanislandinn.com. Rooms start at $175.

Where to eat: The inn’s waterfront restaurant attracts visitors and locals alike for such specialties as creamy oysters in puff pastry and cider-glazed pork with grits.

Kayak With the Ponies

Misty may have been fictional, but the wild ponies of Chincoteague and Assateague remain a symbol of the shore’s independent spirit.

Although it’s unknown how the horses came to settle on the islands, it’s believed they may be descendants of horses left behind when a Spanish galleon sank in the 1500s. Today, there are two distinct herds of about 150 horses—one in Chincoteague, Virginia, and one on the Maryland side, in Assateague. Although there are boat and land tours, the least obtrusive way to appreciate the ponies is by kayak.

Coastal Kayak (877-44-kayak; c-kayak.com) offers tours and rentals. A four-hour tour of Assateague is $45 a person (with Web coupon), a single kayak rents for $25 for two hours.

Make a weekend of it: Bunk where Marguerite Henry wrote Misty of Chincoteague in 1947, at Miss Molly’s. The old boarding house has been converted into a sweet bed-and-breakfast with bikes, boogie boards, and beach chairs. It’s at 4141 Main Street, Chincoteague; 800-221-5620; missmollys-inn.com. Rooms start at $120 a night.

Where to eat: Oyster stew to crab imperial, Chincoteague Inn & PT Pelicans is all about traditional shore cooking. Sit on the deck for wide views of Chincoteague Bay. It’s at 6262 Marlin Street, Chincoteague; 757-336-6110; chincoteague.com/rest/ciptp.

Scenic Route

Two of the prettiest historic waterfront towns on the shore are St. Michaels and Oxford. A scenic alternative to the half-hour drive between them is the ten-minute ride on the Oxford-Bellevue Ferry from either Oxford or the town of Bellevue, seven miles from St. Michaels.

The nation’s oldest privately operated ferry, it’s been making the trip across the Tred Avon River since 1683. Get out of your car and stand at the bow to watch blue herons land on the shore, ospreys hunker in their nests, and hawks swoop for prey.

The ferry (410-745-9023; oxfordbellevueferry.com) runs seven days a week March through November, beginning in Oxford at 9 am; crossings every 20 minutes. Last trip leaves Oxford at 8:30 pm and Bellevue at 8:45. Car and driver cost $9 one way, $14 round trip.

Make a weekend of it: Oxford’s Robert Morris Inn, alongside the Tred Avon, was the 18th-century home of a signer of the Declaration of Independence. The inn also is home to the restaurant James Michener credited with serving the best crab cakes on the shore. It’s at 888-823-4012; robertmorrisinn.com. Rooms start at $110 a night.

Where to eat: A couple from Chicago have reinvented Pope’s Tavern, a former general store, into a gourmet haven. In nice weather sit on the front porch and sample chef Lisa MacDougal’s signature tuna tartare or mussels with homemade frites. It’s at 504 South Morris Street in Oxford; 410-226-5220; oxfordinn.net.

A Night at Andy’s

Andy’s is a favorite of students and professors from nearby Washington College and of music lovers from all over the shore. You never know who’ll be booked there—one night the quirky singer Seamus Kennedy from Belfast, Ireland, another night Washington’s own alternative country band Last Train Home. A plus: fun beer like oyster stout and Granny Smith cider.

Andy’s is at 337½ High Street, Chestertown; 410-778-6779; andys-ctown.com.

Make a weekend of it: In downtown Chestertown, walking distance from the club, is the Imperial Hotel. Double porches, a cozy courtyard, and heated towel racks make this a deal. Rooms start at $105. It’s at 410-778-5000; imperialchestertown.com.

Where to eat: Andy’s is fun and a bargain to boot. Fill up on potato skins (with six toppings) and the club’s famous $6.25 hamburger.

Lighthouses of the Bay

Some of the most historic “houses” on the shore are the least visited because they are far from land.

Although tended lighthouses were once an integral part of the maritime economy of the Chesapeake, they have been either automated or abandoned. History buff Captain Mike Richards can take you on a cruise to look at lighthouses you’d never see if you remain landlocked—like Sharps Island Light, built in 1882 and famous for its 15-degree tilt. You can also glimpse what living in a lighthouse was like inside Thomas Point Shoal, a red-roofed lighthouse built in 1875.

Tours range from $50 to $130 a person, depending on the number of lighthouses visited (up to ten). Contact Chesapeake Lights, 800-690-5080; ches­apeakelights.com.

Make a weekend of it: Richards and his wife, Carol, run the Lazyjack Inn on Dogwood Harbor. Rooms start at $144 April through October. Call 800-690-5080 or see lazyjackinn.com.

Where to eat: The Bridge Restaurant is beside the Knapps Narrows Bridge at the head of Tilghman Island. People come by land and sea for the fresh seafood. Not to be missed: soft-shell crabs from the restaurant’s own soft-shell floats. It’s at 6136 Tilghman Road; 410-886-2330; bridge-re­s­t­aurant.com.

Winetasting

The Eastern Shore is no Napa Valley, but some plucky vintners have been converting fields of corn into grapes.

Little Ashby, a boutique winery that started bottling in 2000, was the first licensed winery on Maryland’s Eastern Shore. The Merlot, Pinot Noir, Chardonnay, and Cabernet Sauvignon are served in local restaurants, as is its smooth red, Super Talbot, a state gold-medal winner.

Surrounded on three sides by water, Little Ashby can be reached by boat, car, or bicycle. Chester, the yellow Lab whose face graces many of Little Ashby’s wine labels, has been known to give tours of the grounds in exchange for a game of fetch.

Nearby, in a converted flour mill, is the newest Eastern Shore winery. Opened in 2006 by two young couples, St. Michaels Winery features small runs of wines, including a smooth Chardonnay and crisp Sauvignon Blanc.

Little Ashby is at 27549 Ashby Drive, Easton; littleashbyvineyards.com. Call owners Warren or Lynne Rich for a tour and tasting, 410-819-8850. St. Michaels Winery is at 605 South Talbot Street, St. Michaels; 410-745-0808; st-michaels-winery.com.

Make a weekend of it: The Inn at 202 Dover, a Gilded Age mansion transformed into an uber-luxe inn, features 600-square-foot suites with steam showers, breakfast in a glass conservatory, and a music room where you can enjoy a cocktail. Rooms start at $375. Call 866-450-7600 or see innat202dover.com.

Where to eat: Scossa is a stylish Italian restaurant that turns out traditional dishes like bresaola with arugula and Parmesan, risotto with shrimp and zucchini, and roast chicken alla cacciatore courtesy of chef Giancarlo Tondin, formerly of Cipriani’s in New York. It’s at 8 North Washington Street, Easton; 410-822-2202; scossarestaurant.com.

Build a Boat

The shore has a long shipbuilding history. Drop in at the Chesapeake Bay Maritime Museum most Saturdays and Sundays to get hands-on experience hanging planks and shaping bow stems under the direction of a shipwright through the museum’s Apprentice for a Day program.

The museum is also a stop for all things bay-related, with exhibits on Native Americans of the Chesapeake, oystering, and crabbing.

The museum is at 213 North Talbot Street, St. Michaels; 410-745-2916; cbmm.org. The apprentice shipbuilding program costs $25 for nonmembers and runs 10 to 4 on weekends.

Make a weekend of it: Five Gables Inn & Spa is a revamped Victorian with cheerful rooms and a small spa. It’s within walking distance of the museum and the boutiques and galleries of downtown St. Michaels. Rooms start at $160. Check out last-minute deals on the inn’s Web site, fivegables.com, or call 877-466-0100.

Where to eat: Hands down, the best place for crabs and beer is the Crab Claw in St. Michaels. The waterfront deck, where waitresses pile Old Bay–coated blue crabs on your paper tablecloth, is made for getting messy. Toss scraps to the rockfish, who can’t resist crab—shells and all. Take Route 33 to Mill Street, turn right, and the restaurant is at the end of the street at Navy Point on St. Michaels Harbor; 410-745-2900; thecrabclaw.com.

When to Go

Time your visit right and you can drink fine wine, see lots of art, or listen to duck calls

There’s no better time to visit the Eastern Shore than during one of its many festivals. Here are a few worth checking out:

April 27 to 29: The St. Michaels Food & Wine Festival is a gourmet’s dream, with tastings of fine wines and spirits, seminars by sommeliers, and cooking demos by top chefs such as Roberto Donna of Galileo. For details: 443-205-2185 or stmichaelsfoodandwinefestival.com.

July 22 to 29: The Plein Air Festival features 50 artists from around the country painting outdoors on the historic streets of Easton through that Thursday. Exhibits, workshops, auctions, and other art-related events round out the week. For details: 410-822-7297 or pleinair-easton.com.

November 9 to 11: The Waterfowl Festival is expected to draw 20,000 visitors. Some 400 artists from around the world exhibit and sell paintings, decoys, photography, sculpture, and folk art celebrating America’s waterways, flora, and fauna. For details: 410-822-4567 or waterfowlfestival.org.