1. Eat Crabs on the Water
Perched on docks overlooking the Miles River, the nearly 60-year-old, family-owned Crab Claw (304 Burns St., St. Michaels) is an Eastern Shore institution, serving steamed crabs, crabcakes, oysters, rockfish, and more from the water, plus other items such as a Beyond Burger. Tip: After feasting, stretch your legs with a stroll along Talbot Street, lined with antiques stores and other small shops.
2. Enjoy Fresh Crabs With Live Music
The menu at Foxy’s Harbor Grille (125 Mulberry St., St. Michaels) includes crabs and other seafood and non-seafood dishes, along with an expansive selection of island-inspired cocktails—including more than a dozen spins on the popular orange crush. Plus, Foxy’s regularly hosts live music. Want to get on the water before or after? St. Michaels’ public boat ramp is just a few blocks from the restaurant, and the folks at Shore Pedal & Paddle (410-745-2320) will meet you there with kayak or paddleboard rentals.
3. Check Out a Waterfront Museum
The Chesapeake Bay Maritime Museum (213 N. Talbot St., St. Michaels) features permanent and rotating exhibits, a schedule of well-loved festivals and events, plus other fun activities on its campus, which includes a museum, a working shipyard, a historic lighthouse, and a floating fleet of historic boats, including log canoes. New this summer: Groups of up to six can charter a two-hour boat tour to see log canoe races in the Miles River ($375).
4. Hike a Waterfront Trail
Pickering Creek Audubon Center (11450 Audubon Ln., Easton) offers more than four miles of walking trails (no bikes!) as well as bird-viewing spots, a pond, and wetlands on 400 acres bordering the creek. Print a trail map before you go or pick one up at the welcome center.
5. Sip Wine on a Creek
The Eastern Shore isn’t widely known for its wineries and vineyards, but there are a few worth a stop. In addition to weekend tastings, Kent Island’s Cascia Vineyards (1200 Thompson Creek Rd., Stevensville), which overlooks Cox Creek, hosts events such as Queen Anne County’s “Thursdays in the Park” summer concert series.
6. Walk to a Hidden Beach
Terrapin Nature Park (191 Log Canoe Cir., Stevensville) is a 276-acre park with a flat 3.25-mile trail that goes through woodlands and wetlands and—what makes it such a hidden gem—winds up at a thin but long sandy beach overlooking the Bay Bridge. Because it’s a nature park, coolers and umbrellas are prohibited, but there are new restrooms and picnic areas—plus plenty of shoreline for dipping toes in the sand. Tip: Just down the street, Bark Barbecue (371 Log Canoe Cir.) offers tasty sandwiches and soft-serve ice cream.
7. Stroll or Ride Around an Island
Wye Island (632 Wye Island Rd., Queenstown) is home to six miles of relatively flat walking and biking trails as well as a nearly 300-year-old holly tree. It’s pet-friendly, too.
8. Enjoy a Sunset Dinner
Overlooking the Tred Avon River with a westward view, Doc’s Sunset Grille (104 W. Pier St., Oxford) is known—and aptly named—for its sunset-over-the-water vistas. The menu features a mix of seafood dishes and “handhelds”—burgers, sandwiches, and wraps—with indoor and outdoor seating and a tiki bar.
9. Grab Dockside Ice Cream
The Scottish Highland Creamery (103 S. Morris St., Oxford) moved inland recently, but you can still enjoy the ice cream—which is so beloved that the catering is popular for local weddings—with a view by strolling across the street to the waterfront Oxford Town Park. For pre-dessert dinner or drinks, Capsize (314 Tilghman St.) serves American fare along with wine, beer, and seasonal cocktails on the water. Also nearby, the Water’s Edge Museum (101 Mill St.) is Talbot County’s first African American arts museum.
10. Bike the Oxford/St. Michaels Loop—and Ride a Ferry
The Oxford/St. Michaels Loop is a 30-mile biking route that goes from St. Michaels to Bellevue, where you hop on the Oxford-Bellevue ferry to Oxford, then bike back to St. Michaels. Note: The trail goes along some main roads, so plan and navigate accordingly—also, the ferry is $6 per biker and accepts cash, check, or Venmo. Tip: While in Oxford, you can refuel with an ice-cream cone at the aforementioned Scottish Island Creamery. A map and other details are in the Talbot County Bike Trails Map, where the trail is listed at map number 5.
11. Enjoy Frozen Drinks on a Fake Beach
At Kentmorr Restaurant & Crab House (910 Kentmorr Rd., Stevensville), you can pretend you’re somewhere else entirely, with your toes in the sand next to a tiki bar churning out frozen drinks. The restaurant offers indoor and open-air covered dining, but there’s a takeout menu for beachgoers, who sometimes (heads up!) are required to pay a cover.
12. Tour a Lighthouse
The Choptank River Lighthousein Cambridge (High and Water sts.) is a 20-plus-year-old replica of the screw-pile structure put there in the early 1900s, after an ice floe destroyed the original one built in the 1800s. The lighthouse—which is open to the public for free (seasonally) and houses a small museum about its history and the area—is at the end of a pier, walking distance to downtown. Afterward, you can stroll a few blocks over to RaR Brewing, which is famous for its draft-beer selection and Chessie smash burger (504 Poplar St., Cambridge).
This article appears in the May 2023 issue of Washingtonian.