Things to Do  |  Travel

Coastal Escape: 25 Things to Do on the Eastern Shore and in Annapolis

Cruise on a skipjack, dine on local seafood, bike by the water, and more.

Head to Annapolis and sail away on Woodwind II. Photograph by Heather Crowder.

Want to get out of town this summer, even for the day? These four great Maryland destinations offer a coastal vacation less than two and a half hours from DC. For each, we’ve listed places and activities we recommend, whether for a day trip or a weekend.



Dine outside on West Street in Annapolis. Photograph by Ken Tom.

The picturesque state capital, home to the U.S. Naval Academy, is known as a hot spot for sailing.

Sail on–or Above–the Bay

Chill aboard the schooners Woodwind and Woodwind II (80 Compromise St.), which ply the Chesapeake Bay for daily sunset cruises. Or soar on a parachute above pretty Thomas Point Shoal Lighthouse with parasailing operator Z Flight Parasail and Watersports (300 Second St.).

Celebrate Civil Rights

Maryland governor Wes Moore declared 2024 to be the Year of Civil Rights. Head to the Banneker-Douglass Museum (84 Franklin St.) to learn about major contributions made by Black Marylanders, including Thurgood Marshall, the first African American to sit on the Supreme Court.

Engage With Artists

Galleries exhibit everything from antique oils to contemporary spins on maritime art. Go beyond the canvas to peek inside studios and take workshops from working artists during the citywide Annapolis Arts Week June 1 through 7.

Stroll and Shop

Around Main Street, you can browse brand-name boutiques as well as local favorites, including Naptown Clothing Co. (107 Main St.) for nautical-themed clothes and Old Fox Books (35 Maryland Ave.), a cozy bookstore with a cafe.

Eat Like a Resident

Sample local seafood with a kick—think chili-crusted oysters—at the Choptank (110 Compromise St.), the glam girl of Annapolis with a stylish dining room on the harbor. For unusual seafood combinations such as anchovies with chocolate, stop by Sailor Oyster Bar (196 West St.),which reopened in February after a fire damaged the hipster haven.

Party Under the Stars

A large swath of West Street, one of the city’s main arteries, closes to traffic during much of the summer. Beneath a canopy of lights, listen to live music and dine outside at some of Annapolis’s best restaurants, including Tsunami (51 West St.), an Asian-fusion hot spot owned by the mayor.

Book a Room With a View

Watch yachts circle Ego Alley from your room at the Annapolis Waterfront Hotel (80 Compromise St.). The property on the harbor has some recent upgrades, including rooms redecorated with a nautical motif.


Talbot County

The Inn at Perry Cabin in St. Michaels,  Maryland.  Photography by Jay  Fleming.

This upscale enclave is home to historic towns with boutiques, galleries, and restaurants, as well as more than 600 miles of waterfront to explore.

Take a Boat Ride

Sip and snack during an hour-and-a-half sail aboard one of the Chesapeake’s famed skipjacks, the Stanley Norman. Built in 1902, the vessel recently joined a fleet of exquisite boats at the Inn at Perry Cabin (308 Watkins Ln., St. Michaels). Nearby, Patriot (213 N. Talbot St., St. Michaels) is a two-story cruise boat that offers history and wildlife tours on the Miles River.

Brunch on the Bay

A new owner has ensured that the Robert Morris Inn (314 N. Morris St., Oxford), which was originally home to a signer of the Declaration of Independence, retains its historic charm. You can enjoy the popular brunch—try the crab Benedict—on the brick porch overlooking the water.

Hit the Shops

Talbot County is known for its stylish boutiques, including Silver Linings Jewelry (203 S. Talbot St., St. Michaels) for statement sterling, the well-curated Flying Cloud Booksellers (26 W. Dover St., Easton), half of which is devoted to kids, and Bountiful Home (803 Goldsborough St., Easton), a home-decor and furniture emporium.

Grab a Cone With a View

The ice-cream shop Scottish Highland Creamery (103 S. Morris St., Oxford) now has a second location in a former general store, still offering creative homemade flavors such as maple bacon. Savor your treats across the street on a bench overlooking the water.

Attend Drive-Worthy Arts Events

The Chesapeake Chamber Music Festival (17 S. Washington St., Easton), June 7 through 15, is a chance to catch concerts in an intimate setting and engage in Q&As with world-class artists. Additionally, this year marks the 20th anniversary of Plein Air Easton, the country’s largest festival of plein air painting, where visitors can interact with artists from around the world as they paint outdoors, July 12 through 21.

Sample an Award-Winning Menu

Chef Harley Peet helms the acclaimed kitchen at Bas Rouge (19 Federal St., Easton), an elegant jewel box of a restaurant—and he’s a James Beard Award winner* for best chef in the Mid-Atlantic. Peet’s menu roams the world for the finest ingredients, from imported kaluga caviar to rockfish caught steps from his kitchen.

Play Overnight

Channel your inner child at Wylder Hotel Tilghman Island (21551 Chesapeake House Dr., Tilghman), a resort that feels like a posh camp for grownups, with cornhole, moonlight s’mores around the fire pit, and cocktail classes, along with a newly installed plunge pool and sauna. Or ratchet up the romance in a waterfront suite at the Inn at Perry Cabin (308 Watkins Ln., St. Michaels), paired with a private wine dinner in a boathouse. The chic resort also has a playful side, with golf, croquet, and tennis, plus loaner bikes for puttering around St. Michaels.


Queen Anne’s County

Libbey’s Coastal Kitchen and Cocktail Bar’s fried green tomato crab tower. Photograph courtesy of Libbey’s Coastal Kitchen and Cocktail Bar.

Across the Bay Bridge, this area is known for fresh seafood and outdoor activities.

Paddle the Bay

Bring your kayak, canoe, or standup paddleboard, or rent one through Dragon­fly Paddle and Fitness, an outfit that will meet you at the best launch site based on conditions. Once you’ve got a paddle in hand, you can explore the creeks and rivers of Kent Island’s extensive water trails.

Sip Wine on the Water

Stop byLove Point Vineyards and Winery (305 River Shore Ln., Stevensville) for tasty, accessible wines on the waterfront. Popular theme days include oyster-pairing Sundays and “Yoga & Wine” on Wednesdays.

Bike by the Bridge

Pack mountain bikes to ride along the Off-Road Trail @ Terrapin Nature Park in Stevens­ville. A smooth and easy 1.2-mile loop is ideal for families, while other paths call to more adventurous riders, thanks to challenging features such as log obstacles and berms.

Ogle Extraordinary Yachts

Check out classic and antique boats at the Chesapeake Bay Motoring Festival, one of the Mid-Atlantic’s premier showcases. The event drops anchor at the Kent Island Yacht Club June 8 and 9.

Catch a Sunset

Dine on oysters, crab, and rockfish plucked right from the water below the dining deck at Libbey’s Coastal Kitchen & Cocktails (357 Pier 1 Rd., Stevensville), in the shadow of the Bay Bridge.

Dream on the Water

Sleep on the water in a Kent Narrows Rentals houseboat that’s more than 630 square feet—as big as many DC apartments—with unencumbered views of the bay from the rooftop. Or stay on land at Kent Island Resort (500 Kent Manor Dr., Stevensville), which recently amped up its waterfront emphasis with a water-sports program, a bay-to-table restaurant, and beach hammocks.



Mural of Harriet Tubman, “Take My Hand”, created by Michael Rosato. Photography by Jill Jasuta.

This edgy, artistic town on the Chop­tank River has a burgeoning downtown with a mix of historic buildings and new spaces.

Party on a Crab Deck

Hit Snappers waterfront tiki bar (112 Commerce St.) for live music and all things crab, from creamy dip to plump crab-cakes, sourced by watermen at the marina next door.

Pay Homage to a Heroine

Detour off Route 50—the main drag—for a photo in front of an engaging mural that’s gone viral. Titled “Take My Hand” (424 Race St.), the acrylic work depicts American abolitionist Harriet Tubman reaching out beyond the wall.

Pick Your Own Flowers

Stalk rows of blooms for the perfect bouquet at Emily’s Produce (2214 Church Creek Rd.), a seventh-generation family farm. Once you’ve selected your flowers, stop by the market for fruits and vegetables, also grown onsite.

Vibe Over Cocktails

Blue Ruin (400 Race St.), a buzzy exposed-­brick bar in the heart of downtown, is pouring creative cocktails with ingredients such as black cherry and star anise; fig liqueur; and root beer.

Book a Family-Friendly Stay

There’s plenty to do at the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina (100 Heron Blvd.), including time at the beach, three pools, beach volleyball, basketball, a game room, a sauna, and a steam room. New this year: Water’s Edge Grill, the main restaurant, has launched a menu heavy on local seafood.

* This post was updated since its original publication, after chef Harley Peet won a James Beard award on June 10, 2024.