Crack Some Crabs Photograph courtesy of Fisherman’s Inn Crab Deck. Butcher paper, wooden mallets, and blue crabs doused in Old Bay are staples, but each crab deck has its own personality. Drive, boat, or walk to the Crab Claw, a charming waterfront spot in downtown St. Michaels (304 Burns St.).  Doc’s Sunset Grille (104 W. Pier St., Oxford) pairs classic crabs and crabcakes with waterfront views. Hushpuppies are a religion at Fisherman’s Inn Crab Deck (3032 Kent Narrows Way S., Grasonville), on a bustling marina near the Bay Bridge. Head to the lower deck at Cantler’s Riverside Inn (458 Forest Beach Rd., Annapolis), tucked away from the crowds on a hill, to see where soft-shell crabs are harvested. Waterman’s Crab House (21055 W. Sharp St., Rock Hall) has a party vibe, with live music as well as boats leading short cruises from the restaurant’s harbor.   Soak In Some History The Frederick Douglass statue outside the Talbot County Courthouse. Photograph courtesy of Talbot County Economic Development and Tourism. America’s Founding Annapolis—briefly the Colonial capital of the United States—is home to a pair of mansions owned by signers of the Declaration of Independence: the Charles Carroll House (107 Duke of Gloucester St.) and the William Paca House (18 Pinkney St.). Abolitionist Trails Honor Harriet Tubman’s legacy on a self-guided tour through Dorchester County, where the Underground Railroad conductor was born. The Harriet Tubman Underground Railroad State Park and Visitor Center (4068 Golden Hill Rd., Church Creek) offers a few routes. Or follow the Frederick Douglass Driving Tour through bucolic Talbot County, stopping at places he labored before becoming an abolitionist hero and statesman. Old Navy Visit the US Naval Academy (121 Blake Rd., Annapolis) to check out the famed crypt of John Paul Jones, an officer in the Continental Navy. Time it right—at noon—to watch the “meal formation,” in which cadets march to lunch accompanied by the drum-and-bugle corps.   Dine in Style Bas Rouge in Easton. Photograph by Francine Zaslow/courtesy of Simoneink. In recent years, the Eastern Shore has become a Mid-Atlantic dining destination, and these restaurants are worth the drive. The European spot Bas Rouge (19 Federal St., Easton), with an intimate 54-seat dining room, and its sister restaurant, the Wardroom (103 N. Washington St., Easton), recently reimagined as a love letter to Italy, are helmed by James Beard Award–winning chef Harley Peet. Both host guest chefs from around the world. Rustic-chic Ruse (209 N. Talbot St., St. Michaels), where James Beard nominee Michael Correll commands the kitchen, turns out a dizzying rotation of seasonal dishes, including vegetables that earn a starring role.   Visit a Farm Berries from Lockbriar Farm. Photograph courtesy of Lockbriar Farm. Bring home some Eastern Shore bounty. Load up on all-summer berries, including elderberries, at Lockbriar Farm (10051 Worton Rd., Chestertown) before cooling off with fruit-studded ice cream. For a family day in the countryside, Emily’s Produce (2214 Church Creek Rd., Cambridge) has games, mini goats, and a market, plus fields of pick-your-own sunflowers and wildflowers. Eco-conscious grownups will enjoy a stroll along fields and marshland at the sustainable waterfront estate Cottingham Farm (28038 Goldsborough Neck Rd., Easton), dipping into the market for non-GMO vegetables, heritage pork, and free-range eggs.   Climb Aboard a Boat Sail a river on the Sultana. Photograph courtesy of Kent County Economic and Tourism Development. Hugging the Chesapeake Bay, this region has more than 600 miles of shoreline to explore. Hoist a sail and steer the ship when you hop onto the Sultana (200 S. Cross St., Chestertown), a replica of a 1768 schooner, which plies the Chester River. When you want to go all in on a nautical shore experience—including cracking crabs—book a dinner cruise on the Choptank River Queen, a paddle-wheel boat that leaves from the dock fronting Suicide Bridge Restaurant (6304 Suicide Bridge Rd., Hurlock). Feeling splurgy? Charter Five Star, a Hinckley yacht that will ferry you from the Inn at Perry Cabin (308 Watkins Ln., St. Michaels) to Annapolis and back again. For a fuss-free experience, rent kayaks at the Chesapeake Bay Environmental Center (600 Discovery Ln., Grasonville), where you’re likely to spot ospreys, bald eagles, and river otters as you paddle. Families can also turn to Capital SUP (655 Americana Dr., Annapolis), which has tandem kayaks you can navigate along tranquil waterways. Those who pre-fer to stay dry while getting on the water can rent a novice-friendly electric boat through Annapolis Electric Boat (300 Second St., Annapolis), where you can get a temporary Maryland boater’s certificate.   Book a Room by the Bay Bay views at Great Oak Manor. Photograph by Jumping Rocks. Water, water everywhere—but that doesn’t mean you’re guaranteed a room with views of it. These three accommodations do offer options for those who want to wake up and see the water. The Chesapeake Bay Beach Club (180 Pier 1 Rd., Stevensville) recently renovated several loft-like rooms with Bay Bridge views. This summer, the resort will unveil the boutique hotel Wilson’s Cove (104 Marina Club Rd., Stevensville), where every room has a balcony overlooking the bay. Reserving a water-view room at Great Oak Manor (10568 Cliff Rd., Chestertown)—a small luxury hotel with a well-stocked bar and library—is like staying with the aristocratic family you wish you had. The hotel’s chef has a pedigree that includes Per Se in New York, and you can pair bay scenery with farm-to-table plates.   Enjoy a Summer Festival Photographs by Mark Sandlin/Talbot County Economic Development and Tourism. Antique and Classic Boat Festival Even if you’re not there to stroke a check, you can still appreciate the jaw-dropping collection of historic and modern vessels. When: June 19–21. Where: Chesapeake Bay Maritime Museum (213 N. Talbot St., St. Michaels). Don’t miss: The artisans tent featuring nautically inspired pieces in all price ranges. Fourth of July Celebration Celebrate the nation’s bisesquicentennial with a parade and other red-white-and-blue festivities. When: July 4. Where: Throughout Annapolis. Don’t miss: Live music and fireworks over the harbor in the evening. Plein Air Festival Watch artists do their thing during the largest outdoor painting event in the country. When: July 10–19. Where: Throughout Talbot County. Don’t miss: The live quick-draw event, where artists create works on the spot. This article appears in the May 2026 issue of Washingtonian.The post Where to Stay, Dine, and Play in Annapolis and on the Eastern Shore This Summer first appeared on Washingtonian. ...read more read less