Blast across the Chesapeake Bay Bridge for a quintessential Eastern Shore vacation minus the crowds. The community offers bay-to-table cuisine, luxurious waterfront accommodations, and shoreside recreation sites.
The Inn at Chesapeake Bay Beach Club
This new hotel helped to establish Kent Island as a vacation destination for travelers seeking upscale waterfront stays. Many rooms, suites, and cottages have views of the Chesapeake Bay, and all are outfitted with plush furnishings. The resort has a campus-like feel that includes a spa, small beach, splash garden, hops garden, chef’s garden, and market stocked with pastries and sandwiches. The hotel restaurant, Knoxie’s Table, is known for its signature cocktails and sourcing from Chesapeake Bay–area farms and marinas. Rates from $209 per night. 500 Marina Club Rd., Stevensville, Maryland
Morning: Did you know that during the early days of fall, Maryland blue crabs are still plentiful? Snag a paper-covered table and order them steamed and topped with Old Bay at the iconic Fisherman’s Inn. Seasonal options include Upper Bay oysters, vegetable crab soup, and regional desserts like chocolate–peanut butter Smith Island cake. While you wait, peruse the inn’s collection of oyster plates, the largest on the Eastern Shore.
Afternoon: Check into the Chesapeake Bay Beach Club to freshen up. Feel yourself relaxing? Don your beach gear and drive to Ferry Point Park. The 5 miles of trails—mostly boardwalks through the marshy wetlands—lead to sandy beaches bordering the Chester River. Stretch out your blanket and watch the boats go by, or play in the shallow water. Don’t forget water shoes and sunscreen.
Evening: Board the Jetty Bus from the hotel to Jetty Restaurant and Dock Bar overlooking the Eastern Bay. This uber-local hangout has a popular happy hour, spins dance music, and features fresh-caught seafood from local anglers who dock at Jetty Marina. Jetty is a dog-friendly bar, so feel free to bring your pooch along. Another great option is The Big Owl Tiki Bar, known for the rockfish tenders and live bands.
Morning: Kent Island is the largest island in the Chesapeake Bay, and Centreville serves as the county seat. Begin your day with an acai bowl at Commerce Street Creamery & Yo Java Bowl, and then stroll through the picturesque town founded 30 years after Captain John Smith began trading with indigenous tribes in 1608. This English settlement was powered by flourishing tobacco plantations, and the residents used boats for their transportation. Check out the white-brick courthouse constructed in 1792, and on the first Saturday of the month, several heritage sites are open to visitors. Grab lunch at the new Amalfi Coast Italian + Wine Bar with delectable panini and flatbreads.
Afternoon: Kent Island is all about being on the water. The options depend on your budget and preferences. The priciest is chartering a boat at a local marina, where a waterman will motor to quiet coves to drop lines tied with crab bait or teach you to cast for the bay’s legendary rockfish. In the middle range are the sunset cruises. For those who prefer to steer their own vessel, rent a kayak at the Chesapeake Bay Environmental Center. The least-expensive route: Haul a bucket of chicken necks and some string and go crabbing off the 600-foot Romancoke Fishing Pier ($2.50/hour fee).
Evening: Many locals say Hemingway’s Restaurant is Kent Island’s best, and along with the fresh, local seafood, you can’t beat the views. From the upper deck, the stunning sunsets contrast with the glowing lights of the Chesapeake Bay Bridge. After dinner, visit Ten Eyck Brewing for a sampling of beer and nonalcoholic drinks in the beer garden.
Morning: For brunch, try local favorite Pupuseria Kent Island, which serves authentic Salvadoran dishes like huevos con chorizo and quesabirria. Then park at Chesapeake Heritage & Visitor Center, where you’ll find maps and information about the Cross Island Trail. Cycle or walk north, passing by wildflower meadows, forests, streams, and wetlands, to reach Terrapin Nature Park, a protected waterfowl sanctuary with beaches facing Annapolis. Bring binoculars for a closer look at the eagles, osprey, and blue heron.
Afternoon: After so much time on the water, you’ll crave one last taste of the bay. Before crossing the Bay Bridge, stop for a crab-cake sandwich and a housemade Nutty Buddy ice cream cone from Harris Crab House & Seafood Restaurant. Now, back to reality.
This story originally ran in our September issue. For more stories like this, subscribe to our monthly magazine.
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