From Bethesda Magazine: Best of Tilghman Island

This historic fishing village offers boating, biking, hiking and fresh-caught local seafood

By Renee Sklarew

July 17, 2026 3:01 p.m. | Updated: July 17, 2026 3:10 p.m.

Department of Tourism, Talbot County, Maryland

This is the fifth part of The Best of The Bay July/August cover story for Bethesda Magazine. St. Michaels was published Monday, Cambridge was published Tuesday, Easton was published Wednesday and Chestertown was published Thursday.

Tilghman Island is a bayside beauty at the southern tip of western Talbot County. Bordered by the Chesapeake Bay, Choptank River and Harris Creek, British seafarers ﬁrst settled here in the 1650s, establishing boat-building and seafood businesses. Even today, many of Tilghman’s 700-plus residents make a living on the waterways. You’ll ﬁnd this close-knit community is welcoming to visitors, who can stay in a mix of accommodations from cozy vacation rentals to casual resorts while enjoying the island’s nature, boating and biking experiences.

Best Bike Rides

Expect to find very few cars on the flat roads around Tilghman Island, making bike rides here fun for all ages and experience levels. Begin with breakfast at Two If By Sea, then ride 22.2 miles on an up-and-back route that takes you out-side of town to Claiborne Landing, a historic village with a public beach and fishing pier. For a shorter option, choose the 3.6-mile ride from Tilghman Watermen’s Museum to the entrance of Black Walnut Point Natural Resources Management Area and back. Free bikes are available to guests of the Wylder Tilghman Island, a waterside resort, or you can rent and have bikes delivered to your vacation rental from Shore Pedal & Paddle in nearby St. Michaels.

Two If By Sea, 5776 Tilghman Island Road, 410-886-2447, twoifbysearestaurant.net

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Claiborne Landing, 23014 Claiborne Landing Road, Claiborne, Maryland

Tilghman Watermen’s Museum, 6031 Tilghman Island Road, 410-886-1025, tilghmanmuseum.org

Black Walnut Point Natural Resources Management Area, 4787 Black Walnut Point Road,410-820-1668, dnr.maryland.gov

Wylder Tilghman Island, 21551 Chesapeake House Drive, 410-886-2121, wylderhotels.com

Best Cocktails With A View

Pull up a barstool at Gina’s at the Bridge to watch vessels pass under the Knapps Narrows Bridge. The Tilghman Island drawbridge is raised and lowered to accommodate larger boat traffic crossing from the Chesapeake Bay to Harris Creek. The indoor space at Gina’s offers panoramic views, and the lower deck is a waterfront Tiki bar with picnic tables and bar games. Don’t miss Gina’s margaritas or the native catfish, caught and processed by Tilghman Island Seafood.

Gina’s at the Bridge, 6136 Tilghman Island Road, 410-886-1096, ginasatthebridge.com

Image Courtesy of Talbot County Maryland

Best Heritage Museum

Visit the Tilghman Watermen’s Museum, which celebrates the legacy of this watermen’s village dating back to the mid-1600s. Located inside one of Tilghman’s iconic W-shaped houses (an architectural style that captures the bay breezes), the museum is operated by volunteers, including local watermen and boat builders. The exhibit on Sharps Island Light Station illuminates Tilghman’s unsung role in military history, while the permanent collection features Tilghman’s seafood industry and displays artifacts from the Indigenous tribes of the Eastern Shore. Open weekends from May through October. Admission is free.

Tilghman Watermen’s Museum, 6031 Tilghman Island Road, 410-886-1025, tilghmanmuseum.org

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Best Way To Get On The Water

Rent a kayak from Tilghman Island Marina to explore Tilghman Island’s waterways. From the marina, you can follow the 2½-mile Three Creeks Trail into the peaceful waters of Back Creek. Hearty kayakers can add 2 additional miles by passing under Knapps Narrows Bridge and paddling into Dogwood Harbor and back. You’re likely to see wildlife, such as schools of fish, rays and waterbirds along the way.

Tilghman Island Marina, 6140 Mariners Court, 410-886-2500, tilghmanmarina.com

Best Eastern Shore Sunset

The Talbot County Fishing and Parking Area adjacent to Black Walnut Point Natural Resources Management Area is one of the only locations on the Eastern Shore with public views of the Chesapeake Bay and Sharps Island Light Station. From the parking area, watch a panoramic sunset stocked with goodies from Tilghman Island Country Store (we recommend the buffalo chicken wrap and fresh-baked cookies), chairs and binoculars. You can also hike the 1-mile Nature Trail through a shady forest and back, keeping an eye out for ducks, eagles and osprey.

Black Walnut Point Natural Resources Management Area, 4787 Black Walnut Point Road, 410-820-1668

Tilghman Island Country Store, 5949 Tilghman Island Road, 410-886-2777

Photo Credits Maryland Port Administration

Best Nature Tour

Sign up for the Poplar Island Tour to see terrapin and cormorant nesting sites on an isolated nearby island. In the early 20th century, Poplar Island was home to about 100 residents, but the 1,100-acre island in the Chesapeake Bay eventually was reduced to about 4 acres by erosion and abandoned. In 2001, the U.S. Army Corps of Engineers began dredging sediment from Baltimore’s shipping channels to rebuild the island habitat. Today, Poplar Islandis a flourishing nature sanctuary and unique place to see preservation in action. The 2½-hour weekday exploration begins with a boat ride to the island and continues in a vintage school bus. The boat departs from a Tilghman Island dock. Reservations are required.Maryland

Environmental Service’s meeting place is at 21548 Chicken Point Road, Tilghman Island, 240-444-4025, poplarislandrestoration.com

This appears in the July/August 2026 issue of Bethesda Magazine.

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Originally published at Bethesdamagazine