1. Enjoy Maryland Blue Crabs at Tickler’s
Nothing says fall like feasting on Maryland blue crabs, and Tickler’s Crab Shack is an expert in fresh-caught seafood. With crabs being extra juicy and tender in the fall months, it’s the perfect time to indulge in seafood. Offering delicious sides, refreshing drinks, and decadent desserts, Tickler’s is one of the best Tilghman Island restaurants.
2. Tilghman Island Day
If you’re looking for a special fall event, Tilghman Island Day is a great choice. This small-town festival showcases the island’s rich heritage, vibrant culture, and a deep-rooted sense of community. Explore booths, sample cuisine, and even watch a boat race at this exciting event!
3. Live Music at Wylder Hotel
With a rotating schedule of events, our charming Chesapeake Bay venue offers an array of live music to suit every taste, from soulful jazz to toe-tapping bluegrass. Weekend nights come alive at Wylder Tilghman Island with captivating performances that create an unforgettable ambiance.
4. S’mores by The Water
In the cooler months, nothing beats a cozy night by the Chesapeake Bay making s’mores. Wylder Hotel Tilghman Island offers bonfires by the water and a build-your-own s’mores package with your choice of wine. Sit back, toast marshmallows, and relax as the sun goes down.
5. Browse Local Shops
If you’re looking for the perfect fall activity on Tilghman Island, we recommend exploring the local shops. Shop for vintage clothes at 2 Vintage Chicks, souvenirs at Tilghman Island Country Store, or fishing gear at Fairbank Tackle. You’ll surely find the perfect gift for yourself or a friend and discover happenings around town.
6. Explore the Tilghman Watermen’s Museum
Immerse yourself in the rich maritime heritage of Tilghman Island at the Tilghman Watermen’s Maritime Museum. This interesting museum honors the island’s strong link to the Chesapeake Bay and celebrates the traditional life of watermen. Step into exhibits showcasing historical artifacts, interactive displays, and informative narratives.
7. Attend Oysterfest at St.Michaels
Celebrate the beloved Chesapeake Bay delicacy at the annual OysterFest in St. Michaels, just 30 minutes from Tilghman Island. This famous festival highlights the area’s strong oyster tradition. It features shucking contests, cooking shows, live music, and—of course—a delectable abundance of freshly harvested oysters.
8. Tilghman Island Marina & Rentals Boat Tour
While less common than in the summer, Tilghman Island Marina & Rentals still offers water tours by request after August. These exclusive tours offer a unique opportunity to cruise along the picturesque waterways, surrounded by the serene beauty of Tilghman Island.
9. Run the Historic Drawbridge Half Marathon
Enjoy the scenery and community of Tilghman Island by participating in the annual Historic Drawbridge Half Marathon. Starting at Wylder Hotel, this half leads to the nearby town of St.Michaels and offers stunning views of the Chesapeake Bay. So lace up your shoes and get ready to enjoy the crisp fall air.