Seasonal Things to Do on Tilghman Island

Explore the natural beauty of Tilghman Island with Wylder Hotel’s specially-curated seasonal guides. Whether you’re looking for a cozy coastal winter retreat, a spring renewal, a sunny summer vacation, or a fall escape, our guides offer the best things to do in each season. Start planning your ultimate Chesapeake Bay trip today with these seasonal guides to the Island!

Summer Things to Do

Soak up the sun this summer with our warm weather guide to Tilghman Island. From bay water adventures, to fresh coastal dining, and bonfire s’mores with a view, we’e highlighted the summer things to do on the Chesapeake Bay.

oysterfest st.michaels

Fall Things to Do

Explore the cooler months on the island with bonfires by the water, fresh oysters, and exploring the local culture. Start planning your fall getaway today!

Woman drinking red wine outside

Winter Things to Do

Plan a coastal winter getaway like no other with our seasonal guide of best things to do and see. Whether you’re looking to take in the holiday lights with a nearby day trip to St.Michaels, relax with a favorite book by the fire, or simply enjoy a savory meal, we’ve found the best things to do this season.

Spring Things to Do

Experience relaxation and adventure with our spring guide to Tilghman Island. Whether you’re looking to relax in a wood-fired sauna, savor fresh seafood, or simply lounge bayside, this guide will help you plan your ultimate getaway.