For those seeking an authentic Chesapeake Bay experience, Tilghman Island offers a strong connection to its working waterfront roots.
This unspoiled island community, just a short drive from St. Michaels, is known for its waterman’s culture, incredible seafood, and endless views of the bay. A weekend here is all about unplugging, exploring the outdoors, and savoring the adventure.
Day 1:
Settle In
Arrive on Friday afternoon, noting the Tilghman’s Pride mural as you cross the drawbridge, before checking into the Wylder Tilghman Island. Once settled, grab a complimentary cruiser from the hotel to explore the island. At only three miles long and one mile across at its widest, you’ll have no trouble navigating. Swing into the Tilghman Island Country Store to pick up any essentials for the weekend. If timing aligns, join the staff for a toast during their weekly wine tasting – Friday@Five.
Return to the Wylder for a relaxing dinner by the water at Tickler’s, where the menu draws on the freshest local products, from both land and sea. After dinner, grab a drink from the bar before hopping aboard a sunset cruise. Watch the sunset melt into the bay and let the island’s serenity set the tone for your stay. End your evening by sitting around the outdoor fire pits, connecting with fellow guests.
Day 2:
Explore the Island
Enjoy a leisurely morning before embarking on a quick, 5-minute bike ride to Two if by Sea Restaurant for breakfast. Pick from morning staples or embrace your proximity to the bay with one of their Maryland blue crab breakfast creations. Continue to stretch your legs with a ride to the Tilghman Island Watermen’s Museum. The museum reflects on the culture of those who have carved out a living on the Chesapeake Bay, reflecting their stories through videos, artifacts, and a significant collection of model boats. Swing into Gina’s at the Bridge for tacos before heading back to the Wylder. Spend the afternoon relaxing by the salt water, heated-outdoor pool before hopping into the panoramic, waterfront sauna. Return to your room for an afternoon refresher before heading to Blue Waterfront Restaurant within the Tilghman Island Inn to dine al Fresco.
Day 3:
A Final Hoorah
Wake early to enjoy a morning paddle amongst Chesapeake Bay views from one of the hotel’s complimentary kayaks or SUPS. Chart your course using the Tilghman Island and Bay Hundred Water Trails Guide. Before departing, stop at the Tilghman Island Country Store for a freshly made breakfast sandwich to fill you for the road. While there, pick up fresh seafood or a memento of your stay. Tilghman Island leaves you with the sense that time moves differently here — slower, calmer, and more connected to the rhythms of the Chesapeake Bay.
Tips for a Memorable Weekend:
Make Reservations: While walk-in guests are always welcome, availability may be limited at times, so a reservation will guarantee your space and eliminate undue stress.
Check our Calendar of Events: Explore our calendar of events to help plan your weekend getaway to coincide with festivals and live performances in the area.Bring Your Dog: The Wylder Hotel and many venues throughout Talbot County are dog-friendly, so depending on your plans, consider bringing your pup with you.
