1. DINE AT TICKLER’S CRAB SHACK & RESTAURANT

What’s a visit to the Eastern Shore without some freshly-caught seafood?

With a rich history of fishing and crabbing dating back to the 1890’s, Tilghman Island residents have long appreciated the flavors and cooking techniques that go into producing a delectable seafood meal.

Located on the grounds of Wylder Hotel, Tickler’s Crab Shack aims to capture that enthusiasm through its expansive menu of delicious fresh seafood, crab cakes, house made pastas, lamb meatballs, filet mignon, and Southern-inspired sides like hush puppies in a casual, yet elegant setting.

Insider Tip: In the Winter, Tickler’s offers several special Holiday events and buffets annually.

2. BIKE THE ISLAND & SHOP FOR GIFTS

At just under 3 miles long and 1 mile wide, exploring the Island via 2 wheels is a favorite for locals and visitors alike!

Stopping to admire sweeping views of the beach, or to peruse local shops for unique finds, it’s easy to make a day out of biking the island. Whether you’re looking for a cute accessory to gift to a friend, or a locally-inspired postcard to send to family, the Tilghman Island Country Store has everything you’re looking for and more.

Insider Tip: Guests of Wylder Hotel can enjoy complimentary beach cruiser rentals with their stay.

3. HOLIDAY LIGHTS & SHOPPING IN ST. MICHAELS

Get in the holiday spirit with an afternoon trip to the nearby waterfront town of St. Michaels for festive shopping in quaint boutiques, vibrant light displays, delicious toasty drinks, live music, and more.

Located just 7 miles from Tilghman Island, St. Michaels is the perfect place for an afternoon spent browsing unique maritime-themed gifts for friends, gorgeous jewelry for yourself, sipping hot cocoa from locally-owned cafes, and enjoying the overall festive setting this holiday season.

Insider Tip: Don’t miss the annual holiday parade for awesome classic cars, llamas, marching bands, and more.

4. COZY UP & LOUNGE AT WYLDER HOTEL

After a day of fulfilling adventure, spend some time cozying up on the grounds of Wylder Hotel with your favorite book, a nostalgic board game, or a toasty bonfire and s’mores overlooking the Chespeake Bay.

With nautical-inspired decor and cozy amber and sea moss candles flickering throughout the hotel, you’ll feel at ease and warm from the inside out, as you sip on a festive cocktail or local brew from Bar Mumbo.

Insider Tip: There’s several cozy nooks and shared spaces to lounge in solo or with your group.

5. FESTIVE EVENTS AT WYLDER HOTEL

Tune in to the festive spirit of Winter with fun and community-based annual events at Wylder Hotel.

Offering various annual events like holiday dinners and Santa pancakes, plus over a dozen pop-up events like open mic nights, live music, paint and sips, gingerbread making, and speakeasy parties, you’ll feel extra cozy and connected to the season.

Keep an open mind to meeting new people through these events, many guests have made lifelong friends and connections here.

Insider Tip: Check the Winter calendar of events on an on-going basis, new events are added each year.