The Wylder Hotel Tilghman Island is exclusively open to wedding guests from Friday to Sunday (i.e., no public). Although on-site rooms are limited to just wedding party and immediate family, we urge EVERYONE to join in at any time and make yourself at home. To-Do: Tickler's Crab Shack & Restaurant, Bar Mumbo, private beach, Adirondack chairs, bonfire pits, saltwater pool, lawn games, hammocks, kayaks, canoes, paddle-boards.
Surrounding the Wylder Hotel, this small watermen's hamlet is a step back in time where life is slow and quiet. Its authentic charm begs you to relax and take a stroll from unobstructed views of the Chesapeake Bay to the mouth of the Choptank River. To-Do: Black Walnut Point Natural Resources Management Area, Tilghman Island Marina & Rentals (jet-skis, pontoon boats, sailboats, cruises, fishing gear), Tilghman Island Country Store, Marker 5, Characters Bridge Restuarant, Tilghman Watermen's Museum.
One of the best small coastal towns in America, St. Michaels boasts a picturesque harbor with houses dating back to the mid-1600's. Walk along Talbot Street to experience outstanding restaurants, galleries and shopping. The area is also home to the Chesapeake Bay Maritime Museum where you can immerse yourself in maritime history. 13 miles from Tilghman Island To-Do: Chesapeake Bay Maritime Museum, river cruise, shopping, Crab Claw Restaurant, Foxy's Harbor Grille, Ruse, Ava's Pizzeria and Wine Bar, The Galley, Eastern Shore Brewery, Lyon Rum Distillery, Gina's Cafe, Justine's Ice Cream Parlour.
The commercial hub of Talbot County and the greater Mid-Shore region, Easton is known for its vibrant culinary and arts communities and historic downtown. Brick-lined sidewalks welcome you to clothing stores, antique shops and plenty of restaurants. 23 miles from Tilghman Island To-Do: Tidewater Inn, Hunters Tavern, The Wardroom, Doc's Downtown Grille, Tiger Lily, Weather Gage, Bonheur Ice Cream and Pie, Easton Antiques & Art Gallery, Sailor.
Listed on the National Registry of Historic Places and one of the oldest towns in Maryland, Oxford serves double duty as a charming port town and home to the bride's parents. Stroll down tree-lined streets steeped in colonial and shipbuilding history. Take the Oxford-Bellevue Ferry - established in 1683, it's the country's oldest privately operated ferry service. Just save time for sunset with a bucket of crab! 33 miles from Tilghman Island To-Do: Doc's Sunset Grille, Robert Morris Inn, Capsize, Oxford Market & Deli, Oxford Social Cafe, Scottish Highland Creamery, The Treasure Chest, Oxford Vintage & Trade, the Strand (beach), Oxford Park.
Home to the United States Naval Academy and the starting point to some of our more competitive sailing adventures, downtown Annapolis deserves at least a detour on your way in or out of the weekend. From the historic state house to Ego Alley and fried oysters to chocolate dipped bananas, this bustling capital has something for everyone. 63 miles from Tilghman Island To-Do: USNA campus tour, Maryland State House Circle, Main Street, City Dock, McGarvey's, Middleton Tavern, Pusser's Caribbean Grille, The Choptank, Chick & Ruth's Delly, Kilwins Chocolate & Ice Cream.