2 hours, 15 minutes
Jutting deep into the Chesapeake Bay and dotted with quaint country cottages, generous patches of undisturbed marsh and greenery, and—yes—the occasional cornfield, bucolic Tilghman Island was, for many years, a working fishing village. These days, vacation and retirement homes abound. Life here slows to an easy pace the second you cross over Knapps Narrows—and isn’t that exactly what summer weekends are for?
After the tumultuous year that was 2020, the real draw of Tilghman right now is consistency—away from the hustle and bustle of the DMV, not too much changes on the tiny 3-mile-long peninsula. That said, the cozy Knapps Narrows–adjacent Tilghman Island Inn is under new ownership—the husband was a chef in DC; the wife is a landscape designer—and debuted extensive renovations and a fresh look last August. Thankfully, the views of soaring bald eagles, ospreys, and great blue herons from the waterfront decks remain the same.
By the beach
Activities largely center on the water, not in it, thanks to seasonal infestations of jellyfish that come and go based on water temperature and salinity. But that doesn’t mean you’ll be left wanting for things to do: Wylder offers paddleboards, kayaks, and canoes to resort guests free of charge, and in high season, sunset cruises ($75 per person) set sail from the onsite marina every Friday and Saturday night. There’s also a heated saltwater pool, which is lined with lounge furniture and offers cocktail service (don’t leave without trying the Grapefruit Crush) on the weekends.
Looking for a little more thrill? At Tilghman Island Marina, an easy 20-minute walk from Wylder, you can rent Wave-Runners, pontoons, and fishing and crab boats. And don’t worry if you left your rod at home—they’ve also got the gear necessary for catching the critters.
Even if you don’t book a room at Wylder, you’ll want to do at least one meal at Tickler’s, the resort’s casual, come-as-you-are indoor/outdoor restaurant. Helmed by chef Jordan Lloyd, former owner of Easton’s Bartlett Pear Inn and an alum of Citronelle, Per Se, and Chopped, the eatery’s Chesapeake classics include Fisherman’s Daughter oysters, Maryland blue crab cake sandwiches, and a delectable jumbo shrimp imperial. (If it’s dinner and a show you’re after, Tickler’s also hosts live music and karaoke.)
Nearby, Two If By Sea is beloved for down-home American cooking and epic brunch portions, and the stuck-in-time Tilghman Island Country Store has a surprisingly gourmet selection of breakfast pastries, deli sandwiches, and desserts—pop in and reward yourself after a long bike ride on one of Wylder’s free beach cruisers through Tilghman’s idyllic bay-water-kissed neighborhoods.
The rest of your waking hours should focus on relaxing on or near the water, but if the weather turns, a bit of shopping is possible—check out 2VintageChics for upcycled furniture and breezy, boho-leaning women’s fashions, or get lost among the stacks at Crawford’s Nautical Books (open weekends only), which is home to more than 12,000 titles dedicated to all things seafaring.
The Tilghman Watermen’s Museum is the best place to go to explore island history and boating artifacts, or you can head over to Dogwood Harbor to see skipjacks in the wild—some of which offer tours during warmer months when they aren’t oystering.
Open-air living was built into the bones of Wylder Tilghman Island, the largest and most amenity-packed overnight option for visitors around these parts. It began life in 1898 as a boarding house for crabbers and fishermen, but reopened as a boutique 54-room resort in 2018. There are no indoor hallways or elevators. The suites are elegant in an understated way—nautical touches include rope-knot doorstops, brass wall sconces, and navy wainscoting—but the real draw is the grassy 9-acre lot, which backs right up to the water with a 25-slip marina, an outdoor bar and dining patio, Adirondack chairs and hammocks, and plenty of socially distant fun for the whole family (think bocce courts, cornhole, lawn darts, ladder golf). The resort is also pet-friendly, and dog owners aren’t shy about taking advantage.
Looking for something even more low-key? Taking in the sunrise over the Choptank River and the sunset on the bay will be the highlight of your stay at Black Walnut Point Inn, a secluded seven-room B&B located on a 58-acre bird sanctuary at the very tip of the island.