Weekending on Tilghman Island: A Pet-Friendly Escape on the Water

Fun awaits on the Chesapeake Bay.

visiting tilghman island

The back dock at Wylder Tilghman Island. Photograph Courtesy Hotel Wylder

Of all the quaint small towns dotting Maryland’s Eastern Shore, St. Michaels gets the most attention. Fewer folks know about Tilghman Island, its sleepier — but even more naturally beautiful — neighbor around the bay. That makes it the perfect home base for a low-key weekend centered on water sports and quality seafood.

Distance from Philly: 2.5 hours

Where to Stay: With outdoor walkways and a distinct lack of elevators, it’s almost as if the Wylder Tilghman Island got refurbished with pandemic living in mind. (Originally built in 1898 as a boardinghouse for crabbers and fishermen, the building reopened as a 54-room boutique resort in 2018.) Suites are infused with classic coastal charm — expect lots of brass fixtures, rattan and navy blue — but the real draw is Wylder’s private nine-acre lot, which backs right up to the Chesapeake and boasts bocce courts, a saltwater pool, and plenty of lounge furniture and firepits. And if you can’t bear a night away from that pooch you adopted during quarantine, some good news: Dogs are welcome. Rates start in the mid-$100s.

What to Do: Get outside, and stay outside (when the weather allows, of course). Wylder guests have gratis access to paddleboards, kayaks and beach cruisers; you can also book sunset cruises that leave straight from the on-site marina. (The more adventurous can rent jet skis and schedule fishing charters at Tilghman Island Marina, a 20-minute walk away.) Another option: nine holes on the new golf course at the nearby Inn at Perry Cabin, a luxury resort best known for appearing in Wedding Crashers.

The Eating-and-Drinking Sitch: You’ll want to do more than one meal at Tickler’s, Wylder’s dockside restaurant that serves up crabcakes, oysters, bourbon smashes and grapefruit crushes to locals and visitors alike. (It’s not uncommon to see groups walk straight from their boats to a table.) Any long bike ride around the hamlet should end with ice cream — or begin with a breakfast sandwich — at the Tilghman Island Country Store, and if you brought Fido along, St. Michaels is full of dog-friendly options for lunch. (Gina’s Cafe is especially beloved for quirky twists on tacos and quesadillas.)

visiting tilghman island

Spirits at Lyon Rum. Photograph by Jaime Windon

Can’t-Miss List

1. Make s’mores at Wylder
Bonfire-ready kits are available for $15 at the front desk.

2. Shop in St. Michaels
Browse one-of-a-kind furniture at Iron Will Woodworks, pick up a book at Chesapeake Trading Company, and grab gourmet canine treats at St. Michaels Pet Supplies.

3. Sail the Selina II
Bookings for dog-friendly sailboat tours begin in late April.

4. Sip spirits at Lyon Rum
Until the tasting room in downtown St. Michaels reopens, you’ll have to settle for curbside pickup or arrange a delivery (free to any Maryland zip code!).

5. Do a last lunch in Easton, Maryland
Between Tilghman and Philly, Bluepoint Hospitality dominates the dining scene with surprisingly upscale eateries. Hit Sunflowers & Greens or Bumble Bee Juice for something light and fresh.

Published as “Bring Your Pet to … Tilghman Island” in the “Road Trip!” guide in the March 2021 issue of Philadelphia magazine.