Wylder Hotel Tilghman Island is located on Maryland’s Eastern Shore, just 20 minutes from St. Michaels in Talbot County. Today’s stylish Wylder has a storied past, beginning in 1898, when the Harrison family built a boarding house for anglers and hunters to escape the city. The vintage hotel expanded over the years, and began attracting celebrities and dignitaries. Guests would take the ferry from the western shore to commune with nature and socialize. The major draw was joining a fishing charter, and afterward, feasting on Chesapeake Bay crabs while sharing fish-tales with fellow lodgers. This under-the-radar destination was hosted by four generations of Harrison’s until the family sold the property.
As they say, the more things change, the more they stay the same. Back in 2018, a new owner, John Flannigan, reopened the hotel as Wylder Tilghman Island, with 54 refreshed rooms and enhanced public spaces. But the Wylder retains what has always made this place so iconic: riverside landscapes and active adventure.
Today, Wylder brings people together to unwind, and very likely, make new friends. There may be something in the water, but looking out at the serene Choptank River, watching dogs play, and dining at Tickler’s Crab Shack for Chesapeake Bay seafood was an undeniable recipe for fun and rejuvenation.
The rooms and suites are casual and unfussy, the patios gracious and comfortable. Everything is enhanced by the scenic views. “Wylder is all about experiencing the whole property. Your room is a classic with all the modern amenities you need, but the focus is on the 9.5 green waterfront acres,” says general manager Kristin Seymour Bram. “We want you to get out of your room and onto the bikes, swinging in the hammock, eating crabs, playing corn hole, swimming in the saltwater pool, paddling a kayak, and listening to live music. We want you to have the full Eastern Shore experience.”
While many Eastern Shore inns and resorts are focused on couples, Wylder caters to families, dog lovers, friend getaways, and locals too. “We have tons of guests who turn us into their second homes and come multiple times throughout the season. We get to know their names, their kid’s names, their dog’s names. When they book, they ask for their favorite room,” says Bram.
Most activities at the Wylder are included in the room rate. We relaxed by the saltwater pool after a session in the rustic wood-fired sauna. Others were cycling around the island on a Wylder bike, stopping for Scottish Highland Creamery ice cream (made in nearby Oxford) at the Tilghman Island Country Store or touring the Tilghman Waterman’s Museum. The canoes, paddleboards, and kayaks are free to guests who can self-launch from the Wylder’s sandy beach. In the off-season, the full breakfast with menu items like frittatas, smoked salmon, and pastries was complimentary. The porch was our favorite place to sit and watch the boats go by.
Chef Chris Mitchell is at the helm of Tickler’s Crab Shack at Wylder. The floating restaurant is equipped with a raw bar where you can watch the hospitality team shuck oysters and steam live blue crabs made to order. Mitchell is deft at reimagining classic Mid-Atlantic dishes, like creamy oyster stew with bivalves from Tilghman Island Oyster Company, or the Shi-Mar Farms’ grass-fed beef burger piled high with onion rings and tomato bacon jam. Other notables include the rockfish, offloaded that day by a local watermen, and crisp hushpuppies. On Friday evening, we tapped our feet to a soulful acoustic performance by guitarist Sam Pugh.
“Tickler’s Crab Shack was built over the water, and on any given Saturday, you’ll have people walking up to the bar in their board shorts and bathing suits,” says Bram. “It’s very ‘come as you are,’ but you’re eating food that you’d expect from a white-linen, fine dining restaurant, that’s all locally sourced. Our goal is to have 80% of our menu coming from within 50 miles from here, and we’re getting really close to achieving that. We have oysters on our menu that never leave this island.”
Guests also enjoy hanging out in Wylder’s Bar Mumbo with its chill but classy atmosphere. In the summer, the hotel’s craft cocktail program features tiki-style drinks, some that incorporate spirits from Lyon Distilling in St. Michaels.
Starting in mid-May, Wylder offers two-hour sunset cruises around Choptank River on a traditional “dead-rise” boat. “The sunset cruise is with a real waterman who literally went fishing that morning, cleaned up his boat, then takes his guests on a cruise that night,” says Bram. “He’s someone who lives and works here and can tell you the history of the area. You even get to experience the Knapp’s Narrows drawbridge going up and down.”
As I chatted with people around the bonfire, the chef came out and spoke to us about crabbing, and everyone watched as the sky turned from soft blue to pink. “So many of our guests bond while their kids make s’mores or their dogs play,” says Bram. “It’s really magical.”
Rates range from $250 to $750 per night, including taxes and resort fee. 21551 Chesapeake House Drive, Tilghman Island, Maryland; 410-886-2121
Feature image by Renee Sklarew
For more stories like this, subscribe to our Travel newsletter.
