A Weekend at the Wylder Hotel in Tilghman Island, Maryland


“You have to get out of the city once per month.”

Since I moved to New York more than two years ago, this has been advice I’ve always taken, yet rarely put into action. This is a city where people are driven to work work work, do more, make more money, and as individualistic as the people are here, the drive to succeed tends to seep into everything you do. 

Then Antarctica happened and blew my mind open. After 12 days offline in brutal nature, I returned with a clear mind, bursting at the seams with creativity. That settled it. While I can’t head off to Antarctica at the drop of the hat, I can and should get offline and into nature whenever I can. 

Then I got an interesting email: an offer to come to Maryland’s Eastern Shore for the weekend and enjoy a stay at the brand new Wylder Hotel on Tilghman Island. It was a doable weekend trip from New York, they pointed out.

And I was intrigued — because I had never considered this destination before. 

Most of the hotel invites I receive are from places I have no plans to visit and I respond with, “Thank you so much! I’ll keep your offer in mind if I plan a trip to Bali/northern Alabama/Novosibirsk, Siberia.” (Bali is pretty much the least likely of those three.)

This one was different. The hotel looked beautiful, it was close by but offbeat, it was located in nature, and I’ve never seen a single travel blog post about this region. Why not say yes? I accepted, we worked out dates, I got strep, we worked out new dates, and in early May I made my trip down to Tilghman Island. 

When you think of weekend getaways from New York, most New Yorkers think of small towns upstate like Hudson, or somewhere on the Jersey Shore, or any of the myriad getaways in New England. Maybe Montreal or DC if you wanted to go further afield. There’s no reason why Maryland couldn’t be on that list as well.

In my mind, it would look just like Wedding Crashers. (“Crabcakes and football — that’s what Maryland does!”) 

Tilghman Island and the Eastern Shore

Slowly the city disappeared around me. A heinous traffic jam in lower Manhattan gave way to the highways of New Jersey, the suburban towns of Delaware and Maryland, and suddenly I was cruising down a rural road, few other signs of civilization around. 

Even though few Marylanders would consider themselves to be Southerners, I noticed the hints of Southern-ness around you. Accents that have the slightest lilt to them, but not a full-on Southern drawl. The presence of grits on menus. And most significantly, people who welcome you warmly and have full-on conversations.

At one point, I accidentally went down a private way and drove into someone’s driveway. I turned around quickly and saw a man in gardening gear approaching. Uh-oh, I thought to myself. I hope he doesn’t yell at me to get off his property.

I rolled my window down to talk to the man. His opener? “Hello, there! Welcome to Tilghman!” We spent a few minutes chatting about Tilghman, the local attractions, and the Wylder Hotel. By the time we said our goodbyes, I felt like I made a new friend.

Tilghman Island is known for its boating culture; it seems like everyone here lives for getting out on the water. If you like to boat — or fish — you’ll be very happy with the opportunities here. But at the same time, it has a lovely throwback look to it — as if it hasn’t changed in decades.

In fact, with the right Instagram filter, it looks like you could be visiting in the sixties or seventies.

The Wylder Hotel

My main goal for this weekend was to relax — and it couldn’t have been easier. The Wylder Hotel, a family-owned property, just opened this past spring. With only 54 rooms on an expansive nine acres, it feels like a bed and breakfast.

This is not the kind of place you stay for a million activities and excursions at a breakneck pace. This is where you come to chill out.

Just look at these grounds.

Five minutes in that hammock and my mind was wiped nearly to Antarctica levels. Seriously. I don’t know what it is about Tilghman, but it has a way of removing all the stresses that impact your life.

On the grounds you have outdoor decks, a hammock, an outdoor fireplace, a bocce court, lawn games, and a saltwater pool. And of course, since this is Tilghman, there’s a marina where you can bring your boat. There’s also a canoe, a paddle board and a kayak available to take out on the bay.

Everything fits into a nautical theme. It’s all brand new and you can feel the love that went into its design.

There are two restaurants in the property: Bar Mundo and Tickler’s Crab Shack.

Breakfast, in the bar, included a fluffy omelet, yogurt parfait, and delicious pastries…

Dinner, also in the bar, had so many delicious dishes on the menu. Two major standouts? The burrata with tomato jam, slathered all over crostini. And that rockfish entree was serious — it’s a fish that eats like meat.

But the absolute best dishes were reserved for brunch the next day. It was Mother’s Day during my visit and they had a special menu for the event. First out came a variety of appetizers — fresh oysters, hush puppies, asparagus, and the most absolutely delicious deviled eggs stuffed with crab.

I would eat those crab deviled eggs every day if I could. They were THAT good.

The main dish? Shrimp and grits. Rich and hearty in all the right ways.

The rooms are simply and elegant. They’re on the small side, but they have everything you need.

Any caveats? Small ones. It would have been nice to have some kind of side table next to the bed — even a simple shelf would have been a help. My bathroom door didn’t fully close; I told John and he said he’d fix it right away.

St. Michaels

A 25-minute drive from Tilghman Island is St. Michaels, an absolutely beautiful village and one of the highlights of my weekend. It’s full of pretty cottages with beautifully manicured yards, shops, boutiques, and restaurants.

I’ve been to little touristy villages all over the United States. They’re filled with gift shops selling novelty items — signs that read “Flip Flops Only,” dish towels that say, “The answer is wine. What was the question?” and the like.

Not St. Michaels. Somehow the shops here are infinitely classier. There are plenty of gift shops hawking wares for your fantasy vacation home, but these stores are actually filled with items I would legitimately put in my house. Beautiful furniture, accessories, and objets d’art. And while there’s obviously a strong nautical theme, it’s far from the only theme in town.

After browsing the shops and galleries, I stop at the Carpenter Street Saloon for lunch. Here in Maryland I’m trying to eat as much crab as humanly possible, and immediately order the “crab balls,” along with an order of shrimp. (Seriously. If something on the menu is called “crab balls,” I’m ordering it.)

“Here, try some Old Bay,” the waitress offers. She shakes out the iconic Maryland seafood seasoning into my hand and encourages me to lick it up. (I giggle to myself. This would not happen in New York.) The shrimp comes with its shells on, drenched in Old Bay, and I’m wondering the etiquette — do I lick it off and discard the shells? Do I put the whole thing in my mouth, shells and all? The world may never know.

And I’m Back

Two nights isn’t enough — but it’s time to go home. 

I can feel dueling spirits fill my body on the drive home. Half of me is infinitely relaxed; the other half is getting tenser by the minute as more gray buildings dot the landscape. Soon I’m craving a frappuccino to stay alert. Little by little, that stress settles in; traffic in New Jersey around the Lincoln Tunnel doesn’t help.

I drop off the car at a garage in Flatiron and hop on the 1 train back to Harlem. An older man sits down next to me on the uncrowded train and says, “Thank you,” into the air for no discernible reason. Then he turns to me and leans in. “Thank you,” he repeats. The hair stands up on the back of my neck. He leans in further. “I appreciate it,” he says. This, as any woman will recognize, has nothing to do with thanking me or appreciating me. This man’s goal is to intimidate me, to tell me that I don’t belong in his space. My body is rigid until he gets off at 42nd St.; at that point, I deflate.

I choose to live in a hard place because the pros outweigh the cons. But I wouldn’t be able to deal with the stress or urban life without making regular visits to the softer places, too. Places like Tilghman. The places where you can sit on a dock and feel your mind go beautifully blank, where waitresses have you lick Old Bay up from your hand, where local homeowners welcome inadvertent trespassers with a smile.


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Essential Info: The Wylder Hotel on Tilghman Island, Maryland, is accessible by car only. High-season rates start at $248 per night.

Tilghman Island is about a four-hour drive from northern New Jersey without traffic; I recommend that you rent your car from Newark Airport or one of the nearby towns like Fort Lee or Teaneck. If you’re leaving from Manhattan, beware the traffic of rush hour. It’s about a two-hour drive from Baltimore or Washington DC, and about a three-hour drive from Philadelphia.

Do note that phone signal around Tilghman Island and the hotel is limited, but the hotel has excellent wifi.

I use travel insurance for all of my trips to protect myself (and my finances) from ruin. For this trip and all my US trips, I used World Nomads, which I highly recommend.

Have you been to Maryland? What was your favorite place? Share away!

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