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  • Writer's pictureLisa

The Seafood-Loving Weekender: Tilghman Island

Updated: Mar 24, 2019

Pool-side service, waterfront views, and crabs straight off the boat: that's what the Eastern Shore does.

In August my husband and I celebrated our second anniversary. When we celebrated our one-year anniversary, we knew we wanted to make a big trip out of it. Your second anniversary, however, is really just the first in a long line of “normal” anniversaries, and can really set the tone for how you celebrate from here on out. So naturally, we decided we had to travel for our second anniversary, too! We chose the Wylder Hotel in Tilghman Island, MD.

Where: Tilghman Island, MD, a small town in the Eastern Shore countryside

Get there: Two-hour drive from DC

Do: Kayak, ride bikes, hang out at the pool, shop in St. Michael’s

Eat: Tickler’s Crab Shack, Bar Mumbo

Stay: The Wylder Hotel

We left for Tilghman Island on a Saturday morning after spending a night in Annapolis. After driving through the bucolic farmland that is the Eastern Shore of Maryland, we crossed over the bridge into the tiny Tilghman Island. Our hotel, the Wylder Hotel, was one of the few there, and was perfectly placed on the water. The concierge greeted us with champagne and led us to an upgraded room that had warm chocolate chip cookies, so I was already won over.

The best welcome!

Despite scarfing down the cookies, we were hungry for lunch, and walked 50 yards from our room to Tickler’s Crab Shack, which serves food from a pavilion on the dock on nice summer days. As we were looking at the menu, we saw a boat pull up to the dock and a waiter meet the captain to collect a basket of fresh crabs. He then brought it back to Tickler’s for the cooks as they prepared that day’s lunch. Decision made.

After lunch, we spent an extremely relaxing afternoon in and by the salt water pool. The Wylder Hotel offers food and bar service there so you never really have to leave--unless you want to try out the harborside Adirondack chairs or hammock for a different place to read or sleep.


Saturday night we ate at the other restaurant on the hotel property, Bar Mumbo. We loved the pickled deviled egg appetizer with crab meat.

At night, the hotel sets up a few fire pits and you can even buy s’mores supplies if you want to roast marshmallows. We ended up just sitting by the fire, exploring the docks, and playing some twilight cornhole set up on the lawn.

The hotel also provides free kayaks, canoes, paddle boards, and bikes you can use. On Sunday morning we grabbed two bikes and biked three miles out to Black Walnut Point, the tip of the island. There are so few cars there and the most commotion we saw was a group of bird watchers getting ready for their trek. Even for a very average cyclist like me it was very relaxing!

Biking back worked up our appetites. We had a complimentary breakfast of pastries, ham, fresh juice, and coffee at Bar Mumbo. Then we jumped in the pool one more time and packed up in the late morning. We had heard great things about the town of St. Michael’s, only 20 minutes away, and decided to head there for lunch.

St. Michael’s has a very cute main street filled with tons of little shops and restaurants. Then if you walk just a few blocks off the main road, you get to the harbor where I imagine many people with much more money than us enjoy using their boats. We elected to grab a quick lunch at Bistro. I normally don’t rave over salads but I had an excellent salad, with a side of some of Collin’s fresh blueberry muffin. =]

The best way to top off our anniversary weekend was a stop at Justine’s Ice Cream Parlor. Even though this was a challenge to eat in the car as we headed back to DC, I was definitely up to the challenge and regret nothing. (Kind of the same as marriage, right?)

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