Celebrate Spring with a Trip to St. Michaels and Tilghman Island

Adirondack chairs by Chesapeake Bay

A few weeks ago I wrote about several things you have to do if you want to hop on a plane for international travel. But there are also many day and weekend destinations that you can reach with a one-or-two-hour drive from your house near the beach. One getaway that’s especially scenic and fun is a trip to Tilghman Island, located just a few minutes from downtown St. Michaels . That’s where our Second Street neighbor, Stacey Chandler, traveled earlier this month. 

Getting there:

Stacey’s key objective for her trip to Tilghman was relaxation. She got off to a great start with an “easy drive” up the Delmarva Peninsula that took less than two hours. After briefly touring St. Michaels’ historic downtown, she and her companion crossed a drawbridge to the island, “which was world’s away” from even the mild hustle and bustle she’s accustomed to in Lewes. 

Checking in . . . 

“We stayed at The Wylder Hotel, which was like staying in a wonderful old house,” Stacey said. “You walk in to what feels like a grand living room. Our suite was known as The Widow’s Walk. We reached it by going outside the main hotel, then walking up steps to a rooftop. It was beautiful – done up in navy blue and white with nautical touches everywhere, including a partial view of the water.”

The Wylder does indeed look like a quaint country estate. It’s fashioned from a circa 1898 boarding house for watermen working the Chesapeake Bay. Today it’s quite grand, taking up 9 acres of the island, which is only three miles long. The hotel property houses a restaurant and bar, a grand lawn for croquet and other games, a firepit, saltwater pool, and a private marina with 25 boat slips, where you can arrange charter fishing trips.

Enjoying the relaxing vibe . . . 

“One of our favorite places on the island was The Country Store, which had everything from t- shirts to groceries to sandwiches to liquor. The people who run it are super friendly and fun to talk to. They also love dogs and won’t blink if you’re joined by yours, without a leash.”

Stacey and her friend also enjoyed sitting back in Adirondack Chairs offering a view across the lawn toward the docks, where they watched numerous oyster boats coming in with their catches. 

“The last thing I wanted to do was pick up my phone. It was just so nice to relax and do almost nothing.”

Dining on local seafood, in style . . . 

Tickler’s Crab Shack & Restaurant and Bar Mumbo are both located at The Wylder. The menu at Tickler’s spotlights fresh seafood, including whatever’s brought in by the docks. , and a bar that promises at its web site to welcome “fellow adventurers, city slickers, boaters and fun locals.”

Because Stacey travelled mid-week in April the restaurant wasn’t open, which created the opportunity to go back over the bridge to St. Michael’s. 

“It’s like a slightly larger version of downtown Lewes,” she said. “With boutique shops and restaurants. On our last trip we had a wonderful lunch at Awful Arthur’s . . . this time we went to Theo’s, which is also in an old house, with dark wood and cool chandeliers and great food.”

After browsing the shops and taking in more water views they returned to Tilghman, “which really feels like a world away because it’s so remote. You definitely won’t go there for the night life. You go to unplug and relax.”

With shopping and sightseeing all around . . . 

One big takeaway from hearing about Stacey’s trip is that a jaunt to St. Michaels and Tilghman Island offers a variety of experiences that could appeal to different people in your family. Checking in to the Wylder, the Black Walnut Point Inn, the Knapps Narrows Inn, or the Lowes Wharf Marina Inn will almost certainly enable you to get a good night’s sleep prior to sightseeing and shopping in St. Michaels’ downtown. 

While you’re there, check out the Chesapeake Bay Maritime Museum, the St. Michaels Maritime Museum, and the motorcycles, trucks and vintage cars at the Classic Motor Museum.

About Christine Davis

Christine grew up in northeastern Pennsylvania in a small town called Pittston, which is located between Wilkes-Barre and Scranton. Upon graduation, she enlisted in the United States Air Force, where she proudly served for eight + years at a variety of bases throughout the world, including Holland, Korea, and New Mexico. While in the Air Force, Christine spent most of her time working in the civil engineering career field where she thoroughly enjoyed meeting and working with such a diverse group of people with varying backgrounds and experiences, and learned so much from each of them. Christine’s last assignment in the Air Force was at Andrews Air Force Base in Maryland, and that’s when she discovered the Delaware beaches. Growing up in PA, her family spent time at the Jersey shore. But once she moved to MD, she became one of those many drivers making the trek across the Chesapeake Bay Friday afternoon to visit the Delaware beaches for the weekend. Upon Christine’s separation from the Air Force, she spent a small amount of time working in Washington, D.C., but it didn’t take long before she was drawn to the quiet, slow pace of Lewes and Rehoboth Beach, “the nation’s summer capital”. Christine moved to Rehoboth Beach in 1999 and finished her degree in Business at Delaware Tech. At the time she was working for a large physician organization when a friend recommended that she become a REALTOR because she loved helping people and loved looking at homes. She was reluctant for quite a while because Christine didn’t think of herself as a salesperson. But after much urging by her friend, Christine decided to get her real estate license in 2003 and has not looked back since. Christine still doesn’t think of herself as a salesperson, but rather a facilitator between buyer and seller, working toward a common goal. Christine aims to make the process as smooth and fun as possible but also educates the buyer and seller along the way so they can make the best decision possible. Christine now lives in Lewes and although she misses the mountains of PA, she thoroughly enjoys spending as much time as possible at the beach, especially Cape Henlopen State Park. Christine’s philosophy in life is that it’s too short. Never spend so much time making a living that you forget how to live.

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