“There’s a ‘soul sigh’ when you cross the bridge to Tilghman Island,” one local explained.

You’ll find little to do if you’re driving over for a day trip. But stay a bit, and the island opens into a world of peaceful adventures.

About Tilghman Island

Just over 800 people live on this island that was first settled in 1659. The island’s name kept changing depending on who owned it.

It’s been Tilghman (pronounced “TILL-man”) since 1752, after the family of Matthew Tilghman, a planter who became one of Maryland’s delegates in the Continental Congress in 1776.

He voted for final approval of the Declaration of Independence but his term ended before it was signed so his signature is not on the document.

The island is just under three square miles at the end of a long peninsula sticking into the middle of Choptank River where it empties into the Bay.

Residents who’ve been there a long time say it’s less than two hours — and 20 years — from Washington, DC, Baltimore, and Philadelphia. Newer residents say it’s more like 50 years from those big cities. But that’s the island’s draw.

The nearest traffic light is about 15 miles away in St. Michaels.

“We’ll never have a Mcdonald’s,” says Bob Zuber, co-owner of the Black Walnut Point Inn at the island’s farthest point. “(Tilghman Island) is not on the way to anything.”

Except for migratory birds and fish.

“This point is in the middle of the Bay,” says Bob. “Anything that flies comes through here.”

There’s a regular timing for the migrations.

Butterfly on Tilghman Island

Porpoises go by at the beginning of summer. Middle of summer, swallowtails. Late summer, purple martins. End of summer, it’s Blue Jays. Monarch butterflies stop through September-October. Then it’s raptors following the smaller birds in the fall. Osprey leave the island in mid-September to head south. Tundra swans stay for the winter.

The island is known locally for sea glass that washes up on its shores.

Being in the middle of the Bay brings all sorts of unique treasures.

What’s on Tilghman Island?

Tilghman Watermen’s Museum

For a look at some of the more interesting items as well as the culture and history of the island stop by the Tilghman Watermen’s Museum (6031 Tilghman Island Road), which started in 2007. 

“As the watermen retired, their stories and experiences were going with them,” according to Hall Kellogg, one of the museum organizers. “This is what we really set out to capture, their experiences as professional watermen.”

Tilghman Waterman's Museum

The museum is a restored “W” house, one of 12 built on the island around the turn of the century. They’re unique to the island, according to locals. Only five still exist.

Dogwood Harbor

Dogwood Harbor (21308 Phillips Road) about mid-island still has rows of watermen’s boats. These are working boats and maybe one of the largest collections in one spot on the Chesapeake Bay.

The Tilghman Island harbor is also home to the nation’s oldest skipjack, Rebecca T. Ruark, built in 1886, a national historic landmark. She’s part of the last working fleet of skipjacks in North America docked in Dogwood Harbor.

Rebecca T. Ruark under sail. (Photo courtesy The Last Skipjack Project)

In 2021, the Rebecca T. Ruark was under repairs in the Tilghman Island harbor.

Another local charter is the former racing yacht, the Lady Patty, built in 1935. She’s docked at a marina by the Knapps Narrow bridge to the island.

Tilghman Island Water Trails

There are also lighthouse tours, kayak tours, and sports fishing charters. All are available during the sailing season, typically April through October.

Talbot County has created water trails around Tilghman Island for kayaking and canoeing. The island has information about outfitters who provide equipment and guides if needed.

Tilghman Island Naval Research Laboratory

Naval Research Laboratory on Tilghman Island, MD

At the end of the island is the WWII-era Naval Research Laboratory. The tower is still in use.

Near the laboratory, the sometimes one-lane road widens into what looks like a parking lot. But there’s no beach or fishing pier. The asphalt was laid there by the state to help watermen dry and repair their pound nets.

It’s one of the last areas of the Bay still doing pound-netting, and just offshore are clusters of posts sticking out of the water that hold the nets. It’s a maze of nets that guide fish into a main holding area. Watermen dip into the trap and pull out what they want, then toss back the rest back into the Chesapeake Bay.

Cycling on Tilghman Island

bicycle on Tilghman Island pier

Tilghman’s is also a popular cycling route from St. Michaels to the island and back, about 15 miles one way if you go to the end of the island.

The highway to Tilghman Island is a bike route and has wide shoulders up to the island; traffic is relatively light.

Tilghman Island Hiking Trails

Boy Scouts have restored some hiking trails near the Black Walnut Inn. The longest is about a half-mile through loblolly, pines, and marsh.

The farthest point on Tilghman Island is on private property, at the Black Walnut Inn. However, they’ve set aside a pretty photo stop just outside the entrance, near the hiking trail.

Tilghman Island Business District

What could be called the downtown section of the island are the remains of what used to be three villages. In the 1940s and 50s, the island, with its packing houses, was the economic engine for Talbot County.

They canned not only oysters, crabs, and fish, but also corn, tomatoes, and beans that were grown inland. The canned goods were shipped by steam engine across the country.

The middle village, Avalon, is the only one remaining. The barbershop became the community museum. The department store is a restaurant. The country market is still a market.

Two If By Sea Restaurant

 Two If By Sea (5776 Tilghman Island Road) is the yellow restaurant in the former general store — one side for dry goods, and the other side a hardware store. Henry Mill (Chef Henry) kept the interior intact and it’s worth a stop by to step back in time.

The restaurant is open only for breakfast and lunch Sunday-Thursday. On Friday and Saturday, Chef Henry gets creative with dinner until 9pm, using herbs and veggies grown in his garden in the back of the store.

His hits include Crabby Eggs Benedict for breakfast and unique sandwiches for lunch. However, he’s known for his Smith Island cakes sold at several of the island’s restaurants.

Tilghman Island Country Store

Just down the street a bit is the Tilghman Island Country Store (5949 Tilghman Island Road), owned by Patricia McGlannan and her husband. It’s a small, full-service market with a deli counter where visitors can buy sandwiches and sides for day tripping. 

The store is known for what the locals call “the world’s best” carrot cake, made by Patricia’s sister-in-law.

They also have the claim to Tilghman’s “tiniest bar.”

“In our case, even though we’re just a country store,” says Patricia, “There’s more going on than you might realize.”

On Friday nights, it’s the gathering place for locals and visitors alike. A wine distributor brings in a variety of bottles for weekly tastings.

“I’ll have 20 people standing around drinking wine before they go out to dinner or entertain at home,” says Patricia.

Even the watermen show up, in their work boots, swearing they don’t drink wine.

Waterfront Dining on Tilghman Island

Tilghman has several waterfront restaurants.

Wylder inn has Tickler’s, a modern crab shack. Tilghman Inn has upscale dining featuring local produce, seafood, and Eastern Shore beef.

For ultimate casual, head to marina restaurants on both sides of the narrows, where you can get crabcakes and cold drafts as well as a fishing charter.

There’s very little to do on Tilghman Island if you’re doing a day-trip drive-by.

“Just popping in will not give you any idea of what there is,” says Patricia, the country store owner. “You have to hang out, park your car, and start walking around to see it.”

And, you have to talk to the locals. Ironically, that can fill a weekend or a week.

Where to Stay on Tilghman Island?

Go the farthest point on the island and you’ll find Black Walnut Point Inn, a private B & B located in a 52-acre bird sanctuary. Owners Bob Zumer and Tracy Staples call themselves “curators” of the historic farmhouse. It’s two houses that have been joined together over the years.

As the tip of the island fell into the bay, the houses kept getting rolled back on logs and were eventually connected. Island deterioration has been slowed by a rocky outcrop installed using state and federal funds.

The inn is a popular wedding destination, so parking near the inn is reserved for guests. But there is some parking outside the gate for the public to explore the sanctuary. 

On the other end of the island is the traditional Tilghman Island Inn  (21384 Coopertown Road), with boat slips.

Midway on the island is Wylder Tilghman Island (21551 Chesapeake House Drive, Tilghman, MD). It’s a boutique hotel and the former Thompson House, originally opened in 1880.

For the more casual, there are B&Bs and local houses available for rent.