How to Clear Your Head: Cycling Historic Tilghman Island

St. Michaels to Tilghman Island Bike Route

The Ride

  • 32 miles roundtrip


  • Moderate
  • Flat

The Payoff

  • Visiting Tilghman Island


  • Start at St. Michaels Nature Park – a cyclists’ scenic downtown by-pass
  • Smooth asphalt highway with wide shoulders – get your speed on
  • Tilghman Island – a step into small-town Chesapeake Bay island life
  • Expand the Ride – by adding Neavitt Landing, another 22 miles roundtrip
  • End at St. Michaels – ahhh, refreshments & relaxation

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Overview of St. Michaels to Tilghman Island

This route seems easier than it really is. Yes, it’s a flat route. But, you’re peddling constantly. There’s no restful coasting. The longer you go, the harder that is.

Then, there’s the wind. There’s a constant breeze from the Chesapeake Bay, and the Bay is just on the other side of farm fields that you’ll be riding by. On a light air day, that’s wonderful. On a breezy day, it’s like going up hill but there’s no down-hill. No coasting.

This route doesn’t have much shade. The trees are cut far back off the road due to the farm equipment, and sometimes cyclists have to share the shoulder with a combine. On hot days, it feels like cycling through Arizona.

Those are just extra challenges.

You can go as fast as you want on the smooth road. And, you get to play on Tilghman Island half-way through the ride.

If you’re on an e-bike, just go and enjoy!!

The St. Michaels to Tilghman Island Route

We start you at the St. Michaels Nature Trail (across the road from a bike shop). It’s a one-mile asphalt-paved trail that acts as a busy downtown by-pass and an easier getaway out of town after the ride. It’s also a very pretty ride.

The trail ends after a mile and a half at Bradley Park. It’s a pretty park with a portable toilet and a playground. Go through the gravel parking lot and turn right.

This is a ride down a traditional St. Michaels neighborhood full of eclectic houses. It takes you to the northern end of downtown St. Michaels. Take a look around at the busy, cool city-center and remember that you’ll be returning to it.

Off you go the other direction toward Tilghman Island.

This is where you get to open up and let those cycling legs go strong. There’s nothing slowing you down except the highway speed limit, and maybe a turning car.

St. Michaels Road to Tilghman Island

There are no convenience stores along the way. There’s Chesapeake Landing restaurant about a quarter of the way, a crab shack that sells water and soda out of its cooler.

That’s the Chesapeake Bay on the other side of this farmhouse

You’re traveling along farms and woods until you get to Knapps Narrows, the stretch of water separating Tilghman Island from the mainland. That’s your highest elevation. Going over the bridge.

The road narrows considerably on the other side of the bridge. There are no shoulders. You’re on county lanes the rest of the way through the island.

Tilghman Island

Tilghman Island sits between the Chesapeake Bay and the Choptank River, at the southernmost top of Talbot County. It is literally in the middle of the Chesapeake Bay, making it a lay-over stop for migratory flying things, such as butterflies and birds.

Watermen reign, pristine landscapes abound, and crowds only exist at the annual crab feasts and docking contests.

Talbot County Tourism Office

The island is dominated by watermen, but it also caters to wealthy tourists who don’t want to be noticed. That means Tilghman Island has an amazing number of foody restaurants with very fresh Chesapeake Bay seafood.

But you’re on a bike and that’s okay too. Check out the Tilghman Island County Store. They make sandwiches, and will broil up a crab cake to go with a beer if you’re inclined. There’s Tickler’s Crab Shack up the road a bit as well as Two If By Sea, a sandwich shop by day that still looks like the country store it used to be.

Tilghman Island Country Market on Tilghman Island, MD

The most dramatic water views are at the tail-end of this ride just past the community of Avalon. That section used to be the town of Fairbank, but now it’s a nature preserve. The unusually wide road there is for professional fishermen to dry-out their pound-nets.

You’ll also find great views by wandering down some of the side roads of the island.

If you have time, check out Dogwood Harbor. It’s full of deadrise boats, the crabbing and oystering boats used by professional watermen. There are also historic skipjack sailboats docked at that harbor.

Museums are open on the weekend. The Tilghman Island Watermen’s Museum is in what’s called a “W” House, built in the shape of the letter “W” and thought to be unique to the island.

Watermen's Museum on Tilghman Island, MD
Tilghman Watermens Museum open on weekends

Ride Back to St. Michaels

If you need a convenience stop, there’s a city park on the mainland side of the bridge with portable toilets. It also has a nice walkway to a Chesapeake Bay overlook.

Tilghman Back Creek Park

This is when you remind yourself that a seat at a fun bar or restaurant awaits you at the end.

Settle in for the ride back. The wind that didn’t seem so bad on the way out could turn into a challenge, depending on which way it’s blowing. And hot will seem hotter.

But if it’s a gorgeous day and you’re not tired out, check out the Neavitt Landing route on your way back (another 22 miles). The landing is beautiful.

Not much to the village of Neavitt, but it does have a shady park with a water fountain.

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