Small Town USA: A Guide to the Towns of Talbot County

Easton, Oxford, St. Michaels, Tilghman Island and Trappe are our main destinations, each with unique features that make Talbot County a hub for the arts, history, maritime heritage, eating and shopping. Just about 90 minutes from both Baltimore and Washington, Talbot County towns make for the perfect Chesapeake Bay escape—they’re destinations for relaxation and exploration. It’s easy to navigate from one to the next, dining, discovering the local flavor, attending concerts and festivals and admiring the 600 miles of picturesque shoreline.


Located just off of Route 50, Easton is the county seat and our epicenter of culture. Its world-class Academy Art Museum, Historic Avalon Theatre, renowned art galleries, boutiques, fine-dining restaurants, coffee shops, boutiques and seasonal events lure visitors from far and wide. Easton welcomes international artists, musicians and tourists with carefully curated and award-winning festivals—there’s no question why it’s been named one of the Top 100 Small Arts Communities in America.

The headwaters of the Tred Avon River start as just a trickle outside Easton and lead directly to Oxford, a maritime community with water on three sides. One of the oldest towns in America, it was one of the first ports in the state of Maryland, and boats still sometimes outnumber cars. The Oxford-Bellevue ferry, a fun way for visitors to get out on the water, is the oldest privately owned ferry in the country. Oxford offers the charm of a quaint, historic town with superb restaurants, plenty of room for a stroll—and one of the country’s top handmade ice cream parlors.

Just 10 miles from Easton on Route 33, St. Michaels sits on the Miles River and prides itself on its maritime heritage. The Chesapeake Bay Maritime Museum highlights the area’s rich history and offers both educational exhibits and some of the Shore’s most anticipated festivals and events. It’s home to its own brewery, winery and distillery. Highly acclaimed restaurants, one-of-a-kind shops, and some of the area’s best shopping will leave you lingering. But its bike trails and easy water access will make you want to wander.


Past St. Michaels, off the beaten path at the end of a peninsula on the Bay, Tilghman Island is watermen’s country. Probably the most low-key town in the county, it offers local seafood, scenic views and a friendly feel year-round. Tilghman Island is also well known for its Seafood Festival and Tilghman Day. Looking for a little adventure? Rent a kayak and hit the newly designated water trails. Launch sites are easily accessible and the trails can offer a day full of exploration.

Route 50 cuts directly through Trappe, a tiny town on the rise. In addition to a bookstore and quilt shop, notable restaurants give visitors tasty reasons to stop. Trappe’s Bill Burton Fishing Pier is a draw for local visitors and a welcome respite for travelers every day of the year. Stretch your legs with a walk along the pier, cast a line for an afternoon of fishing, enjoy a picnic lunch or explore the adjacent walking and biking trails along with your pets.

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This content originally appeared in the 2016 Talbot County Travel Guide. Download the entire guide here.

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