Outdoor dining

Things to Do in St. Michaels, Oxford and Easton

Fall in love with these quintessential Eastern Shore towns.

Outdoor dining

St. Michaels, Oxford and Easton are all located on Maryland’s Eastern Shore, and each offers something unique for visitors. St. Michaels maintains its historic nautical identity and Easton, known as the cultural capital of the Eastern Shore, boasts a vibrant arts scene. In Oxford, you’re sure to find a laid-back and quiet escape. Oxford offers water views at every turn, plus picturesque brick sidewalks and beautifully restored 18th, 19th, and early 20th century homes.

Read on for our favorite things to do in St. Michaels, Oxford and Easton.

Historic Inns
Historic Inn on the Eastern Shore
The Inn at Perry Cabin by Belmond

Book a room at a historic inn on your trip to the Eastern Shore. If you’re looking for water views, opt for The Inn at Perry Cabin by Belmond in St. Michaels. It stretches across 25 acres of waterfront, and offers a sprawling lawn—the perfect place to relax with a drink while watching sailboats glide by on the Miles River. In Easton, The Tidewater Inn traces its routes back to 1712 and in Oxford, you’ll find the oldest full service Inn in America—Robert Morris Inn 1710. It’s the childhood home of a signer of the Declaration of Independence and one of the many historic options to check out in the area.

Links at Perry Cabin
The Links at Perry Cabin Inn
Joann Dost

This 18-hole championship course in St. Michaels is designed by legendary Pete Dye. It offers a setting of mature shade trees and soft dunes and culminates with an unforgettable finishing stretch in view of the majestic Chesapeake Bay.

Chesapeake Bay Maritime Museum

Maritime history, motors or Colonial memorabilia? Here, you don’t have to choose! St. Michaels, Oxford and Easton are home to a variety of museums that are worth a stop. The Chesapeake Bay Maritime Museum in St. Michaels offers numerous outdoor and indoor exhibitions, a Museum Store and marina. Also in St. Michaels, the Classic Motor Museum boasts a vintage collection with anything from farm tractors to fine examples of the cars that have fueled American’s love affair with the automobile. In Oxford, the Oxford Museum preserves a diverse collection of artifacts and memorabilia that chronicles more than 300 years of Oxford’s colonial and American history.

Breweries, Wineries & Distilleries
Maryland Spirits Month

When you’re ready to wet your whistle, head to the Old Mill in the heart of St. Michaels, where a trifecta of craft companies await. The Eastern Shore Brewing Company strives for the perfect pint with seasonal specialties. The tasting room at St. Michaels Winery offers premium boutique wines that reflect the Chesapeake Bay and Lyon Rum prepares splendid rum and rye whiskey in ultra small batches.

Shopping and Retail Stores
Boutique shopping

St. Michaels is a great place to shop local with independently owned shops and boutiques thriving along the town’s charming streets. You'll find everything from cocktail attire to thrift, antique stores to home décor and kitchen shops. In Oxford, make sure to visit the Mystery Loves Company bookstore, which overflows with tomes from the mystery genre in addition to a great selection of regional titles.

Hiking / Biking Trails
Heron on Dock at sunset

Easton’s open spaces, historic sites, and stunning waterfront vistas make it a magnet for cyclists. Several bike routes have been designed to showcase the best of Talbot County, including the popular 38.2-mile Chesapeake Views loop, which leads to unobstructed views of the water. Pick up a brochure at any of the half-dozen bike rental centers in the county or download a bike trail map from TourTalbot.org. In Oxford and St. Michaels, the 29.6-mile long Premier Bike Trail is recognized as one of the best in the Mid-Atlantic region. The route includes the historic town of Oxford, the crossroads of Royal Oak with its antique stores and post office (where you will find a cannon ball that lodged in a nearby oak tree during the War of 1812) and the delightful town St. Michaels with its many shops and restaurants.


St. Michaels is known for its Chesapeake Bay bounty featuring fresh locally caught fish, crabs and oysters, but don't be surprised if you find Italian, Irish, and Scottish-inspired restaurants too. In fact, one of the country’s best homemade ice cream stands, the Scottish Highland Creamery is located in Oxford and was voted one of the top 5 ice cream shops in the United States according to TripAdvisor.

African-American History Attractions
Frederick Douglass statue by Talbot County Courthouse

African-American history threads all corners of Easton. Frederick Douglass, a great American hero, abolitionist and native son is commemorated in a bronze statue in front of the county’s majestic brick courthouse. There’s also a self-guided trail that weaves through side streets, highlighting those who made an impact on the town’s history.

Arts & Entertainment
Avalon Theatre Easton

The Avalon Theatre, an Art Deco gem in Easton, is the go-to place to catch live music and theater. There are also free outdoor performances in downtown Easton and musical events like the Chamber Music Festival throughout the summer. Easton is also home to many galleries and art studios and one of the Mid-Atlantic’s premier art centers, the Academy Art Museum, which has a stellar permanent collection (including artists such as Pierre Bonnard, Robert Rauschenberg, and Martin Puryear). The Museum welcomes more than 50,000 visitors annually to experience exhibitions, concerts, lectures, programs, and classes for all.

In Oxford, enjoy art for a good cause with Oxford Picket Fences. During the summer, picket fences painted by local artists are displayed throughout the town at various businesses. In the fall, the fences are auctioned off and the proceeds benefit charities of the artist’s choice.

Festivals & Events
Artist painting landscape
Talbot County Tourism

There are many festivals that take place throughout the year in St. Michaels, Oxford and Easton, including:

  • Plein Air Easton (July): At the center of the modern plein air movement, it is the largest and most prestigious juried plein air painting competition in the United States. Many of the world's most accomplished artists have Easton at the top of their wish list of competitions.
  • Waterfowl Festival (November): This is the granddaddy of all waterfowl festivals, attracting artists, collectors, and hunters from around the world for exhibits, workshops, music, and Chesapeake Bay cuisine. Come for an autumn weekend trip to Easton to find a new decoy, view the latest wildlife art, see retrievers in action, listen to the maestros of duck and goose calling. The annual Waterfowl Festival is a wonderful celebration of Maryland's Eastern Shore sporting tradition and conservation.
  • Oxford Day (April): The annual Oxford Day celebration includes a plant sale, boat rides and a hometown parade.
The Oxford-Bellevue Ferry
Oxford-Bellevue Ferry

The Oxford-Bellevue Ferry, in service April through November, is the most scenic approach to the colonial-era town of Oxford. It crosses the gentle Tred Avon River and is the perfect choice when traveling from St. Michaels or Easton. Captains Tom and Judy Bixler will welcome you aboard America’s oldest privately owned ferry which began its service in 1683.