Maine’s Eastern Shore is home to several charming Eastern Shore Maryland towns to see, including our nearby neighbors Easton, Oxford, and St. Michaels, Maryland. These small towns have the biggest heart with wonderful small-town charm.

Easton, Maryland

Easton, Maryland, “the 8th Best Small Town in America” has both casual and gourmet dining; unique boutiques from collectibles to fine antiques; eclectic art galleries; several public golf courses; The Avalon Theatre, and a historic Town Center.

During the Fall and Summer on Saturdays, the Easton Farmers Market features local vegetables, fruit, plants, jewelry, paintings, freshly baked breads and other vendors with live music. Visit their visitor’s site for more info:

Oxford, Maryland

Oxford was officially founded in 1694, making it one of Maryland’s oldest towns. It’s located about 15 minutes from The Anchorage near the mouth of the Tred Avon River which served as an important port of entry for British trade vessels in Colonial times. 

With picturesque streets, historic homes with beautifully tended gardens, it’s an Eastern Shore Maryland town perfect for a stroll. The Scottish Highland Creamery is a great place to stop for some homemade ice cream. There are a couple waterfront restaurants including Doc’s Sunset Grill and Capsized.

The 300 year old Oxford-Bellevue Ferry has both car and walk on/bike availability. The ferry is in service April through November and is the perfect choice when traveling to St. Michaels. Visit the Port of Oxford’s website for more Info:

St. Michaels

Historic St. Michaels dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. The current St. Michaels is hip, historic, laid back, and has a variety of activities from fishing, boating, cruises, biking, visiting some of the unique shops, or the Maritime Museum for a taste of history. It’s also filled with history including historical quaint homes and is a great walking town.

St. Michaels is also a Foodie heaven. There are many outstanding restaurants for Fine Dining, Casual Dining, Restaurants on the water, Steak houses, Italian food, a winery and brewery, Coffee Houses, Ice Cream Parlors, and of course plenty of places to enjoy seafood. Learn more at St. Michael’s website: