Talbot County - Easton, Saint Michaels & Oxford

Filled with charming streets and historic buildings, these Eastern Shore towns have a friendly atmosphere and are great for weekenders and full time residents alike.


Welcome to Talbot County!

Luxury living on the most picturesque part of Maryland’s Chesapeake Bay!
Easton, Saint Michaels, and Oxford are small towns located in the beautiful natural setting of Talbot County on Maryland’s eastern shore. Filled with charming streets and historic buildings, these towns have a friendly atmosphere that warmly welcomes tourists and new residents alike.
Rich in history dating back to 1677, these towns encapsulate the quintessential seaport village associated with the gorgeous Chesapeake Bay. These towns were once vibrant shipbuilding and fishing centers and now boast the largest collection of restored 18th-century homes in the state.
The idyllic seaports are well-known for their waterfront sunsets, graceful white-sailed boats, birding trails, and restaurants serving up heaps of local oysters and crabs. Tourists and residents alike frequent the shops and galleries along Talbot Street, go crabbing at Tilghman Island, or attend the area’s frequent festivals. This is sure to be an area you’ll fall in love with!

What to Love

  • A sailor’s paradise
  • Small, quiet towns with gorgeous waterfront views
  • Great schools and strong athletic programs
  • Many houses are weekend homes for affluent buyers

Local Lifestyle

These towns are lauded for being quiet, while still serving up some great dining, waterfront views, and real estate prices. Lots of residents are boat-owners or outdoorsmen who take full advantage of the close proximity to the water.

Dining, Entertainment & Shopping

There are plenty of places to eat, drink and shop in Talbot County. Bas Rouge, Scossa, and Banning’s Tavern (great cocktails here!) in Easton are popular local favorites for dinners out with friends and family while Ava’s Pizzeria & Wine Bar and Foxy’s Harbor Grill in Saint Michaels are practically institutions – you will fall in love with their colorful decor and family-owned feel. Oxford has some awesome waterfront restaurants like Capsize OXMD, Latitude 38, and Doc’s Sunset Grille for some great Maryland crab.
Easton Marketplace and Shoppes at Easton will be your go-to place for retail chains while Saint Michaels and Oxford have more locally-owned specialty shops like The Preppy Redneck, Oxford Vintage & Trade, the Modern Bulldog and so many other fun stores.

Things to Do

Living in this area means warm, sunny summers and mild winters. The water is the main draw for residents because living here means you love to sail…or at least love to watch the sailboats go by. Many dock their vessels at Saint Michaels Marina or in Oxford at Safe Harbor.
The community has a lively performing arts scene, with theater productions regularly held at the Talbot County Historical Society Auditorium and the Avalon Theatre. Cinema fans can see new releases at Easton Premier Cinemas in the Tred Avon Square Shopping Center. Each July, Talbot County is home to Plein Air Easton, the largest and most prestigious juried plein air painting competition in the United States.
Easton is home to one of the oldest places of worship in the state of Maryland, the Third Haven Meeting House, which was built in the 17th century. The 19th-century Trinity Cathedral is another popular place of interest for tourists.
A popular annual event in Easton is November’s Waterfowl Festival which supports wildlife and habitat conservation, education, and research, as well as features music, food, exhibits, and kids’ activities. There’s a year-round Amish Country Farmers Market that features fresh produce, meats, furniture, and hand-crafted items. Pet lovers enjoy Thursday dog walks at the Adkins Arboretum, where they join Arboretum staff for a stroll around the best paths for your pets. The annual Saint Michaels WineFest is a beloved and lively weekend for local residents – if you’re a wino, you will have a blast with this one!


Easton, Saint Michaels, and Oxford have great local schools and are operated by the Talbot County Public School District. As with most of Maryland, lacrosse and sailing are popular sports amongst kids here! For private school options, Saints Peter and Paul High School is known for its rigorous academic and athletic programs.

Work With Us

Follow Me On Instagram