Talbot County’s cultural identity comes from the unique history, character, and setting of each of its small towns and villages. From quaint picket fence-lined streets to bustling brick sidewalks to working watermen and agricultural villages, you’ll find the tie that binds them is the Chesapeake Bay. Here you’ll find the diversity of the American landscape all in our region of Maryland’s Eastern Shore.
Home to sophisticated small towns, waterman’s villages, and more than 600 miles of Chesapeake Bay waterfront, Talbot County is the perfect balance of rural simplicity and urban refinement. Here you’ll find a season for art, film, food, music, and cultural festivals and a season for quiet and calm, ranking this as a go-to destination for both action-packed adventures and relaxing retreats. Accessible by car, boat, and small plane make a visit here ideal for a long weekend or extended stay for travelers from D.C., Philadelphia, New York, and beyond!
Deemed the “big city” of Talbot County, Easton is as sophisticated as it is lively. Featuring a world-class theater, renowned art galleries and impeccably curated museums, it’s the heart of the Shore’s arts and culture scene. This mini metropolis draws international artists, musicians, and cultural connoisseurs to a series of acclaimed festivals each year. And it’s a foodie town to boot, chock-full of hidden culinary gems. Come for a show, stay for a week – this art lovers’ retreat is rated among the Top Ten Best Small Towns and Top 100 Small Arts Communities in America.
Like an old-fashioned postcard, Oxford is picture perfect. Surrounded by water with Town Creek to the east and the Tred Avon River to the north and west, the town’s waterways bustle with the passing of yachts, sailboats, powerboats, and its own Oxford-Bellevue Ferry. Author James Michener even penned the novel Chesapeake in this peaceful nautical oasis. Take a stroll back in time as you navigate the tree-lined streets, peppered with historic homes and picket fences, charming inns and taverns, and a local ice cream creamery. It’s a quiet escape with water views around every turn.
Though its picturesque setting earned national attention as the backdrop for the movie Wedding Crashers, St. Michaels’ physical beauty offers only a glimpse of its idyllic charm. Nestled along the Miles River in the heart of the Chesapeake, the historic waterfront town provides itineraries for from romantic getaways, family vacations, “girls” shopping weekends, and more. Home to museums and boutiques, gourmet restaurants and crab shacks, and plenty of adventure by land or by sea, foodies, sailors, wine connoisseurs, and art enthusiasts alike will lose themselves in all the town has to offer.
A quintessential historic American waterfront village, Tilghman Island is just off the beaten path on the southernmost tip of Talbot County. Watermen reign, pristine landscapes abound, and crowds only exist at the annual crab feasts and docking contests. Nestled between the Chesapeake Bay and the Choptank River, the island offers serene vacations marked by fishing, crabbing, boat rides and relaxation. This waterman’s territory brims with unmatched hospitality and is just the place to leave your stress behind — and sample the Chesapeake Bay’s best seafood.
With a population of just over 1,000 and an area of just under 3 square miles, Trappe is one of Talbot County’s smaller towns — but it has an outsized history. A vacation in Trappe is a quiet escape that isn’t without its charms. Opt for a stay at a vacation rental on the water and enjoy the seclusion of a private estate. It’s a great home base for your stay in Talbot County.