Cruisin’ the Great Talbot County Loop: Stop 2 – Oxford

The picture-perfect town of Oxford offers a graceful waterfront and is home to brick-lined streets anchored by history and great restaurants. 

Get Moving

Bicyclists holding a map in Oxford.

Oxford is located on the banks of the Tred Avon River, making this the perfect place to explore by water. Local vendors will meet at your launch site with a rented paddleboard, kayak, or inflatable boat. Land lovers can rent bikes to explore the town on wheels. While you pedal, you can embark on The Oxford Museum’s audio tour of the town, which chronicles life from the 18th and 19th centuries and tells the story of founding father Robert Morris. It even includes a stop at a beloved bookstore, housed within an old bank, that specializes in mysteries, and a visit to the free Water’s Edge Museum, which celebrates the founding Black families of America through artwork.

Relax on the Waterfront

Mother's Day walk on The Strand Beach in Oxford, Maryland.

Call it the unofficial town square—Oxford Town Park is where dogs scamper on the lawn, kids pump their legs on swings, friends set up picnics, and couples comb the beach. Wade into tranquil waves at The Strand Beach, a family (and dog) friendly spot that fronts some of the most beautiful historic homes in town. 

Dine Well

Guests dining at Doc's Sunset Grille at sunset in Oxford, Maryland.

From relaxed party vibes with cocktails and live music, to a popular crab deck, Oxford’s waterfront restaurants offer the perfect perches to catch a sunset. You can take in more of the town’s history over dinner at one of the historic inns. Oxford is one of the best places to dine by the water and catch a spectacular sunset.

Book a Historic Stay

Oxford Town Clock

For a quaint and quiet stay, Oxford is the perfect setting. Stay in the waterfront home of a signer of the Declaration of Independence and dine downstairs in front of a cozy fireplace. There’s even a quiet getaway just for adults with its own stretch of beach. Author James Michener wrote much of his famous novel “Chesapeake” in Oxford.

Ferry Across the Water

Departing Oxford can be an experience all its own, as you cross the Tred Avon River aboard the Oxford-Bellevue Ferry, which first began operating in 1683. Cars, pedestrians, and cyclists can travel aboard. As you head to your next destination on the Great Talbot County Loop, you are guaranteed beautiful water views accompanied by osprey swooping overhead.

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Talbot County farm field with red barn.

Cruisin’ the Great Talbot County Loop

The Great Talbot County Loop – It’s here you’ll find the best of the Chesapeake culture and cuisine, much of it bound together by a ribbon of backroads that string together the small-town pearls of Easton, Oxford, St. Michaels, and Tilghman Island.

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Sunday
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Monday
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