Tucked along the Tred Avon River, Oxford is one of Maryland’s oldest towns and among the most peaceful places on the Eastern Shore.
A weekend here is all about slowing down, soaking in the waterfront views, and savoring small-town charm.
Day 1:
Settle In
Arrive Friday afternoon and check into the waterfront Sandaway Suites & Beach. After settling in, take a gentle walk along the town’s quiet streets, lined with sailboats, charming cottages, and flower-filled gardens. Utilize the Oxford Museum’s free audio tour to guide your walk and learn the area’s history.
For dinner, indulge in a Chesapeake favorite at the waterside Doc’s Sunset Grille. After dinner, enjoy an Orange Crush, Maryland’s official state cocktail from the rooftop bar and take in the sunset over the river — a simple, yet unforgettable Oxford tradition.
Day 2:
Explore the Area
Saturday morning, ease into your day by taking advantage of Sandaway’s breakfast delivery option. When you’re ready to venture out, work with Easton Cycle and Sport to rent a kayak to explore the Tred Avon River. If you prefer to stay on land, have a bicycle delivered to take to the open road.
After returning your equipment, grab a sweet treat from Scottish Highland Creamery and drive aboard the Oxford–Bellevue Ferry, the oldest privately operated ferry in the United States, offering gorgeous views of the Tred Avon River and a sense of timeless connection. From Bellevue, enjoy a short ride to St. Michaels for an afternoon of shopping along Talbot Street. In the evening, stay in St. Michaels for dinner or if you’d prefer a quiet setting, return to Oxford and pick up a homemade meal and bottle of wine from the Oxford Market to enjoy from the private beach at Sandaway Suites.
Day 3:
A Final Hoorah
On Sunday, grab coffee and a baked good from Oxford Social before heading next door to enjoy the waterfront views from Oxford Town Park. Watch the early morning sailboats cross the waters before wandering through town to take in the views of historic homes and quiet lanes a final time. Oxford’s magic lies in its tranquility — a place where time feels slower, the scenery more vivid, and every moment a reminder to pause and breathe deeply.
Tips for a Memorable Weekend:
Adults Only: Sandaway Suites & Beach is an adults-only property. Some of the options mentioned are add-ons, so please inquire when making your reservation. Vendors, such as Easton Cycle & Sport, may require advanced reservations.
Confirm Hours and Availability: Some amenities in Oxford are not available year-round or may close early. It’s best to confirm hours in advance to avoid any surprises.
