Fresh winds, bright water, and the season’s first easy cruise.

As winter fades along Maryland’s Eastern Shore, spring arrives in Oxford with steady breezes, sunlit river views, and the welcome return of boating season. The historic waterfront town comes alive as sailboats and cruisers fill the Tred Avon River, dogwoods and daffodils bloom along quiet streets, and outdoor dining and dockside strolls become part of the daily rhythm. With mild temperatures, scenic harbor views, and a relaxed coastal charm, spring is the perfect time to experience Oxford, whether you arrive by land or water for a day trip, weekend getaway, or extended stay.

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24 HOURS IN OXFORD, MD.

Morning
Arrive by land or water (find tide tables here) and stretch your legs with a walk along the Strand and the town docks. Start the day with coffee and breakfast at Oxford Social, watching boats come and go.

Lunch
Pick up sandwiches, snacks, or picnic fare at the Oxford Market & Deli and enjoy lunch at Town Park overlooking the Tred Avon River.

Afternoon
Visit the Oxford Museum and the Water’s Edge Museum to learn about the town’s maritime roots. If visiting between April and November, take the Oxford–Bellevue Ferry for a short, scenic river crossing.

Dinner
Dock-and-dine or drive to Doc’s Sunset Grille for fresh seafood, casual cocktails, and sunset views over the marina. Or head to the other side of our little peninsula for waterfront dining at Capsize.

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36 HOURS IN OXFORD, MD.

Day One
Follow the 24-hour itinerary.

Day Two – Morning
Enjoy breakfast at Oxford Social, then walk or bike a portion of the Oxford–St. Michaels Trail as spring flowers come into bloom.

Lunch
Lunch at Capsize OXMD, known for seasonal menus and relaxed waterfront dining.

Afternoon & Evening
Browse local shops and galleries.

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72 HOURS IN OXFORD, MD.

Add a third day on the water. Rent kayaks or paddleboards, or simply enjoy a quiet morning on the dock. Visit the Oxford Community Center for a play, classes, or performances if available. End the day with dinner at Pope’s Tavern for Italian-inspired dishes and local wines.

SEE ALSO: A Relaxing Weekend in Oxford, Maryland, Talbot County Office of Tourism

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A WEEK IN OXFORD, MD.

Plan your visit around Oxford Day in late April, featuring boat displays, music, and community celebrations. Spend mornings on the water, afternoons exploring museums and trails, and evenings dockside at Doc’s Sunset Grille or Capsize. This is an ideal week for boaters looking for a calm harbor and walkable dining.

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SEE MORE:

Food & Drink
Places to Stay
Shop and Play
Marinas & Marine Services