Long days, warm water, and slow Chesapeake living.
Oxford, Maryland, offers a simple kind of summer along the Chesapeake. The town is small, walkable, and built around the water. Days tend to revolve around coffee, a walk along the harbor, time on the river, and dinner by sunset.
Whether you have 24 hours or a full week, Oxford makes it easy to slow down and settle into a steady rhythm.
Start with breakfast in town, spend the afternoon on the water, and end the day with live music or a waterfront meal. With a ferry ride to Bellevue and easy access to nearby St. Michaels, the town also makes a good base for exploring the Mid-Shore. Here is how to spend 24 hours, 36 hours, 72 hours, or a full week in Oxford.
24 HOURS IN OXFORD, MD.
Morning
Breakfast and coffee at Oxford Social, followed by a leisurely waterfront walk. Be sure to check for any upcoming sailing races taking place throughout the summer along our abundant waterfront, including the Strand and Oxford Park.
Lunch
Lunch from The Oxford Market & Deli or a casual meal at Capsize OXMD.
Afternoon
Kayak, paddleboard, or relax at the marina. Stop for ice cream at Scottish Highland Creamery.
Dinner
Dinner and live music at Doc’s Sunset Grille, one of Oxford’s most popular summer gathering spots.
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36 HOURS IN OXFORD, MD.
Day One
Follow the 24-hour itinerary.
Day Two
Take the Oxford–Bellevue Ferry and explore the opposite shore, then return for lunch and a relaxed afternoon. Enjoy dinner at one of our waterfront dining establishments.
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72 HOURS IN OXFORD, MD.
Add a day trip by bike or ferry to nearby St. Michaels. Return to Oxford for sunset drinks and a quiet evening along the docks.
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A WEEK IN OXFORD, MD.
Spend the week mixing water activities with unhurried meals.
Stay at one of our vacation destinations. Enjoy strolling our streets to shop, explore, and take in all the history and sweeping waterfront views our town offers.
Attend summer events at the Oxford Community Center, enjoy sunset sails, and dine your way through Doc’s Sunset Grille, Capsize OXMD, and soon-to-be-open new eateries and more. Ideal for boaters seeking a peaceful Chesapeake port, with all our marinas and maritime businesses listed here.
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See more about the businesses and services available in Oxford, Maryland by visiting our member directory here.