Ultimate 5-Day Getaway in Oxford, Maryland Itinerary

Start your day with a delicious breakfast at Grape and Grain, where you can also explore their selection of fine wines and artisanal spirits. After breakfast, visit the Oxford Exchange to browse the works of local artists and craftsmen.

For lunch, head to Latitude 38 and indulge in their fresh seafood and nautical atmosphere. Spend your afternoon at the Bachelor Point nature area, taking a leisurely walk and observing the native wildlife.

Dine at Mason's, a restaurant with a focus on seasonal and local ingredients, providing a true taste of the region. Cap off the night with a visit to the Rabbit's Ferry House, a historic site with a story to tell.

Enjoy a hearty breakfast at Robert Morris Inn to fuel up for the day. Then, step back in time at the Academy Art Museum in Easton, where you can admire a diverse range of art collections.

Satisfy your appetite with a sumptuous lunch at Capsize in St. Michaels, followed by a visit to the Chesapeake Bay Maritime Museum to explore the rich maritime history of the region.

Return to Oxford for an elegant dinner at Scossa Restaurant & Lounge, celebrating the culinary arts. Wind down with a leisurely walk through the Oxford Strand, reflecting on the day's discoveries.

Begin with breakfast at Pope's Tavern before embarking on a day trip to Tilghman Island. Explore the quaint island, visit the Phillips Wharf Environmental Center, and enjoy the fresh seafood at Characters Bridge Restaurant.

Return to Oxford and spend a relaxing afternoon at Bellevue State Park, surrounded by nature. For dinner, indulge in the culinary creations at Mason's, known for its innovative dishes and welcoming atmosphere.

Conclude your day with a serene walk through the Oxford Strand, under the soft glow of the streetlights, taking in the peaceful ambiance of the waterfront town.

Enjoy a final breakfast at Grape and Grain, where you can also pick up some last-minute gifts. Take a scenic drive to Tred Avon Yacht Club and Oxford-Bellevue Ferry, savoring the coastal views.

For lunch, return to the heart of Oxford and dine at Latitude 38, soaking in the laid-back atmosphere and enjoying the flavors of the Chesapeake Bay. Spend your final afternoon visiting the Oxford Museum or simply meandering through the town, capturing its essence.

As the sun sets on your Oxford getaway, have a memorable farewell dinner at Robert Morris Inn, where the combination of historic charm and culinary excellence provides the perfect ending to your journey. Reflect on your experiences with a quiet walk along the Oxford Strand, the waterfront's gentle lullaby bidding you adieu.