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The Choptank is the largest of Chesapeake’s Eastern Shore rivers and played a major part in Harriet Tubman’s dangerous journeys north on the underground railroad to smuggle enslaved people to freedom. Today, boaters enjoy exploring all 68 miles of the Choptank and encountering the many beautiful anchorages along the way. Riverboat cruises are also a fun way to fully appreciate the surroundings and learn more about this unique river with all its twists and turns.
Experience the charm of an authentic watermen’s village on the Eastern Shore with a trip to Tilghman Island. Popular activities include sailing and fishing on the bay, dining by the water, or taking a leisurely stroll down the tree-lined streets. There are plenty of little shops to peruse in town, as well as museums and historic landmarks. This relaxing getaway is perfect for anyone who enjoys a slower pace and plenty of time to explore the surroundings.
Established in 1683, the Oxford-Bellvue is still transporting passengers on the oldest privately-owned ferry route in the country. Guests have the option to transport their cars, motorcycles, bicycles, and even RVs on the ferry to spend a day in nearby St. Michaels exploring shops, museums, and other fun attractions. Don’t miss the chance to experience this historic journey with your crew.
Plan to spend your next weekend getaway at the historic Robert Morris Inn, the oldest full-service inn in America. Built in 1710 as a residence and converted to an inn in 1800, many of the rooms were occupied by the country’s Founding Fathers and other dignitaries, including Robert Morris and George Washington. Guests can book a stay at the inn, enjoy a meal, and even take a cooking class to get a fascinating glimpse into the colonial era and America’s early years as a new nation.
For a great dock n’ dine option, head straight to Doc’s seafood restaurant and bar. Situated right on the water in Oxford, Maryland, this lively spot offers indoor and outdoor dining, live entertainment, delicious bites, and–you guessed it–front row seats to gorgeous seaside sunsets. The menu at Doc’s covers a wide range of cuisine– from freshly prepared seafood dishes to burgers, BBQ baby back ribs, sandwiches, and more.
Located right next to Town Park, this bustling cafe is a local gathering place to enjoy specialty coffee, ice cream, and baked goods. Oxford Social has a cozy, rustic atmosphere and is designed to promote conversation and connection. A great little spot to catch up with a friend, or make a pit stop before starting your day.