What makes exploring this area particularly distinctive is the deep history that is woven into the landscape. When you are cycling Wildlife Drive and the surrounding roadways, paddling the refuge water trails, and walking the trails, you are exploring the very same scenery that Harriet Tubman traversed in her efforts to lead enslaved African Americans to freedom along the Underground Railroad.

Maryland’s Lower Eastern Shore is a region where history, culture, and nature come together in remarkable ways. From the sandy beaches and winding marsh creeks of the lower Chesapeake to the mysterious black waters of the Pocomoke River and the quiet coastal bays behind Assateague Island, this area offers endless opportunities to connect with both the outdoors and the state’s heritage.

The Pocomoke River and its watershed make up the ultimate playground for outdoor enthusiasts on Maryland’s Lower Eastern Shore. The Pocomoke is the perfect backdrop for camping, fishing, paddling, hunting, birding, hiking, and even mountain biking.

From the Wicomico River to the Pocomoke Sound, this corner of the Chesapeake offers some unique hiking options, ample paddling opportunities, and some of the best sunsets in all of Maryland. We’ve rounded up some of our top picks to help you get outdoors and make the most of the area.

The Dogfish Inn sits right at that sweet spot. Nestled in the historic district, this stylish boutique hotel is just a short walk or bike ride from some of Delmarva’s best trails, beaches, and waterways.