Byways and Trails

Whether you are a history buff, nature lover, biker, kayaker, baseball fan, shopaholic, foodie, we have something for you here.  Colonial and maritime heritage, outdoor adventure, shopping, dining, and a year full of fabulous events await.  Paddle a tidal run, fish the Bay, savor some seafood and climb to the top of a lighthouse!

Cultural Trails

Southern Maryland TRAILS: earth, art & imagination Your guide to all things handmade, homegrown and authentically Southern Maryland.

Paddle Trails

Southern Maryland provides paddlers with hundreds of miles of shoreline along the Potomac and Patuxent Rivers and the Chesapeake Bay to explore.  

Rail Trails

Indian Head Rail Trail– Enjoying Charles County Naturally Three Notch Trail – St Mary’s County Chesapeake Beach Rail Trail – Calvert County

Star Spangled Banner Trail

Discover the War of 1812 on the Star-Spangled Banner National Historic Trail – a path tracing troop movements through historic places, inspiring landscapes, charming waterfront towns, and waterways of the Chesapeakek Bay region. The trail offers many ways to experience the drama of the war and tell the stories of its people.

The Patuxent Wine Trail

Enjoy rural beauty and sophisticated tastes The Patuxent Wine Trail presents the wineries of Calvert and St. Mary’s Counties, bounded by the Patuxent and Potomac Rivers and the Chesapeake Bay.

Captain John Smith Chesapeake National Historic Trail

 History and nature intersect in the Chesapeake Bay to create a place with endless potential for discovery. 

Potomac Heritage National Scenic Trail

Linking the Potomac and upper Ohio river basins from the Chesapeake Bay and Potomac tidewater to the Allegheny Highlands, the national scenic trail network lets you retrace-by foot, bicycle, horse, or boat-the corridor that George Washington considered essential to the Nation’s development.

Civil War Trail: Escape of an Assassin

Roll through the country side checking-out Maryland Civil War Trail wayside markers along the way.  Each tells a unique story.  The Maryland Civil War Trails map and guide: John Wilkes Booth, Escape of an Assassin, has more information on sites in Charles and St. Mary’s Counties. The following locations in Charles and St. Mary’s Counties are … Continue reading Civil War Trail: Escape of an Assassin

Chesapeake Bay Gateways and Watertrails

The Chesapeake Bay Gateways and Watertrails  is a partnership of over 150 parks, museums, historic sites, and water trails  in the Chesapeake  Bay region that provide an opportunity to experience the uniqueness of the Bay’s rich natural and cultural heritage. The following locations in Southern Maryland are part of the trail.

Religious Freedom National Scenic Byway

The Religious Freedom National Scenic Byway is more than just a glimpse of history.  Visitors traveling along the Byway as it winds through Southern Maryland’s scenic roads can immerse themselves in the natural and cultural spaces that shaped the early story of a cherished American Right.  Along this Byway you will discover the story of … Continue reading Religious Freedom National Scenic Byway

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