The Indian Head Rail Trail is Charles County’s exciting new recreational trail. A generous gift through the Department of Interior’s Federal Lands to Parks Program, Charles County has completed converting this abandoned railroad corridor into a 13-mile bike trail. Connecting the Town of Indian Head to Route 301 in White Plains, the IHRT traverses approximately halfway across the County.

Patuxent Wine Trail— The state's only linear wine trail includes six wineries along a north-south route in Calvert and St. Mary's counties. A seventh winery is west of this route in Leonardtown.

Southern Maryland Trails - The Southern Maryland Trails: Earth, Art, Imagination is your guide to all things handmade, home-grown, locally harvested and authentically Southern Maryland!

'To the Point'— Starting in Historic St. Mary's City— Maryland's birthplace— this 30-mile route extends to the 1828 lighthouse at Point Lookout State Park, site of a Civil War museum and nature center. The park is also part of the Chesapeake Bay Gateways Network.