Driving Tours

  1. View looking down the road through treesAfrican American Heritage Trail

    Discover the stories that shape the fabric of Southern Maryland. Explore the history behind compelling individuals, establishments, and organizations and how their stories helped shape the region. The profound history of African Americans resonates throughout the three counties of Calvert, Charles and St. Mary's.

  2. Arts & Antiques Trail

    Featuring several prominent art galleries, antique boutiques and community theater groups, Calvert County's arts and antiques scene is dynamic, unique and rich with talent. Meander through quaint shops along the Calvert County Arts & Antiques Trail to find the perfect souvenir!
  3. Barn Quilt TrailBarn Quilt Trail

    The mission of the Calvert Barn Quilt Trail is to connect our community and visitors by promoting Calvert County's agricultural heritage, local history and artistic talent through the exhibition of hand-painted wooden quilt squares on barns and buildings throughout Calvert County. Barn Quilt Trail Map and Brochure.

  4. Calvert Birding Trail

    Calvert County has had over 330 reported bird species. Most of the county is rural and habitats include tidal wetlands, freshwater marshes, beaches, forests, meadows, bay and river shorelines and even a cypress swamp. Calvert County is home to both common and notable bird species. See our Calvert County Birding Page to find out more.  
  5. Calvert county beer and wine trailCalvert County Beer and Wine Trail

    Maryland’s smallest county plays a big role when it comes to the fine art of fermentation. Every aspect of the region’s charm is on display at our local wineries and breweries. Roam the trail and sample superb wines in a restored tobacco barn, on the slopes of a rolling vineyard or along the banks of a pristine creek. Cold, fresh beer is also part of the Chesapeake Bay lifestyle.
  6. Captain John Smith TrailCaptain John Smith Trail

    The Captain John Smith Chesapeake National Historic Trail offers countless opportunities for recreation and discovery. Take to the water by kayak, sailboat or boat. Bicycle or hike along woodland trails, or follow winding roads through rural landscapes and historic villages. Visit places that celebrate American Indian heritage and watch wildlife in marshes, waterways and forests. Captain John Smith Trail Map and Brochure.

  7. Patuxent ChallengePatuxent Challenge

    The Patuxent River is the largest river completely within Maryland: 115 miles long, a watershed of over 900 square miles. It was designated one of Maryland’s most scenic rivers in 1968 and is full of history, culture, and natural beauty. By completing challenges, you will experience a different Patuxent River with each activity as it changes from its headwaters to the Chesapeake Bay. Calvert County offers three challenges: paddle a kayak or canoe from Lower Marlboro Wharf, fish at Kings Landing Park or take a hike along the Patuxent River at Jefferson Patterson Park. Patuxent Challenge Map

  8. Patuxent Wine TrailPatuxent Wine Trail

    The Patuxent Wine Trail presents the wineries of Calvert and St. Mary's counties. The birthplace of Maryland, the area is rich in history and flavor, home to many historical landmarks, lighthouses and quaint waterfront towns

  9. Cypress SwampRoots & Tides Byway

    Explore the timeless traditions and deep maritime roots of Western Shore towns along the Chesapeake Bay. Go sailing, bird watching, museum hopping or just relax on a sandy beach.

  10. Oyster TrailSouthern Maryland Crab & Oyster Trail

    Southern Maryland abounds with quintessential crab houses and wharves that echo traditions from yesteryear. The placid scenes betray the hard labor that underlies the watermen’s lives. Experience catching your own crabs or harvesting oysters, or just learn about the Chesapeake Bay and the life of a waterman on a Watermen’s Heritage Tour. Several tours are based out of Solomons Island, which is a favorite port for sailors. The island has its own vibe.

  11. Star Spangled Banner TrailStar-Spangled Banner Trail

    The Star-Spangled Banner National Historic Trail is a 560-mile land and water route that tells the story of the War of 1812 in the Chesapeake Bay region. It connects historic sites in Maryland, Virginia and the District of Columbia and commemorates the events leading up to the Battle for Baltimore, the aftermath of which inspired Francis Scott Key to write our National Anthem. The trail traces American and British troop movements, introduces visitors to communities affected by the war and highlights the Chesapeake region’s distinctive landscapes and waterways. Congress established the Star-Spangled Banner Trail in 2008. Watch this video from VisitMaryland.org to learn more. See the route map and brochure.

  12. Sweet Treat TrailSweet Treat Trail

    From sweet kettle corn made right before your eyes, to extreme milkshakes, the Calvert County Sweet Treat Trail satisfies any sweet tooth!