Driving Trails


Partial image of African American Heritage Guide cover

African 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.
Southern Maryland African American Heritage Guide (PDF)

Circle icon that reads "Calvert Arts & Antiques Trail"

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!
Interactive Arts & Antiques Trail Map

A large red barn with a quilt painted on it, part of the Barn Quilt Trail

Barn 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 (PDF)
Barn Quilt Website

Birding trail sign at the entrance to the boardwalk trail

Calvert County Birding Hot Spots

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 Hot Spots Page to find out more.    
Interactive Calvert County Birding Hot Spots Map

local beer

Calvert 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.
Flag Pond boardwalk to a dock that overlooks the water and a sunset

Captain 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
Captain John Smith Trail Website

Kayakers at Kings Landing

Patuxent 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
Patuxent Challenge Website

Wine bottles in a row

Patuxent 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.
Patuxent Wine Trail

Exhibit at the Railway Museum with a kangaroo from the carousel, cardboard cutouts and signage

Roots & 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.
Website & Trail Map 

Oyster shells

Southern 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.
Crab & Oyster Trail Website

Star Spangled Banner Trail

Star-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.
Route Map and Brochure
Star-Spangled Banner Trail Website

Sweet Treats Trail graphic with a donut, popcorn, cookie and icecream

Sweet Treat Trail

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