Trail Town
Annapolis
Anne Arundel County, DMV
State capital
About Annapolis
Annapolis is Maryland’s historic capital and a scenic waterfront city located where the Severn River meets the Chesapeake Bay. With a compact downtown of colonial architecture, cobblestone streets, and maritime heritage, Annapolis blends American history with a vibrant culture of sailing, education, and small-town charm. The United States Naval Academy is located here, drawing visitors year-round to its campus, museum, and ceremonial events. Annapolis also serves as a regional hub for trails, parks, and waterfront recreation, making it a natural stopover for long-distance trail users and outdoor travelers.
Trail Access
The Annapolis area offers multiple connections for trail users seeking scenic corridors and bike-friendly paths. The Baltimore & Annapolis Trail links Annapolis and Baltimore via a roughly 13-mile paved corridor, providing a regional connection for cyclists and walkers.
Locally, Annapolis is served by city parks and waterfront pathways along the Severn River, as well as smaller community trails and links into broader networks across Anne Arundel County. Nearby sections of the South Shore Trail (part of the East Coast Greenway and ultimately the 9/11 National Memorial Trail) are in development and will further enhance connections to regional trail systems
Trail Services & Facilities
Bike Shops
436 Chinquapin Round Rd, Annapolis, MD 21401
(667) 225-4482
2138 Generals Hwy Annapolis, MD 21401
(410) 266-7383
Food & Dining
Seafood • 400 Fourth St, Annapolis, MD 21403
Traditional American • 12 Market Space, Annapolis, MD 21401
Restaurant/Bar • 25 Market Space, Annapolis, MD 21401
Cafe • 35 Maryland Ave, Annapolis, MD 21401
Lodging
Full-Service Hotel • 173 Jennifer Rd, Annapolis, MD 21401
Hilton Garden Inn Downtown Annapolis
Full-Service Hotel • 174 West St, Annapolis, MD 21401
Boutique Hotel • 86 State Cir, Annapolis, MD 21401