4.1
(20)
791
riders
25
rides
Road cycling in Queen Anne's County offers diverse landscapes, from level to gently rolling farmland, making it accessible for various abilities. The region is characterized by its extensive waterfront along the Chesapeake Bay and its tributaries, providing scenic views. Cyclists can explore dedicated paved trails and numerous road routes that traverse farmlands, meadows, and wooded areas. The topography generally features minimal elevation gain, ideal for smooth road cycling experiences.
Last updated: July 7, 2026
4.0
(1)
28
riders
46.9km
01:47
30m
30m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
26
riders
50.6km
02:24
50m
50m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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11
riders
77.3km
02:56
40m
40m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.7
(3)
39
riders
44.1km
01:44
40m
40m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
28
riders
49.3km
02:00
70m
70m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
21
riders
19.8km
00:54
30m
30m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(4)
23
riders
31.7km
01:20
40m
40m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
19
riders
60.1km
02:36
310m
310m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
77.8km
03:07
170m
170m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
72.6km
03:04
390m
390m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Queen Anne'S County
The Maryland State House in Annapolis is the oldest U.S. legislative building still in active use for legislative purposes. Construction began in 1772 and took until 1797 to complete. Its striking feature is its large wooden dome—built entirely without nails. The U.S. Congress of the Confederation met here between 1783 and 1784. Today, the building is located on the grounds of Fort Williams Park and is managed by the State House Trust.
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Sandy Point State Park spans 786 acres and is open to the public. It is a great stop to take in the beauty of the northwestern shore of the Chesapeake Bay. People visit this beach for swimming, fishing, crabbing, picnicking, and boating along the mile-long sandy beach. Lifeguards are on duty during the summer months, and the park is also home to the historic Sandy Point Farmhouse and provides access to the adjacent Corcoran Woods forest preserve with four miles of hiking trails.
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Eastern Neck National Wildlife Refuge was established in 1962, and many migratory birds can be spotted here. It is a very wild and picturesque area.
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Tolchester Beach Road dead ends at the coast. There is a rocky shoreline that offers great views onto the water.
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Tolchester Beach Road dead ends at the coast. There is a rocky shoreline that offers great views onto the water.
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Eastern Neck National Wildlife Refuge was established in 1962, and many migratory birds can be spotted here. A very wild and picturesque area.
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Queen Anne's County offers diverse landscapes, primarily characterized by level to gently rolling farmland. You'll find extensive waterfront views along the Chesapeake Bay and its tributaries, as well as routes winding through farmlands, meadows, and wooded areas. The topography generally features minimal elevation gain, making it ideal for smooth road cycling experiences.
There are over 25 road cycling routes in Queen Anne's County, catering to various preferences and skill levels. These include dedicated paved trails and numerous road routes that showcase the region's natural beauty.
Yes, Queen Anne's County features popular paved, off-road trails. The Cross Island Trail is a notable 7-mile route, and its companion, the South Island Trail, also spans 7 miles. These trails are relatively flat and well-maintained, suitable for all ages and abilities.
Absolutely! You can combine the Cross Island Trail and the South Island Trail for a longer ride. This creates a round trip of approximately 28 miles, offering varied scenery from Terrapin Nature Park to Romancoke Fishing Pier.
Yes, Queen Anne's County has many routes suitable for beginners and families due to its generally flat to gently rolling terrain. For example, the Saint Michaels to Oxford loop is an easy 29.1-mile path, and the Swan Cove loop from Stevensville is an easy 20 km route, both offering pleasant rides.
Many routes offer scenic views and pass by notable attractions. You can cycle past Matapeake Park, which features a public beach and fishing pier, or explore areas near Swan Cove. The Cross Island Trail also offers views of Terrapin Nature Park, known for its panoramic Chesapeake Bay vistas.
Parking is available at key access points for popular trails. For the Cross Island Trail, you can find parking at Terrapin Nature Park. For the South Island Trail, Matapeake State Park serves as a convenient starting point with parking facilities.
The spring and fall months generally offer the most pleasant conditions for road cycling in Queen Anne's County, with mild temperatures and beautiful scenery. Summer can also be enjoyable, especially along routes with shaded sections or water views, though it can be warmer.
Yes, there are several loop routes available. Examples include the Roadbike loop from Claiborne, the Swan Cove – Bennetts Point Landing loop from Stevensville, and the Matapeake Park loop from Stevensville, providing circular journeys through the scenic landscape.
The area is highly rated by the komoot community, with an average score of 4.25 stars from over 19 reviews. Reviewers often praise the diverse landscapes, from quiet farmlands to scenic waterfronts, and the accessibility of routes for various abilities, including dedicated paved trails.
While much of Queen Anne's County is gently rolling, there are routes that offer more challenge. For instance, the Severn River views – Baltimore & Annapolis Trail loop from Skidmore is a moderate 74 km route with more elevation gain, providing a more demanding experience for advanced cyclists.
Yes, many road routes in Queen Anne's County offer a blend of scenery. The 'Grasonville Flatlands' route, for example, combines woods, farms, and residential areas, and also provides opportunities to visit the Chesapeake Bay Environmental Center.


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