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Road cycling routes
United States
Maryland

Queen Anne'S County

The best road cycling routes in Queen Anne's County

4.1

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791

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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.

Best road cycling routes in Queen Anne's County

  • The most popular road cycling route is Cross Island and Kent Island South Trails, a 31.5 miles (50.6 km) trail that takes 2 hours 24 minutes to complete. This moderate route combines two popular paved trails, offering views of the Chesapeake Bay and winding through diverse natural settings.
  • Another top favourite among local road cyclists is Saint Michaels to Oxford loop, an easy 29.1 miles (46.9 km) path. This route provides a scenic journey through charming towns and along the waterfront.
  • Local road cyclists also love the St Michaels: Tilghman Island and Neavitt Landing, a 48.0 miles (77.3 km) trail leading through coastal landscapes and rural roads, often completed in about 2 hours 55 minutes.
  • Road cycling in Queen Anne's County is defined by gently rolling farmland, extensive waterfront views, and dedicated paved trails. The network offers options for easy, moderate, and challenging ability levels.
  • The routes in Queen Anne'S County are highly rated by the komoot community with an average score of 4.25 stars from over 19 reviews. More than 800 road cyclists have used komoot to explore Queen Anne'S County's varied terrain.

Last updated: July 7, 2026

4.0

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#1.

Saint Michaels to Oxford loop

46.9km

01:47

30m

30m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

4.7

(3)

39

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

5.0

(2)

21

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

5.0

(4)

23

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Queen Anne'S County

Road Cycling Routes around Stevensville

Road Cycling Routes around Kent Narrows

Road Cycling Routes around Grasonville

Road Cycling Routes around Chester

Road Cycling Routes in Love Point State Park

Hiking in Queen Anne's County

Cycling in Queen Anne's County

Running Trails in Queen Anne's County

Tips from the Community

Marius
June 1, 2025, Maryland State House

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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beautiful beach! 😍

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mtm05005
July 23, 2024, B&A Trail

The Baltimore & Annapolis (B&A) Trail is a 13-mile rail trail that connects Baltimore & Annapolis. It is fully paved and runs along an old railroad corridor.

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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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Frequently Asked Questions

What kind of terrain can I expect when road cycling in Queen Anne's County?

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.

How many road cycling routes are available in Queen Anne's County?

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.

Are there dedicated paved cycling trails in Queen Anne's County?

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.

Can I combine trails for a longer road cycling experience?

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.

Are there road cycling routes suitable for beginners or families?

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.

What are some interesting landmarks or natural features I can see along the road cycling routes?

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.

Where can I park for road cycling routes in Queen Anne's County?

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.

What is the best time of year to go road cycling in Queen Anne's County?

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.

Are there any loop road cycling routes in the area?

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.

What do other road cyclists enjoy most about cycling in Queen Anne's County?

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.

Are there any challenging road cycling routes for experienced riders?

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.

Can I find routes that offer a mix of woods, farms, and residential areas?

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.

Most popular routes in Queen Anne's County

Hiking in Queen Anne's County

Most popular attractions in Queen Anne's County

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Didn’t find what you were looking for?

Check out more Road cycling routes throughout Queen Anne'S County below and find the perfect route in your destination.

StevensvilleLove Point State ParkChesterKent NarrowsGrasonville

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