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Routes
Road cycling routes
United States
Maryland
St. Mary'S County

Leonardtown

The best road cycling routes around Leonardtown

5.0

(12)

47

riders

11

rides

Road cycling around Leonardtown features a landscape characterized by gently rolling terrain and a mix of open countryside and parkland. The region offers routes with moderate elevation changes, suitable for various fitness levels. Distances range from shorter loops to longer excursions, providing options for extended rides through the local environment.

Best road cycling routes around Leonardtown

  • The most popular road cycling route is Roadbike loop from Leonardtown, a 29.4 miles (47.4 km) trail that takes 1 hour 57 minutes to complete, offering a substantial loop with varied scenery.
  • Another top favourite among local road cyclists is Roadbike loop from Wildewood, an easy 21.4 miles (34.5 km) path. This route features a generally flat profile, making it accessible for many riders.
  • Local road cyclists also love the Greenwell State Park loop from Saint Andrews Church, a 30.1 miles (48.4 km) trail leading through parkland and rural roads, often completed in about 2 hours 14 minutes.
  • Road cycling around Leonardtown is defined by open countryside, parkland, and gently rolling hills. The network offers options for easy road bike trails Leonardtown as well as more challenging road bike trails Leonardtown for different ability levels.
  • The routes in Leonardtown are highly rated by the komoot community with an average score of 5.0 stars from more than 10 reviews. More than 40 road cyclists have used komoot to explore Leonardtown's varied terrain.

Last updated: April 26, 2026

7

riders

#1.

Roadbike loop from Leonardtown

47.4km

01:57

280m

280m

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

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Easy

4

riders

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

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

Moderate

5.0

(5)

8

riders

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

Easy

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

Easy
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Tips from the Community

Andrus
February 25, 2024, Greenwell State Park

This state park near the mouth of the Patuxent River offers a wide array of activities. You have hiking, biking, fishing, and kayaking. There's also the historic Rosedale Manor House and Bonds-Simms tobacco barns available to tour for those interested in the local history.

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Frequently Asked Questions

How many road cycling routes are available around Leonardtown?

Leonardtown offers a selection of around 10 road cycling routes. These routes cater to various preferences, with options ranging from shorter, easier rides to longer, more moderate excursions through the local landscape.

Are there easy road bike trails in Leonardtown suitable for beginners?

Yes, Leonardtown is well-suited for beginners, with 8 out of 10 routes classified as easy. An excellent option is the Roadbike loop from Wildewood, which is 34.5 km long and features a generally flat profile, making it very accessible for many riders.

Are there challenging road bike trails around Leonardtown?

While most routes are easy, there are a couple of moderate options for those seeking a bit more challenge. The Greenwell State Park loop from Saint Andrews Church is a moderate 48.4 km trail that leads through parkland and rural roads, offering a good workout with some elevation changes.

What are the typical lengths of road cycling routes in Leonardtown?

Road cycling routes in Leonardtown vary in length, typically ranging from approximately 25 km to nearly 50 km. For instance, the Roadbike loop from La Grande Resort RV is about 25.6 km, while the Roadbike loop from Leonardtown covers 47.4 km.

What kind of scenery can I expect on road cycling routes near Leonardtown?

Road cycling around Leonardtown is characterized by a mix of open countryside, parkland, and gently rolling hills. You'll experience varied scenery, from rural roads to routes passing through areas like Greenwell State Park, offering a pleasant and diverse riding environment.

Are there loop road bike trails in Leonardtown?

Yes, many of the road cycling routes in Leonardtown are designed as loops, allowing you to start and end your ride in the same location. Examples include the popular Roadbike loop from Leonardtown and the Retention pond โ€“ Drainage Pond loop from Leonardtown.

What do other road cyclists enjoy the most about road cycling in Leonardtown?

The road cycling experience in Leonardtown is highly rated by the komoot community, with an average score of 5.0 stars from over 10 reviews. Riders often praise the region's varied terrain, which includes a good mix of open countryside and parkland, and the availability of routes suitable for different ability levels.

When is the best time to road bike in Leonardtown?

Given the gently rolling terrain and mix of open countryside, spring and autumn are generally excellent times for road cycling in Leonardtown. The milder temperatures and vibrant foliage (in autumn) can enhance the riding experience, though routes are accessible throughout much of the year.

Are there family-friendly road cycling routes in Leonardtown?

Many of the easy-rated routes in Leonardtown are suitable for families, especially those with some cycling experience. The generally flat profile of routes like the Roadbike loop from Wildewood makes it a good choice for a family outing.

Where can I find less crowded road cycling routes in Leonardtown?

While specific crowd levels can vary, exploring routes that venture further into the rural countryside or through less central park areas might offer a quieter experience. The Greenwell State Park loop from Saint Andrews Church, for example, takes you through parkland and rural roads, potentially offering more serene sections.

Are there road cycling routes with viewpoints in Leonardtown?

The gently rolling terrain of Leonardtown means that many routes offer pleasant views of the surrounding countryside and open landscapes. While there aren't specific 'viewpoint' routes listed, the elevated sections on some trails will provide scenic vistas of the region's natural beauty.

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Browse the best Road cycling routes in other regions.

WildewoodLexington ParkSaint Mary'S River State ParkSalem State ForestCaliforniaGreenwell State ParkCallawayNew Towne Neck State Park

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