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.
Last updated: April 26, 2026
7
riders
47.4km
01:57
280m
280m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4
riders
34.5km
01:21
130m
130m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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6
riders
48.4km
02:15
200m
200m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(5)
8
riders
34.6km
01:28
170m
170m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3
riders
25.6km
01:05
100m
100m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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