5.0
(7)
295
riders
37
rides
Road cycling routes around Upper Marlboro traverse a landscape characterized by established parklands, local ponds, and a network of trails. The region features gently rolling terrain, making it suitable for various road cycling experiences. Elevations are generally modest, with no significant peaks over 200m.
Last updated: May 21, 2026
21
riders
45.7km
01:54
220m
220m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
18
riders
86.8km
04:21
650m
650m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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14
riders
54.4km
02:18
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
93.5km
03:56
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
33.9km
01:34
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Upper Marlboro
This is a lovely spot with a nice boardwalk, where you can walk along the pond's perimeter and enjoy the surrounding parkland. There is a picnic area, and a fishing pier, making it an ideal spot for a peaceful respite amidst the city's hustle and bustle for lunch, or spending the afternoon.
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Watkins Regional Park in Upper Marlboro, Maryland, spans over 850 acres and offers a diverse range of attractions for visitors of all ages. One of its standout features is the Wizard of Oz-themed playground, where children can follow the Yellow Brick Road through imaginative play structures like Dorothy’s house, the Emerald City, and ruby slipper slides. This playground not only provides entertainment but also incorporates educational elements to promote literacy and learning through play.
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This is a lovely spot with a nice boardwalk, where you can walk along the pond's perimeter and enjoy the surrounding parkland. There is a picnic area, and a fishing pier, making it an ideal spot for a peaceful respite amidst the city's hustle and bustle for lunch, or spending the afternoon.
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Dower House Pond is a pretty pond with lily pads and a small stream flowing out of it right on Rosaryville Road in Maryland. This is a pretty spot to ride past and look out for birds and other animals.
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there's rarely alot of car traffic, so the streets are recommended
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very few people in the morning & early afternoon.
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The road cycling routes in Upper Marlboro are primarily categorized as easy or moderate. The region features gently rolling terrain with modest elevations, making it accessible for various skill levels. There are no routes classified as difficult in this area.
Yes, komoot offers a selection of over 30 road cycling routes around Upper Marlboro. These include 14 easy routes and 20 moderate routes, providing options for different preferences and fitness levels.
For an easier ride, consider the Pj's coffee – Watkins Regional Park loop from Marlboro Village, which is 28.4 miles long. Another accessible option is the Watkins Regional Park – Watkins Regional Park loop from Marlboro Village, covering 20.9 miles.
For those seeking a longer, moderate challenge, the Folly Branch Trail – WB&A trail loop from Upper Marlboro spans 57.1 miles. Another excellent moderate option is the School House Pond – Schoolhouse Pond loop from Upper Marlboro, which is 53.9 miles long and passes by local water features.
Road cycling routes in Upper Marlboro traverse a landscape characterized by established parklands, local ponds, and a network of trails. The terrain is generally gently rolling, with no significant peaks, offering a pleasant riding experience.
Many routes in the area pass by or near notable attractions. You might encounter Watkins Regional Park, which is a central feature for several routes. Other natural highlights include Northampton Lake and the Patuxent River Park - Jug Bay Natural Area.
Yes, many of the road cycling routes in Upper Marlboro are designed as loops. Examples include the popular Pj's coffee – Watkins Regional Park loop from Marlboro Village and the longer School House Pond – Dower House Pond loop from Upper Marlboro.
Given the region's climate, spring and fall generally offer the most comfortable conditions for road cycling in Upper Marlboro, with milder temperatures and pleasant scenery. Summer can be warm and humid, while winter may bring colder temperatures and potential for ice.
The road cycling routes around Upper Marlboro are well-regarded by the komoot community, with over 300 road cyclists having explored the area using komoot. Riders often appreciate the varied terrain, the network of established trails, and the scenic parklands and local ponds.
Yes, the prevalence of easy and moderate routes, combined with the gently rolling terrain and established parklands, makes Upper Marlboro suitable for family-friendly road biking. Routes that utilize dedicated trails or pass through parks like Watkins Regional Park are often good choices for families.
Many routes originate from or pass through key locations like Marlboro Village or near Watkins Regional Park. Specific parking information is often detailed within individual komoot Tour descriptions, but public parks and community centers typically offer designated parking areas for trail access.


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