The best road cycling routes around Plymouth
4.3
(3)
132
riders
38
rides
Road cycling routes around Plymouth offer a diverse landscape, characterized by coastal stretches, inland waterways, and wooded areas. The region features a mix of flat sections and rolling terrain, providing varied experiences for road cyclists. Elevation gains are generally moderate, with routes traversing areas around ponds and through state forests. This geography supports a range of road cycling experiences, from leisurely rides to more challenging excursions.
Best road cycling routes around Plymouth
- The most popular road cycling route is College…
Last updated: July 2, 2026
19
riders
45.7km
02:03
250m
250m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
16
riders
57.4km
02:57
330m
330m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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6
riders
142km
06:20
610m
610m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
4.0
(1)
12
riders
32.8km
01:29
220m
220m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
7
riders
80.3km
03:55
370m
370m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Other adventures around Plymouth
Tips from the Community
Rocky Pond is one of several ponds in Myles Standish State Forest. This is a great pond for a break during a ride, as you can access it from Bare Hill Road.
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Myles Standish State Forest is covering over 12,400 acres, and is one of the state’s largest and most important protected areas. It is home to many rare habitats and species, including the globally rare Pine Barrens ecosystem, sensitive frost pocket habitats, scores of coastal plain kettle ponds, and 42 rare and endangered plants and animals.
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Leonard's Pond, spans 54 acres in Rochester. Situated to the west of Mary's Pond, it marks the confluence of the west and east branches of the Sippican River, with the Sippican River flowing onward as the outflow from the pond. At this point you gain lovely views looking across the peaceful pond.
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New Long Pond, a 23-acre pond within Myles Standish State Forest in Plymouth, Massachusetts, lies northeast of East Head Reservoir and southwest of College Pond and Three Cornered Pond. Its water quality is compromised by the presence of non-native aquatic plants. With the road running right next to the pond, you get the chance to take a good look of it whilst cycling past.
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Jump off the bike and walk down the footpath to find College Pond. College Pond is one of the many lakes in Myles Standish State Forest. The 53-acre (21 ha) pond has a swimming beach and picnic area on its north shore. It has an average depth of 10 feet (3 m) and is as deep as 24 feet (7.3 m) in places.
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Powder Point Bridge is an intriguingly long wooden bridge. If you happen to cross it at the same time as a car, the sound of the wooden boards rattling with the weight of the vehicle is something to behold. Fear not, it will hold the weight of all of you and has done since 1986 when the bridge was rebuilt following a fire. The previous structure was built in 1892.
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Frequently Asked Questions
How many road cycling routes are available in Plymouth?
There are over 35 road cycling routes around Plymouth, offering a wide range of options for different skill levels and preferences.
Are there easy road cycling routes suitable for beginners or families in Plymouth?
Yes, Plymouth offers 15 easy road cycling routes. These routes typically feature flatter terrain and shorter distances, making them ideal for those new to road cycling or looking for a relaxed ride.
What kind of terrain can I expect on road cycling routes in Plymouth?
Road cycling routes in Plymouth feature a diverse landscape, including coastal stretches, inland waterways, and wooded areas. You'll find a mix of flat sections and rolling terrain, with generally moderate elevation gains as routes traverse areas around ponds and through state forests.
Are there challenging road cycling routes for experienced cyclists in Plymouth?
For experienced cyclists seeking a challenge, there are 2 difficult routes in the Plymouth area. One notable option is the Myles Standish State Forest – Rocky Pond loop from Kingston, which covers over 88 miles (141 km) with significant elevation changes.
Can I find loop road cycling routes in Plymouth?
Many road cycling routes in Plymouth are designed as loops, allowing you to start and end at the same point. Examples include the College Pond – Three Cornered Pond loop from Plymouth and the Rocky Pond – East Head Pond loop from Plymouth.
What are some scenic road cycling routes near the coast in Plymouth?
For scenic coastal views, consider the Duxbury Beach Reservation – Powder Point Bridge loop from Kingston. This route offers beautiful vistas and passes by the notable Powder Point Bridge.
Are there any attractions or points of interest along the road cycling routes in Plymouth?
Yes, many routes pass by or are near significant attractions. You might encounter historical sites like Plymouth Rock or Plimoth Grist Mill. Routes also often circle beautiful natural features such as College Pond and pass through areas like Myles Standish State Forest.
What is the best season for road cycling in Plymouth?
The spring, summer, and fall months generally offer the most pleasant conditions for road cycling in Plymouth. Spring brings blooming landscapes, summer provides warm weather, and fall showcases vibrant foliage, making these seasons ideal for exploring the region's diverse routes.
Are there road cycling routes that pass by ponds or through state forests?
Absolutely. Many routes in Plymouth are designed to highlight the region's natural beauty, including its numerous ponds and state forests. The New Long Pond – Three Cornered Pond loop from Plymouth North High School is a great example, as it navigates through areas rich with these features.
What do other cyclists say about road cycling in Plymouth?
The road cycling experience in Plymouth is highly regarded by the komoot community, with an average rating of 4.0 stars. Cyclists often praise the diverse scenery, from coastal paths to serene pond-side routes, and the variety of options available for all skill levels.
Are there options for longer road cycling tours in the Plymouth area?
Yes, for those looking for longer rides, Plymouth offers several extended routes. The Myles Standish State Forest – Rocky Pond loop from Kingston is a substantial option, covering over 88 miles (141 km) and providing a full day's adventure.
Where can I find parking for road cycling routes in Plymouth?
While specific parking details vary by route, many road cycling routes in Plymouth start from public areas, parks, or trailheads where parking is generally available. It's advisable to check the starting point of your chosen route for the most convenient parking options.
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