4.8
(13)
572
riders
59
rides
Road cycling routes in Myles Standish State Forest traverse a landscape characterized by extensive pine and oak forests, numerous freshwater ponds, and generally flat to gently rolling terrain. This region, located in Plymouth County, offers a network of paved roads suitable for road cyclists seeking routes with minimal elevation changes. The forest's composition provides a shaded environment for much of the year, with routes often winding past its many natural water bodies. The area's topography makes it particularly well-suited for accessible road cycling.
Last updated: May 21, 2026
20
riders
23.7km
01:15
110m
110m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
11
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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19
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3
riders
9.15km
00:35
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
31
riders
117km
05:29
530m
530m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
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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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A lovely stretch of road running through the forest that remains reasonably flat throughout. Perfect for getting your head down and the speed up.
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The Claire Saltonstall Bikeway, named after the former Massachusetts senator, was established to promote cycling and outdoor recreation. Since then, it has become a beloved pathway for cyclists, offering stunning views and access to recreational amenities.
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This quiet undulating road is a joy to cycle on, with plenty of room little traffic. The road is surrounding by pine trees, giving a feeling of being immersed in the woods whilst cycling along it.
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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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Myles Standish State Forest offers a range of road cycling routes suitable for various skill levels. Out of 70 available routes, 21 are rated as easy, 46 as moderate, and 3 as difficult. This means there are plenty of options for both beginners and experienced riders.
Yes, Myles Standish State Forest is well-suited for beginners, with 21 easy-rated road cycling routes. A great option to start with is the New Long Pond – Three Cornered Pond loop from East Head Pond, which is 12.6 miles (20.3 km) long and offers a scenic ride around several ponds.
For experienced riders seeking a challenge, Myles Standish State Forest does offer some more demanding routes. One such route is the Long Pond – Tremont Mill Pond loop from Long Pond, which is a difficult 72.3-mile (116.4 km) ride with over 1,700 feet (520 m) of elevation gain.
The routes vary significantly in length. Many popular routes are in the 12-15 mile (20-24 km) range, such as the College Pond – Three Cornered Pond loop from College Pond at 13.2 miles. However, there are also much longer options, like the challenging Long Pond – Tremont Mill Pond loop from Long Pond, which extends to 72.3 miles.
Absolutely. The forest's generally flat to gently rolling terrain and numerous easy-rated routes make it an excellent choice for family road cycling. The paved roads and shaded environment provide a pleasant and safe experience for riders of all ages.
The best times for road cycling are typically spring and fall, when temperatures are mild and the foliage is vibrant. Summer can also be enjoyable, especially with the shade provided by the extensive pine and oak forests, though it can get warm. Winter cycling is possible but requires appropriate gear due to colder temperatures and potential for snow or ice.
Road cycling routes in Myles Standish State Forest wind through extensive pine and oak woodlands and past numerous freshwater ponds. You'll encounter natural beauty like Charge Pond, East Head Pond, and College Pond. The Myles Standish State Forest Headquarters is also a notable point of interest.
Yes, many of the road cycling routes in Myles Standish State Forest are designed as loops, offering a continuous and scenic ride without retracing your path. Examples include the New Long Pond – East Head Pond loop from Massasoit National Wildlife Refuge and the College Pond – Three Cornered Pond loop from Long Pond.
Myles Standish State Forest offers various parking areas throughout the park, typically near trailheads, ponds, or visitor centers. Specific parking information can often be found on the individual route pages or by checking the state park's official website for detailed maps and access points.
The komoot community highly rates road cycling in Myles Standish State Forest, with an average score of 4.3 stars from 17 reviews. Riders often praise the quiet, shaded roads, the beautiful pond views, and the generally flat terrain which makes for a relaxing and accessible cycling experience.
For a comfortable road cycling trip, it's advisable to bring plenty of water, snacks, a basic repair kit (spare tube, pump), and a helmet. Given the extensive forest, a map or GPS device is also recommended. Depending on the season, layers of clothing are useful, and sunscreen is always a good idea.
While some routes, especially those around popular ponds, can see more activity, the vastness of Myles Standish State Forest means you can often find quieter sections. Exploring routes further from main entrances or during off-peak hours (weekdays, early mornings) can lead to a more secluded experience.


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