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Routes
Road cycling routes
United States
Massachusetts
Plymouth County

The Pinehills

The best road cycling routes around The Pinehills

4.7

(3)

158

riders

25

rides

Road cycling routes around The Pinehills offer diverse terrain within a community dedicated to preserving natural beauty. The area features undulating topography, including geological formations like kames and kettles, and is nestled within a large pine ecosystem. Many routes utilize well-paved surfaces, winding through hilly landscapes that connect different parts of The Pinehills. This environment provides varied road cycling experiences, from gentle rides to more challenging ascents.

Best road cycling routes around The Pinehills

  • The most popular road cycling route…

Last updated: June 27, 2026

31

riders

#1.

Long Pond – Tremont Mill Pond loop from Long Pond

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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Hard

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Cycling around The Pinehills

Tips from the Community

Hans
September 5, 2024, Leonards Pond

If you love “silent” looks

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Alex
February 20, 2024, Fearing Pond Road

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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Alex
February 20, 2024, East Coast Greenway

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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Alex
February 20, 2024, Leonards Pond

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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Alex
January 26, 2024, New Long Pond

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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Alex
January 26, 2024, Long Pond

Long Pond, a 211-acre cold water pond in Plymouth, Massachusetts, lies to the east of Myles Standish State Forest, Halfway Pond, and Round Pond. Positioned west of Route 3 at Exit 3 and The Pinehills, northwest of Bloody Pond, and north of West Wind Shores, it features an average depth of 46 feet and a maximum depth of 100 feet. Fed by groundwater and an inlet from Little Long Pond, the pond drains through its bottom.

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Amy
January 26, 2024, Charge Pond

Charge Pond is a warm water lake in Myles Standish State Forest. There are several campgrounds around the lake where you can stay. The lake has clear water, sandy beaches, BBQ areas and a pavillion. Covering 23 acres (9.3 ha) and with an average depth of 6 feet (1.8 m), it's a great spot to enjoy water sports. Note: the lake is only open to campsite guests.

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Frequently Asked Questions

How many road cycling routes are available in The Pinehills?

The Pinehills offers a diverse selection of over 25 road cycling routes. These routes cater to various fitness levels, ranging from easy, shorter rides to more challenging, longer excursions across the region's unique landscape.

What kind of terrain will I encounter when road cycling in The Pinehills?

The Pinehills is characterized by its natural undulating topography, featuring geological formations known as 'kames and kettles' left by the last ice age. You'll cycle through hilly terrain and ancient pine ecosystems, with most routes utilizing well-paved surfaces that connect different parts of the community. This provides a varied and scenic cycling experience.

Are there any easy or family-friendly road cycling routes in The Pinehills?

Yes, The Pinehills offers 10 easy road cycling routes, making it suitable for beginners and families. These routes typically cover shorter distances with minimal elevation gain, allowing for a relaxed ride through the scenic pine forests and past kettle ponds. An example is the New Long Pond – East Head Pond loop from Massasoit National Wildlife Refuge, which is 14.8 miles long.

Where can I find challenging road cycling routes in The Pinehills?

For experienced cyclists seeking a challenge, The Pinehills features routes with significant elevation gain and longer distances. The most difficult route is the Long Pond – Tremont Mill Pond loop from Long Pond, which spans 72.3 miles (116.4 km) with over 520 meters of elevation gain, requiring very good fitness.

What are some scenic landmarks or points of interest along the road cycling routes?

While cycling in The Pinehills, you'll pass through beautiful natural landscapes, including ancient pine forests and kettle ponds. Some routes may take you near Charge Pond, East Head Pond, or College Pond. The area also integrates attractions like the Village Green with shops and restaurants, and the Mirbeau Inn & Spa with its Monet-esque gardens, offering pleasant stops.

What is the best time of year for road cycling in The Pinehills?

The Pinehills offers enjoyable road cycling conditions through much of the year. Spring and fall provide pleasant temperatures and vibrant foliage, making them ideal. Summer is also popular, though it can be warmer. While some routes may be accessible in winter, conditions can vary, so it's best to check local weather and trail conditions for ice or snow.

Are there any loop routes for road cycling in The Pinehills?

Yes, many of the road cycling routes in The Pinehills are designed as loops, offering a continuous and convenient cycling experience. Examples include the College Pond – Three Cornered Pond loop from Long Pond and the Bentley Loop Trail – Charge Pond loop from Chiltonville.

Where can I park my car when road cycling in The Pinehills?

Parking options are available at various points around The Pinehills, often near the starting points of popular routes. For example, routes like the New Long Pond – Three Cornered Pond loop can be accessed from areas near Plymouth North High School. Specific parking details are usually provided on individual route pages.

Are there cafes or places to eat near the road cycling routes in The Pinehills?

Yes, The Pinehills community is designed with amenities that cater to visitors. The Village Green serves as a central hub with shops, restaurants, and a coffee shop, providing convenient stops before or after your ride. These establishments are easily accessible from many of the area's cycling routes.

What do other road cyclists enjoy most about cycling in The Pinehills?

The road cycling routes in The Pinehills are highly rated by the komoot community, with an average score of 3.8 stars from over 5 reviews. Cyclists often praise the well-paved surfaces, the serene atmosphere of the pine forests, and the diverse terrain that offers options for all skill levels, from gentle rides to challenging ascents.

Is public transport available to reach The Pinehills for cycling?

While The Pinehills is primarily a residential community, public transport options to the immediate area may be limited. It is generally recommended to travel by car to access the various cycling routes and their starting points. Check local transit authority websites for the most up-to-date information on routes and schedules to Plymouth, MA.

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