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The Pinehills

The Pinehills

The best road cycling routes around The Pinehills

4.1

(7)

250

riders

rides

Want to go road cycling around The Pinehills? We’ve reviewed all of the road rides around The Pinehills to identify the best. Explore them all here, and find your perfect road cycling route around The Pinehills.

Last updated: December 23, 2025

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1. Tremont Mill Pond – Leonards Pond loop from Toll Brothers At the Pinehills

118km

05:33

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

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2. Three Cornered Pond – New Long Pond loop from Toll Brothers At the Pinehills

64.3km

02:59

260m

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

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Moderate

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2.0

(1)

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3. Long Pond – Fearing Pond loop from Toll Brothers At the Pinehills

29.6km

01:24

170m

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

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Moderate

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4. New Long Pond – Three Cornered Pond loop from Plymouth

82.0km

04:02

370m

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

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Moderate

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5. New Long Pond – East Head Pond loop from Toll Brothers At the Pinehills

24.0km

01:21

110m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

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The best road cycling routes around The Pinehills

1. Tremont Mill Pond – Leonards Pond loop from Toll Brothers At the Pinehills

2. Three Cornered Pond – New Long Pond loop from Toll Brothers At the Pinehills

3. Long Pond – Fearing Pond loop from Toll Brothers At the Pinehills

4. New Long Pond – Three Cornered Pond loop from Plymouth

5. New Long Pond – East Head Pond loop from Toll Brothers At the Pinehills

Most popular routes around The Pinehills

Most popular attractions around The Pinehills

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