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Bike touring routes & trails

Berkshire County

Mill Pond loop from Great Barrington

Bike touring routes & trails

Berkshire County

Mill Pond loop from Great Barrington

Intermediate

2

riders

Mill Pond loop from Great Barrington

03:10

50.5km

250m

Intermediate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: August 13, 2025

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Includes a segment in which cycling is not permitted

You'll need to dismount and push your bike.

101 m in total

Waypoints

A

Start point

Parking

Get Directions

1

5.30 km

Housatonic River Access

Nature Reserve

2

18.3 km

Mill Pond

Highlight • Lake

Mill Pond is a large reservoir just off the side of Bow Wow Road. The body of water is fed by Hubbard Brook, and you actually bike right by the …

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3

26.5 km

View of the Housatonic River on U.S. Bicycle Route 7

Highlight (Segment) • Viewpoint

The U.S. Bicycle Route 7 (USBR 7) is a super good, north-south bike trail that follows the Western New England Greenway through Connecticut, Massachusetts, and Vermont. This section in Massachusetts …

Tip by

B

50.5 km

End point

Parking

Way Types & Surfaces

Way Types

29.4 km

17.8 km

2.49 km

730 m

100 m

< 100 m

Surfaces

23.3 km

21.8 km

5.26 km

191 m

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Elevation

Elevation

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Weather

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Thursday 30 October

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100 %

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Nearby routes

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Intermediate

5.0

48

Copake Iron Works Furnace – Rudd Pond loop from Hillsdale

02:46h

45.4km

200m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Expert

17

Housatonic River Reservoir – Card Pond loop from West Stockbridge

02:46h

42.9km

510m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Easy

5.0

12

Bike loop from Hillsdale

00:51h

13.3km

60m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Expert

9

Beautiful View of the Valley – New Concord Meeting House loop from Chatham

05:02h

68.2km

940m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Intermediate

5.0

4

Gould Meadows loop from Stockbridge

01:50h

27.2km

320m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Intermediate

5

Mill Pond loop from North Canaan

02:49h

47.3km

350m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Expert

5

Gould Meadows – Olivia's Overlook loop from Pittsfield

05:15h

83.7km

890m

How to understand each route’s difficulty level

Hiking

Bike

Mountain Bike

Road Bike

Running

Up to 2 hours and 1,000 ft. of elevation gain. Great for any fitness level.Easily-accessible paths. Suitable for all skill levels.
Corresponds approx.to SAC 1.

Up to 5 hours and 3,000 ft. of elevation gain. Requires good fitness.Mostly accessible paths. Sure-footedness required.
Corresponds approx. to SAC 2-3.

More than 5 hours long or 3000 ft. of elevation gain. Requires very good fitness.Sure-footedness, sturdy shoes and alpine experience required.
Corresponds approx. to SAC 4–6.

Technical difficulty rating based on the Swiss Alpine Club (SAC) Hiking Scale.

Expert

4

Olivia's Overlook – Hancock Shaker Village loop from West Pittsfield

02:59h

47.9km

510m