Routes

Planner

Features

Updates

App

Get the App

Berkshire County

Berkshire County

The Top 20 Attractions in Berkshire County

There are plenty of places to see and visit in Berkshire County. Whether you love hiking or cycling, Berkshire County is a region where 20

hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.

Last updated: December 15, 2025

Veterans' War Memorial Tower at the summit of Mount Greylock

Highlight • Monument

Visible from afar, the Veterans War Memorial Tower at the top of Mount Greylock was erected in 1934 in memory of all who served the U.S. during World War I. …

Tip by

See hikes here

Send to Phone

Save

Bascom Lodge

Highlight • Mountain Hut

The Bascom Lodge was built in the 1930s at the summit of Mount Greylock. It was managed by the Appalachian Mountain Club for 16 years until 2000 when it came …

Tip by

See hikes here

Send to Phone

Save

Get recommendations on the best single tracks, peaks, & plenty of other exciting outdoor places.

Ashuwillticook Rail Trail

Highlight (Segment) • Trail

Converted from an old railroad track, the Ashuwillticook Rail Trail is now a 10 foot wide, 14.2 mile, paved multi use trail meandering along the Cheshire Reservoir while offering sublime views of Mt. Greylock.

Tip by

See rides here

Send to Phone

Save

Thunderbolt Shelter, Mount Greylock

Highlight • Mountain Hut

The Thunderbolt Shelter was built in 1940 as a warming hut for skiers using the Thunderbolt Trail. This historic stone building is currently only used as a winter/emergency shelter for those attempting Mount Greylock during the off-season.

Tip by

See hikes here

Send to Phone

Save

U.S. Bicycle Route 7 — Cheshire Reservoir section

Highlight (Segment) • Cycleway

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

See rides here

Send to Phone

Save

Gould Trail

Highlight (Segment) • Trail

The Gould Trail is a popular route to the summit of Mount Greylock, the tallest mountain in Massachusetts, up its eastern flank. This trail climbs up through hardwood forests, which are exceptionally beautiful in the fall, parallel to Peck's Brook.

Tip by

See hikes here

Send to Phone

Save

Ashuwillticook Rail Trail Head

Highlight • Cycleway

Located just north of Adams, the Ashuwillticook Rail Trail Head sets a lovely tone for the rest of your ride along the trail, perfectly smooth and easy to use for families.

Tip by

See rides here

Send to Phone

Save

Cheshire Reservoir

Highlight • Lake

Cheshire Reservoir captivates riders with its tranquil beauty. The scenic reservoir, nestled in the Berkshires, offers stunning views along the route. Cyclists can enjoy a peaceful ride surrounded by nature, …

Tip by

See rides here

Send to Phone

Save

Benedict Pond

Highlight • Lake

Benedict Pond was once part of the Civilian Conversation Corps (CCC) construction project. This included building an earth dam to create the approximately 14-acre Benedict Pond.

Here you can go …

Tip by

See hikes here

Send to Phone

Save

Mount Greylock State Reservation Visitor Center

Highlight • Rest Area

The Mount Greylock State Reservation Visitor Center is located on the southern side of the long mountain and a great place to stop before your hike. There are people available …

Tip by

See hikes here

Send to Phone

Save

Already have an account?

Other adventures in Berkshire County

The Appalachian Trail — America's most iconic long-distance hike

Hiking Collection by

Jamie S.

The Long Trail — America's oldest long-distance path

Hiking Collection by

Jamie S.

Most popular routes in Berkshire County

Hiking in Berkshire County

Easy hikes in Berkshire County

Waterfall hikes in Berkshire County

Cycling in Berkshire County

Running Trails in Berkshire County

Road Cycling Routes in Berkshire County

Gravel biking in Berkshire County

MTB Trails in Berkshire County

Most popular attractions in Berkshire County

Lakes

Mountain Peaks

Natural Monuments

Waterfalls

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures around London and beyond.

Join komoot Now

Didn’t find what you were looking for?

Are you keen on exploring more awesome places nearby? Browse our guides:

Great Barrington Lee Williamstown Cheshire Lenox Dale Adams Pittsfield Housatonic North Adams Lenox

Explore more

Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:

Suffolk County Middlesex County Norfolk County Essex County Barnstable County Worcester County Hampshire County Plymouth County Bristol County Dukes County Franklin County Hampden County Nantucket County

The Top 20 Attractions in Berkshire County

Veterans' War Memorial Tower at the summit of Mount Greylock

Bascom Lodge

Ashuwillticook Rail Trail

Thunderbolt Shelter, Mount Greylock

U.S. Bicycle Route 7 — Cheshire Reservoir section

Gould Trail

Ashuwillticook Rail Trail Head

Cheshire Reservoir

Benedict Pond

Mount Greylock State Reservation Visitor Center

Other adventures in Berkshire County

Most popular routes in Berkshire County

Most popular attractions in Berkshire County

Get inspired with the komoot mobile app

Didn’t find what you were looking for?

Explore more

Get ready to conquer new peaks

We value your privacy ⛰️

We value your privacy ⛰️