Hiking Trail Guide

Hike the Trails of Berkshire County
in Western Massachusetts

Whether you are planning a leisurely stroll, a hike with the kids, or a strenuous uphill workout, you will find a hiking trail in the Berkshires that is just right.

Hiking one of the many trails in Berkshire County is one of the best ways to see all the beauty this area has to offer. From mountain vistas, waterfalls, lakes and streams, to wildlife in their natural habitat, you’ll find just what you are looking for… and more.

Don’t forget to bring a camera for those wonderful photo moments that are sure to be plentiful.

And, remember the number one rule…

…“Leave no trace.”

Keep the surroundings beautiful for the next person to enjoy.

No matter where you are in the Berkshire area, a hiking trail may be found close by. These trails range from short and easy to long and difficult. So, you can always find one that is just right for you.

When you go hiking, make sure you have the proper hiking apparel.

And, to be sure you'll find your way, we have provided links to topographic maps for each trail you choose to explore.

To find a hiking trail in Northern Berkshire County you may go to:

Williamstown:

1. Pine Cobble Trail

2. Stony Ledge Ski Trail

3. Williams Trail

4. Mountain Meadow Preserve

5. Hopkins Memorial Forest Trail

6. Hopper/Money Brook Trail to Mt. Greylock

7. Roaring Brook/Hopper Trail

North Adams:

1. Natural Bridge State Park Trail

2. Mount Williams

3. Appalachian Trail: North Adams to Mount Greylock

4. March Cataract Falls Trail

5. Cascades Trail

6. Busby Trail

7. Savoy Mountain State Forest

Clarksburg:

1. Pond Loop Trail and Horrigan Road Trail Clarkburg State Forest

Florida:

1. Bog Pond Trail

2. North Pond Loop Trail

Adams:

1. Bellows Pipe to Ragged Mountain

2. Gould Trail

3. Thunderbolt Ski Trail

4. Mount Greylock

Cheshire:

1. Cheshire Harbor Trail

For a hiking trail in Central Berkshire County you may go to:

Lanesboro:

1. Mount Greylock

2. Rounds Rock

3. Circle Trail and Deer Hill Trail

4. Hopper Trail and Overlook Trail

Hancock:

1. Hancock Shaker Village Trail

Windsor:

2. Notchview Reservation Windsor State Forest

Pittsfield:

1. Pittsfield State Forest

2. Berry Pond Trail

3. Taconic Skyline Trail

4. Turner Trail

5. Canoe Meadows Sanctuary

6. Brickhouse Mountain Trail

Richmond:

1. Stevens Glen

Hinsdale:

1. Housatonic River Greenway Trail

Dalton:

1. Appalachian Trail: Dalton to Cheshire

Washington:

1. Appalachian Trail: Washington to Dalton

2. Washington Mountain Meadow

Lenox:

1. Pleasant Valley Sanctuary

2. Shadowbrook

And, to find a hiking trail in Southern Berkshire County you may go to:

Lee:

1. Upper Goose Pond Trail

2. October Mountain State Forest

Becket:

1. Appalachian Trail: Finerty Pond & October Mountain State Forest

2. Becket Land Trust Historic Quarry & Forest

Stockbridge:

1. Ice Glen

Tyringham:

1. Appalachian Trail: Tyringham to Goose Pond to Becket

2. Tyringham Cobble Trail

3. McLennan Reservation

4. Ashintully Gardens

Housatonic:

1. Squaw Peak

Great Barrington:

1. Monument Mountain

2. Bartholomew's Cobble

3. East Mountain

4. Wild Cat Trail

Monterey:

1. Benedict Pond Loop Trail

Sheffield:

1. Appalachian Trail: Sheffield to Jug End

2. Race Brook Falls and Mount Everett

Egremont:

1. Indian Trail

2. Alander Mountain Loop

New Marlboro:

1. Dry Hill

2. Questing

Mount Washington:

1. Ashley Hill Trail

2. Bash Bish Falls and Mountain Trail

3. Sages Ravine



As you can see, there are many trails to hike in the Berkshire area. Your job is to decide which hiking trail to take.


And, then…ENJOY!!!

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