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Top 3 Best Fall Hikes in Berkshires

Best Fall Hikes in Berkshires - Autumn Trees
Matt Claiborne
Matt Claiborne
August 12, 2022

The Berkshires are home to impressive vistas and beautiful fall foliage. Hiking is a great way to see fall colors while enjoying the crisp fall air.

Experience the Best Fall Hikes in Berkshires

The Berkshires are known for their natural areas and fabulous landscapes. Fall is the perfect time to experience Berkshire’s beauty and see the stunning annual nature show known as fall foliage. The leaves turn shades of yellow, orange, and red. Mountain vistas and forests look like an artist’s canvas. Hikers can walk flat, paved trails or head to the mountains to experience the best fall hiking in the Berkshires.

Ashuwillticook Rail Trail

Ashuwillticook Rail Trail

The Ashuwillticook Rail Trail is over 12 miles long and features varied views. City planners created this scenic trail by paving an old railroad track. The repurposed trail is 10-foot wide, and bikers, hikers, rollerbladers, cross-country skiers, and walkers are welcome.

The trail goes through Cheshire, Lanesborough, and Adams. Hikers can stop in each charming town, enjoy a meal or refreshment, or choose a different part of the trail to complete each visit. In addition to towns, the trail features views of the scenic Hoosic River and Cheshire Reservoir.

Along the trail, hikers might see a variety of birds and wildlife. In the fall, hikers are rewarded with beautiful colors and perfect hiking temperatures.

There are several picnic areas and restroom facilities along the trail.

Monument Mountain

Monument Mountain

Monument Mountain features breathtaking views. The trail leads hikers to the mountain’s impressive 1.642-foot peak. Hikers will be awed by the fall color views in the Housatonic River Valley below.

Monument Mountain has been a sacred part of the Mohican people’s culture for millennia. Members of the Mohican tribe left stone offerings on the mountain top, which created the original monument. White settlers destroyed the monument and forced the Mohican people from the area. The monument has since been recreated on the Mohican Monument Trail.

This beautiful and sacred place has inspired artists and authors. The mountain inspired William Cullen Bryant to write the Monument Mountain poem in 1815. Herman Melville, author of Moby Dick, and famous local author Nathaniel Hawthorne were also inspired by hikes on Monument Mountain.

Monument Mountain has several miles of trails suited for various abilities and ages. Visitors can enjoy a quick walk or take a longer hike to experience the area.

Mount Greylock


Mount Greylock’s summit rises to 3,491 feet and is the highest peak in Massachusetts. If you climb the peak on a clear day, you can see across five states and up to 90 miles away.

Author Henry David Thoreau climbed Mount Greylock’s peak in 1844. Thoreau spent about 36 hours in the area, but Mount Greylock’s astounding beauty left a long-lasting impression on him and shaped his life and later writings.

Mount Greylock has dozens of trails for all ages and abilities. You can spend a few hours or all day hiking and enjoying the spectacular fall foliage and heavenly views. In addition, you can take a fall foliage driving route through Mount Greylock State Reservation.

Experience Family Friendly Hikes in The Berkshires

Many of our favorite hiking trails are pet-friendly. Dogs are welcome in the Berkshires, so plan a trip with your pet and experience the best of the Berkshires with your fur babies today.