In the Berkshires, you’ll find incredible trails for all skill levels, leading to roaring waterfalls, rocky mountain peaks, and breathtaking overlooks that make every step worth it.
Whether you’re up for a challenging climb to a 3,000-foot summit or an easy walk to a picture-perfect lookout, there’s a trail here with your name on it.
Ready to find your next favorite hiking spot?
Here are the 7 best hiking trails in the Berkshires that deserve a spot on your adventure list!
1. Mount Greylock State Reservation
Mount Greylock State Reservation spans 12,455 acres and is home to the state’s highest peak, Mount Greylock, which rises 3,491 feet and offers stunning mountain views.
For an unforgettable hike, tackle the 6.5-mile Cheshire Harbor Trail, which climbs 1,925 feet, starting on a flat gravel path before ascending steeply toward the summit.
At the top, you can visit the 93-foot Veterans War Memorial Tower, built between 1931 and 1932, and stop by Bascom Lodge for a meal when it’s open for the season.
If you’re looking to explore more, follow part of the Appalachian Trail, which runs 11.5 miles through the reservation, and keep an eye out for wildlife along the way.
2. Hoosac Range Reserve
For a peaceful hike with awesome views, explore Hoosac Range Reserve in North Adams, which spans 989 acres of wooded trails and rugged cliffs.
The highlight is the 1.5-mile Sunset Rock Loop via Hoosac Range Trail, which follows a wooded path with gentle uphill sections and occasional rocky stretches.
Once you reach the overlook, you’ll see North Adams spread out below, surrounded by rolling mountains that look especially beautiful as the sun sets over the valley.
If you want to soak in the scenery a little longer, bring a picnic or visit in October when the towering trees glow with yellow, red, and orange fall colors.
3. Olivia’s Overlook at Yokun Ridge Reserve
Another fantastic hiking spot with a much easier start is Olivia’s Overlook at Yokun Ridge Reserve, where you can enjoy jaw-dropping views of Stockbridge Bowl.
The 3.5-mile Burbank Trail Loop is a great choice to explore the area, taking you through peaceful woodlands, past Monks Pond, and along a forested ridge.
You can also follow the 1.8-mile Charcoal Trail Loop, which features steep climbs, historic charcoal mounds, and rocky overlooks above the surrounding countryside.
It’s the kind of place where you can lose track of time as you relax, admire the stunning landscape, and capture beautiful photos along the way.
4. Monument Mountain
Next is Monument Mountain in Great Barrington, where a 1,739-foot summit, quartzite ridges, and a fascinating literary history make for an unforgettable hiking trip.
Here, you can take the 2.4-mile Hickey and Peeskawso Peak Loop, which climbs through quiet forests and rocky slopes, offering glimpses of the mountains along the way.
At the top, you’ll be rewarded with sweeping views of the Housatonic Valley, the Berkshires, and distant peaks of the Taconic and Catskill ranges.
Fun fact: Famous writers Herman Melville, Oliver Wendell Holmes Sr., and Nathaniel Hawthorne hiked this mountain together in 1850, giving book lovers another reason to visit.
5. October Mountain State Forest
In the town of Washington, you’ll find October Mountain State Forest, which spans more than 16,400 acres, making it Massachusetts’ largest state forest.
It’s packed with winding trails, rushing streams, hidden waterfalls, and towering hardwood trees that turn brilliant shades of orange and yellow in autumn.
For a fun hike, explore the 0.8-mile Gorge Trail, which follows a steep path along the edge of a rocky gorge filled with lush vegetation and colorful mushrooms.
At the end, you’ll reach Felton Lake, where grassy picnic areas and calm waters offer a relaxing break and a chance to spot wildlife along the shore.
6. Bash Bish Falls State Park
If you loved the streams at October Mountain, Bash Bish Falls State Park in Mount Washington offers an even bigger thrill with Massachusetts’ tallest single-drop waterfall, plunging 60 feet.
The cascade splits around a massive boulder, sending two powerful rushes of water into an emerald pool below, surrounded by rock formations and lush green trees.
You can reach it from two starting points: a challenging 0.6-mile round-trip hike from Massachusetts or a moderate 1.5-mile round-trip trail from New York.
Whichever route you choose, bring your camera to capture the gorgeous waterfall, but remember that swimming and climbing on the rocks are prohibited for safety reasons.
7. Mount Everett State Reservation
Lastly, Mount Everett State Reservation, stretching across Mount Washington and Sheffield, takes you to one of the Berkshires’ most spectacular mountain summits.
The star here is Mount Everett, which rises 2,624 feet above sea level and offers unforgettable views stretching across Massachusetts, Connecticut, and New York.
If you’re up for a challenge, hike the 7.5-mile Mount Race and Mount Everett Trail, which takes you past Race Brook Falls and up steep slopes along the Appalachian Trail.
Afterward, slow things down with a peaceful walk through the reservation’s old-growth forest, which covers 530 acres and features hemlocks, white pines, and hardwood trees.
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