11 Best Hikes in the Berkshires

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One of the most fun activities in New England is hiking, no matter what state you’re in! If you find yourself in western Massachusetts, you’re in luck; the best hikes in the Berkshires are incredible and often overlooked by people visiting the area.

The Berkshires refer to a mountainous area in Western Massachusetts. This area is known for its incredible views and charming small towns. This is also the best spot to see fall foliage in all of Massachusetts!

Aerial view of the Berkshire Mountains in Autumn

Stevens Glen

A wooden bridge surrounded by woods

For one of the easier best hikes in the Berkshires, head to Stevens Glen. Located in West Stockbridge, this 1-mile loop trail is great for all ages.

Even if you’ve never been hiking before, you’ll be able to do and enjoy this one. Dogs are also allowed on the trail so that you can bring your furry friend along for the beautiful walk.

There’s a slight elevation gain of just 229 feet. The hike won’t take more than an hour at most unless you often stop along the trail to take in the beautiful scenery.

Be sure to be on the lookout for the waterfall that the path is named after!

Hoosac Range

The Hoosac Range Trail is a bit longer of a hike, but the views are breathtaking at the top. It’s excellent for moderate-level hikers, and similar to Stevens Glen, dogs are also allowed to go on the trail.

This trail is just over 6 miles long and is an out and back trail, meaning that you’ll come back down the same way that you go up. There are about 1,000 feet of elevation gain, so the hike is decently uphill.

The Hoosac Range Trail is located in North Adams. You’ll want to make sure that you wear comfortable and stable hiking shoes on this hike because it’s known for being rocky and sharp at times.

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Olivia’s Overlook via Charcoal Trail

Hikers walking a trail with walking sticks

Olivia’s Overlook via Charcoal Trail is arguably one of the best hikes in the Berkshires! It’s another moderate-level hike, but it’s relatively short. The entire loop trail is only 2 miles long, and it’s located in Richmond. 

The elevation gain is only 500 feet, and dogs are allowed on the trail. Once you get to the top of the summit, you’ll look out and be rewarded with a view of rolling mountains and all-around incredible scenery.

You’ll want to make sure that you bring your camera!

One pro tip for hiking here is to check the weather before you go. It’s best to do this hike when the weather is drier, meaning don’t do this hike right after it snows or rains. You might slip!

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Alford Springs Father Loop

The Alford Springs Father Loop is slightly over 4 miles long and is a moderate-level trail. Unlike some of the other trails on this list, this is a great trail that you can do no matter the time of year for the most part.

The trail is a loop trail, so you’ll see different views the entire time you’re hiking. Elevation gain is just under 800 feet, so it is pretty uphill over the 4 miles you spend hiking.

In addition to hiking, this trail is also often used for snowshoeing, horseback riding, running, and cross-country skiing.

Along the trail, take the time to look out for extraordinary wildlife in the area. This is also an excellent all-around trail for bird watching.

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Finerty Pond via Appalachian Trail

A sign post on a path in the Appalachian Trail

The Appalachian Trail is one of the most well-known hiking trails in the country, but it would take a while for you to hike the whole thing. Instead, experience a chunk of the Appalachian Trail by hiking to Finerty Pond.

This trail is 6 miles and has an elevation gain of 1,400 feet, so it is very much uphill. It’s moderate level and is an out and back trail, but the views are so great that you won’t even mind seeing the same scenery twice.

At the end of the hike, you’ll be brought to the beautiful Finerty Pond. Keep in mind that this is the main view of the entire hike, and the majority of the hike is through the woods.

Housatonic Flats

Hike the Housatonic Flats Trail in Great Barrington, Massachusetts, for an easy and charming hike! This hike is barely 1 mile long and is more of a walking trail than a hiking trail. The elevation gain is only 6 feet!

This loop trail is perfect for all ages since it’s easy beginner level. That means that kids can easily go along this trail with you, and they’ll enjoy the fantastic scenery and views just as much as you. 

Along the trail, keep an eye out for the wildflowers and birds in the area. In addition to hiking, this trail is often used for cross-country skiing.

Pine Cobble Trail

Two hikers with backpacks walking through the woods

This moderate-level trail in the Clarksburg State Forest in Williamstown is one of the best hikes in the Berkshires! It’s barely 3 miles long but has an elevation gain of 1,200 feet.

Despite being very much uphill for the majority of the trail, the views of the rolling hills at the top are truly unbeatable.

It’s an out and back trail and is often used for snowshoeing during the winter months. Many past hikers say that this is one of the better-marked trails they’ve done, so it’s nearly impossible to get lost. This is great for you first-time hikers!

Like some other hikes on this list, make sure that you wear sturdy hiking shoes because parts of the trail are very rocky. 

Race Brook Falls and Mount Everett

For you expert-level hikers reading this, hike this trail! The Race Brook Falls and Mount Everett Trail is located in Mount Everett Statae Reservation in Sheffield, Massachusetts.

Despite being only 6 miles long, the elevation gain is over 2,000 feet, making this a hard-level hike. It’s an out-and-back trail most famous for being home to a breathtaking waterfall that you’ll see along the route.

The trail, despite being difficult, is known for its great upkeep and clear markers. For experienced hikers, this trail probably won’t take more than five hours.

Because of its difficulty, it is best to hike this one with a group. Cheek the weather before your hike, too!

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October Mountain Loop

This 7-mile hike in October Mountain State Forest near Lee, Massachusetts, is one of the best hikes in the Berkshires. It’s moderate level, so if you’ve been hiking before, you should be able to do this hike to enjoy the epic scenery easily.

The trail is a loop trail with just over 1,5000 feet in elevation gain. Throughout the year, the October Mountain Loop is used for hiking, snowshoeing, offroading, and mountain biking. So, you may come across lots of other people enjoying the trail!

Despite being moderate level, this trail is kid-friendly, and dogs are allowed on the trail. Unlike some other trails on this list, October Mountain Loop doesn’t have a summit but will bring you pretty high up the mountain.

The Cascades Trail

A large waterfall descending into a rocky body of water

The Cascades Trail in North Adams is another easy trail in the Berkshires! It’s barely 2 miles long and has only 275 feet of elevation gain, so it’s more of a walk than a hike, honestly. However, just because it’s easy does not mean that the views pale compared to some other trails on this list. 

A waterfall is the main feature of this trail, which is where it got its name. The hike is dog and kid-friendly. Throughout the trail, you can go bird watching and explore a lot of great nature. A

lot of the trail is within a forest, so even on a hot summer’s day, you may be able to cool off pretty quickly.

Basin Pond

A body of water next to fall trees reflecting in the water

Basin Pond in October Mountain State Forest is a moderate-level trail that is both kid and dog-friendly. It’s just over 2 miles long with 200 feet of elevation gain and is an out and back trail. 

This trail, in particular, is different than the other best hikes in the Berkshires because it’s prominently within a forest! So, the views are slightly different, but hiking or walking the trail is still very much worth it.

This trail is well marked and has excellent scenery along the way. It’s also easily accessible, so you won’t have to look too hard to find the trailhead.

The Berkshires are filled with so many amazing hikes, and they range in difficulty. Even if you’re a beginning hiker, you’ll be able to enjoy the epic scenery in the Berkshires that you genuinely won’t want to miss.

When you go on your hike, be sure to pack a backpack with everything you’ll need during it. This includes water, snacks, and other essentials. It’s always best to be prepared, and you’ll use a lot of energy on a hike, even if you don’t realize it!

Which of the best hikes in the Berkshires do you most want to hike?

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