One of the most fun activities in New England is hiking, no matter what state you’re in! If you find yourself in the Berkshires of 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 a great spot for leaf peeping fall foliage in Massachusetts!
Rounds Rock Trail
If you’re looking for great kid friendly Berkshires hikes, Rounds Rock Trail is a good one! Located in Mount Greylock State Reservation, this beautiful .9 mile loop trail is an easy way to get out and see some gorgeous Berkshires views.
Also on this Berkshires hike is a memorial and the remains of an airplane crash from the 40s, so in addition to being a lovely scenic hike, it’s a pretty interesting one, too.
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 if you’re looking for dog friendly hiking trails in Massachusetts, add this one to the list!
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!
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 on leash.
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.
Olivia’s Overlook via Charcoal Trail
Olivia’s Overlook via Charcoal Trail is absolutely 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 Berkshires scenery.
You’ll want to make sure that you bring your camera!
One pro tip for hiking this Berkshires spot 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.
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, and it is considered a kid friendly Berkshires hiking trail.
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; it’s a great Berkshires trail for bird watching.
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 Berkshires hiking 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 with some rocky sections, so mind your step!
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.
Bash Bish Falls Trail
One of the most beautiful places in Massachusetts, Bash Bish Falls is a Berkshires treasure! Whether you approach from the Massachusetts side or the New York side, you’ll be treated to beautiful waterfall views.
It is easier to approach from the parking lot on the New York side, as the MA trailhead is a bit steep and can be challenging at points, especially after a lot of rain. Do be aware that in order to see Bash Bish Falls at its most dramatic, you need to go after a rainy period.
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, so definitely add this one to your list of best Berkshires hikes with kids!
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.
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 scenic Berkshires views of the rolling hills at the top are truly unbeatable.
It’s an out and back Berkshires hiking 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 Berkshires trail! The Race Brook Falls and Mount Everett Trail is located in Mount Everett State 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.
This Berkshires 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 this is a challenging trail, it is best to hike this one with a group. Check the weather before your hike, too!
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, off-roading, 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
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.
If you’re looking for waterfalls in the Berkshires to hike to, this is a great option!
This great Berkshires hiking trail is located in a pretty cool spot: right up the hill from the Clark Art Institute! If you decide to make it an indoors/outdoors kinda day, start off exploring man-made art at the Clark Art Institute before heading out the doors and up the hill to explore the beautiful natural art of this Berkshires trail.
The loop is only 1.9 miles and is considered a fairly easy Berkshires, so this would be a great hike for the kids. Pro tip: Hug the museum on the way up so you can come back down with full expansive valley views; those Berkshires scenic views are everything, especially if you’re hiking in the fall!
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 Berkshires hiking trail will keep you mostly within a forest, so the views are slightly different, but hiking or walking the trail is still very much worth it.
This Berkshires 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.
March Cataract Falls Trail
Located in New Ashford, March Cataract Falls Trail is a beautiful Berkshires waterfall hike that is a 2.5 mile out and back trail that is considered to be moderately challenging.
Leashed dogs are allowed but be aware that this is a very popular waterfall hike in the Berkshires, so you’re likely to run into several other hikes on your way out and back from this gorgeous waterfall!
The Berkshires are filled with so many amazing hikes, ranging in difficult from easy to hard. Even if you’re a beginning hiker, you’ll be able to enjoy the epic scenery in the Berkshires with one of the hiking trails above.
When you go on your Berkshires MA 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 from the list above do you most want to hike?
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Amy is the founder of New England with love. A proud Vermonter, she hopes to share her love of New England and help you find the best adventures in the region. Amy is also blogger/founder at Two Drifters, where she writes alongside her husband about romantic and couples travel, relationships, honeymoons, and more. When not working on websites, Amy is probably reading, cuddling with her husband, son, and cats, & drinking a maple latte.