Hiking in the Berkshires

Looking for the best hikes in the Berkshires? Great, we’ve got you covered.

So, you love hiking and you’re headed to the Berkshires. Good choice! Located in western Massachusetts, this popular vacation destination is well known for its wide range of outdoor activities. This area is sprinkled with quaint villages and towns, fresh food, amazing scenery, and more. It’s the perfect destination for hikers of any experience level.

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Hiking in the Berkshires is an amazing experience, no matter which trails you choose to check out. As a bonus, this is the perfect place for waterfall enthusiasts, as there are plenty to explore. But what are the best hikes near the Berkshires? We’re here to help you out.

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Housatonic Flats

Let’s start with an easier Berkshires hike. The Housatonic Flats trail in Great Barrington is only a 1-mile long round-trip. It will only take you about 30 minutes to complete. This makes it perfect for beginner hikers as well as for families with little ones.

This hiking trail will provide some great views of the Housatonic River and take you through lush forest. You’ll probably spot some wildlife along the way, as well, including deer, otters, beavers, and birds. It’s a great spot for birdwatching, so be sure to bring your binoculars.

Stevens Glen

This is one of the Berkshires waterfall hikes you won’t want to miss. A little less well-known than some of the other Berkshire waterfalls, Stevens Glen tends to be a little less crowded. This 1.5-mile semi-loop is an easy to moderate hike and will take you a little over an hour.

After you hike through the woods and across the wooden bridge, you’ll come to a short uphill trek. Once you reach the magnificent waterfall, you can take the stairs down to the observation platform to get some photos. This platform provides the best view of the falls that you can get, so be sure not to skip it!

Basin Pond

Basin Pond is one of the more difficult places to go hiking in the Berkshires. Tread carefully if you’re hiking with children or people with limited mobility. Walking the trail is fairly easy, but there are some places where you’ll have to cross streams via stepping stones. As a result, this is a 3 on the difficulty scale.

Round-trip this hike is 2.5 miles and should take about 2 hours to finish. Along this trail, you’ll pass by scenic wetlands, a boulder field, and five streams if you take the long way. You can also take advantage of the wildlife viewing deck, perfect for birdwatching. This trail is also known for its many great picnic locations, so be sure to pack lunch for everyone!

Bash Bish Falls

One of the most famous of the Berkshires waterfall hikes, Bash Bish Falls is an easy 0.4-mile loop. Bash Bish Falls is an 80-foot waterfall and is typically described as the state’s most dramatic. However, because of its popularity, it’s also one of the most crowded hiking trails, so be prepared for company. You’ll take a path along the edge of Bash Bish Brook and pass through dense forest and climb stone stairs. Then, you’ll reach the highlight: the falls.

The Cascade Trail

Another one of the most famous Berkshire waterfalls, this trail is located in North Adams. The Cascade Trail is an easy hike that’s 1.2 miles roundtrip. It should take you less than an hour depending on how long you stop at the falls.

You’ll follow the Notch Brook all the way to the falls which plummet 45 feet down into a shallow pool. If you visit during the summer, this is the perfect watering hole to cool down. This trail is just a few minutes from the downtown area of North Adams, but there is limited parking. You may have to walk a bit before starting your hike.

Race Brook Falls

This is another one of the best hikes near the Berkshires, even if it’s a bit more difficult. This is a 4.3-mile hike that provides you with amazing views of the 5 sets of waterfalls sprinkled throughout.

This hike is best suited for experienced hikers though, as there’s a 1700-foot elevation gain on the trail. But, it’s totally worth it for the views! Once you’re done, you can continue your hike to the summit of Mt. Everett or Mt. Race if you want.

Bob’s Way

Bob’s Way is one of the most famous hikes in the Berkshires. This fantastic Berkshires hike has multiple loops, so choose the areas you want to explore and hike as long as you want. Your route can be anywhere from 1.75 miles to 2.5 miles long depending on what you decide.

This moderate hike will take you an hour or two to complete depending on what routes you take. It may take you even longer if you decide to stop and enjoy the views for a while! You’ll pass through forested hills, old foundations and walls, beaver ponds, and wetlands. The highlight of the hike is Dave’s Bench, a stone seat that overlooks the beautiful scenery. This area used to be a heron rookery and is still full of diverse wildlife. So, take a seat and enjoy the view.

Alford Springs

This is one of the best hikes near the Berkshires because of all the diversity it has to offer. It’s perfect for all levels, as you can choose between the Mother Loop, the Father Loop, and the Saddle Trail. The Mother Loop is a little less than 2.5 miles roundtrip and should take an hour and a half. This is a pretty traditional moderate hike.

You’ll walk through beautiful forests, explore an apple tree field, and pick your way over old foundations. The Father Loop will take you about 3 hours and is 4.3 miles roundtrip. This is a difficult hike, so come prepared. However, the challenging hike is worth it as you’ll have incredible views to the north, south, and east. You’ll walk through the woods and be rewarded with an amazing view of Mt. Greylock.

The Saddle Trail is the easiest of the options, and this is the perfect hike if you’re bringing the kids. It’s a one-way 1-mile hike and it’s rated as moderate, so it should take about 30 minutes. You’ll cross a meadow before heading up the Taconic Range, where you’ll have a beautiful view of Tom Ball Mountain.

This trail also connects right to the Father Loop if you’re feeling ambitious and looking to lengthen your hike.

Where to Stay in the Berkshires

The best hikes near the Berkshires can be pretty spread out, so finding a place to stay can be challenging. We’ve got a few suggestions for you for when you go hiking in the Berkshires:

What to Bring with You When Hiking in the Berkshires

The most important part on a hike, your feet. Look after them with a solid pair of hiking boots! Ankle support is a must, and a waterproof boot doesn’t go amiss either.
Water, water, water! Invest in a decent reusable bottle, the market is saturated with them during this plastic-free age, and ensure you take enough to keep you well hydrated.
If the sun is out, keep that face youthful from the rays with sunscreen and a hat that covers it. Future you will thank you.
Clothing. You want to be comfortable, the right temperature and perhaps need something with a little more give if you plan to be scrambling over rocks.
Always check the weather before you head out. Layering up with breathable material is always a safe bet.
Trekking poles are recommended for some paths, it’s up to you if you think you’d be more comfortable with them. Many are foldable so don’t take up much space in your bag.
A portable first aid kit is a good idea. You want to look after yourself and a little portable pack with the essentials ensures you are covered for any situation.
Something to carry this all in, a neat lightweight pack. Take a look at our hiking backpack round up to help you choose the right one!