12 Best Hikes in the Berkshires: Hills, Waterfalls, Views, and More!

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Imagine escaping in the brisk mountain air of the Berkshires; fiery colored leaves or fresh snow on top of it all. Whether you are an experienced walker or just want an enjoyable weekend break these tracks will suit your needs.

Prepare yourself for breathtaking views, lush landscapes, and a chance to take your mind off things.”So put on your comfortable shoes and be prepared for the Best Hikes in the Berkshires at a time.

So in this blog post, we will some of the best hikes in the Berkshires, and apart from that we will also tell you about its features, length, and Address.

12 Best Hikes in the Berkshires 

We have found you the Best hikes in the Berkshires which you must hike once in your life. 

#1 Mount Greylock Hike 

Best Hikes in the Berkshires

Climbing the highest peak in Massachusetts, Mount Greylock is a rewarding challenge for an ambitious hiker. The Bellows Pipe Trail stretches for about 5. 9 miles and gradually progresses through various zones including the forest and the mountainous rock terrains.

It allows you to have eye witness on mountains and valleys or any other big structure on a clear day at the top. Do not leave without visiting the Stone War Memorial with its historical background, check also the visitor center. The trip can be considered one of the most challenging and, simultaneously, the most outstanding in the Best Hikes in the Berkshires.

  • Special features: Tallest Mountain, Offers panoramic views and historic sites like the War Memorial Tower.
  • Difficulty: Moderate to Difficult
  • Length: 12.5 miles (round trip)
  • Elevation Gain: 2,490 feet
  • Address: Adams, MA 01220, United States
  • Where: Find it on Google Maps

#2 Pine Cobble

Best Hikes in the Berkshires

Pine Cobble Trail is a 1.6-mile difficult hike located in Williamstown, Massachusetts. One can hike through oak forests before reaching the quartzite cobbles summit, providing a bird’s eye view of mountains and valleys. This is one of the famous trails with an easy ascent to explore.

This walk takes about 3.5 miles back and forth such that it lies within the Monument Mountain reservation; very easy! There was history behind this simple stroll. This trail also deserves to be on the Best Hikes in the Berkshires.

  • Special Features- Amazing views of the Hoosac Valley and the Taconic Mountains. 
  • Difficulty: Moderate to Difficult
  • Length: 3.5 miles (round trip)
  • Elevation Gain: 1,200 feet
  • Address: 163 N Hoosac Rd, Williamstown, MA 01267, United States
  • Where: Find it on Google Maps

#3 Flag Rock Mountain

Best Hikes in the Berkshires

Notably one of the best hikes in the Berkshires is the Flag Rock hike where you will find superb views and great rock formations. If you cannot go to other more popular places but at the same time you would like to take some walks enjoying the views of the Berkshires, this route is ideal for such an activity.

Another important feature of hiking through Squaw Peak is that you wake up to wonderful vision when in that facility, especially on a clear day one sees the Housatonic River Valley, Taconic Mountains, as well as Catskills. Perhaps this is the right place to have a cup of coffee and get surrounded by the atmosphere of Berkshires’ calmness. Great Barrington lists a variety of activities to engage in including the nal fun, shopping, and eating places. Ensure you plan to venture downtown after your hike for complete excitement.

  • Special Features: See the tallest waterfall in Massachusetts (80ft!) on a scenic hike through the woods. 
  • Difficulty: Moderate
  • Length: 3.4 miles (round trip)
  • Elevation Gain: 870 feet  
  • Address: Sam Snead Hwy, Hot Springs, VA 24484, United States
  • Where: Find it on Google Maps

#4 Bash Bills Falls 

Best Hikes in the Berkshires

Bash Bish Falls, situated in Mount Washington, Massachusetts, remains one of the Best Hikes in the Berkshires region especially because it features a one hundred-and-seventy feet waterfall drop which is the highest in the state of Massachusetts with the drop exceeding 80 feet into a calm pool at the base of the waterfall. It is just a 2-mile round-trip by foot lasting for approximately an hour through the short, beautiful wooded gorge.

Watch out for rocky parts around the falls on the way up; they can be treacherous so beware! Nature enthusiasts and photographers flock to these beautiful falls; however, no swimming is allowed here to preserve cleanliness and safety within the vicinity. 

  • Special Features: Massachusetts’ highest single-drop waterfall and offers panoramic views.
  • Difficulty: Easy to Moderate
  • Length: 2 miles (round trip)
  • Elevation Gain: 300 feet
  • Address: Bash Bish Falls State Park, Falls Road, Mount Washington, MA 01258
  • Where: Find it on Google Maps

#5 Laura’s Tower Trail

Best Hikes in the Berkshires

Laura’s Tower is one of the best hikes in the Berkshires especially for those who cannot walk much. They are a short walk ideal for organizing a power walk before catching a delicious meal in the charming Stockbridge village. As such, the location of this trailhead is easy to find and won’t leave you in a quandary. Finally, you will rise to the mountaintop for some time, then take a steep and short climb with barriers to the top of the tower. 

If the sky is clear, one can see up to mountains of many distances on the horizon; after taking the view of the scenery, one will need to hike in the same way but in a backward direction to reach the same point. For those who may wish to take a break and enjoy the fresh Stockbridge air before going on other tours around the village, this is an excellent opportunity to do so.

  • Special Features: Amazing Views of Mountains, the best spot for a picnic and you can also see lots of birds.
  • Difficulty: Easy to Moderate
  • Length: 1.5 miles (round trip)
  • Elevation Gain: 300 feet
  • Address- Stockbridge, MA 01230, United States
  • Where: Find it on Google Maps

#6 The Cobbles

Best Hikes in the Berkshires

The Cobbles are located in Williamstown, Massachusetts, and offer a tough but short trail hike. This 1.6-mile round-trip hike is worth doing because it is really that beautiful. Despite demand, the trail passes through areas of oak trees before arriving at a picturesque quartzite-cobbled summit. 

Think of a vast expanse of mountains and valleys to be reached and conquered! This sharp incline is ideal for those who wish to achieve elevation in a relatively short period as well as those who are experienced climbers.

  • Special Features: Great view from the top, lots of trees and animals to see, and easy parking and starting point. 
  • Difficulty: Moderate
  • Length: 2.5 miles (round trip)
  • Elevation Gain: 600 feet
  • Address: Main Street, Cheshire, MA 01225 United States
  • Where: Find it on Google Maps

#7 Spruce Hill Trail

Best Hikes in the Berkshires

Fed up with the routine Berkshires vacation, seeking for history blend? Take a stroll through one of the first established trails in the park, the Spruce Hill Trail. There is a fairly tough 1.5-mile loop trail in Richmond, Massachusetts with moderate elevation in mixed pine and oak woods.

Stunning views of the valley and spectacular nature that is great for a picnic or just a few quiet moments. This trail is ideal for those who like nature and history, especially if you want to take a short but truly refreshing break.

  • Special Features: Best Picnic Spot, Stunning Views of the Valley, and easy trails for walking and hiking. 
  • Difficulty: Moderate
  • Length: Approximately 3 miles (round trip)
  • Elevation Gain: Approximately 700 feet
  • Address- 179-5 Raycroft Rd, North Adams, MA 01247, United States
  • Where: Find it on Google Maps

#8 Mount Everett

Best Hikes in the Berkshires

Mount Everett which is situated in Mount Washington, Massachusetts is certainly one of the best hikes in the Berkshires. It is one of those mountains where one can trek and enjoy the cool top view. Climbing this trail takes about two hours longer than shorter trails like the Hanksville Valley Overlook.

This hike will take roughly 2.5-3 hours and involves approximately 2.5 miles with an elevation gain of around 900 ft vertically. You’re going to be inside trees that are ten years old, which I found interesting. Many people hike the Mount Everett trail because it’s not too challenging but is still rewarding with elaborate views of the Berks.

  • Special Features: Features a hike through old-growth forest to a summit with expansive views of the surrounding area. 
  • Length: 2.5 miles (round trip)
  • Difficulty: Moderate
  • Elevation Gain: 900 Feet 
  • Address: Mt Washington, MA 01258, United States
  • Where: Find it on Google Maps

#9 Alander Mountain, Mount Washington

Best Hikes in the Berkshires

Nature lovers must visit Alander Mountain in Mount Washington, Massachusetts as it is one of the best hikes in the Berkshires. The trail gives you great thrills and offers a great view from the top.

Basically, if you’re doing both sides of the trails, it is 6 miles long. It’s not really difficult but very exhausting. On top of that, you can have a look at an excuse for an amazing view in Best Hikes in the Berkshires that is simply beyond words. Anyone who wants to experience hiking in the Berkshires should consider visiting Alander Mountain.

  • Special Features: Spectacular views from the summit, traverses through beautiful forest, and great scenery at the top of the trail.
  • Length: 5.8 Miles 
  • Difficulty: Moderate 
  • Elevation Gain: 1200 feet 
  • Address: Mt Washington, MA 01258, United States
  • Where: Find it on Google Maps

#10 Mount Race and Race Brook Falls 

Best Hikes in the Berkshires

When it comes to the best hikes in the Berkshires, Mount Race and Race Brook Falls are worth visiting. Mount Race offers an exciting hike owing to its being paved with rocks and a thrilling view once on top. This trail covers six miles round trip so just tighten your waistband and get ready for some pulse-racing moments ahead.

You go through forests and waterfalls that make the scenery spectacular throughout the journey. And then there is Race Brook Falls which is a slightly easier trail of about two miles round trip. This trail takes you through a quiet forest with beautiful views, especially the waterfall which is a bonus for Best Hikes in the Berkshires.

  • Special Features: Offers breathtaking views from the summit, rocky terrain, and diverse flora and fauna.
  • Length: Approximately 6 miles round trip.
  • Difficulty: Moderate to challenging 
  • Address: 716-732 S Undermountain Rd, Sheffield, MA 01257, United States.
  • Elevation Gain: Around 1,500 feet.
  • Where: Find it on Google Maps

#11 Money Brook Trail

Best Hikes in the Berkshires

Among the best hikes in Massachusetts’ Berkshires is Money Brook Trail. It is about six miles long and provides a hike that can vary from moderate to rugged, with gains of around 1,500 feet in elevation. 

Along this trail, there are lovely woods you will walk through, some rivers that you might pass by, and some wonderful waterfalls to look at. Some wildlife may be seen. The top of the trail presents an amazing display of mountains and valleys below it all. Anyone who loves nature or hiking would be fun exploring Best Hikes in the Berkshires.

  • Special Features: Scenic trail along a brook with waterfalls and old-growth forest.
  • Length: Around 6 miles round trip.
  • Difficulty: Moderate to challenging.
  • Elevation Trail: 1500 Feet 
  • Address: Notch Rd, Williamstown, MA 01267, United States
  • Where: Find it on Google Maps

#12 Pleasant Valley Wildlife Sanctuary

Best Hikes in the Berkshires

Pleasant Valley Wildlife Sanctuary is one of the best hikes in the Berkshires, Massachusetts. This vast ground consists of forests, meadows, and swamps where numerous animals live.

It offers about 7 miles of very comfortable trails. One may encounter birds, deer, and other animals on the way. You can come across signs that provide information about nature and history. People are particularly fond of bird watching here as there are more than 200 different types! This is a good place to have some rest and enjoy wildlife.

  • Special Features: Well-maintained trails, diverse habitats, and educational opportunities.
  • Length: Around 7 miles round trip.
  • Difficulty: Easy to Moderate
  • Elevation Trail: 1500 Feet 
  • Address: 472 W Mountain Rd, Lenox, MA 01240
  • Where: Find it on Google Maps

Things to keep in mind when hiking the Trails in the Berkshire-

Following is the list of those things that you should take care of while hiking the trails in the Berkshire

  • Check current trail conditions before going out. Trails may be soft, wet, frozen, or icy depending on the weather and weather pattern of the particular season.
  • It said it is always a good idea to check the local weather forecast because it is possible for the temperature to fluctuate when in the Berkshires. 
  • Bring layers of clothing so in case of a change in the weather bring an extra jacket or coat and a raincoat or windbreaker in case you get rained on or the wind picks up.
  • Bring sturdy walking shoes or hiking boots with good grip to navigate through loose, irregular, or slippery surfaces.
  • It is recommended to take enough water for drinking to help with the issue of hydration, especially during long trails or very hot weather. Make sure that you carry along snacks so that you can be able to have what to eat whenever you feel hungry when hiking.
  • Let someone know that you will be hiking, the specific trail, and your expected time of return. 
  • It is good practice to have a simple first aid kit, a map, or GPS and be sensitive and cautious, especially in moments that may come across wild animals.

What is the best time to hike in the Berkshires?

If you are asking me what time of year is the best for hiking in the Berkshires, well that depends on what you like. It could be fantastic in spring (May-June) as it has nice weather and is less crowded – not yet decided. Just be ready for some early muddiness though. 

The summer (June-August) is ideal for hot hikes but also the busiest time. Although some trails may close due to hunting, fall (September-October) will make you think of magic with its multicolored leaves and mild temperatures – no decision made on this one too. 

Winter (November-March), however, turns the mountains into a snowy paradise where you can have solitude even if maybe some snowshoeing too. For a perfect combination of weather, scenery and lesser traffic, you might want to consider late spring or early fall. 


The Berkshires are home to such scenery and are one of the best destinations for hikers of all abilities. Going from the easy crisscross strolls to the tough climbs with beautiful views, these trails have it all. 

Every given step on a trail can lead to the discovery of a new trail, a breathtaking cascade of water, a field of wildflowers, or stories of the history of an old structure. Therefore, to answer the above question: What are you waiting for? So why not go and start your own Berkshire trail and make your adventure out of it? 

Some FAQs

What are the must-visit Trails in the Berkshires?

Some of the most famous trails include the Pine Cobble, Mount Greylock trails, Flag Rock Mountain, and Bash Bish Falls State Park.

Are there any easy hikes for families near the Berkshires Mountains?

There are a few options here like the Ashuwiltikook Rail Trail, Kennedy Park, and the Laura Tower Trail.

What should you bring on a hike in the Berkshires?

As such it is essential that one has some items like water, snacks, a map or GPS device, proper footwear, layered clothing items, sunscreen lotion; insect repellent cream; a first aid kit, etc.

What are the most challenging hikes in the Berkshires?

For experienced hikers seeking a challenge, the Bellows Pipe Trail on Mount Greylock, the Taconic Crest Trail, and the Race Brook Falls Trail are known for their steep ascents and rugged terrain.

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