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12 Best Hikes in the Berkshires

12 Best Hikes in the Berkshires Wholly Rewarding For All Ages

By Sometime Traveller

Forget about searching for the best hikes in the Berkshires – we’ve done all the work for you! This list has everything you need to plan the perfect hiking adventure. Berkshires is located approximately 120 miles, approximately 2.5 hours, from Boston and 140 miles, approximately 3 hours, from New York City. As soon as you arrive in the Berkshires, you can feel the magic of nature surrounding you. This place is globally known as a hiker’s paradise it has trails for every mood and every skill. You can simply enjoy a relaxing walk, a thrilling climb, or a stunning view through hiking; it totally depends on what you prefer to do. 

In this blog, we have listed 12 of the best hikes in the Berkshires, highlands located in western Massachusetts and northwestern Connecticut in the United States. 

You will get to know what to expect, what to bring, and what to see on each hike. So put on your hiking shoes, grab your water bottle, and get ready to discover the best hikes in the Berkshires. You will have an unforgettable experience!

12 of Our Favorite & Must-Do Hikes in the Berkshires

  1. Monument Mountain
  2. Mount Race and Race Brook Falls
  3. Bash Bish Falls
  4. Mount Everett
  5. Balance Rock Loop Trail
  6. Mount Greylock
  7. October Mountain
  8. Glendale Falls
  9. Tyringham Cobble
  10. Natural Bridge State Park
  11. Bartholomew’s Cobble
  12. Mount Tom

Now, we will discuss each hike in detail, including its length, elevation gain, difficulty, etc. Everyone can choose a hike according to their taste and ability, whether they are novices or professionals, solo adventurers or family-friendly people, or lovers of nature or history.

Your Guide to Amazing Hikes in the Berkshires

1. Monument Mountain

Length: 2.5 miles 
Elevation Gain: 594 feet  
Difficulty: Moderate  
Trail Type: Loop  
Parking: Monument Mountain Reservation Parking
Special Features: Quartzite cliffs, panoramic views, Devil’s Pulpit

The Monument Mountain hike is a hands-down winner on a short list of the best hikes in the Berkshires. This loop around Peeskawso Peak, better known as Monument Mountain, provides hikers with stunning panoramas of the Housatonic River Valley, Mount Greylock, and the surrounding hills. The trail is a combination of Hickey and Indian Monument Trails. 

You will encounter rocky scrambles, granite slab staircases, and white quartzite outcroppings as you travel upward. Don’t forget to take the brief detour to Devil’s Pulpit. These cliffs, which climb 400 feet above the trees, are worth seeing.

Keep your eyes peeled for peregrine falcons, the fastest birds on earth, soaring gracefully overhead. 

2. Mount Race and Race Brook Falls

Length: 5.7 miles  
Elevation Gain: 2,214 ft
Difficulty: Hard  
Trail Type: Out and back  
Parking: Mt Race
Special Features: Waterfall, open views, Appalachian Trail

If you are looking for a more intense hike in the Berkshires, Mount Race, and Race Brook Falls are the paths for you. The awesome waterfall, as well as the spectacular views from Mount Race, part of the renowned Appalachian Trail, are guaranteed to delight hikers. The hike begins with a challenging ascent up Becket Mountain before heading to Race Brook Trail, where hikers will discover the splendid Race Brook Falls, prancing down numerous levels. 

Take the Appalachian Trail to the summit of Mount Race, which provides a memorable panorama of the eastern Berkshires and beyond. It’s really one of the best hikes in the Berkshires, marrying natural beauty with a satisfying adventure.

 3. Bash Bish Falls

Length: 1.5 miles  
Elevation Gain: 534 ft
Difficulty: Easy  
Trail Type: Out and back  
Parking: Bash Bish Falls
Special Features: Waterfall, state park, New York border

Yet unconquered to many a tourist, Bash Bish Falls is the tallest and most well-known waterfall in Massachusetts. Your path to the falls is gentle and fascinating, leading you along a well-kept rut through the wood next to Bash Bish Brook. Finally, you reach a lookout that provides a beautiful view of the 80-foot waterfall tumbling into a quiet pool encircled by rocks. Located in Bash Bish Falls State Park, this stop features not only one of the best hikes in the Berkshires but many more routes, as well as towns and camping. The Berkshires combine the best of nature and outside obstructions.

4. Mount Everett

Length: 5.5 miles  
Elevation Gain: approx. 2000 feet  
Difficulty: Hard  
Trail Type: Out and back  
Parking: Mount Everett State Reservation  
Special Features: Fire tower, views, Appalachian Trail

Explore one of the best hikes in the Berkshires by tackling Mount Everett, the area’s second-highest peak after Mount Greylock. This rewarding trek along the Appalachian Trail offers stunning panoramic views. The trail winds through dense forest and rocky terrain, providing a challenging but enjoyable experience. 

Along the way, take a break at the tranquil Guilder Pond, a serene lake nestled amidst the trees. As you continue, reach the summit of Mount Everett, where a fire tower awaits. Climb to the top for a breathtaking 360-degree view of the Berkshires, the Catskills, and the Hudson Valley.

5. Balance Rock Loop Trail

Length: 0.3 – 0.8 miles  
Elevation Gain: 364 feet  
Difficulty: Easy  
Trail Type: Loop  
Parking: Balance Rock Loop Trail
Special Features: Rock formation, state forest, accessible trail

Another great hike in the Berkshires is the one to Balance Rock. This incredible formation consists of a big rock balanced on top of a smaller one, very much like a sculpture, and it is literally impossible to understand how it is not falling. The trail is super short and easy, passing by a paved road in the middle of the forest. 

The rock itself is walkable around to see it from different angles and is astonishing in front of it, as it is actually much bigger than it appears to be. The place is Pittsfield State Forest, as it has other great hikes, camping areas, and even a pond where you can swim in summer.

6. Mount Greylock

Length: 5.5 miles  
Elevation Gain: 3,491 feet 
Difficulty: Hard  
Trail Type: Out and back  
Parking: Mount Greylock 
Special Features: Highest peak in Massachusetts, war memorial, views, state reservation

One of the best hikes in the Berkshires leads to Mount Greylock, the highest peak in Massachusetts. At 3,491 feet above sea level, it promises one of the most strenuous but rewarding trekking experiences. The trail starts on a lovely Cheshire Harbor Trail while you hike through the magnificent forest. 

Additionally, you will cross several streams before you join the Appalachian Trail. The trail ends in a 93-foot granite tower, serving as a war memorial and lighthouse with unique panoramic views of the Berkshires: Green, White, Adirondacks, and White mountains. The hiking location is called Mount Greylock State Reservation, where you can access many other walking/outdoor getaways, including miles of hiking trails, camping spaces, and a warm lodge.

7. October Mountain

Length: 6.7 miles  
Elevation Gain: 170 to 2,650 feet
Difficulty: Moderate  
Trail Type: Loop  
Parking: October Mountain State Forest
Special Features: Lake, views, state forest, campground

October Mountain is also home to the best hike in the Berkshires, the Schermerhorn Gorge Trail. It’s the largest state forest in Massachusetts, covering 16,500 acres and offering all sorts of trails for all skill levels and seasons. This relatively easy hike winds around the Finerty Pond with scenic views of the hills, making for an enjoyable stroll. 

But a single, steep hill at the end of the hike can provide a bit of a challenge. The trail is frequented by babbling streams, wetlands, and strange rock formations. Additionally, the October Mountain State Forest offers camping, fishing, boating, and snowmobiling facilities.

8. Glendale Falls

Length: 0.3 miles  
Elevation Gain: 98 feet  
Difficulty: Easy  
Trail Type: Out and back  
Parking: Glendale Falls
Special Features: Waterfall, picnic area, Trustees of Reservations property

Glendale Falls, one of Massachusetts’ most magnificent and scenic waterfalls, is just a short, fast, and simple yet great hike in the Berkshires. You will find the dirt path along the brink of Glendale Brook, where the water spills and plunges over 155 feet and numerous precipices and pools. 

The waterfall is most stunning in spring when the water is at its height and fall when the foliage around the shower is vibrant. At the falls’ base, look at the rocks and pools or have a tranquil picnic at close stone tables and benches. Massachusetts keeps its nature natural at Glendale Falls, managed by the Trustees of Reservations.

9. Tyringham Cobble

Length: 2.1 miles
Elevation Gain: 429 feet
Difficulty: Moderate
Trail Type: Loop
Parking: Tyringham Cobble Park
Special Features: Views, meadows, Trustees of Reservations property

One of the best hikes in the Berkshires, the moderate and beautiful Cobble Trail, encircles the Peak of Cobble Hill. From the edge of the pathway is a spectacular panorama of the Tyringham Valley and the surrounding hills. This easy trail through meadows and woodlands is soft and primarily smooth by regular sections of steep and rocky terrain. The top of the summit offers a superb view of the valley’s fields, farms, hills, and remote mountains. 

10. Natural Bridge State Park

Length: 1 – 4 miles
Elevation Gain: 98 to 1768 feet
Difficulty: Easy
Trail Type: Loop
Parking: Natural Bridge State Park 
Special Features: Natural bridge, marble quarry, state park

A historical treat to the people is the Natural Bridge State Park, North America’s only natural white marble arch. The Marble Quarry Trail is deemed one of the finest hikes in the Berkshires, providing breathtaking views of the natural bridge, marble quarry, and Hudson Brook. The effortlessly accessible pathway is level and paved, with stairs and other bridges throughout. Discover the park’s history and geology while walking through it, which was once a vibrant marble mine.

For more of the park’s offerings, visit the visitor center, relax with a picnic, or go fishing. Marble Quarry Trail at Natural Bridge State Park offers an unforgettable blend of natural beauty plus history and is not to be missed at any cost.

11. Bartholomew’s Cobble

Length: 3.5 miles
Elevation Gain: 472 feet
Difficulty: Moderate
Trail Type: Loop
Parking: Bartholomew’s Cobble Reservation
Special Features: Views, rock formations, Trustees of Reservations property

Undoubtedly, this hike at Bartholomew’s Cobble falls among the top hikes in the Berkshires. With its benign elevation gain, combined with nice views of the Housatonic River and beautiful Taconic mountains, the hike became a popular place among fans of the great outdoors. Hiking along the Ledges Trail, visitors walk across this magnificent landscape and pass by peculiar rock formations and dense forest. 

Although the trail’s character is mainly mild and easy, visitors may expect some exciting and challenging steep, rocky parts of the path. A highlight of the trek is encountering the cobble, a remarkable cluster of quartzite and marble outcrops teeming with diverse flora and fauna. 

12. Mount Tom

Length: 4.2 miles
Elevation Gain: approx. 4000 feet
Difficulty: Moderate
Trail Type: Out and back
Parking: Mt Tom 
Special Features: Fire tower, views, state reservation

A refreshing addition to the list of the best hikes in the Berkshires, Mount Tom offers a more moderate but equally challenging opportunity with unbeatable views of the Connecticut River Valley and its neighboring mountains. Drawing on the Metacomet-Monadnock Trail, Mount Tom invites hikers to climb to the summit of the Holyoke Range. 

The majority of the pathway involves passing through thick woods on the rock-geared ridges and turning the stone steps or boulder expanses. There are even small switchbacks on the ledges. Set within the boundaries of the Mount Tom State Reservation, visitors can also expand their hiking journey down numerous other trails to camping sites and a peaceful lake.

Now that you know what are the best hikes in the Berkshires let’s cover some important information you need to know:

When is the best time to go hiking in the Berkshires?

In conclusion, the best time to go hiking in the Berkshires depends on your preference and what kind of hiking you enjoy. In the spring, you’ll see the greenest trees, in the summer, you get to attend the festivals, in the fall, you’ll see the most amazing foliage, and in the winter, you’ll get snow. Wherever you go, you’ll be in awe of the natural beauty. 

However, according to the locals, the fall is the best time to go hiking in the Berkshires. During fall, nature is truly colorful and refreshing. You can also enjoy apple picking as fall is less busy and more affordable than other seasons, so you can do a peaceful and relaxing hike.

Essential Things to Know Before You Go Hiking in the Berkshires

Before embarking on your hiking adventure in the Berkshires, it’s crucial to be well-prepared. Here are some essential tips to ensure a safe and enjoyable experience.

  • Check the weather forecast and dress accordingly.
  • Bring enough water and snacks to stay hydrated and energized throughout your hike.
  • Wear sturdy hiking shoes with good traction to navigate varying terrain.
  • Study the trail map and plot your route before heading out.
  • Pack essential gear such as a first-aid kit, sunscreen, insect repellent, and a flashlight.
  • Notify someone of your hiking itinerary and anticipated return time.
  • Respect nature and leave no trace by properly disposing of trash.
  • Be mindful of wildlife and follow guidelines for encounters.
  • Stick to marked trails to prevent getting lost or harming fragile ecosystems.
  • Pace yourself and take breaks as needed to avoid exhaustion.

Map of Hiking Trails in Berkshires

We have created a Google map to help you find the best hikes in the Berkshires more easily. With it, you can easily find the trails that are close to you and see their ratings and photos. 

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Some Interesting Facts about Hiking in Berkshires

  • The Berkshires, located in western Massachusetts and Connecticut, are renowned for their scenic landscapes, charming towns, and rich history and culture.
  • Offering a variety of hiking trails suitable for all levels and seasons, from easy walks to challenging climbs, visitors can explore waterfalls, mountain views, and more.
  • Berkshire County alone boasts 90 miles of the Appalachian Trail and 800 miles of mapped trails.
  • Notable waterfalls in the Berkshires include Bash Bish Falls, Race Brook Falls, Glendale Falls, and Wahconah Falls.
  • The region is also home to impressive rock formations, such as Balance Rock, Natural Bridge, and Bartholomew’s Cobble.
  • Mount Greylock, at 3,491 feet, is the highest peak in both the Berkshires and Massachusetts and offers panoramic views.
  • Well-maintained and accessible hiking trails in the Berkshires often feature parking areas, picnic spots, and visitor centers.
  • The Berkshires offer diverse scenery and experiences year-round, from spring wildflowers to fall foliage, summer swimming, and winter snowshoeing.


How many hiking trails are there in the Berkshires region?

The Berkshires boast over 100 hiking trails, offering a diverse range of experiences from strolls to challenging mountain ascents, making it a haven for outdoor enthusiasts of all skill levels.

What is the most picturesque trail in Massachusetts?

The Mount Greylock Hiking Trail offers breathtaking vistas and serene woodland paths, making it a top choice for nature enthusiasts seeking scenic beauty in the Bay State.

Which fall hikes in the Berkshires offer the best foliage experience?

The Bash Bish Falls Trail and Monument Mountain Trail are renowned for their stunning autumn colors, making them top picks for the best fall hikes in the Berkshires region.

What are some of the most challenging hikes in the Berkshires region?

The Race Brook Falls Trail is among the most challenging hikes in the Berkshires, featuring steep ascents, rugged terrain, and rewarding summit views for experienced hikers seeking a strenuous adventure.

Are the Berkshires hiking trails dog-friendly?

Yes, many trails welcome dogs, but it’s wise to check leash policies and trail regulations before bringing your furry friend along for the hike.

Do any hiking trails in the Berkshires have fees?

Some trails in state parks or private reserves may require nominal entrance fees to support maintenance and conservation efforts.

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