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Awesome Day Hiking in the Berkshires of Massachusetts

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The Berkshires in western Massachusetts and northern Connecticut are known for their small New England towns, world-class art and cultural offerings, and heart-pumping outdoor activities. Hiking in the Berkshires is a great way to spend a day outdoors, and there are hundreds of miles of trails for every skill set.

Waterfalls are plentiful in these hills, as are small ponds, lush meadows, and bald mountain summits. Here are some of the best trails for day hiking in the Berkshires — perfect for novice hikers, families, and casual adventurers.

A blue silhouette of Massachusetts with a star marking the Berkshires.

Hiking in the Berkshires: Northern Region

The following hikes are located in the Northern Berkshires, just south of the Vermont border, and include the towns of Williamstown and North Adams.

Pine Cobble Trail, Williamstown, MA

A woman sits next to a black dog at the top of Pine Cobble Mountain in Williamstown, Massachusetts.
The Pine Cobble Trail in Williamstown is very dog-friendly.

The Pine Cobble Trail in Williamstown takes you to the Pine Cobble summit at 1,894 feet, before hooking up with the Appalachian Trail that heads south to Georgia or north to Maine. From the summit, you’ll have a 360-degree view of the surrounding mountains, as well as the towns of Williamstown and North Adams.

The trail is a steady climb, with one small section that is relatively flat. It ascends through a lovely oak forest, which is particularly beautiful in the fall foliage season. Wildflowers and mountain laurels are abundant in the spring. The summit is characterized by “cobbles,” or rounded outcroppings that are perfect for picnicking and relaxing.

Difficulty level: Moderately strenuous. A workout for casual hikers, but easy for preteen boys…
Length of trail: 3.2 miles (round trip)
Dogs: Yes
Fee: Free
Notes: The trailhead is located in a residential neighborhood in Williamstown, and can be reached from downtown. Here is a link to the Google map and here is a link to the Pine Cobble Trail Map on Alltrails.

The Clark Art Museum Trails, Williamstown, MA

A family hikes through the meadow at the Clark Art Institute in Willamstown, MA
Kids love exploring the meadows behind the Clark. Photo credit: Massachusetts Office of Tourism

If you happen to be visiting The Clark Art Institute to check out world-class, classical art exhibitions, be sure to take time to head up the hill and explore the trails. Actually, even if you don’t care a bit about art, you should come walk these trails, which are lovely in all seasons.

Meander through meadows and manicured woods, and take in the incredible views of the Berkshire Mountains. There are several trails here, crisscrossing 140 acres, which can be combined to create the perfect walk. All of the trails are easy on the legs and well-manicured.

Difficulty level: Easy
Length of trail: Depends
Dogs: On leash
Fee: Free to walk the trails. There is a fee to visit the museum
Notes: Visit The Clark Art Institute website for information about visiting. Here’s a link to the Google map.


Read Next: The Best Family-Friendly Museums in the Berkshires


The Cascades Trail, North Adams, MA

Cascade Waterfall, the end of The Cascades Trail in North Adams, Massachusetts, USA.

The Cascades Trail begins at the end of a small, residential street and follows the Notch Brook to a lovely cascading waterfall. It is just minutes from downtown North Adams, and the whole trail can be completed in under an hour. The walk is an easy one, with just one tricky spot where you have to scramble along the riverbank for about 30 feet. The Cascades Trail ends just before you come to the falls. For the best view of the cascades, you must hike into the gorge, possibly scrambling a bit on the rocks to get closer.

The Notch Brook Cascade is a highly seasonal waterfall, but when the river is full, you will be rewarded with lovely horsetail falls that drop about 45 feet into a nice shallow pool. In the summer months, it’s deep enough to cool off in, but probably not swim. Unless, of course, you’re a dog.

Difficulty level: Easy, except for one small section where you have to scramble along the bank. Perfect for small children, as they will enjoy playing in the stream if the weather is nice.
Length of trail: 1.2 miles (round trip)
Dogs: Yes
Fee: Free
Notes: The parking area for the Cascades Trail is in a residential area and there is only room for 1-2 cars. For detailed directions, here’s a link to the Google map and to the Cascades Trail Map on Alltrails.

Sunset Rock, North Adams, MA

The hike to sunset rock totals 1.6 miles and features some stunning views of North Adams and the surrounding valleys. As the name suggests, this is a great spot to watch the sunset — just be sure to bring a flashlight or headlamp for the hike back down.

The sunset rock hike is part of the longer Hoosac Range trail, which leads to Spruce Peak and totals 6 miles. The Hoosac Range trail ascends up a series of switchbacks to sunset rock. It is not particularly steep, but it is all uphill. This is suitable for families with elementary-age kids and is gorgeous during the fall foliage season.

Difficulty level: Moderate. It’s all uphill but isn’t very steep.
Length of trail: 1.6 miles (round trip)
Dogs: Yes
Fee: Free
Notes: The trail map can be found here. The trailhead is located on route 2, about four miles east of North Adams. Here is a link to the Google map.

March Cataract Falls, Williamstown, MA

March Cataract Falls in Williamstown, MA
March Cataract Falls by cerebros1 via Flickr

You can reach Mt. Greylock’s loveliest waterfall by hiking 1.5 miles on an easy trail through a mixed hardwood forest. I won’t go into too much detail here because I’ve covered March Cataract Falls in a separate post. The falls are fullest in the spring, and dry to almost a trickle in the fall, but the colorful leaves more than make up for it.

Difficulty level: Easy
Length of trail: 3 miles (round trip)
Dogs: Yes
Fee: Free
Notes: The trailhead is located next to Sperry Road Campground on Sperry Road, which is closed from November to June. Here is a link to the Google map and the March Cataract Falls Trail Map on Alltrails.

Hiking in the Berkshires: Southern Region

These hikes are located south of Pittsfield, Massachusetts, and one south of the border in Connecticut.

Stevens Glen, West Stockbridge, MA

This 1.25-mile loop takes you through a deep, dark hemlock forest, across two footbridges, and eventually, through a birch forest to Stevens Glen, where you’ll find a very narrow gorge with a 40-foot, ribbon-thin cascade that is gorgeous in the spring. The spur trail takes you to a nice viewing platform with a bench for relaxing. Retrace your steps on the spur trail until you return to the loop. If you visit in the summer, be sure to spend some time barefoot in the streams.

Difficulty level: Moderate. The loop is flat and easy. The spur trail to the glen is uphill.
Length of trail: 1.2 miles (round trip)
Dogs: Yes
Fee: Free
Notes: The trail map can be found here. The trailhead is located on Lenox Branch Road. Click here for the Google Map.

Bash Bish Falls, Mt. Washington, MA

A long exposure shot of Bash Bish Falls
Bash Bish Falls is the highest single-drop waterfall in Massachusetts

I couldn’t create a hiking in the Berkshires post without including Bash Bish Falls. This is the highest single-drop waterfall in Massachusetts, and it’s a looker! Visitors can either park at the base of the falls in New York or the top of the falls in Massachusetts. The falls are located in Bash Bish Falls State Park in Massachusetts, but very close to the border. The hike down to the base of the falls from the Massachusetts parking area is a very steep ⅓ of a mile. If you park in the lower lot, the hike is easy and just ⅔ of a mile with an elevation gain of 150 feet.

Although swimming is technically not allowed, we witnessed plenty of bathers under the falls in the summer, so you’ll have to use your judgment on whether that rule is meant to be broken. Alcoholic beverages are not allowed in any Massachusetts state parks. There are more extensive hiking opportunities in Washington State Forest, just south of the falls or in Taconic State Park across the border in New York.

Difficulty level: Easy
Length of trail: 1.5 miles (round trip)
Dogs: On leash
Fee: Free
Notes: Detailed information and a trail map can be found on the Bash Bish Falls State Park webpage. Here is the Google Map location for Massachusetts parking area.

Monument Mountain Reserve, Great Barrington, MA

The far-reaching view from Devil's Pulpit on Monument Mountain in Great Barrington, MA.
The view from Devil’s Pulpit on Monument Mountain in Great Barrington.

This is a new hike for us, but we love it! Monument Mountain is a 503-acre preserve managed by The Trustees. There are several trails on the preserve, but all of them are easy to moderate and under three miles. I think the best views can be found along the Peeskawso Peak Trail, and there are several small waterfalls along the Hickey Trail. If you choose the 1.5-mile Mohican Monument Trail, you’ll pass the remains of ancient Native American trails, stone walls of former sheep pastures, and old woods roads.

Honestly, no matter what path you choose, you will experience lovely woodland trails. Fair warning, though – these trails are popular with both locals and visitors, so I recommend hiking in the early morning. There is a $6 fee for parking at the trailhead.

Difficulty level: Easy to moderate
Length of trail: all under 3 miles
Dogs: On leash
Fee: $6 for parking
Notes: Detailed information, directions, and a trail map can be found on The Trustees website.

Insider Tip: We included the hike up Monument Mountain on our detailed 3-day itinerary for Stockbridge, MA. If you are planning a longer visit, be sure to check it out.

A long distance view of the mountains from Bartholomew's Cobble in the Berkshires
The long-distance view from Bartholomew’s Cobble. Photo credit: phoca2004 via Flickr

This is what hiking in the Berkshires is all about — gorgeous, long-distance views, dancing streams, hardwood forests, and lush meadows. Bartholomew’s Cobble was named a National Natural Landmark in 1971 and encompasses 329 acres through many different ecosystems, as well as five miles of well-marked hiking trails.

The Ledges Trail is our favorite, a .5-mile loop that takes visitors around the “cobbles” and past several caves. If you want a bit more exercise, consider hiking to the top of Hulbert’s Hill, which provides stunning views of the surrounding mountains and valleys.

Difficulty level: Easy to Moderate
Length of trail: 5 miles of trails can be combined based on your time and stamina.
Dogs: No
Fee: $5 for parking
Notes: Bartholomew’s Cobble is maintained by The Trustees of Reservation — visit their website for a detailed trail map. Here’s a link to the Google map.

If you’ve never explored the Berkshires of Western Massachusetts, we urge you to visit for at least a couple of days. The Berkshires are within a day’s drive of New York City, Boston, Montreal, and Philadelphia, and there is so much to do. We often head to the Berkshires for the food, the concerts, and the incredible art, but hiking in the Berkshires is our number one reason for visiting.

No matter why you come to explore the Berkshires, be sure to take some time for outdoor adventures. For more awesome day hiking ideas in the Berkshires, I highly recommend AMC’s Best Day Hikes in the Berkshires.

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A collage of photos featuring the best day hiking in the Berkshires of Masachussets.

Our Favorite Resources for Road Trips and Outdoor Adventures

These are the resources we use for planning road trips, saving money while traveling, and shopping for outdoor gear. 

Car Rentals: While we use our own car most often for road trips, we also enjoy flying into major airports and then renting a car for more regional road trips. We use Kayak to compare prices and find deals from dozens of car rental agencies at once. 

Flights: We use Kayak or Skyscanner to search out flight deals. Money-saving tip: If you find yourself using the same airline over and over again (we are huge Southwest fans), consider joining their loyalty program and getting an airline credit card. With our Southwest Rewards Visa, we earn a few free flights each year. 

Hotels: When it comes to lodging, we seek out small boutique hotels or quirky roadside motels. First, we search for hotels on TripAdvisor so we can read reviews from other travelers. Then, we use Booking.com to make reservations (they have the best prices, plus a flexible cancelation policy).

Camping: Camping is one of our favorite things to do on long road trips. It allows us to explore the outdoors, cook our own food, and save money. We use They Dyrt Pro to find campsites and read reviews before booking on Recreation.gov or state park websites. 

Glamping and Vacation Rentals: For weekend getaways and shorter vacations, we love glamping (check out our glamping resource guide). We book glamping properties through Tentrr, Hipcamp, and Airbnb. For cabins and vacation rentals, we like to use VRBO (they have fewer fees and a better cancelation policy than Airbnb).

Guides and Maps: If we are visiting a new region, we usually invest in a Moon Travel Guide for the area. We pass them on to friends and family after our trip.  If we are planning on hiking, we also purchase a Falcon guide in the Best Easy Day Hikes series.

Outdoor Gear: We are REI Co-Op members. It cost us $20 for a lifetime membership, but we get a yearly dividend based on our purchases, plus great deals and coupons throughout the year. REI also has a great return policy.

Check out our complete guide for planning a road trip on a budget

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