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13 Best Hikes in the Berkshires; Views, Waterfalls, & More!

Written by Kristen, Writer/Photographer


Looking for the most scenic hikes in the Berkshires?! Check out this round-up of the best Berkshire hikes all with great views and/or waterfalls!

This hike is #3 on our list 😍

Located in western Massachusetts the Berkshires is a county that runs from the southern point of Egremont to the very top of the state in North Adams.

I’ve lived in New England all my life and was lucky enough to live in the Berkshires for 4 years. I loved my time living there from the small communities to the hiking and beautiful scenery.

While I live back in Connecticut now, I often make the 1-2 hour drive up to the Berkshires to hike and visit a favorite cafe along the way!

When I’ve had a rough work week or just feel the need to get away, the Berkshires is the first place I think to escape to. My fiance, Jared, likes to say – “does someone need a Berkshire weekend?” and usually I do! 👀

The Berkshires is a beautiful area with tons of hikes and trails to choose from so let’s get to our best of the Berkshires hiking list! ⬇️⬇️

Each hike includes several favorite places you can head to after for a latte, pastry, or lunch!

For each hike you’ll find:

  • a parking description & GPS coordinates 🚙
  • a link to the hike on AllTrails 🔗
  • mileage and difficulty 🥾
  • special features of each trail 🌅
  • and where to eat after! 🥐☕️

I plan to keep adding to this list so bookmark this page and return when you’re ready for a beautiful hike in the Berkshires!


  • Miles: 5.7 miles 🥾
  • Elevation Gain: 1,676 ft elevation gain 📈
  • Level: Hard
  • Parking: Pull off along Rt 41/S Undermountain Rd, on a busy day cars will be parked parallel to traffic all along the street here (GPS Coordinates 42.0895, -73.41122)
  • Special Features: Wide open view facing east 🌅 and Race Brook Falls 💦
  • Where to go after: I love stopping at the Marketplace Cafe ☕️ in Sheffield on way back to CT. Or stop by the amazing and historic Race Brook Lodge to check out the inn or eat at their 18th century tavern.

A big big view and waterfall, too, on this hike! It most certainly deserves a spot on this best hikes in the Berkshires list. Though tough, I’ve done this hike countless times from a winter sunrise or sweltering summer climb (see below) and each time it’s worth it!


While this hike is rated ‘Hard’ on AllTrails it’s mainly a non-technical uphill walk except for a short scramble section at the end where you may use your hands to help you up.

At just 0.9 miles in you’re rewarded with the (usually raging) Race Brook Falls. Though not the tallest waterfall in MA (that’s further on this list!) this is a tall fall I always stop to admire. It’s a great spot to take a break and reinvigorate yourself for the rest of the climb.

From Race Brook Falls you’ll continue with a steady incline, passing Race Brook Campsites and at 1.9 miles you’ll meet up with the Appalachian Trail (white blazes). Turn left onto the AT and continue with the final mile of the hike.

At the top, enjoy the sweeping, wide-open views looking east over Mount Everett State Reservation. It’s a great place for lunch and to spend some time. It will be hard to leave this summit but when you do, turn around and enjoy the no longer uphill steps, back down the way you came.


  • Miles: 5.9 miles 🥾
  • Elevation Gain: 2,244 ft elevation gain📈
  • Level: Hard
  • Parking: Parking lot off of Gould Rd (GPS Coordinates: 42.62714, -73.14522)
  • Special Features: Tallest ⛰ in MA, 360-degree views at the top, Bascom Lodge, and tower/monument
  • Where to go after: Click here for coffee shops, diners, and restaurants to stop at in Adams.

At 3,491 feet, Mount Greylock is not only the tallest mountain in Massachusetts but also the tallest in all of southern New England! A must-do hike in the Berkshires and top spot on our Berkshire hikes list.

It is the hike that’s the furthest north on this best of the Berkshires hiking list. So, unfortunately, I don’t make it up there as often since it is about 2 hours from me.

I’ve climbed Mount Greylock twice; in winter on New Year’s Eve day and in the fall in October. Neither disappointed!

Though similar mileage and elevation to the Bellows Pipe route linked above, I have also done the Gould Trail in the winter and loved that one, too.


“The 12,500-acre Mount Greylock Reservation is the oldest Massachusetts wilderness park. The park spans five towns with the Mount Greylock summit in Adams. The reservation includes the state’s only subalpine taiga-boreal forest. Old-growth forests including remarkable stands of red spruce up to 120′ can be seen.

From late May through November 1, you can drive to the summit on two recently restored roads (weather permitting). The views are spectacular from the summit and several other spots along the roads.” ~exploreadams.com

In addition to the noteworthy views atop Greylock, there are two other reasons to hike up. From the top of the Veterans War Memorial Tower (built 1932) you’ll enjoy a five-state view from the highest point in Massachusetts.

And then Bascom Lodge, built from stone and red spruce from Mount Greylock, is open seasonally for dining, lodging, and events. Bring cash up to buy treats at the lodge! :))


  • Miles: 5.8 miles 🥾
  • Elevation Gain: 1,200 ft elevation gain📈
  • Level: Moderate
  • Parking: Parking lot just off of West Street (GPS Coordinates: 42.0863, -73.46205)
  • Special Features: Wide open views 360 degrees mainly facing west toward New York
  • Where to go after: There isn’t anywhere too close here so I would head into Millerton NY to check out Harney & Sons Tea & Cafe or another cafe there or head into South Egremont to Mom’s County Cafe! (check hours)

The epic views on this hike in the southern Berkshires earn this hike a permanent spot on this best hikes in the Berkshires list! For me in CT, it is conveniently located in the southeastern corner of Massachusetts almost on the border of New York.

I’ve hiked Alander countless times and in every season. It’s a beauty when you catch the mountain laurel in bloom in early summer when the hills in the distance are blanketed in green. But it’s got breathtaking and wide wide-open views to the Catskills and is worth it in any season.


The summit of Alander Mountain is just east of the Massachusetts/New York border.

The trail is rolling for the first two miles before the more continuous climbing begins to the top.

For the first 1.9 miles it’s a mostly flat trail will just rolling elevation. You’ll cross a pretty stream at the beginning before the views start to open up the closer you get to the top.

After the 1.9 mile walk you’ll start the climb up with about 650 feet of elevation for the next 0.9 miles.

There will be a couple trails shooting off to the left so just stay straight all the way up to Alander Mountain.

In the late spring there are super pretty mountain laurel bushes along the top.