Why the Berkshires?
The Berkshires of Western Massachusetts is known for its world-class cultural attractions, farm-to-table food scene, and excellent options for outdoor recreation including many great short day hikes!
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We’ve put together a list of 8 of our favorite short day hikes in the Berkshires. Most of these hikes are free, most allow dogs, all of them can be done in a few hours, and together they make a pretty compelling case for the Berkshires as one of New England’s most underrated outdoor hiking destinations!
The Hikes at a Glance
| Trail | Distance | Elevation Gain | Cost | Dogs |
|---|---|---|---|---|
| Bash Bish Falls | ~1.5 mi RT | ~300 ft | Free | Yes, leashed |
| Monument Mountain | 2.5 mi loop | 672 ft | $6–10 parking | Yes, leashed |
| Ashintully Gardens & Titus Mansion Ruins | 1.2 mi loop | ~230 ft | Free | No |
| The Cascades | 2.1 mi RT | 265 ft | Free | Yes, leashed |
| Tannery Falls | 0.5 mi loop (summer) / 4.6 mi (winter) | 170 ft / 708 ft | Free | Yes, leashed |
| Cheshire Cobbles | 1.5–2.9 mi RT | 872 ft | Free | Yes, leashed |
| Mount Greylock | ~6 mi RT | ~2,200 ft | Free | Yes, leashed |
| Mount Frissell | ~2.4 mi RT | ~900 ft | Free | Yes, leashed |
Bash Bish Falls — The Tallest Waterfall
~1.5 mi round trip | ~300 ft elevation gain | Free | Dogs: Yes, leashed
Bash Bish Falls is the tallest single-drop waterfall in Massachusetts, dropping about 60 feet into a crystal-clear pool at the base. And in our opinion, it’s also one of the most photogenic waterfalls in New England. The most scenic approach is from the New York side via Taconic State Park, which has a large parking lot and an easier, more gradual trail to the falls. The Massachusetts side is shorter but steeper and more rugged.
Note: Access to the base of Bash Bish Falls is no longer permitted. Several fatalities had occurred throughout the years, and the ecologically fragile area was also suffering from overcrowding, so the decision was made to restrict access to the upper viewing platform in 2020.
Monument Mountain — The Historic One
2.5-mile loop | 672 ft elevation gain | $6-10 parking (free for Trustees members) | Dogs: Yes, leashed
The 1,642-foot summit of Monument Mountain in Great Barrington offers views of Housatonic River Valley, the Taconic range, and the Catskill Mountains. The pale quartzite geology makes the upper ridge particularly interesting. Take the Hickey and Peeskawso Peak Loop and make sure to include the short spur trail to Devil’s Pulpit overlook for a view of an impressive tall outcropping of rocks.
We went for a Father’s Day hike with my dad in mid-June, and the mountain laurel lining the trails was in full bloom and was gorgeous!
Monument Mountain is sacred to the Mohican people, who left stone offerings on the summit creating the “monument” for which it’s named. The original monument was later destroyed after the Mohicans were dispossessed and forced from the area, though it was recreated near the Mohican Monument Trail.
The mountain was also the inspiration for William Cullen Bryant’s 1815 poem “Monument Mountain,” and authors Nathaniel Hawthorne and Herman Melville spent a notable afternoon here together — an encounter that sparked a friendship and influenced the writing of Moby-Dick.
Note: Stay on marked trails to prevent soil erosion. Exercise caution – rocky cliffs provide great views but also come with risk with sheer and sudden drop offs on the summit ledges.
Ashintully Gardens and Titus Mansion Ruins — The Hidden Gem
1.2 mi loop | ~230 ft elevation gain | Free | Open April–November| Dogs: No
Tucked away in the quiet town of Tyringham, Ashintully Gardens combines serene formal and informal gardens, fountains, and sweeping mountain views from the dramatic ruins of the Titus Mansion, a 35-room “Marble Palace” that burned down in 1952.
The front terrace, foundation, and four Doric columns are still standing and open to explore. It’s equal parts peaceful garden stroll and ruin exploration, and it’s completely free (though donations are welcome!).
The Cascades — The Local Favorite
2.1 mi out-and-back | 265 ft elevation gain | Free | Dogs: Yes, leashed
The Cascades Trail in North Adams is a beloved local waterfall hike. But even though I grew up just 20 minutes away, I never knew it was there until I noticed a small sign for it on our way back to Vermont a few years ago. It’s short, pretty, and ends at a lovely cascading waterfall as the name suggests.
The trail requires a few stream crossings, so bring waterproof footwear or be prepared to get your feet wet. In winter and early spring, microspikes are recommended.
Note: There’s no official parking at the trailhead — park at the YMCA and walk a short section through a quiet residential neighborhood to reach the trail. Please be respectful of the neighborhood.
The Cobbles — The Appalachian Trail Sampler
1.5 mi out-and-back from Notch Road (or 2.9 miles from town center) | 872 ft elevation gain | Free | Dogs: Yes, leashed
The Cobbles in the small quaint town of Cheshire is a great hike for anyone who wants a taste of the Appalachian Trail without committing to a months-long trek. The AT runs right through downtown Cheshire and connects to the Cheshire Cobbles trail. If you start at the Notch Road Trailhead, you’ll first pass by a peaceful waterfall. The payoff at the top of The Cobbles is a great view of the Berkshire Hills and Mount Greylock, Massachusetts’s highest peak.
Note: Two parking options — Railroad Street in town for the longer approach, or Notch Road for a shorter, steeper start.
Tannery Falls — The Forested Waterfall
0.5 mi loop | 170′ (summer) or 4.6 miles | 708′ (winter, when access road closed) | Free | Dogs: Yes, leashed
Tannery Falls in Savoy Mountain State Forest is a picturesque waterfall in the middle of a quiet woods. A short loop trail leads to a beautiful multi-tiered waterfall tucked into the forest. In summer, it’s barely half a mile from the parking area. In winter, when the access road closes, it becomes a longer 4.6-mile round trip. If taking the longer route, don’t miss the short detour to the glacial Balance Rock along the way.
Bring microspikes and be prepared for stream crossings and mud in the winter and early spring.
Note: Swimming is not permitted.
Mount Greylock — The Highest Peak
~6 mi round trip via Bellows Pipe Trail | ~2,200 ft elevation gain | Free | Dogs: Yes, leashed
At 3,491 feet, Mount Greylock is the highest point in Massachusetts earning it a spot in the New England High Points Hiking Challenge. On a clear day, the summit views stretch into five states. From late May to mid-October, the auto road opens to vehicles. If hiking isn’t your thing, the drive up alone is worth it, granting access to the Veterans War Memorial Tower and Bascom Lodge at the summit.
I grew up in the town next door, so Greylock holds a special place in my heart and I’ve hiked it more times in my life than any other mountain (and many of those times were before I even liked hiking).
(It is also the fantastical location of Ilvermorny, the American School of Witchcraft and Wizardry, for all you Harry Potter fans!)
Mount Frissell — The State Line Quirk
~2.4 mi round trip | ~900 ft elevation gain | Free | Dogs: Yes, leashed
Mount Frissell’s underwhelming forested summit is in Massachusetts… but this hike is most often done for what lies just beyond it.
This trail is the easiest access to the highest point in Connecticut which is on the side of Mount Frissell. The hike to hit both the Mount Frissell summit and the Connecticut high point is a fun 2.5-mile out-and-back trail with ridge views, mossy woods, and a bit of scrambling.
Bonus: If you also want to hike to the highest peak in Connecticut, the Bear Mountain trailhead is right across the road from the Mount Frissell trailhead. This is a separate 2.4-mile round trip with 640 feet of elevation gain. Checking off both the Connecticut high point and high peak in a single day is very doable and quite satisfying!
Tips for Hiking in Western Massachusetts
Download offline maps. All of these trails are pretty well-marked, but cell service is spotty so we recommend downloading AllTrails maps before you leave.
Consider a Trustees membership. At $80/year, the Trustees household membership covers parking and entrance to 120 total properties across Massachusetts, including Monument Mountain. The funds help to protect places of ecological, scenic, and historic importance across the state, and it pays for itself quickly if you’re planning multiple visits to Trustees properties throughout the year.
Pack microspikes for winter/early spring visits. Several of these trails — particularly the Cascades and Tannery Falls — involve stream crossings and steep sections that are icy in the winter and early spring. Microspikes make a significant difference.
Where to Stay
TOURISTS is a charming 46-room riverside property inspired by the classic American roadside motor lodge, with a focus on incorporating nature into its unique design. This is a great option for Greylock and the Cascades and could also work for the Cobbles and Tannery Falls.
The Porches Inn at Mass MoCA features lovely art-filled restored Victorian row houses across from the iconic Massachusetts Museum of Contemporary Art (AKA Mass MoCA, one of the largest centers for contemporary visual and performing arts in the U.S.). Stays include breakfast, and access to the heated pool, hot tub, and sauna. This is another great option for Greylock and the Cascades.
The Red Lion Inn is a charming and historic centerpiece of the lovely town of Stockbridge, Massachusetts. The Red Lion Inn features an outdoor pool, hot-tub, and on-site dining options. From here, you’ll have easy access for hiking Monument Mountain and Ashintully Gardens.
Buttonball Inn – located in the picturesque town of South Egremont, MA, this late 18th century, 12-room inn blends historic charm with modern comforts. The Buttonball Inn features private bathrooms, a shared kitchen, and an on-site restaurant with outdoor seating and live music. Perfectly situated between Monument Mountain and the area of Bash Bish Falls and Mount Frissell, it’s a great base if you’re planning to do all three!
Full transparency, we have lots of family in the Berkshires, so we’ve never actually had a need to stay in any of these places, but we’ve heavily researched them, they get great reviews, and we hope to stay at all of them ourselves someday!
We’ve spent countless hours exploring the Berkshires throughout the years, and they keep surprising us the more time we spend in them! Whether you’re chasing waterfalls, expansive summit views, or a bit of literary history, there’s more here than most people expect… and that’s before you even factor in the world-class cultural attractions and farm-to-table food scene that the region is famous for. We hope this convinces you to explore this corner of New England. The Berkshires are waiting!
