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50 Family-Friendly Berkshire County Hiking Trails

Dive into our Berkshire backyard with hikes for all ages and skill levels

By Taylor Staubach - Berkshire Family Hikes October 1, 2022

Berkshire County hiking and trail guide for parents and kids looking for family-friendly adventures and day trips in Western Massachusetts. For hike reviews, outdoor activities, and more, visit our partner site www.berkshirefamilyhikes.com.


As a mom of two very busy and active children, we began hiking in the Berkshires every chance we could get. Maybe you've followed some of our adventures over on Berkshire Family Hikes or inspired you to get outdoors with your own family. We've put together a list of 50 Kid-Friendly Hiking Trails in the Berkshires and you can find the first 25 of our favorites below. Need more Berkshires hikes idea? Check out PART 2 HERE will include 25 more, as well as recommendations from local readers and hiking enthusiasts.


NOTE: As the state releases new guidelines, please practice social distancing guidelines and know that we try to keep these lists as updated as possible, but some of the trails may not have opened yet. If you see a change, please email me at taylors@macaronikid.com.

1. Appalachian Trail, Various access from VT to CT
There are countless short hikes and dozens of easy access points along the trail across the county. A few kid favorites are the Hinsdale branch with its obstacle-course-like stretch of rustic boardwalks and bridges (accessible from Pittsfield Rd in Hinsdale), the two-mile hike to Ice Gulch, where snow remains well into July or August and kids can explore the rustic trail-side shelter or write a note on the logbook (take 23 East from Great Barrington to Lake Buel Rd; parking available about 1 mile down; follow trail markers to the Gulch), and the Upper Goose Pond stretch of the trail, where six-bunk Upper Goose Pond cabin, complete with an outhouse, porch, and tent platforms is located (accessible from Washington Mountain Rd in Washington or County Rd in Becket). The cabin is set up for thru-hikers only, but it’s still cool to check out. There is even a canoe available for short-term borrowing.

2. Ashintully Gardens, Tyringham
Follow the well-maintained half-mile trail to the ruins of the “Marble Palace”, the Georgian-style mansion destroyed by fire in 1952, whose Doric columns still stand surrounded by the majestic Ashintully Gardens — the thirty-year labor of love of music composer John McLennan.

3. Ashmere Lake Dam, Hinsdale/Peru
Nestled in the hidden backroads of Hinsdale and Peru, the Ashmere Lake Dam is an engineering marvel. The trail to the right of the public boat ramp is perfectly flat and takes you directly over the dam (watch out for goose poop), giving adventurers unbeatable views of the south side of Ashmere Lake and an up-close opportunity to explore a modern working dam or to fish for bass from an idyllic perch fifteen feet above the dam’s rocky shoreline. (Take Rt 143 in Hinsdale to right on Creamery Rd. Merge left onto Middlefield Rd/Skyline Trail, and then take next left on Hickingbotham/Smith Rd. Look to your left of the dark brown gate of DCR entrance to Ashmere Lake State Park.)

4. Ashuwillticook Rail Trail, Lanesboro, Cheshire, Adams
This 11.2-mile biking/walking trail runs parallel to Route 8, through Lanesboro, Cheshire, and Adams. With multiple parking areas and bathrooms along the way, this ten-foot-wide paved trail the perfect go-to activity even during the dreaded Berkshire “mud season”. It’s the perfect spot for parents pushing strollers, toddlers pushing doll strollers, and bikers, scooter-riders, or roller-bladers young and old. Two favorite family-friendly stretches include the stretch alongside Cheshire Reservoir (just a short trek to the Whitney Farms kid-friendly play area) and the parking area at Russell Street Field in Adams, which has ample parking, tennis courts, a fabulous new play structure, bike racks, and is a short walk to coffee/food/bathrooms/snacks in downtown Adams. (Follow Rail Trail signs on Route 8, taking a left on Prospect St, to left on Harmony St.)

5. Balance Rock State Park, Lanesborough
A 165-ton limestone boulder, balanced impossibly on a tiny stone, covered with decades of graffiti? What more can we say? The photo ops are endless. Follow Route 7, past Pontoosuc Lake. Left on Bull Hill Rd. Left on Narragansett Ave. Right on Balance Rock Rd. Follow the signs to the parking area.

6. Bartholomew’s Cobble, Sheffield/Ashley Falls
Designated a National Natural Landmark in 1971, the cobble is a rare geological formation of twin rocky knolls, rising 1,000 above the surrounding meadows. Abundant with wildlife, it is home to hawks, bald eagles, turtles, and over 800 species of unique plants. Opened daily, year-round.

7. Bash Bish Falls, South Egremont
It’s just a short hike from the parking area (just before the “Welcome to New York State” sign) on Bash Bish Falls Road in Mount Washington State Park, to the county’s most spectacular waterfall, the 80-foot drop if Bash Bish Brook, segmented by a giant boulder, into a crystal clear basin (said to be as deep as the waterfall is high). Follow the massive mountain-side staircase to the bottom of the falls for the best photo ops or a picnic beside the falls. Nearby trails are well-marked and vary in grade and intensity.

8. Basin Pond, Lee
An easy hike on well-maintained trails, past dramatic boulders with natural stepping stone stairs and bridges over streams and brooks. Gorgeous view of the twice-dammed Basin Pond, which eventually broke loose, flooding the surrounding area. A wooden lookout over the dam ruins is the perfect place to stop for pictures or a trail-side snack. Route 20 to Becket Road. Parking well-marked with blue DCR signage. Trail maps available on site.

9. Beartown Mountain, Monterey
The perfect day trip for families with kids of all ages! Bring your bathing suits and pack your lunch and sand toys. There is a $5 charge to park (during summer season), but the well-groomed trails, spotless picnic tables, clean bathrooms, swimming area, and soft sand beach on the 35-acre Benedict Pond are all yours for the day (or night if you’re up for camping). The 1.5 Benedict Pond Loop Trail is a must. Set your GPS for 65 Blue Hill Road.

10. Becket Quarry Walk, Becket
A spectacular self-guided outdoor quarry museum and nature preserve, marked by dozens of stone pillars highlighting the history of this long-abandoned quarry, including industrial-sized turn of Century drills, winches, derricks, and mining vehicles. Not to mention a massive marble staircase rising to a cathedral-like arrangement of birch trees with unbelievable views of the water-filled quarry below. Trails open in daylight hours year-round. Take Route 20 to 456 Quarry Road, Becket.

11. Berkshire Fish Hatchery, New Marlborough
This National Treasure nestled in South County offers an amazing local opportunity for kids to learn about watersheds, ecosystems and the conservation of our county and nation’s fishery resources. Start your visit by stopping by the information kiosk and picking up a trail map. Three trails skirt the property and lead visitors past a variety of trailside spectacles including, aquifers, “fish tents”, plank bridges, quartzite rock slides, and a giant glacial crater made of sand and gravel. Hatchery located at 240 Hatchery Rd. Open for tours most days from 9 a.m. – 4 p.m.

12. The Boulders Preserve, Dalton
This great nature area with a variety of trails has an enormous pay-off! Climb huge glacial erratics and have a picnic at the top. Who needs a park when nature provides such great slides? Trails can be accessed from Gulf Road or Dalton Ave.

13. Buckley Dunton Lake, Becket
This reservoir on the southeast corner of October Mountain was created when a portion of forest area was flooded. (Rumor has it that the bass can be found hiding among the drowned tree stumps.) Park on the far side of the dam, near the picnic table, for easy access to the trail that skirts the lake or to launch your kayaks from the paved boat launch. Accessible from Becket Rd/Yokum Pond Rd. You will see Buckley Dunton entrance and sign just before a large brown maintenance garage.

14. Canoe Meadows, Pittsfield
Hike the trails, take in a free program or tour the gardens at Canoe Meadows Wildlife Sanctuary located along the banks of the Housatonic River on Holmes Road in Pittsfield.

15. Cascades Trail, North Adams
An easy hiking trail that rewards visitors with a stunning view of the 40-foot waterfall. Whether you have an hour or an entire day, this trail provides the perfect backdrop for an outdoor family adventure. Park at Braxton School off of Route 2 and walk to the trailhead at the end of Marion Avenue.

16. Clark Art Trails, Williamstown
The home of one of the most extraordinary art collections in the world is set in an extraordinarily beautiful 140-acre rural setting. The parking area behind the Lunder Center is perfect for families looking to explore the Woodland and Meadow Trails. There are accessible bathrooms just inside the Lunder Center and a cafe with outdoor seating and incredible views of the entire campus. There is no charge for hiking and exploring the grounds. The campus is located at 225 South Street.

17. Cheshire Cobble Trail, Cheshire
Park on Furnace Hill Rd for a 1.2 mile (mostly uphill) round-trip hike to the Cobbles (boulders made of white Cheshire quartzite). From the parking area, follow the footpath to the trail, marked with Appalachian Trail markers and yellow paint. Gorgeous view from the top, but keep young kids well back from the edge!

18. Dorothy Frances Rice Forestry Preserve, Peru
The main trail is an old farm road closed to vehicles, but very stroller friendly. Avoid the lure of the pastel-painted arrows marking the other trails until you make it to the red cape-style ranger station/welcome center at the end of Rice Rd (about a 1/4-mile) where you’ll also find a grouping of low benches, the site trail map, a rustic wishing well and a grove of apple trees. Every trail on the property measures one mile or less, so you can just pick a color and go, knowing it’ll circle back to where you started (Pond Trail is a must). Take Rt 143, through Hinsdale, straight up (literally) to the center of Peru, where you can’t miss the red and white weather tower. Head toward the tower by turning onto South Rd. Follow the road until it forks sharply to the right. Straight ahead you will see the parking area and entrance gate to the preserve.

19. Dry Hill, New Marlborough
Explore 1.5 miles of trails off of Old North Road (Harmon Rd), through the forest, thickets, vernal pools, and wetlands. Trails are open year-round. Low bush wild blueberries free for the taking during blueberry season.

20. Field Farm, Williamstown
Park to the right as you enter the property at 554 Sloan Rd, where trail maps are available. The pond trail is a quick loop, complete with wooden bridges and perfect for small kids. The 1 mile North Trail will guide you past spectacular outdoor sculptures and unbeatable mountain views. And, the Caves Loop will capture young explorers' imaginations as they watch the small stream disappear into a series of underground caves.

21. Fountain Pond State Park, Great Barrington
While parking directly beside the pond on Route 7 is available, we recommend continuing on toward Great Barrington center and parking toward the back of the lot behind Berkshire South (15 Crissey Rd) where you will see a loop-shaped gravel path, leading to an information kiosk and trail map. From there, follow the well-maintained rambling trail north to Fountain Pond. Don’t be discouraged by the first stretch, which is the steepest. The trail levels off quickly and bridges and boardwalks will keep your feet dry in the wet areas.

22. Greylock Glen, Adams
Hike the 1.5 Greylock Glen Meadow loop and take in the stunning view of Mount Greylock and the surrounding mountains. Climb the massive black willow, explore the remnants of an abandoned ski area, and enjoy lunch in the gazebo overlooking the pond. Gould Road

23. Hilltop Orchards/Furnace Brook Winery, Richmond
Hikers, cross-country skiers, and snowshoers are welcome to explore the full 200-acre property on the professionally designed Johnny Mash I & II Trails (3.2 miles). Open daily from 9 – 5, at 508 Canaan Rd/Rt 295.

24. Hopkins Memorial Forest, Williamstown
A 2,600-acre preserve, with over 15 miles of walking, skiing, and snowshoeing trails, open to the public. Horseback riding allowed on Ford Glen Brook and Carriage Road trails. All wheeled and motorized vehicles, including bicycles, prohibited.

25. Jug End State Reservation, Egremont/Mount Washington
Parking is available on Jug End Rd in Egremont. The 2-mile Jug End Trail Loop (blue triangle trail markers) will probably take you an hour or two. To start, cross over the bridge to the right of the parking area, and head west.


(FIND FAMILY-FRIENDLY HIKES # 26-50 HERE)

Reader Comments & Suggestions:

  • "Wow, great list! You’ve hiked a lot with your kids! Also note, Pownal, VT for Mountain Meadows." — Silvia C.
  • "Don’t forget Windsor Jambs in Windsor, Mass. off Route 9 in Windsor. — Barbara