We recently shared 25 of our favorite Berkshire hiking trails (FOUND HERE), but the Berkshires is so chock full of outdoor spaces, so we had to add 25 more!
For hike reviews, outdoor activities, and more, visit our partner site www.berkshirefamilyhikes.com.
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 kellym@macaronikid.com.
26. Kennedy Park, Lenox
A great place for families looking to bike, hike, cross-country ski, and more, with over 14 miles of groomed, town-maintained trails. Dogs welcome on leashes. Parking available at the Arcadian Shop, on Rt 7, the Church on the Hill on Main St, West Dugway Rd, and behind the Department of Public Works at 275 Main Street.
27. Keystone Arch Bridges, Becket/Chester/Middlefield
Take the Jacob’s Ladder Scenic Byway/Rt 20 (the Country’s first auto road over a mountain range, completed in 1910) to the Keystone Arches, built for the railroad in 1833 and 1841, and the oldest bridges of their kind in the U.S. Parking for the 2.5-mile Keystone Arch Bridge (KAB) Trail is available at the crossroads of Herbert Cross and Middlefield Roads in the town of Chester.
28. Lake Mansfield, Great Barrington
A 29-acre lake surrounded by the 29-acre Lake Mansfield Forest. The swimming area is roped in and relatively shallow and the sand is soft and clean. The hiking trails are flat and well maintained with a few cool climbing opportunities on gigantic trailside boulders. Cross country skiers, snowshoers, and skaters are welcome during the winter season. Parking is available (no sticker required) at the beach area on Lake Mansfield Rd.
29. Laura’s Lookout/Ice Glen, Stockbridge
Turn left onto Route 7 off of Main Street and take the 2nd left on Park St. Parking available at the end of the road. Cross the bridge and take a left to follow the riverside trail (an easy walk perfect for smaller kids). Another fun option with kids is to follow the left handrail alongside the river before crossing the bridge. It will take you past an old stone furnace and either to the rear parking lot of the Stockbridge Town Hall or the backside of the Stockbridge Town Playground. The trail, over the bridge, into the woods will fork to the left to “Laura’s Lookout," a metal fire tower that can be climbed for a panoramic view of Stockbridge and the Monument Valley (1.5 miles round trip). The other fork will lead hikers to Ice Glen, a glacial ravine that holds ice until mid-summer (1-mile round trip). (Note: Park St has a small picnic/playground area perfect for a post-hike snack.)
30. McLennan Reservation, Tyringham
Follow Main Rd in Tyringham to the bottom of Fenn Rd (you’ll see a red barn with a split rail fence on the corner). There is no parking on Fenn, so park alongside Main Rd and begin your excursion to the reservation with an easy 1/2-mile walk up Fenn, where you will spot the Trustees of Reservations signage and the start of the 1.5-mile trail. Hikers who make it to the top will be rewarded with sweeping views of Hale Pond and 600 acres of unspoiled forest and wetlands.
31. Monument Mountain, Great Barrington
One of the county’s most well-traveled hiking trails, with sweeping views stretching from the Catskills to Mt. Greylock. A hike to the 1,642-foot Squaw Peak summit of Monument Mountain will not disappoint. With a rapid elevation gain and steep unguarded ledges, you may want to skip the summit with smaller kids.
32. Mount Everett/Race Brook Falls, Sheffield
Begin your hike at the paved parking area off of Route 41 in Sheffield, where you will see signage and a trail map. The three-tiered Race Brook Falls is the highlight of the Mt. Everett State Reservation. Once you’ve visited the falls, you can cheat and drive to the 2,624-foot summit of Mt. Everett (by following the summit road when open) and take in the expansive view of Massachusetts, New York, and Connecticut. Parking is also available at Guilder Pond, where it’s just a 3/4-mile trek to the summit.
33. Mount Greylock, Adams/Lanesborough
Beginning in Adams, the Thunderbolt Trail is the steepest and shortest route to the 3,491-foot peak, but families with kids will likely want to cheat and make the 8-mile drive to the summit (open for the season on May 16). The $5 parking fee is well worth the 60 to 90-mile million dollar view and easy trail access from the top. Bring your own picnic or stop in at Bascom Lodge for a bite to eat (http://www.bascomlodge.net/default.aspx). Even on the warmest days, bring an extra layer of clothing. Temperatures inevitably drop about 10-degrees at the summit. Check out the DCR’s list of suggested day hikes on the mountain.
34. Mountain Meadow Preserve, Williamstown/Pownell, VT
Walk from Massachusetts to Vermont along this beautiful scenic trail, with views of Mt. Greylock and the Hoosac Valley. Offering four miles of trails, the preserve is a must-try for cross country skiers. Follow Route 7 North to the Mason St. entrance of the preserve, where you will find a small parking area and trail map.
35. Natural Bridge State Park, North Adams
This stunning geological gem will take your breath away. Follow trails past 550 million-year-old marble bridges and arches, and to traverse a series of stone stairs and metal gangways over incredible waterfalls, caverns, and gorges. With endless climbing and exploring opportunities, Natural Bridge State Park is a natural playground that will capture your child’s curiosity and spark their sense of adventure. Restrooms and an ongoing nature exhibit can be found in the visitors’ center, beside the parking area. Follow Route 8 to McCauley Road. $5/day parking fee
36. Notchview, Windsor
Located on Route 9 in Windsor, Notchview is known for its twenty-five miles of Nordic ski trails, but it’s 3,000 acres of wooded passages, historic hayfields and pastures, stone walls and cellar holes will have you coming back to hike and explore year-round. Open from sunup to sundown year-round. The Budd Visitor Center with cafe and snowshoe/ski rental shop is only open in winter, but Adirondack trail-side shelters and restrooms are accessible year-round.
37. October Mountain State Forest, Becket/Lee/Lenox
October Mountain is the largest State Forest in Massachusetts, with 16,500 acres of winding woodland trails that circle past lakes, reservoirs, marshlands, and geological formations. With 27 miles of trails, ATV’s and snowmobiles are welcome on the mountain, with proper permits. Campsite and Yurt rentals are available year-round. There are nine designated parking areas on the mountain, including Woodland Rd and Willow Hill Rd in Lee and Becket Rd (Finnerty Pond Trail) and Country Rd in Becket.
38. Old Mill Trail, Hinsdale
The parking area for the trailhead of this must-try hike for families is at the junction of Rt 8 and Old Dalton Road. Peppered with beautifully constructed bridges and hedged with cool sites, like the old dam, an abandoned vintage auto, old mill ruins, jutting boulders, a weather-protected trail journal, and a stone stairway, the trail skirts 1.5 miles of the East Branch of the Housatonic River, the first 1/2 mile of which is handicap accessible and great for strollers!! After your hike, cross Old Dalton Rd and enjoy a soft serve of SoCo Creamery ice cream in Hinsdale Trading Co.’s riverside gazebo.
39. Olivia’s Lookout & Shark Rock, Richmond/Lenox
If you have small kids, you have a moral obligation to drive to Lenox Road/Richmond Mountain Road from Route 183 in Lenox to Swamp Road in Richmond to see SHARK ROCK. Nearby hiking trails include Yukon Ridge North, Yukon Ridge South, Burbank Trail, Charcoal Trail, the Michael H. Walsh Trail, and Steven’s Glen. After checking out Shark Rock, Olivia’s Lookout (about 1.5 miles from Route 143 on the Lenox side) offers a stunning view of Stockbridge Bowl and is the perfect backdrop for more photo ops. You can also hop on the Burbank Trail from here, a 3.2-mile loop that circles Monks Pond and the 1850’s Gorman Homestead. The Yukon Ridge South trailhead is also just across Lenox Rd from Olivia’s Lookout parking area.
40. Pittsfield State Forest, Pittsfield
Explore over 30 miles of Taconic Mountain Range trails or fish at 2,150-feet above sea level, in Berry Pond, one of the highest bodies of water in Massachusetts. The Pittsfield State Forest offers camping at the Berry Pond (top of the mountain) and Parker Brook (base of the mountain) campground. Swimming and picnicking are also available in the natural cold spring pool at LuLu Brook on 1041 Cascade Street. $5 daily parking fee.
41. Pleasant Valley Wildlife Sanctuary, Lenox
Birds, bridges, bullheads (catfish), beavers, and boardwalks. Your kids are going to love exploring Pleasant Valley. Set on 1,142 acres, with over 7 miles of trails, you can visit again and again and experience a different adventure and spot new wildlife each and every time. Check out their website for info on summer nature camps and family programs! The parking area is located at 472 W Mountain Rd.
42. Questing, New Marlborough
Follow an old wooded road, mowed meadow passages, and forested footpaths past cellar holes, stone walls, and the remnants of a long-abandoned Colonial settlement of Leffingwell, where the first Colonial settlers of New Marlborough were born. The parking area is located on New Marlborough Hill Road. Questing offers over 2 miles of hiking/walking trails and is open year-round.
43. Race Brook Falls, Sheffield
Set in the Mt. Everett State Reservation, Race Brook features five distinct falls, including a “horsetail”, “slide”, “fan”, “plunge” and 100-foot “cascade”. Begin your hike at the paved parking area off of Route 41 in Sheffield, where you will see signage and a trail map. Swimming is prohibited, but wading through the shallow water at the base of the falls is possible for those looking for the perfect photo angle. Note: The trail to the higher portions of the falls may be too steep for smaller children. Hikers (and dogs) are welcome year-round but mud may be prohibitive in early spring.
44. Savoy Mountain State Forest, Florida
Savoy Mountain is the home to over 50 miles of wooded hiking trails, as well as North Pond (sandy beach with restrooms), South Pond (year-round camp and cabin rentals available), Bog Pond (floating bog islands!!), and Tannery Falls (a series of smaller waterfalls feeding into a dramatic 50-foot cascade). Parking on the mountain is available at 260 Shaft Road.
45. Sheep Hill, Williamstown
The Sheep Hill Land trust maintains trails around Williamstown and near its headquarters at a 50-acre former dairy farm. In support of the conservation of open, accessible space, they offer public access to miles of hiking trails, as well as educational children's and family programs in a truly unique setting. The entrance to Sheep Hill is at 671 Cold Spring Road, about 1.2 miles south of Williamstown Center.
46. Snowhole, Williamstown/New York State Line
A fifty-foot chasm, where MA, NY, and VT meet in the Taconic Mountain range, known for its summer snow. The trail leading to a cave, well maintained by Williams College Outing Club. Caving equipment recommended for those who dare to enter. Flashlight recommended for parents to allow kids to peer inside of this geological wonder.
47. Steven’s Glen, Richmond
A 128-acre parcel of land, with family-friendly hiking trails featuring wild blackberry bushes, natural stone steps, rustic benches and bridges, an observation deck, and magnificent views of gorges, glens, and falls. A small parking area is available on Lenox Branch Rd/Lenox-West Stockbridge Rd, where you will see the Natural Resource Council signage and nearby trail map.
48. Tamarack Hollow, Windsor
This highland valley nature and cultural center is a 32-acre conservation area in the center of Windsor, with a unique and ecologically sensitive forest ecosystem. Parking is available at 1515 Savoy Hollow Road for hikes on the property and neighboring conservation lands in Windsor and Savoy.
49. Tyringham Cobble, Tyringham
Walkthrough mountain meadows and follow the Loop Trail past ancient bedrock formations to the summit for panoramic views of the Tyringham Valley. Explore over 2 miles of trails, including a portion of the Appalachian Trail, and help yourself to the wild strawberries and blueberries growing in the meadows. Challenge little hikers to find “Rabbit Rock” and to create names for other unusually shapes rock formations. Parking is available at 20 Jerusalem Road (off of Tyringham/Main Rd). If visiting the Cobble on a Saturday, stop in at the Tyringham Free Public Library (10 am-noon) at 118 Main Rd for a close look at the Ordovician marble and Precambrian gneiss from the Cobble used in the stonework above the library fireplace.
50. Wahconah Falls State Park, Dalton/Windsor
It’s just a short walk from the parking lot to the best view in the park, where several small falls meet at an outcropping of gneiss to form a spectacular 40-foot cascade. The nearby 1/2-mile Loop Trail is an easy trek that will take you to the top of the falls and through the shade of the surrounding conifer forest. Follow the river’s edge a bit downstream and you will find the perfect picnic/rest area beside the pools formed in the rock basins below the falls. The park entrance is located on North Street/Wahconah Falls Road. No parking fee, porta-potty has been available in the past.
Reader Suggestions & Comments:
- "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
