The Berkshires covers over 2,100 square miles of beautiful terrain and needless to say it can be challenging to decide where to start your explorations. In an effort to demystify the process, our friends at the Berkshire Natural Resources Council have put together a list of the 10 best hikes in our beautiful county. They even go so far as to break down difficulty, length and the best season to make the venture. Read along to help you plan your next outdoor adventure in the Berkshires!
Trail difficulty rating:
All time estimates are for walking in dry weather. Difficulty ranges from 1 to 5
1– Easy walking for everyone. Gentle grades, smooth footing, shorter distance.
2 – Easy walking, but with some uphill and downhill sections that will get the heart pumping!
3 – Moderately strenuous, but no problem for anyone who can walk for an hour and climb a few flights of stairs without needing to rest.
4 – Strenuous due to length and/or terrain; this may be a test if you’re not accustomed to 2-3 hour hikes.
5 – Difficult. Steep, sustained climbs and descents, uneven footing, and sheer length make this a trail for those with complete confidence in their stamina and fitness.
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Alford Springs - Winter favorite
Mountain Rd., Town of Great Barrington, Massachusetts 01230Mother Loop: 2.4 miles; 1.5 hours
Father Loop: 4.3 miles; 2.5 hours
Difficulty: Walking, 3; Skiing, 4
Features: Blackberries in summer, noteworthy backcountry Nordic skiing in winter, with challenging ascents and descents. Gorgeous views of Alford Valley and beyond. Good hunting reported.
Especially good in: Winter
Description of property: The sloping eastern shoulder of the ridge is heavily forested and these deep woods hold clear streams and abundant wildlife. In season, blackberries abound, and these are one reason black bears love this property. Luckily they are not acclimated to humans, so if you see them, they’ll be running in the opposite direction. A bobcat may dash across your path, and big bucks are known to roam these hills and stream valleys. Be aware that hunters and non-hunters share this property. Wear blaze-orange during hunting seasons and take all necessary care.
Skiing: On a winter’s day, there’s nothing more delightful than skimming along that ridgeline trail high above the valleys, watching the woods fly by. From the ridge’s high point to the parking area is a nice long descent, made quickly on skis. You’ll pass the Connector Trail intersection again and descend a bit more steeply to the old log landing area. Done this way, you’ll do about 600’ of vertical over 4.3 miles. Normally this route takes about 2-3 hours of hiking. A fit skier might navigate the loop in a little more than an hour.
Click here for trail maps and more information about Alford Springs!
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Hoosac Range- Fall favorite
2441-2599 Mohawk Trail, North Adams, Massachusetts 01247Sunset Rock: 1.6 miles, 1.25 hours | Difficulty: 2
Spruce Hill: 6 miles round-trip; 4 hours | Difficulty: 3
Features: High elevation long views: prepare for the sublime! Cool rock cliffs formed by “glacial plucking” with trees twisted into fantastical forms by wind and ice. Blueberries at Sunset Rock and open ledges near Spruce Hill in summer. Awesome spring snowshoeing. Migratory raptors in fall, great viewing at Spruce Hill.
Especially good in: Fall
Description of the property: From the Hoosac Range Trail you will look out over valleys and towns far below, hike three miles to the open rock summit of Spruce Hill or walk a shorter inner loop to Sunset Rock – all the while delighting in dramatic schist ledges, user-friendly stone steps, carefully designed switchbacks, and the tenacity of a forest that survives the insults of wind and ice on these magnificent 760 acres.
Native Americans first used the Mohawk Trail (now Route 2) to travel through the northern Berkshires between the Hudson and Connecticut rivers. Today a drive east 4.5 miles on Route 2 from North Adams through the “Hairpin Turn” to the top of the ridge brings you to a unique place known as “the Western Summit.” Just beyond the Wigwam cabins on the same side of the road is a large parking area where a BNRC welcome sign and an information kiosk mark the entrance to the trail.
Click here for trail maps and more information about Hoosac Range
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Basin Pond - Summer favorite
4-22 Becket Road, Becket, Massachusetts 01223Distance: 2.5 miles: 2 hours
Difficulty: 3 (easy walking, but does include a couple of stream crossings on step-stones)
Features: Beautiful wetlands, with a wildlife viewing deck in the sun. Trail crosses a boulder field which provides a great place for kids to climb and hide on trailside rocks.
Especially good in: Summer
Description of property: Surrounded by 2200′ high mountains to the north and east, Basin Pond is a large south-sloping drainage area adjacent to October Mountain State Forest in Lee . Hemlocks, oaks and hardwoods abound, but most unique is a boulder-strewn “natural amphitheater” which the trail traverses. Elevation is minimal, but wear sturdy shoes – rocks can be slippery!
It’s a Jackson Pollock rock canvas arrayed around you, and you can’t help but be amused at the way the boulders are scattered so “artfully.” The trail takes a deliberate path through the biggest “array” and in one case passes right next to a huge and dramatic boulder that is perfectly designed for a photo op.
If you walk both sides of the loop you’ll have the delight of navigating five lovely stream crossings, one with a sturdy stone cap for crossing. Stop and listen to the play of water as the brooks tumble and cascade through rocks and chutes.
You might wonder, “What are all these rocks doing here?” Geologically, they are called a talus slope, which is an often concave landform associated with an accumulation of broken rock fragments at the base of crags, mountain cliffs, or valley shoulders. You’ll find no crags or cliffs here though–just a gently sloping topography that rises to higher land north of the BNRC property at Finerty Pond and the Appalachian Trail.
The trail drops down slightly to the “pond,” although you might rather call it a wetland, marshland or swamp. We have beavers to thank for the beautiful waters that stretch out below.
Click here for trail maps and more information about Basin Pond
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Stevens Glen - Spring favorite
76 Stevens Glen Road, Richmond, Massachusetts 01254Loop Trail: 1.5 miles, 1.25 hours
Difficulty: 2
Features: 19th century tourist attraction, reborn for the 21st century including a waterfall through romantic rock cleft, stream to dabble feet on hot day, a viewing platform with bench for reflection. Deep hemlock forest also awaits.
Especially good in: Spring
Property description: Go when the light is filtering through the tall pines and hemlocks or go when their boughs are laden with snow. Here are glades that are deep with big trees. At any time of year Stevens Glen is a magical place, shifting light and space through a filter of greenery, and trading off light and dark as you make your way along the clearly marked trail. Stop a minute any place here and let your senses breathe in the quiet.
Since 1998, Stevens Glen has offered visitors access on carefully designed trails. Bridges over Cone Brook and Lenox Mountain Brook allow for easy crossings; a series of steeper stone steps there is a sturdy bench upon which to rest; the trail is laid out to visit the most scenic interior views, and the dramatic ravine is safely penetrated by stepping down to a railed platform. Here the Glen itself is a jagged cleft of gray-green rock that rushes Lenox Mountain Brook through crags and slides to the level landscape below. One has to admire the tenacity of trees growing straight out of the sides of the ravine and the lone birch that clings tightly to its fragile base.
Stevens Glen fully deserves our description of it as a “hidden gem,” and many visitors have told us it is “a perfect little hike.” A 1.4 mile roundtrip will take you over several bridges on the way to a platform with a great view of roaring Lenox Mountain Brook, cascading through the tight confines of dramatic Stevens Glen.
Click here for trail maps and more information about Stevens Glen
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Olivia’s Overlook at Yokun Ridge - Fall Favorite
1289 Richmond Mountain Rd, West Stockbridge, Massachusetts 01254Note: Yokun Ridge is the central hub of a multi-spoked trail network. There are multiple options extending north and south from there.
Walsh Trail: 1.5 mile roundtrip; 1 hour | Difficulty: 1
Features: Gentle walking through a 100-plus year old forest with views of Monument Mountain.
Walsh/Charcoal/Brothers loop: 4 miles; 2 hours | Difficulty: 3
Features: Charcoal pits (can you spot them?) and a run alongside Shadow Brook, named by Nathaniel Hawthorne. Remarkable stone work on trail itself. Also includes the Tri-town monument: where Stockbridge, Lenox and Richmond meet…Berkshires’ answer to Four Corners.
Especially good in: Fall
Property Description: You’ve seen the vista from Olivia’s Overlook, but did you know that it’s also the trailhead for more than 6 miles of hiking trail? From here you can access: Walsh (easy access), Charcoal, and Burbank Trails. Those trails connect to Brothers Trail, lead you to Monks Pond, or are very near to Jackson Pond’s boardwalk.
Since its construction, the Brecher boardwalk has tempted trespassers eager to see where it leads. The answer: stunning views of Jackson Pond.
Olivia's Overlook is at the center of the 734-acre Yokun Ridge Reserve. This popular overlook is also the trailhead for the 6 miles of trail that BNRC maintains on Yokun Ridge. Trails range from the easy access Walsh Trail (a gradual climb to stunning views all the way to Great Barrington) to the long inter-locking loops of the Burbank and Brothers Trail. You’d like to spend some time at a quiet pond? Hike the Burbank Trail down to Monks Pond. If you’re hiking with a little one, let them explore the pools of Shadow Brook on the Brothers Trail. If you’re a bird watcher, park at the boat launch on Route 183 and walk over to Jackson Pond where BNRC maintains a boardwalk through the wetland there.
The bulk of the Yokun Ridge Reserve is made up of parcels donated by the Stokes family, the original owners of the Shadowbrook Estate. Other donations were made by local families who loved these hills just as you do.
Click here for trail maps and more information on Yokun Ridge
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Brothers Trail at Yokun Ridge - Fall Favorite
Baldhead Road, Lenox, Massachusetts 01240This is an alternate access point to Yokun Ridge
Burbank Trail Loop: 4 miles; 2 hours
Difficulty: 3
Features: Serene Shadowbrook Reservoir, aka Monks Pond, holds views across Lenox Mountain and the town reservoirs. Great running, mountain biking and skiing loop!
Especially good in: Fall
Property description: At the center of the 734-acre Yokun Ridge Reserve is Olivia’s Overlook. This popular overlook is also the trailhead for the 6 miles of trail that BNRC maintains on Yokun Ridge. Trails range from the easy access Walsh Trail (a gradual climb to stunning views all the way to Great Barrington) to the long inter-locking loops of the Burbank and Brothers Trail. You’d like to spend some time at a quiet pond? Hike the Burbank Trail down to Monks Pond. If you’re hiking with a little one, let them explore the pools of Shadow Brook on the Brothers Trail. If you’re a bird watcher, park at the boat launch on Route 183 and walk over to Jackson Pond where BNRC maintains a boardwalk through the wetland there.
The bulk of the Yokun Ridge Reserve is made up of parcels donated by the Stokes family, the original owners of the Shadowbrook Estate. Other donations were made by local families who loved these hills just as you do.
Click here for trail maps and more information on Yokun Ridge
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Clam River - Summer favorite
87-107 Sandisfield Road, Sandisfield, Massachusetts 01255Loop Trail: 1 mile, 30 minutes
Difficulty: 1
Clam River Trail: 3 miles Roundtrip, 1.5 hours | Difficulty: 2
Features: Beautiful, romantic stream valley, canyon-like in spots with access to Clam River. Old stone foundations and millworks along this cold water stream. Abundant wildlife.
Especially good in: Summer
Property description: With 1.5 miles of frontage on the Clam River, this reserve offers great opportunities for anglers and anyone looking to avoid summer heat. “Why,” the visitor asked, “is the river called the Clam River?” Whereupon a BNRC staff member stepped into the river, reached down, and pulled up a clam – actually a mussel, but let’s not be pedantic. You don’t often hear about bivalves in the Berkshires, but there are an abundance of surprises on this splendid 550-acre Reserve. The Clam River Reserve consists of five separate parcels on the lively Clam River in Sandisfield. The northern parcels are bisected by Hammertown Rd, which on older maps is labelled “Montville-Beech Plain Road”.
Click here for trail maps and more information on Clam River
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Hillow Fields - Spring Favorite
236 Perry Peak Road, Richmond, Massachusetts 01254Loop Trail: 2 miles round trip, 1 hour
Difficulty: 1
Features: Walk mowed paths through open fields – truly a rarity! Long views that are both sun-splashed and windswept, stunning in all seasons. Great birdwatching, particularly in spring. Mellow spot for picnicking.
Especially good in: Spring
Property description: The 139-acre Reserve comprises beautiful hay fields full of bobolinks, pretty hardwood forests, the banks of Sleepy Hollow Brook and provides magnificent views of the entire length of Yokun Ridge. A 2-mile walk on mowed paths through the fields will get you the views. A longer, more strenuous hike into the woods could get you some blueberries!
Click here for trail maps and more information on Hollow Fields
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Bob's Way - Spring Favorite
MA-23, Monterey, Massachusetts 01245Loop Trail: 2.5 miles; 1.5 hours
Difficulty: 2
Features: Multiple loops, so it’s easy to customize your walk with fabulous beaver pond views. Formerly a heron rookery, still teeming with wildlife. Dave’s Bench, a stone seat created from bedrock ledge and artisanal stonework sits atop with the best view of the house!
Especially good in: Spring
Property Description: Three gentle ‘stacked loop’ trails totaling about 2.5 miles, highlighted by Dave’s Bench and a beautiful beaver swamp.
The trail at Bob’s Way was designed for both the casual walker and the avid hiker. You can climb up and over a small peak to Dave’s Bench or for a more relaxing walk, take the low road that circumnavigates the property. The 2.5 miles of this Peter Jensen designed trail can be described as having a series of loops, somewhat resembling a figure eight. However you choose to describe it, you have three loop-trail opportunities with a variety of pleasing destinations. New Trex trail signs, located at every junction, will help keep you on your intended route on this 229 acre property.
Click here for trail maps and more information on Bob's Way
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Steadman Pond - Summer favorite
54-56 Tyringham Rd, Monterey, Massachusetts 01245Loop Trail: .25 miles; 10 minutes round trip
Difficulty: 1
Features: Pond in beautiful setting, excellent bass fishing. Swimming raft and rowboat await! Terrific bird watching. Great picnic and hangout spot.
Especially good in: Summer
Property description: High on a pretty hillside on the way from Tyringham to Monterey lies the lovely 73-acre Steadman Pond Reserve. You’ll find there an open meadow and a quiet pond sheltered by the steep walls of surrounding hillsides. Bring the family – it’s a mellow spot for a picnic.
A short walk down a mowed lane along the forest edge will bring you to the 12-acre pond. Here there are birds and wildlife, fine fishing, and the chance to paddle about (if one brings a boat). If you swim, you do so at your own risk. No skinny-dipping please – you share this spot with others.
The pond is about 15’ deep in the middle but can get weedy during the summer. A feeder stream enters on the south end, and at the north end a concrete dam retains the impoundment. Watch for newly chewed snags and teeth-sawed saplings along the shore; beavers have moved in, and they have built a new lodge along one edge.
The pond nestles comfortably at the bottom of a steep slope. This land, which was conserved in partnership with the Massachusetts Division of Fisheries and Wildlife and the Monterey Land Preservation Trust, eventually links up to the Beartown State Forest. It’s all open for your exploration, but there are no marked trails. The wood roads through the forest were last used for logging in 2005. These roads, along with other trails, may be overgrown and hard to follow.
Near the pond’s outlet you’ll find the remains of an old stone bridge and a newer but deteriorating old logging bridge that spans the brook. If you decide to wander further into the hardwood and hemlock forest, make sure you have with you and can use a compass and topo map, and remember that hunting is allowed during the spring and fall seasons.
Steadman Pond is beloved by locals. It is a place many appreciate as a quiet sanctuary. No one appreciates this peaceful place more than Sarah Hudson, who together with her brother Barclay Hudson, made the gifts that conserved Steadman Pond and its surroundings.
We have no real enforcement power, but we endorse Sarah Hudson’s wish that Steadman Pond remain an electronics-free zone – a place of respite and reflection.
Click here for trail maps and more information on Steadman Pond
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Housatonic Flats - Spring favorite
439 Stockbridge Rd, Great Barrington, Massachusetts 01230Loop Trail: 1 mile; 30 minutes
Difficulty: 1
Features: Views of pastoral Housatonic River, birdwatching, dog walking. Super easy place to “air out” in a short time.
Especially good in: Spring
Property description: The Housatonic Flats Reserve boasts over ½ mile of frontage on the Housatonic River that is perfect for wildlife viewing and fishing. There is a mown path skirting oxbow wetlands and tall floodplain forests of cottonwood and red and silver maples. Keep an eye out for wood ducks, beaver, otter, and large carp patrolling the river’s edge.
Click here for trail maps and more information about Housatonic Flats
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