OUTDOOR ADVENTURE
BerkshiresOutside.org A brand new, comprehensive clearinghouse of trailheads, boat launches, and access points to outdoor recreation in the Berkshires.
BERKSHIRE HIKING & BIKING
STOCKBRIDGE, MA TRAILS
Laurel Hill Association Trails
Within walking distance of downtown Stockbridge, located at the end of Park Street.
Ice Glen Trail: A climber over, under and around giant boulders in a glacial ravine 1 mile round trip. The sides of the glen are covered with old stand pine and hemlock. The crags and crannies of the rocks are said to harbor ice and snow into the summer. At the north end of the glen is a flat rock face with an inscription from the donor, David Dudley Field. At the south end of the glen is reputedly the tallest pine in Massachusetts.
Laura’s Tower Trail: A quiet 1.5 mile round trip, wooded assent, starting out through old stand pine and hemlock. Midway up, a boulder outcropping gives a hint of the wonders of Ice Glen. Nearing the end of the climb is a large section of birch interspersed with mountain laurel. A metal tower at the summit provides a panoramic view of the middle Berkshires, including Mount Greylock to the north, the highest point in Massachusetts. On a clear day, one can see 68 miles west to the New York Catskills, and 50 miles north to the Green Mountains in southern Vermont.
Mary V. Flynn Trail: An easy 1.2 mile round-trip walk in the woods and along the Housatonic River, on a wide, packed-gravel trail, built mostly on the bed of the old Berkshire Street Railway trolley line. Starting with a 100 foot boardwalk, the trail goes through birch, pine, cottonwood and invasive euonymus, traverses two wooden bridges, and meets the river near a railed section. At the end of the wide trolley bed portion, a narrower section traverses two, smaller bridges as it loops back along the river through fern beds to the main trail
Bowker’s Woods is also a property of the Association. It is divided into two sections. The upper trail is located across the entrance to Norman Rockwell Museum, Rte 183, Stockbridge, MA – There is an old, indistinct trail that goes northwest from the pond. It extended over to Mohawk Lake Road, but crosses one of the sold parcels and is now private property. The lower trail, located about a mile outside downtown Stockbridge on Glendale Middle Road, is a mile plus loop that offers pleasant views and a cool calming atmosphere, gently sloping stand in the oxbow of the Housatonic River. The railroad arcs east and west through the property. Just north of the railroad are the remnants of the old Berkshire Street Railway line. This property comprises three of several parcels acquired via trust from the will of Robert R. Bowker, one of the founders of the American Library Association.
Bullard Woods
Located at the intersection of Hawthorne Road and Hawthorne Street, across from the Linde Center in Stockbridge, MA. Bullard Woods conservation property is owned by the Stockbridge Bowl Association. It is 42 acres, open to the public with 1.25 miles of hiking trails that begin at the parking lot at Hawthorne Road and lead to the shoreline. A bridge fords a stream in the woods, and the public can walk through the woods, across the Tanglewood connector and continue on to Gould Meadows, exiting on Route 183. There are picnic tables near the water, and visitors are asked to leave no trash behind.
Gould Meadows
110B Interlaken Road, Stockbridge, MA – Gould Meadows conservation property is owned by the Town of Stockbridge. It is 95 acres, open to the public with .6 miles of public trails. It is a nice walk to the Stockbridge Bowl, open field and benches for relaxing with parking lot at entrance.
Appalachian Trail
30 Rockwell Road, Lanesborough, MA – The Appalachian Trail provides hiking for both the long-distance or day hiker, traveling over Mount Everett in the south, all the way up and through Mount Greylock in the north.
Ashuwillticook Rail Trail
in the town of Lanesborough, MA – This 11-mile rail-trail offers the opportunity for walking, biking, skating, and cross-country skiing. The trail passes through the Hoosic River Valley.
Bash Bish Falls State Park
Next to the Mount Washington State Forest – Bash Bish Falls is about 60 feet and is one of Massachusetts’ highest single-drop waterfalls. An easy hike with incredible views.
Beartown State Forest Trail
69 Blue Hill Rd, Monterey, MA – This 12,000 acre forest is the perfect place to visit no matter the season. Swim, boat, or fish in Benedict Pond. In the winter, you can ice skate, cross-country ski and snowmobile. The 1.5 mile Benedict Pond loop is a must in any season.
Berkshire Natural Resource Council
Berkshire County, Massachusetts – A wide variety of hiking and walking trails for all levels . Please see the BNRC Trials page .
Kennedy Park
91 Pittsfield Rd, Lenox, MA – Kennedy Park is a town-owned and maintained hardwood forest whose groomed trails snake their way through 502 acres of tree lined forest. Excellent for casual strolling, hiking, mountain biking, horseback riding, even cross country skiing and snowshoeing in the winter.
Monument Mountain
Rte 7, Great Barrington, MA – Monument Mountain, is incredibly popular among Berkshire adventurers. Get rewarded with views of Beartown State Forest and Taconic Range once you reach the top.
Mount Greylock
30 Rockwell Road, Lanesborough, MA -The beauty of this mountain can be taken in while hiking or from the comfort of your vehicle. Hike or drive to the top for amazing views of the region. Trail Map
October Mountain
317 Woodland Rd, Lee, MA – Bordering the towns of Washington, Becket, Lee and Lenox, October Mountain’s 16,500 acres make it the largest state forest in Massachusetts. Forest trails are available for hiking, mountain biking, cross-country skiing, and off-road vehicle use.
Olivia’s Overlook Trail
1289 Richmond Mountain Rd, West Stockbridge, MA – 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.
Pleasant Valley Wildlife Sanctuary
Located in nearby Lenox, MA, – This wildlife sanctuary is an easy, family-friendly hike. Explore more than seven miles of forests, meadows, and wetlands. Visitors can also take advantage of guided tours, bird walks, and canoe trips.
OUTDOOR GARDENS, ART WALKS & MUSEUM GROUNDS
Discover the beautiful gardens, grounds, and scenic views in our area. Most of our gardens, museums and historic sites are open for use of their outdoor grounds with restrictions. There is plenty of space and abundant fresh air that provides great venues for visitors to explore. Check out each venue’s website for their offerings.
Here are some highlights:
Bidwell House Museum There are approximately six miles of trails on the 190+ acre property of the Bidwell House Museum. Trails are generally easy to moderate, and the six miles of trails on the property can be combined to form loops from 1/2 mile to over 3 miles. They can be enjoyed free of charge for hiking, historic interpretation, passive recreation, nature viewing, cross country skiing, or snowshoeing.
Clark Art Institute On the museum grounds, visitors will find a reflecting pool and several lawn chairs. Then, on the north side of the building, there are numerous picnic tables underneath the shade of tall trees. This is an excellent place to relax, eat lunch, and chat with friends or family on warm summer days. Beyond the museum, an extensive network of hiking trails spreads throughout the surrounding forests and fields and open free of charge. The top of Stone Hill, an active cow pasture south of the institute, features expansive scenic views of Williamstown and the surrounding Berkshires. Visitors can also hike through dense woodland toward Kite Hill, which has further views of the nearby mountains.
Norman Rockwell Museum Plan an outing to Norman Rockwell Museum’s beautiful 36-acre campus set above the Housatonic River. Site of the former Linwood Estate and later a working dairy farm, the property features rolling hills, wooded areas, historical buildings, and stunning Berkshire vistas, including river views and trails. Museum admission is not required for enjoying the campus. Explore the property using paved paths (with modest to medium inclines) as well as field paths that meander down to the Housatonic River, where the Riverside Meditation Bench offers a spot for reflection. Wander among specimen trees (identified with labels) and flower gardens with native plantings. An apple grove with trees planted for each of the Rockwell grandchildren is another campus highlight; please pick an apple during autumn apple season.
The Mount Visitors to The Mount can go can traverse the grounds, walking through maintained garden pathways with unique plants at every turn. These gardens are a spectacle, but the songbirds and pollinators they create habitats for are a hidden bonus of this landscape. The grounds are open year round free of charge.
SCENIC DRIVES
Take a look at foliage forecasters online.
The Mohawk Trail Williamstown to Westminster (Route 2) Begin in Williamstown, just 9 miles east of the best vista around, the Hairpin Turn at the Clarksburg/North Adams line with views of Adams, North Adams, Clarksburg and Williamstown. (If you haven’t already visited, drive up Mount Greylock on your way by.) Hop out briefly at the Hoosac Range trailhead about a mile past the Hairpin Turn and take a quick walk to Sunset Rock, looking down on North Adams. Don’t worry, it’s certainly not the only spectacular view along the almost 70-mile byway. Follow the Deerfield River from Charlemont to Shelburne, and when you get to Greenfield, stop and explore Rocky Mountain Park along the Connecticut River. From Westminster, check out Wachusett Mountain State Reservation for 360-degree views from this 2,006-foot peak.
Jacob’s Ladder Scenic Byway (Route 20) Russell to the Lee/Lenox town line The Jacob’s Ladder Scenic Byway is a shorter fall drive, only 35 miles through Russell, Huntington, Chester, Becket and Lee. It’s short, but it has the distinction of being the first mountain crossing built by the state for automobiles. October Mountain State Forest and Chester-Blandford State Forest are convenient stops to add to your day. Another highlight along this byway are the Keystone Arches, stone railroad bridges built around 1840 without mortar or steel reinforcements. A 2.5-mile trail offers a chance to hike and see the bridges up close.
Mount Greylock Scenic Byway Lanesborough to North Adams (Rockwell Road, North Adams Road, Notch Road) There’s more to Mount Greylock than just the peak! Take this short, 16-mile drive from Lanesborough to North Adams, perfect for catching some foliage if you can’t make a day of it. And if you’ve got the time, don’t miss out on the 70 miles of hiking trails available in the reservation. Be aware, during peak season, the road to Mount Greylock can be congested, and foot traffic can be heavy at the summit. Sorry, but the Visitor Center, in Lanesborough, is currently closed due to COVID-19 precautions. Parking fees apply.
PICK YOUR OWN APPLES & BLUEBERRIES and Holiday Offerings (cut trees and decorations)
Windy Hill Farm is a destination in the Berkshires and beyond for its pick-your-own operations, both blueberries and apples, on the scenic hillside of our family farm. Since establishing our farm in 1980, they’ve offered superb crops of a diverse range of apples annually. The season begins around late August with tart, crunchy Paulared and Ginger Gold varieties. Typically they have over 25 varieties to follow, including several heirlooms as well as our own fresh-pressed, all-natural unpasteurized sweet cider blend. PYO blueberry fields are another highlight for Windy Hill customers each summer. The blueberry season usually begins around early July. In the winter holiday season they offer holiday garland, cut trees, and decorations.
CANOEING, KAYAKING & WHITEWATER ADVENTURES
Crab Apple Whitewater – Enjoy an outstanding white-water rafting adventure on the Deerfield River. But even if you’re taste for adventure runs a little milder, this outdoor outfitter has a trip that is just right for you.
Berkshire Canoe Tours – “Quietwater” paddling means scenic canoeing or kayaking on lakes, ponds, and relatively calm rivers. Western Massachusetts has some splendid rivers and lakes for “quietwater” canoeing. Berkshire Canoe will take you there, and even help provide you with a boat and gear.
Canoe Meadows – Here’s an opportunity to take a naturalist-guided canoe trip along the Housatonic River from April to October.
Local Lakes – There are also a number of other nearby lakes for canoeing and kayaking. They include the Stockbridge Bowl in Stockbridge, MA, Goose Pond in Tyringham, MA, Beartown State Forest in Monterey, MA and Lake Buel in Great Barrington, MA.
The Stockbridge Bowl, also known as Lake Mahkeenac, is a 372-acre artificially impounded body of water. Above the lake’s north side with sweeping views to the south is Tanglewood, the summer home of the Boston Symphony Orchestra. Stockbridge Bowl is the largest lake within the Town of Stockbridge, with a public boat ramp making the lake accessible to all. Throughout the year, the lake is extensively used by canoers, kayakers, sailers, swimmers and fishermen. The Bowl is also home to the Mahkeenak Boating Club, a venerable sailing and social club with a three-story boathouse on the western side of the lake.
GOLFING & TENNIS IN THE BERKSHIRES
Stockbridge Golf Club in Stockbridge, MA is a private Club with golf, tennis and dining. Guest staying at one of several local inns may inquire about enjoying the club during your visit.
PUBLIC BEACHES IN THE BERKSHIRES
Beartown State Forest Trail
69 Blue Hill Rd, Monterey, MA – This 12,000 acre forest is the perfect place to visit no matter the season. Swim, boat, or fish in Benedict Pond. In the winter, you can iceskate, cross-country ski and snowmobile.
Lake Mansfield in Great Barrington, MA features a 29-acre pond with an adjacent 29-acre Conservation Forest with a 1/4 mile walking loop trail. The pond is open to the public for seasonal recreation. Visitors are welcome. A parking area provides access to the sandy beach front, grassy shaded picnic area, swings, and forest trails. Portable toilets are available May through September. Visitors to the Lake Mansfield Recreation Area enjoy swimming, boating, picnicking, fishing, walking trails and nature watching
BERKSHIRE ZIPLINING AND ADVENTURE PARKS
Berkshire East in Charlemont, MA offers a thrilling ride on their Thunderbolt Coaster, a mountain coaster unlike any other!
Catamount Adventure Park located in Hillsdale, NY – An exciting aerial forest adventure that provides a variety of courses that are fun for all ability levels. With 12 treetop courses of varying difficulties, you are challenged to cross bridges, climb ladders, obstacles and zip lines.
Jiminy Peak in Hancock, MA offers an off season aerial adventure park, a mountain adventure park and mountain biking.
Ramblewild located in Lanesborough, MA is a tree-to-tree adventure destination, eight aerial obstacle courses meander through the trees at various heights and include 15-17 elements including high wires, zip lines, rope ladders, log cargo nets and suspended bridges.
BERKSHIRES SKIING, SNOWBOARDING & TUBING and SKATING & SLEDDING
Within a 5- to 30-minute drive, downhill ski areas include Otis Ridge, Ski Butternut, Jiminy Peak, Bousquet, and Catamount.
ICE SKATING, SNOW SHOEING, DOWNHILL & CROSS COUNTRY SKIING & ICE FISHING
The Stockbridge Bowl, is incredibly popular place to skate and ice fish in the winter months. There are points of access but your best bet during the winter months is the boat ramp at 106 Interlaken Rd
Beartown State Forest Trail
69 Blue Hill Rd, Monterey, MA – This 12,000 acre forest is the perfect place to visit no matter the season. In the winter, you can ice skate, cross-country ski and snowmobile. The 1.5 mile Benedict Pond loop is a must in any season.
Lake Mansfield in Great Barrington, MA features a 29-acre pond with an adjacent 29-acre Conservation Forest with a 1/4 mile walking loop trail. The pond is open to the public for seasonal recreation including ice skating and ice fishing in the winter season.
Kennedy Park
91 Pittsfield Rd, Lenox, MA – Kennedy Park is a town-owned and maintained hardwood forest whose groomed trails snake their way through 502 acres of tree lined forest. Excellent for cross country skiing and snowshoeing in the winter.
Otis Ridge Ski Area Otis Ridge, located nearby Stockbridge, is an exciting destination for those seeking a day on the ski slopes. The ridge offers 17 slopes, 5 lifts/tows, and night skiing on many of the trails. If you are learning to ski, this is a great place, with various terrain, plus a snowsport school running many evenings and offering private lessons. When you are ready to take a break from the slopes, you can visit the Grouse House to refuel. Ample parking is available.