Berkshire Camino, LLC
Lee, MA – Experience the Berkshires on foot with locally curated, expertly guided half-day town-to-town walking tours and multi-day hiking journeys inspired by pilgrimage walks on the Camino de Santiago in Spain.  Berkshire Camino is solo-traveler friendly.

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

Upper Bowkers Woods is also a property of the Association 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.

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 cross-country ski and snowmobile. The 1.5 mile Benedict Pond loop is a must in any season.

Berkshire Natural Resource Council
Berkshire County, MassachusettsA 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, MAMonument 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.


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.


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.

Wyndhurst Manor & Club (Formerly Cranwell Resort) in Lenox, MA is an 18-hole historic par 69 course, 10-acre driving range, with scenic views of the Berkshires. One-on-one golf instruction is also available for beginners. The manor also has a spa and indoor/outdoor pool for guests.


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 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


Ski Butternut About 15 minutes from Stockbridge, Ski Butternut offers snow tubing, downhill skiing, and lessons for all ability levels.


Spirit Ballooning
Based out of Canaan, CT – Spirit Ballooning launches their hot air balloons from various locations in the Berkshires. Take off any time of the year for unparalleled views of the Berkshire Mountains region.


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.


Discover the beautiful gardens, grounds, and scenic views in our area.  Most of our gardens, museums and historic sites reopened, although on a more limited basis than usual. Some are open for use of their outdoor grounds with restrictions and timed entry. There is plenty of space for social distancing and abundant fresh air that provides great venues for visitors to explore.  Check out each venue’s website for their offerings. Tanglewood: Grounds open Wednesdays, 9 am-Noon, Saturdays & Sundays, 10-4. Pre-registration is required. Jacob’s Pillow: You are welcome to stroll the lovely grounds in beautiful Becket. Download a self-guided tour map and discover the history and legends of these historic grounds.


The drive-in movie pulls up to three locations in the Berkshires.

Berkshire International Film Festival (Lenox) – The Berkshire Drive-In, on the campus of Shakespeare and Company in Lenox, shows films Thursday through Sunday nights starting July 23. Tickets are $15 per person. Find the schedule at HERE 

Berkshire Theatre Group Sunset Cinema (Pittsfield) – Family friendly movies in the comfort and safety of your vehicle at the Taconic High School Parking Lot. A food truck will be on site with concession offerings. To purchase tickets ($25 per car) or view the calendar, go to HERE

Mahaiwe (Great Barrington) – On the campus of Bard College at Simon’s Rock, the Mahaiwe presents drive-in movies Thursday through Saturday nights. Tickets are $25 per vehicle and MUST per purchased in advance. Concessions will be available from SoCo Creamery and Berkshire Food Co-op. Find out more at HERE