Skiing is a favorite activity in the Berkshires and has been an important component of the local tourism industry for as long as Tanglewood has been. In 1935, the first of the famous “ski trains” left Grand Central Station in New York bound for Bousquet’s in Pittsfield, MA, where the rope tow was perfected and night skiing was introduced on Dec. 24, 1936, by U. S. Ski Hall of Fame honoree Clare Bousquet. By 1945, Bousquets featured 10 rope tows. Olympic skiers Heidi Voelker, Krista and Kim Schmidinger began skiing at Bousquets.

Skiing the Thunderbolt trail Mt. Greylock

Berkshires skiing lore also includes the legendary Thunderbolt Ski Run, a world class downhill trail carved into the east slope of Mt. Greylock in 1934 by the Civilian Conservation Corps, under the direction of the Mt. Greylock Ski Club. Today, Berkshire county residents and visitors to the Berkshires have several choices for downhill skiing and snowboarding, as well as for cross-country skiing.

Cross Country Skiing and Snowshoeing in the Berkshires

Canterbury Farm Ski Touring

• 1986 Fred Snow Rd.
• Becket, Mass
• 413-623-0100
• 13 miles of ski trails
• canterbury-farms.com/

Cranwell Resort, Spa and Golf Club

• Rt. 7
• Lenox, Mass
• 413-637-1364
• 10km groomed trails
• cranwell.com

Hilltop Orchards – Cross Country Ski and Snowshoe

• Rt. 295 / 508 Canaan Rd.
• Richmond, Mass
• 413-281-2028
• hilltoporchards.com

Notchview Reservation

• Route 9
• Windsor, Mass
• 413-684-0148
• 19 miles of ski trails
• thetrustees.org

Pineridge Cross Country Ski

• 1463 Plank Road
• Petersburgh, NY 12138
• 518-283-3652
• 35km groomed trails
• pineridgexc.com

Berkshires downhill and cross-country ski areas

This map shows locations and driving directions for skiing in the Berkshires; downhill skiing areas and cross county skiing areas are marked with distinctive icons. Each area also is listed below the map. Get more information, including contact information and links to the ski areas on our Berkshires skiing page.

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How to get to the Berkshires

Here are inks for local and regional public transportation depots and stops, plus where to get Peter Pan bus and Amtrak train schedules and tickets: how to get to the Berkshires.

Ashuwillticook Rail Trail closed until August 2020

MassDOT Announces Temporary Closure of Southern Section of Ashuwillticook Rail Trail – The southern section will be closed to the public beginning on Monday, March 16. The closure is necessary to facilitate Phase I of the resurfacing project that seeks to upgrade an 11-mile section of the rail trail.

Bicycling in the Berkshires

Bicycling in the Berkshires is getting better for visitors and locals because of the development by the MA Dept. of Conservation and Recreation of the The Ashuwillticook Rail Trail, which is overseen locally by the Berkshire Bike Path Council. Berkshire Regional Planning Commission (BRPC) and the Berkshire Bike path Council (BBPC) help the Boston Metropolitan Planning Organization (MPO) gather information regarding the popularity of multi-use trails state wide. The data we collect is used to advocate for greater trail development.

Imagine Mount Greylock as the hub of a network of trails, that re-purpose abandoned railroads, and that use other rights-of-way for the creation of a veritable wonderland for persons eager to power their own way through the Berkshires.

The Ashuwillticook Rail Trail is a former railroad corridor converted into a 10-foot wide paved, universally accessible, passive recreation path. The Ashuwillticook runs parallel to Route 8 through the towns of Cheshire, Lanesborough, and Adams. The southern end of the rail trail begins at the entrance to the Berkshire Mall off MA Rte. 8 in Lanesborough and travels 11.2 miles north to the center of Adams. Parking lots and restrooms are available at selected locations along the way.

The rail trail passes through the Hoosic River Valley, between the Mount Greylock and the Hoosac Mountain Ranges. Cheshire Reservoir, the Hoosic River, and associated wetlands flank much of the trail offering outstanding views of the scenery and abundant wildlife. The name Ashuwillticook (ash-oo-will-ti-cook) derives from the Native American word for the south branch of the Hoosic River and literally means “at the in-between pleasant river,” or in common tongue, “the pleasant river in between the hills.” The name was adopted for the trail as a way to reconnect people to local history and the natural environment.

Sept. 28, 2013 article by Dave Read

While the Apple Squeeze was underway in the commercial district, we visited the coolest cultural venue in Lenox, the Frelinghuysen Morris House & Studio, and then took a late afternoon hike through Bullard Woods, which abuts Stockbridge Bowl. It was the sort of early fall day in the Berkshires that attracted old money types in the first place, including the parents of George L. K. Morris, whose ancestor was a signer of the Declaration of Independence.

Video of Black bears in Bullard Woods

We encountered 4 black bears near the main trail that leads down to Stockbridge Bowl, including 3 cubs that scooted up a tree after hearing the rustle of hikers. The Flip video camera is fun and handy, but we’re considering an upgrade that would enable a closer look at these beautiful animals.

Frelinghuysen Morris House & Studio

While Lenox is linked to the Gilded Age, often by errant amateurs who don’t get the joke Mark Twain made when he coined the term, what George L.K. Morris and Suzy Frelinghuysen created was decidedly un-Gilded. It is the first Modern structure to be built in New England, tucked into the hillside below the his parent’s old-world style mansion, Brookhurst.

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Fall hike in Bullard Woods from Lenox to Stockbridge Bowl

Bullard Woods, open to the public and owned by the Stockbridge Bowl Association is accessible from Lenox, MA located near Tanglewood at the conjunction of Hawthorne Rd and Hawthorne St. It is an ideal place for an early fall hike affording views of ancient trees, black bears, and afternoon sun reflecting on Stockbridge Bowl.

Article by Dave Read

The best time to visit New England in the fall is when there are special events and cultural activities scheduled in the Berkshires of Massachusetts. With climate change and local weather conditions making it impossible to predict with much precision when leaf colors will be at their peak, the fall foliage season in towns popular with tourists and visitors, including Lenox, Lee, Stockbridge, Great Barrington, West Stockbridge, Williamstown, North Adams, Hancock, and Pittsfield features a variety of Autumn celebrations and events.

Bullard Woods

We had an encounter with four black bears during a hike in Bullard Woods near Tanglewood on Sept. 28 and got some video that shows them scampering up a tree. Bullard Woods, just a couple miles from the center of Lenox, is an ideal place to hike during October when the fall foliage around the shore of Stockbridge Bowl reaches the peak of colorful brilliance. Video and photos: Bullard Woods hike

Bartholomew’s Cobble

Bartholomew’s Cobble is a great place to visit any time of year; if you are planning a fall hike in the Berkshires, this property of the Trustees of Reservations, located just south of Sheffield, offers a wonderful variety things to see and discover along 5 miles of trails on 60 acres that contain the greatest concentration of biodiversity in the country. Video and photos: Bartholomew’s Cobble hike.

September 2013 Berkshires Fall Foliage events

• Jazz concert – The Parker/Byrd Trio – Fri., Sept. 6, 2013, 8PM – Pittsfield, MA
• North Adams – Berkshire Food Festival — September 15, 2013 – 12-4pm
• Lee – Founders’ Weekend — Friday, Sept. 20, 2013
• Pittsfield – HSV Trail Races – Sept. 21, 2013
• Lenox – Tub Parade — Noon – Saturday, Sept. 21, 2013
• Lee – Founders’ Weekend — Saturday, Sept. 21, 2013
• Lee – Founders’ Weekend — Sunday, Sept. 22, 2013
• Lenox – Apple Squeeze — All day – Saturday, Sept. 28, 2013
• Lenox – Apple Squeeze — All day – Saturday, Sept. 29, 2013
• Pittsfield – Country Fair at Hancock Shaker Village – Saturday, Sept. 28, 2013
• Pittsfield – Country Fair at Hancock Shaker Village – Sunday, Sept. 29, 2013
• Lenox – Brock Trot — 7AM registration – Sunday, Sept. 29, 2013
• Adams – Annual Fall Run to Charlemont — 11AM – Sunday, Sept. 29, 2013

October 2013 Berkshires Fall Foliages events

• Stockbridge – Berkshire Harvest Festival — 10AM – 5PM – Sat. Oct. 5, 2013
• Stockbridge – Berkshire Harvest Festival — 10AM – 5PM – Sun. Oct. 6, 2013
• North Adams – Fall Foliage Parade – 1PM – Sunday, Oct. 6, 2013
• Pittsfield – Pittsfield CityJazz Festival – Oct. 11 – 20, 2013

Bicycle rides, walks, and hiking in the Berkshires

Besides the organized and/or scheduled events listed below, those interested in hiking on their own may find the following post useful for maps and camping information for the Berkshires section of the Appalachian Trail.

• Berkshire to Boston Cycling Tour September 19 – 22, 2013; Berkshire Bike Path Council
• Heritage Walks, Upper Housatonic Valley.
  • Saturday & Sunday – September 21 & 22, 2013
  • Saturday & Sunday – October 5 & 6, 2013

Fall theatre in the Berkshires

• The Beauty Queen of Leenane runs through Sept. 15, 2013 at Shakespeare & Co. in Lenox.
• Accomplice – Sept. 21 – Nov. 10, 2013 -at Shakespeare & Co. in Lenox.
• Barrington Stage Co. presents Scott and Hem in the Garden of Allah , World Premier by Mark St. Germain, through Sep 29, 2013.
• Berkshire Theatre Festival schedules Mary and Edith: Musings by Women a Century Apart for a fall run at the Unicorn Theatre in Stockbridge – Oct. 4 – 20, 2013.

WordFest 2013 at The Mount

The Mount, in Lenox, has scheduled a series of free readings on Thursdays: September 5, 12, and 19; then Friday September 20 – Literary Death Match!, Saturday, September 21 reading by Pulitzer Prize-winning poet Mark Strand.