Bob’s guidebook
Things to do in the Berkshires
Year-round: Mass MOCA museum in N. Adams; Colonial Theater in Pittsfield; antique shops;
Summer: mini-golf (Rt. 7 Lanesborough); Pontoosac Lake boat rentals; Jacob's Pillow Dance Festival; Tanglewood; Norman Rockwell Museum; Donnybrook Golf course; Ashuwillticook Rail Trail.
Winter: Jiminy Peak Ski area; Butternut Ski area; ice fishing; snowshoeing.
Walk, bike, or rollerblade this beautiful 12 mile rail trail, beginning in Pittsfield and ending in North Adams. There are several access points, many offering restrooms; all have free parking. The trail passes along Cheshire Lake in Lanesborough and Cheshire (my favorite section). My advise is to hop on at the Farnums Rd. parking lot and head north. You can also fish from the pier near the parking lot. The trail is wide and was recently re-paved in 2022. I've sighted plenty of wildlife while rollerblading (including black bears and Eagles). Keep your eyes open.
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Ashuwillticook Rail Trail
Rail TrailWalk, bike, or rollerblade this beautiful 12 mile rail trail, beginning in Pittsfield and ending in North Adams. There are several access points, many offering restrooms; all have free parking. The trail passes along Cheshire Lake in Lanesborough and Cheshire (my favorite section). My advise is to hop on at the Farnums Rd. parking lot and head north. You can also fish from the pier near the parking lot. The trail is wide and was recently re-paved in 2022. I've sighted plenty of wildlife while rollerblading (including black bears and Eagles). Keep your eyes open.
This is a great local winery located in Richmond, Mass. Enjoy a tasting and buy a bottle to go. They boast a spectacular view of Richmond Pond and the mountains beyond. There is entertainment every weekend. In the summer, the music moves outdoors. They also have food trucks on most weekends.
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Balderdash Cellars
81 State RdThis is a great local winery located in Richmond, Mass. Enjoy a tasting and buy a bottle to go. They boast a spectacular view of Richmond Pond and the mountains beyond. There is entertainment every weekend. In the summer, the music moves outdoors. They also have food trucks on most weekends.
A 15 minute drive away awaits Bousquet Ski Area. It's a great family mountain that invested loads of money recently on a new lodge, additional snow making, new lift, etc. They even have concerts in the summer outside their beautiful new lodge.
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Bousquet Ski Area
101 Dan Fox DrA 15 minute drive away awaits Bousquet Ski Area. It's a great family mountain that invested loads of money recently on a new lodge, additional snow making, new lift, etc. They even have concerts in the summer outside their beautiful new lodge.
Cities and towns
Home of the largest museum in the northeast (believed), with 250,000 sq ft. of space. Re-purposed Sprague Electric complex. General admission is only $17±. There is frequent live entertainment, a cafe, and an adjacent brewpub.
North Adams also boasts Natural Bridge State Park, a short trail along a river gorge. It's free admission.
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North Adams
Home of the largest museum in the northeast (believed), with 250,000 sq ft. of space. Re-purposed Sprague Electric complex. General admission is only $17±. There is frequent live entertainment, a cafe, and an adjacent brewpub.
North Adams also boasts Natural Bridge State Park, a short trail along a river gorge. It's free admission.
Visit Lenox, Mass., the joule of the Berkshires. Home of Tanglewood, a popular entertainment venue (summer home of the Boston Pops), with gorgeous grounds. Or attend one of the popular artist concerts. Lawn tics are only $30±.
Explore Edith Wharton home on Plunkett St., turn of the century mansion with impeccable grounds for $20.
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Lenox
Visit Lenox, Mass., the joule of the Berkshires. Home of Tanglewood, a popular entertainment venue (summer home of the Boston Pops), with gorgeous grounds. Or attend one of the popular artist concerts. Lawn tics are only $30±.
Explore Edith Wharton home on Plunkett St., turn of the century mansion with impeccable grounds for $20.
Mount Greylock access road begins in Lanesborough- highest peak in Mass. - site seeing, hiking, snowmobiling, waterfalls.
Lanesborough also has a mini-golf (and driving range). A little further south is a nice beach area along Pontoosuc Lake which is open to the public. There is also a boat launch area and boat rental area along Pontoosuc Lake.
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Lanesborough
Mount Greylock access road begins in Lanesborough- highest peak in Mass. - site seeing, hiking, snowmobiling, waterfalls.
Lanesborough also has a mini-golf (and driving range). A little further south is a nice beach area along Pontoosuc Lake which is open to the public. There is also a boat launch area and boat rental area along Pontoosuc Lake.
A quaint, walkable little town with several restaurants and shops. It is also home to the Mahaiwe Theater.
MA-57, Great Barrington, MA, USA
A quaint, walkable little town with several restaurants and shops. It is also home to the Mahaiwe Theater.
Food scene
Beautiful lake-side dining in the summer (open year-round) on nearby Pontoosuc Lake (less than 5 miles south)
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Proprietor's Lodge
22 Waubeek RdBeautiful lake-side dining in the summer (open year-round) on nearby Pontoosuc Lake (less than 5 miles south)
Located 3 miles south. Extensive beer selection, wings, outdoor dining.
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Olde Forge Restaurant
125 N Main StLocated 3 miles south. Extensive beer selection, wings, outdoor dining.
American & Italian bites such as wood-fired pizza, veal marsala & hamburgers. Locate on Rt. 7 in Pittsfield.
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Zucchini's
1331 North StAmerican & Italian bites such as wood-fired pizza, veal marsala & hamburgers. Locate on Rt. 7 in Pittsfield.
Krispy Cones Ice Cream
585 S Main StPopular local ice cream (and much more).
Excellent coffee and breakfast spot located just down the road on Rt. 7. Drive-through only.
Greylock Grounds Coffee Drive-Thru & Cafe
Excellent coffee and breakfast spot located just down the road on Rt. 7. Drive-through only.
A blue collar, American fare restaurant in downtown Lenox. The prices are reasonable and the food excellent. Arrive early in the summer to beat the crowds.
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The Olde Heritage Tavern
12 Housatonic StA blue collar, American fare restaurant in downtown Lenox. The prices are reasonable and the food excellent. Arrive early in the summer to beat the crowds.
A really cool Mexican restaurant located just over the N.Y. border. Great food, great service, outdoor bar and kitchen, fire pits, entertainment. A hidden gem of sorts.
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Norte Azul Cantina
15952 NY-22A really cool Mexican restaurant located just over the N.Y. border. Great food, great service, outdoor bar and kitchen, fire pits, entertainment. A hidden gem of sorts.
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Mt. Greylock
Drive to the summit of Mt. Greylock, the highest peak in Massachusetts. Parking at the summit is only a few bucks. Views of 3 states on a clear day. You can even enjoy dinner and jazz on the summit (Sundays only in the summer). Pick up a trail map at the Visitor's Center 2 miles away.
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Ramblewild Adventure Park
Book ahead for Ramblewild Adventure Park, a high-ropes course in the trees, located less than 2 mis away. It is expensive, but well worth it. There are various levels of difficulty.
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Hiking options:
Pick up a trail map before setting out. Or install the All Trails App. on your phone. Mount Greylock has many hiking options, including the Appalachian Trail. My all time favorite is Stony Ledge trail (from Williamstown). It doesn't go to the summit, but the Ledge overlooks a spectacular ravine.
For something much flatter, try Field Farm on Sloan Rd. in Williamstown. Take a short drive to Great Barrington and hike Monument Mountain. This a very popular hike with excellent views from the summit.
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Music scene
There are countless venues for live music. MassMOCA in N. Adams has regular year-round shows at 3 separate venues on campus. The Bascom Lodge on the summit of Mt. Greylock has jazz bands outside on Sunday evenings in the summer. The Stationary Factory in Dalton has regular bands. Of course there's Tanglewood in Lenox for popular artists and classical music. And there are dozens of small bars/restaurants with talented local musicians.
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farm stands
Visit one of the many local farm stands in the area for anything from fresh flowers to locally grown vegetables, honey, cheese, etc. Most are open summer and fall, but some are year round.