The Berkshire County Bucket List
Welcome to The Berkshire Shopper’s Berkshire County Bucket List —a comprehensive list of things to do and see throughout the Berkshires. Carefully selected by our editorial staff, we combed Berkshire County to put together the ultimate list of well-known and lesser known places to visit and things to do and see this summer.
Whether you’re taking a scenic walk, enjoying a beautiful waterfall, listening to live music, going blueberry picking on top of a mountain, or just sitting and relaxing on the famous porch of the Red Lion Inn, there’s no shortage of things to do and experience.
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Hike to the top of Monument Mountain in Great Barrington as the sun sets. It can be a challenging hike, but with its breathtaking views of the surrounding Housatonic River Valley, you’ll have a front-row seat to one of the most gorgeous sights available the Berkshires that will make all that hard work worth it.
Check out a band at the Down County Social Club. This Sheffield spot is one of the coolest venues in the entire county. Tucked away in a New Orleans-style speakeasy, this intimate spot gets you face to face with some of the region’s best talents. The venue also offers open mic nights, so take the opportunity to show off your musical talents, too.
Take an adventure from tree to tree at Ramblewild in Lanesborough. Test your limits in a hemlock grove with more than 130 individual elements on eight courses will challenge even the most experienced outdoor adventurer.
If you’re a movie buff of any kind you must stop into the Triplex Cinema. Located in the heart of downtown Great Barrington, the Triplex offers three screens and a bold roster of Hollywood, independent and arthouse films. It’s also the host of the ever-growing annual Berkshire International Film Festival.
If you’re into beer — and who isn’t—and great food, stop into the Barrington Brewery on Stockbridge Road. The brewery offers a wide variety of beers brewed on-site, while the restaurant has a friendly atmosphere, along with an extensive menu.
Visit the beautiful Bash Bish Falls. This spot is not too difficult to hike and the pay-off is a magnificent waterfall that, when the water is flowing, will leave you floored with the raw power behind it.
Stop in at the Animagic Museum of Animation. A quirky museum in Lee, this spot showcases local talent and their role in animation and special effects in some of the biggest movies of the last 30 years from 2001: a Space Odyessey to The Matrix.
Take a train ride on the Hoosac Valley Service at the Berkshire Scenic Railway Museum. The rail serves as a living history exhibit for folks to explore the region.
Take a walk through Lake Mansfield, a beautiful pond with a small beach area and a boat launch. It’s especially lovely in the fall, with leaves changing and plenty of bird watching opportunities.
There’s no better place to end the day on Main Street, Great Barrington than a night of food and drink at The Well. This Great Barrington bar is always packed with animated locals and a friendly and hilarious staff that make you feel like you just walked into Cheers.
Reserve a campsite at Clarksburg State Park. The park offers 368 acres of outdoor opportunities.
Go window shopping on Railroad Street in Great Barrington. With everything from kitchen supplies, art galleries and clothing boutiques you’ll find yourself something to draw your interest along the town’s busiest spot for commerce. We recommend JSW’s Art Supply store for all of your crafting needs in a small, quaint space.
Sit at the counter at Joe’s Diner. Re-enact the famous Norman Rockwell painting “The Runaway,” at this Lee staple. The diner (and Joe) are featured in the famous piece.
Visit October State Mountain and search for the Wildman. The grounds at October State Mountain offer beautiful scenes that are some of the best in the Berkshires. And according to urban legends the preserve is also home to the Berkshires very own Bigfoot.
Travel along the Berkshire Beer and Cider Trail. With ten spots starting down at Big Elm Brewery in Sheffield and headed all the way to Northshire Brewery Inc. in Bennington, Vermont, you’ll find a bevy of amazing artisan brewers and cider makers.
Eat a SoCo Creamery ice cream cone. This is a must, and not just in the summertime. No one does ice cream better in the Berkshires than SoCo, with plentiful flavors and toppings it’s nirvana in a cone.
Laura’s Tower is a twenty-minute ascent at the end of Park Street in Stockbridge. The top of the metal tower provides a panoramic view of the 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.
Forking right at the end of Park Street in Stockbridge instead of hiking up to Laura’s Tower you can proceed to Ice Glen, a beautiful walk where you walk towards the tallest pines in Massachusetts through rocks and boulders where you can sometimes find snow or ice on a summer day, thus the name, a mystical haven.
Bowl a few frames at the Cove Bowling Alley in Great Barrington. This funky and fun location looks and feels straight out of the golden era of bowling. Rumor also has it that this location was the inspiration for the Cohen brothers’ classic, “The Big Lebowski.”
Snap a selfie in front of Lulu Cascade in Lanesborough. This waterfall sits in a natural ravine surrounded by trees.
Visit the Berkshire’s best kept secret — The Dream Away Lodge in Becket. The site that inspired Alice’s Restaurant is alive and well with great food and great music throughout the year. Be sure to sip a glass of wine by their fire pit and star-gaze at the clear, summer sky.
Make a South County historical site day trip. With the birthplace of W.E.B. Du Bois in Great Barrington, the site of Shays’ Rebellion in Sheffield, Mumbet’s Walk to Freedom and a number of significant Colonial American history locations throughout the Berkshires is the perfect place for any history buff. You can also view an “Alien Citing” plaque and memorial at Monument Park in Sheffield, don’t let it spook you!
Stop into the Starving Artist Café for a delicious crepe and a cup of coffee. When you’re finished, enjoy the work of local artists in the café’s gallery space. Located on Lee’s wonderful Main Street, the Starving Artist Café is a must for crepe-craving coffee lovers.
For an exciting night out at the theater, catch a show at the Mahaiwe Center for the Performing Arts, which is billed as the leading year-round presenter of performing arts, film and educational programs for the Berkshires and neighboring communities. A lovely restored French Renaissance Revival theatre, the Mahaiwe features numerous dance, music, theatre, opera and film events year round.
Stop in for an exquisite dinner at the Prairie Whale, a casual-but-funky Main Street staple focused on farm-to-table fare. Their grass-fed burgers are fantastic and a must-try.
Head over to the Guthrie Center, located in the former Trinity Church in Vandeusenville where Alice Brock — of Alice’s Restaurant fame — and her husband Ray lived for many years. Berkshire native and folk legend Arlo Guthrie founded the center in 1991 to provide a place to bring people together for spiritual, cultural and educational exchange.
Pay a visit to Windy Hill Farm, a diverse horticultural operation consisting of a 7-acre apple orchard, a one-acre blueberry field, eight acres of field-grown specialty ornamental nursery stock, a retail garden center and a full-service landscape department.
Visit Ski Butternut for its annual Berkshires Arts Festival. Featuring musical acts and the works of local artists and more, the Berkshire Arts Festival is a staple of the Berkshires’ summer offerings.
If you’re a camper, head over to Prospect Lake Park, which is open from the first weekend in May through Oct. 15 and is set along 2,000 feet of wooded lakeshore. The park offers 125 shaded or sunny campsites accommodating everything from the smallest tent to a 36-foot RV. There are also cabins for rent.
Hit the best pool in South County at the Kilpatrick Athletic Center at Bard College at Simon’s Rock in Great Barrington. Open to the public for a fee, the center boasts an Olympic-size swimming pool as well as racquetball, yoga classes, rock climbing, weights and aerobic workouts.
If you’re a dog owner, take your furry best friend to Egremont’s French Park. A haven for pets and people alike, you’re sure to have a wonderful day out in the Berkshire summer sun
Spend the day at Jacob’s Pillow in Becket. The world’s best dancers descend on this slice of Becket forest every summer, giving Berkshire residents and guests alike the rare opportunity to experience global dance in a beautiful, natural setting.
Head to Egremont and listen to a live show at The Barn. This rustic barn space provides a special setting for visiting and touring musicians. Their tavern is also home to several on-tap beers and delicious food. For those that are feeling brave, there’s an open mic every Wednesday that’s free of charge.
Take a painting or ceramics class at IS183 Art School in Stockbridge.
Listen to the distant sounds of a Boston Symphony Orchestra concert from a boat in the middle of Stockbridge Bowl.
Kayak or paddle your canoe at Goose Pond Reservation in Lee.
Indulge your french fry craving and enjoy a box of garlic and truffle fries from Great Barrington’s roadside Bistro Box. Sit at the picnic table, play some field games, and enjoy the summer shade.
Visit the dreamy Berkshire Botanical Gardens in Stockbridge.
Swim and sun yourself at the gorgeous Sandy Beach at Laurel Lake. Pretend you’re a $1,000-a-day guest at Canyon Ranch in Lenox.
Take in a show at Barrington Stage Company. With nine shows on two different stages this season, there will surely be something for everyone to enjoy.
There’s no need for snow to enjoy Bousquet. Whether you take in 18 holes on their disc golf course, go down their water slides a few times or take to the air at the Aerial Adventure Park, Bousquet is the place for some fun in the sun.
Hike Mount Greylock, the state’s highest peak and the site of Ilvermorny, the American version of Hogwarts. Herman Melville and Henry David Thoreau each famously took inspiration from the mountain and its impressive vistas.
Stop and smell the coffee at No. Six Depot Café in West Stockbridge.
Play one of more than 100 of Gunnar Schonbeck’s unconventional instruments, which are on display at the Massachusetts Museum of Contemporary Art, in an exhibit aptly titled “No Experience Required.” The collection includes drums made from aircraft fuselages, a towering 9-foot banjo, a steel-string harp, and ukuleles made from coconuts.
Hike the Jones Nose trail on Mount Greylock and witness stunning views of Berkshire County and beyond. The trail brings hikers through varied terrain, including woods, fields, and clearings.
Get a beer card started at the Olde Forge Restaurant in Lanesborough.
Take a boat out on to Onota Lake and see the beauty of the Berkshires from a different angle.
Spend a day visiting a magnificent Gilded Age mansion like Ventfort Hall in Lenox or Naumkeag in Stockbridge.
Get a Kripalu Day Pass and see what’s on the Rest & Relaxation schedule. Take a yoga class, attend a workshop, go kayaking, or go for a hike.
Grab a book and tuck yourself up against a tree in Otis State Forest.
Watch the New Baroque Soloists at St. John’s Episcopal Church in Salisbury, CT, part of the area’s Northwest Music Association summer concert series,that takes place on Wednesdays at 5 p.m.
Pick up some original pottery, weaving, candles, furniture, jewelry and more at Mountain Goat Artisans in Williamstown.
Have some kielbasa, kapusta, golumbki or pierogi at the annual Polish Picnic on the grounds of St. Joseph’s Church.
Tour the sculpture gardens at The Mount on a beautiful day; then return on a cloudy day for a guided tour of the country home author Edith Wharton called her “first real home.”
See a performance at MASS MoCA in North Adams. One of the best arts centers in the Northeast, MASS MoCA also offers an amazing lineup of musical acts. With a multitude of spots to see a show, the experience is every changing.
Grab your binoculars and go birding at Mass Audubon Canoe Meadows Wildlife Sanctuary.
Pick up a new skill or trade at BCC. Berkshire Community College offers courses throughout the summer, open to folks of all ages.
Visit Arrowhead, the home of Herman Melville, the great 19th century American author, and see where he wrote his timeless classic “Moby Dick.” Check in on the Berkshire Historical Society’s heritage breed chickens and goats while you’re there.
Take a stroll through Pittsfield and admire the results of the Artscape initiative, designed to “enhance the overall character” of the downtown space, beautifying the thoroughfare with breathtaking paintings and sculptures.
Grab some friends and try an escape room at Greylock Bowl & Gold and celebrate the win — or cry over the loss — with a burger and beer at PUBLIC eat+drink, a gastropub in North Adams.
Go to a First Fridays Arts Walk and a Third Thursdays event in downtown Pittsfield. The events feature great food, music and art, and are always a lively affair with plenty of food to sate your appetite.
Canoe down the 149-mile Housatonic River. Use a boat launch at Fred Garner Park or Decker Landing to begin your journey.
Spend a day at the Pleasant Valley Sanctuary. Set amid more than 1,000 lush acres in the Berkshires, Pleasant Valley’s varied trails wind through forests, meadows, wetlands, and along the slopes of Lenox Mountain, making this site an excellent location for easy to strenuous hiking.
Ride your bike down the 11-mile Ashuwillticook Rail Trail from the Berkshire Mall to the center of Adams. Enjoy views of the Cheshire Reservoir and Hoosic River along the way.
See a flick at Images Cinema, a historic venue showing classic, independent and foreign films both indoors and outdoors over the summer.
Test your endurance with the Notchview Ultra in Windsor. Runners can join together to run, celebrate and test their limits for as much as three days or as few as three hours.
Visit the North Adams Public Library. With a rich 130-year history and the commendable distinction of being the state’s first “green” library with solar panels on the roof and geothermals in the basement, it highlights how the Berkshires combine the old and new with class.
Stroll through Wahconah Falls State Park in Dalton and capture its scenic waterfall and post it to Instagram with the #bucketlistintheberkshires.
Take a hike or bike through the Pittsfield State Forest, and be sure to make an adventure out of the Berry Pond when you come through this 11,000-acre forest with 30 miles of trails.
Dine el fresco with some fish tacos and a beer at the Purple Pub in Williamstown.
Go out for a night on the town. A walk through downtown Pittsfield will present a plethora of options for a night of revelry.
Moo-sey on over to Cricket Creek Farm in Williamston to meet the livestock.
Sample some maple syrup or even maple cream at Sweet Brook Family Farms in Williamstown.
Head to Pittsfield for the 4th of July Parade, which is one of the biggest in New England. This year’s theme for the parade is Past, Present and Future, connecting the eras of life in Berkshire County.
Behold the Natural Bridge in North Adams, the only naturally formed white marble arch and man-made white marble dam in North America.
Say “cheese!” at the Cheshire Cheese Press monument and learn about the Cheshire Mammoth Cheese — a gift from the town to President Thomas Jefferson in 1802.
Visit Housatonic’s Ramsdell Library for its Sunday afternoon hours; a popular program that always makes the most for local families. Reading takes no holidays.
Take a dance class with Moving Arts Exchange (MAX) or another one of the Berkshires’ treasured arts nonprofits. There are options for dance professionals or the complete novice so long as you’re willing to move, grow, and learn.
Take the kids to Whitney’s Farm Market and Country Gardens, where they can enjoy a petting zoo, play space, and dairy bar while you shop for plants and produce.
Strike a yoga pose with next to a goat at Hancock Shaker Village in Pittsfield. Goat Yoga allows participants to connect with nature and themselves through fitness. Bring a towel, mat and an open mind.
Go see one of America’s oldest community theaters and take in a production by the Town Players of Pittsfield, who are now in their 98th season of entertaining the Berkshires.
Check out a Pittsfield Suns game at historic Wahconah Park. Erected in 1919, the park has been the home field for 16 different teams from summer ball all the way up to AA, with a number of Major Leaguers making their home in Pittsfield. Go see tomorrow’s stars today.
Get lost in an exhibit at The Clark in Williamstown. Between the institute’s library, expansive collections and lecture offerings, any museum-goer is sure to have a good time.
across the border:
Just a few miles north of the point where New York, Vermont and Massachusetts meet lies a rare geophysical feature called the Snow Hole, a 50-foot chasm in the Taconic Mountains that stays icy year-round. Fairweather hikers beware – the trail up can get steep.
Bite into a grass-fed beef burger at the Grazin’ Diner in Hudson; a classic retro-style atmosphere with booths and tables that would make Norman Rockwell proud.
Take a day trip to Winstead, Connecticut, the hometown of longtime consumer advocate Ralph Nader. Don’t skip the museum he founded there: The American Museum of Tort Law.