Here are some of our favorite places to go depending on how adventurous your family is!
Pumpkin carving
Family Harvest Festival in the Berkshires
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Benedict Pond
65 Blue Hill Rd., Monterey, MassachusettsBenedict Pond in Beartown State Forest is the perfect family getaway. It is a pond without any development on its shores and is great for canoeing and kayaking. The water is clean and there are plenty of nearby trails to hike on including a section of the Appalachian Trail.
Insider's Tip: For the adventurous and organized family, camping is also an option here, but sites fill up fast.
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Berkshire East Mountain Resort
66 Thunder Mountain Rd., Berkshire, Massachusetts 01339No matter the season, there is excitement to be found at Berkshire East. From a mountain roller coaster to world-class mountain biking and aerial adventure, the summer is very active on the mountain. In the winter, the snow sports activities are abundant and understated, so it is a great spot if you are looking to avoid the crowds of the larger resorts.
Insider's Tip: Be sure to experience the white water adventure if you are there as it is some of the best and most reliable in New England.
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Blue Riders Stables
15 Farm Ln, Great Barrington, MassachusettsBlue Riders Stables is the most reputed spot for children and families to go riding and take lessons. You can even learn how to ride without a saddle here. Safety is a top priority and the staff is very kind.
Insider's Tip: Parents should really join in on the fun for shared family experiences make them even more special.
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Candle Lanes
255 North St., Pittsfield, Massachusetts 01201For those rainy days or evenings when relaxing does not seem to an option or appealing to the family, get some bowling in at this local favorite bowling alley. It's not fancy, but it is very charming.
Insider's Tip: Pittsfield has some great restaurants for the family. Check them out in our food section.
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Catamount Aerial Adventure Park
17 Nicholson Road, South Egremont, Massachusetts 12529Located in a beautiful rural area of the Berkshire Mountains, Catamount Aerial Adventure Park is an exciting aerial forest adventure that allows you to experience an unmatched variety of tree-top courses that are fun for all ability levels. Situated near the base of the ski resort the aerial park lies in an all-natural setting far from the noises of cities and suburbs. The park is sited between several ski trails among hundreds of trees whose canopy is waiting for you to explore. With 12 courses of varying difficulties you are challenged to cross bridges, climb ladders, maneuver through obstacles and soar on zip lines.
Insider's Tip: Make sure your child is old and big enough to participate as it is only for ages 7 and up with the suggested minimum height is 48″ and maximum weight is 265 pounds.
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Catamount Ski Area
78 Catamount Rd,, Town of Egremont, Massachusetts 12529If you like night skiing, this is definitely the place to do it. It is a beautiful mountain with some varied terrain which is great if you are just taking up snowboarding, for instance. There is one trail that is almost two miles long and with a vertical drop of 1,000 feet.
Insider's Tip: Catamount sometimes has special deals so be sure to check with their latest promotions.
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Great Barrington Farmers’ Market
18 Church Street, Great Barrington, MassachusettsThis is a great place for the whole family with food to eat, goods to look at and live music to dance and listen to. If you want a good insight into the culture of the local community, this event is a must. It is located right in downtown and is accessible to the toy store and ice cream shops.
Insider's Tip: Bring cash to this event, as many vendors here do not accept cards.
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Greylock Bowl & Golf
Our center contains 30 classic wooden lanes with modern automatic scoring, which provides a unique and accessible experience for both casual and league bowlers! They offer a totally interactive experience for all ages. They have bowling, golf simulators, pool, darts, air hockey, corn hole and an array of games for everyone to enjoy.
Insider's Tip: This is a great spot for indoor adventure, but if you are looking for actual versus simulated golf, you may want to look at some of the other sites such as Bousquet.
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Hawthorne Valley Farm Fall Festival
327 County Route 21C, Ghent, New YorkLocated just over the border, this is one of the best family events of the year in the region with games, activities and best of all-- puppet shows! For over 20 years, Hawthorne Valley has offered the Fall Festival as a free public event to thank our donors, customers, volunteers, community members, and local vendors for their support and partnership. The Festival is the perfect opportunity to get to know the area and experience the beauty of autumn in Columbia County. Over the years, the Festival has grown into a seasonal favorite with over 3,000 people attending
Insider's Tip: Carve your own pumpkin and be sure to check out the hay bale maze
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Housatonic Flats Trailhead
439 Stockbridge Rd, Great Barrington, Massachusetts 01230This is a great way for the whole family to experience the natural heritage of the southern Berkshires. It is not remote, but rather located just on the outskirts of the town of Great Barrington. Despite this proximity, the trail leads to some very scenic sections of the Housatonic River.
Insider's Tip: Although this river looks very pristine, it is not suitable for swimming. If it is swimming you are seeking, try the Green River further to the south.
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Jack's Hot Dog Stand
12 Eagle Street, North Adams, Massachusetts 01247Open the door to Jack's Hot Dog Eagle Street eatery and several things hit the consciousness: the sizzle of a hot grill, the crowd jam-packed at the counter, and the organized chaos guided by cook and business owner Jeff Levanos. This place has been around for more than a century!
Insider's Tip: Every month, Jack's Hot Dog Stand holds a contest to see who can eat the most hot dogs in one sitting.
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Kennedy Park
91 Pittsfield Rd., Lenox, MassachusettsThis is a great local park with a very wild feel. It is large and borders some of the most wild sections of Lenox. It is located right near Pleasant Valley Wildlife Sanctuary as well. There is some great skiing to be experienced in these woods in the colder months and great mountain biking in the warmer seasons.
Insider's Tip: The entrance to the park is walkable from the center of historic Lenox.
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Monument Mountain
600 Stockbridge Rd., Great Barrington, MassachusettsThis hike is a Berkshire rite of passage. From the 1,642-foot summit of Squaw Peak, you’ll enjoy views as far north as Mount Greylock, near the Vermont border, and, in the western distance, the Catskills of New York. Hawks (and even the occasional bald eagle) soar gracefully above the serene Housatonic River Valley spreading below.
Insider's Tip: This hike gets very crowded during the busy times of year so if you are seeking quiet, you may want to look elsewhere. There is also a parking fee.
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Mount Greylock State Reservation
30 Rockwell Road, Lanesborough, MassachusettsMake no mistake of it, there is no easy trail up Mount Greylock. There is however, a road and yes, you can take your whole family up this tallest peak in Massachusetts. Be sure to get out and hike from the summit though, as the woods here are breathtaking. For those families with more mature children, the Cheshire Harbor Trail is the easiest way up and is about 6 miles round-trip.
Insider's Tip: Occasionally there are events at Bascom Lodge on the summit so you can coordinate your trip accordingly or even spend the night there.
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Pleasant Valley Wildlife Sanctuary
472 W Mountain Rd., Lenox, MassachusettsSet amidst 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. While exploring, there’s a good chance you will see evidence of the sanctuary’s most visible wildlife resident, the beaver, via dams, dens, or lodges.
Insider's Tip: There are educational programs for the whole family here so check their calendar for events.
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Ramblewild
Ramblewild
110 Brodie Mountain Rd, Lanesborough, Massachusetts 01237At Ramblewild, the focal point is a central wooden platform about ten feet above ground from which eight aerial obstacle courses originate, meandering from tree to tree at various heights through the forest. Each course consists of 15-17 elements (high wires, zip lines, balancing logs, rope ladders, cargo nets, suspended bridges, etc.) that meander through a pristine hemlock forest. Their tree-to-tree challenge courses are designed to have a profound impact on visitors’ self-confidence and happiness.
Insider's Tip: There are usually coupons out there for Ramblewild, so be sure to search before your trip.
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Ski Butternut
380 State Rd, Great Barrington, Massachusetts 01230This is a great all terrain ski area with one of the best ski schools in the area. There is also a great tubing park if you are looking for something different from skiing and snowboarding. It is located right near downtown Great Barrington.
Insider's Tip: Since it is located so close to town, the option to eat lunch in town is very possible.
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Stockbridge Bowl (Lake Mahkeenac)
55 Interlaken Rd, Lenox, MassachusettsAlthough this lake is artificially dammed, it is a very beautiful natural area. It is very shallow which results in an abundance of weeds in the height of summer. This can make swimming less pleasurable in certain times of year. It is a great lake to explore by boat with wonderful views up to Olivia's Overlook and the surrounding Berkshire Hills.
Insider's Tip: This is a very inhabited lake in the summer months so if it is peace you are after, you may wish lo look at one of the surrounding lakes.
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Photo: Jon Titus
Tanglewood
297 West St., Lenox, Massachusetts 01240Tanglewood, on a vast, green property in the Berkshires region of Massachusetts, is the summer home of the Boston Symphony Orchestra and the Boston Pops. From spring through fall, Tanglewood hosts a large variety of live music performances. Today Tanglewood annually draws over 350,000 visitors. Each season offers not only a vast quantity of music, but also a vast range of musical forms and styles, all of it presented with a regard for artistic excellence that makes the festival unique.
Insider's Tip: Keep an eye out for the Family Fun Fest which includes unique opportunities for the whole family such as an instrument park!
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