things to do with kids in berkshire

7 Outdoor Things to Do with Kids in the Berkshires

Going on a family road trip to the Berkshires this summer? Are you looking for outdoor activities for you and your kids in the Berkshires? The Berkshires is an ideal road trip destination for families in the Northeast because it is a quick drive from NYC and Boston. The drive from NYC to the Berkshires is approximately 3 hours and the drive from Boston to the Berkshires is 2 hours and 45 minutes. I find the 3 hour drive very manageable for road trips with kids. Whether you go in the summer or winter, the Berkshires is a family friendly vacation destination. There are so many outdoor activities for kids in the Berkshires. Here are things to do with kids in the Berkshires this summer.

Things to Do with Kids in the Berkshires this Summer

There are a lot of things to do with kids in the Berkshires this summer from canoeing to kayaking to horseback riding. Kids of all ages will enjoy being active and outdoors in the Berkshires this summer. Below are 7 outdoor things to do with kids in the Berkshires. Even if your family is not “outdoorsy”, these kid friendly outdoor activities in the Berkshires are not extremely challenging. They are fun outdoor activities for kids.

Canoe with Kids on the Housatonic River

Canoeing is a family friendly activity in the Berkshires. Take a guided canoe tour with your kids on the Housatonic River. You will enjoy canoeing on the tranquil river as you admire the natural wildlife and the picturesque Housatonic river. Book a guided canoe tour with Berkshire Canoe Tours. The guides at Berkshire Canoe Tours will take you and your family through a 2 hour canoe tour on the Housatonic river. Their canoe tours are suitable for both novice and experienced paddlers. If you are looking for a kid friendly outdoor activity in the Berkshires, definitely consider taking the kids canoeing! Berkshire Canoe Tours starts at the Decker Boat Ramp at 298 New Lenox Road, Lenox, MA. Phone: 413-329-6017

canoe in the berkshire with kids

Kayak with Kids on Onota Lake

Kayaking with kids is a fun way to spend your afternoon in the Berkshires. Rent a kayak from Onota Boat Livery. Their dock is located on Onota Lake so there is no need to transport the kayaks. Single kayaks and tandem kayaks are available for rent from Onota Boat Livery. The kayak rentals are availably for hourly rentals, 4 hour rentals or 8 hour rentals. If you want a bigger boat, you can rent a rowboat which fits 3 people so you can paddle as a family on Onota Lake. If you are looking to fit 4 people, you can rent a canoe so mom, dad and 2 kids can all fit in one canoe to explore Onota Lake. Just know that Onota Lake is a big lake (617 acre), if you have little kids or you are not too keen on paddling, you may want to consider renting a motorized boat instead. There are motorized fishing boats for rent that are small in size (similar to canoes) and even comes with a paddle so your kids can do some paddling then when they get tired, you have the convenience of being on a motorized boat. Exploring Onota Lake with a hand steered motorized fishing boat is a lot easier than manually paddling! Life vests are included in all rentals. Onota Boat Livery rentals are available on a first come/first served basis. Onota Boat Livery at 463 Pecks Road, Pittsfield, MA. Phone: (413) 442-1724

onota lake berkshire with kids

Bike with Kids on a Paved Bike Trail in the Berkshires

Take the kids biking on a kid friendly bike trail through scenic Berkshires. Ashuwillticook Rail Trail is the perfect bike trail for kids because it is a paved and level bike trail. The 12 mile bike trail starts at Lanesborough and will take you through picturesque Berkshire pond, Hoosic River, woods and farmlands. Pack a picnic lunch so you can stop for a break during your Berkshires family bike ride. Ashuwillticook Rail Trail parking and entry points are located at Lanesborough, MA and Adams, MA. Bike rentals are available from Berkshire Outfitters. Berkshire Outfitters is located 300 yards from Ashuwillticook Rail Trail at Rt. 8 Grove St., Adams, MA. Phone: (413) 743-5900

Ashuwillticook Rail Trail Parking and Trail Access

Below are the trailhead entry points to the Ashuwillticook Rail Trail. There are also parking available at Ashuwillticook Rail Trail.

Lanesborough Trailhead: To reach the Lanesborough trailhead from I-90, take Exit 2 to the toll plaza and bear right onto US 20/Housatonic St. toward Pittsfield. In 0.7 mile turn right onto Main St. Go 0.4 mile, and turn slightly left to remain on US 20 W. Go 10.2 miles and turn right in Pittsfield onto MA 9/East St. toward Dalton/Northampton. Go 1.4 miles and continue straight onto Merrill Road, and then go 1.8 miles and bear left onto MA 8/Cheshire Road. Go 1.5 miles and turn left onto US 7/MA 8 Connector Road. Parking is on the left and the right after the turn.

Adams Trailhead: To reach the Adams trailhead, follow the directions above to MA 8/Cheshire Road. Go 12.1 miles north on MA 8/Cheshire Road, and turn left onto Center St./Park St. In 0.3 mile, turn right onto Hoosac St., and then take an immediate right onto Depot St.

To reach the Adams trailhead from the intersection of MA 2 and MA 8 in North Adams, head south on MA 8/State St. Go 5.5 miles and turn left onto Hoosac St. Take an immediate right onto Depot St. Parking is on the left. Cross Hoosac St. and continue 1.2 miles north to reach the endpoint on Lime St.

biking with kids in the berkshire

Go Horseback Riding with Kids in the Berkshires

Take your kids horseback riding in the Berkshires. Undermountain Farm located in Lenox, MA offers horseback riding lessons and trail rides for kids and for the entire family. Private lessons are available starting at 1/2 hour to get your kids comfortable on horseback. There is also an Introduction to Trail Riding which is great for novice riders because you will spend 30 minutes in the riding ring and 30 minutes on the trail. Although their trail rides are only available for riders 15 years and older. If you are looking to go horseback riding as a family in the Berkshires, there is family package for mom, dad and kids to learn the basics of horse care and to go horseback riding as a group. Pony rides are also available at Undermountain Farm. Horseback riding is a fun, kid friendly, outdoor activity to enjoy beautiful Berkshires. Undermountain Farm is located at 400 Under Mountain Road, Lenox, MA. Phone: 413-637-3365

undermountain farm berkshire with kids
Photo Credit: Undermountain Farm

Go on a Pontoon Boat with Kids in the Berkshires

Want to spend a day on a pontoon boat with kids on a lake in the Berkshires? Rent a pontoon boat for a relaxing day on Pontoosuc Lake. You can rent a pontoon boat by the hour or rent a pontoon boat for the entire day from Berkshire U-Drive Boat Rentals. Each pontoon boat can fit 6-10 people so you can even invite another family to join you on the pontoon boat. Pontoosuc Lake is a beautiful lake in Pittsfield, MA, you will enjoy cruising around the lake with kids. Pack a cooler with food and drinks for snacks and lunch aboard the pontoon boat. Kids will love taking a dip in the lake. If you are looking for an outdoor activity with kids in the Berkshires, definitely consider renting a pontoon boat for a relaxing day on the lake. Make your reservations in advance. Berkshire U-Drive Boat Rentals is located at 1651 North Street, Pittsfield, MA. Phone: (413) 281-4196 

pontoon boat things to do with kids in berkshire

Go on a Ropes Course with Kids in the Berkshires

Challenge the kids on a ropes course in the Berkshires. Jiminy Peak Mountain Resort known for family friendly skiing in the Berkshire, transforms part of the mountain into an aerial adventure park during the summer months- complete with rope bridges, swinging logs and zip line course for kids and adults. The ropes courses at Jiminy Peak Aerial Adventure Park are suitable for kids ages 6 years and up. It is a self-guided, elevated outdoor ropes course through the trees with varying levels from “beginner/easier” to “advanced” aerial courses. Jiminy Peak Aerial Adventure Park is located at 37 Corey Rd Hancock, MA. Phone: 413-738-5500

Ride a Mountain Coaster with Kids in the Berkshires

Go on a high speed Mountain Coaster with kids in the Berkshires! Jiminy Peak Mountain Coaster is an alpine roller coaster with thousands of feet of twisting, turning fun through the woods! You control your speed, enjoy the mountain views and take a leisurely ride or be a daredevil with speeds up to 23 mph. Adults can ride with kids ages 3 years and up. You can buy tickets for single rides or buy a pass to go on the other Mountain Adventure Park rides. The other rides at Jiminy Peak’s Mountain Adventure Park are Alpine Slide, Scenic chairlift rides, Giant Swing and a Euro Bungy Trampoline. There is also a rock climbing wall and a kids ropes course at Jiminy Peak Mountain Adventure Park. If you are looking for fun outdoor activities with kids in the Berkshires, definitely plan an afternoon at Jiminy Peak Mountain Adventure Park. Jiminy Peak Aerial Adventure Park is located at 37 Corey Rd Hancock, MA. Phone: 413-738-5500

things to do with kids in berkshire jiminy peak
Photo Credit: Jiminy Peak

Family Friendly Hotels in the Berkshires

Condo Hotels in the Berkshires

Below are family friendly condo hotels in the Berkshires. Staying at a condo hotel in the Berkshires is a great option for families traveling with kids because you will get more space and you will have a full kitchen.

Jiminy Peak Mountain Resort

If you are looking for family friendly hotels in the Berkshires, then definitely consider staying at Jiminy Peak Mountain Resort. The units at Jiminy Peak Mountain Resort are condo-style accommodations with full kitchens right on the mountain. You can book 1 bedroom units or larger. It’s convenient to stay right at Jiminy Peak Mountain Resort because you have easy access to mountain biking, hiking, Jiminy Peak Aerial Adventure Park and Jiminy Peak Mountain Adventure Park.

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook is a family friendly hotel in the Berkshires located at Jiminy Peak. Club Wyndham Bentley Brook hotel rooms are condo hotels with full kitchen. You can book a studio, 1 bedroom or 2 bedroom units at Club Wyndham Bentley Brook hotel. There are 2 pools at The Club Wyndham Bentley Brook, an indoor pool and a heated outdoor pool overlooking the slopes. There is also a large outdoor hot tub under a covered gazebo. Guests can also enjoy the Movie Theater, Arcade room and Arts and Crafts room at the Club Wyndham Bentley Brook. The hotel is very family friendly, it organizes family friendly activities for their guests such as Arts and Crafts, movie nights and family game nights/competitions. The Wyndham Bentley Brook is definitely a kid friendly hotel in the Berkshires.

Vacation Village Berkshires

Located down the road from Jiminy Peak, Vacation Village Berkshires is a large resort family friendly resort in the Berkshires built on top of a hill facing Jiminy Peak. The units at Vacation Village Berkshires are condo-style units with a full kitchen. There are a lot of family friendly amenities at this Berkshire hotel such as indoor and outdoor pools, movie theater, basketball court, outdoor hot tub, playground, fire pit, barbeque grills and an indoor arcade room. Even though it is a big resort in the Berkshire, the units are located in small 3 story buildings so you are only sharing the floor with a few units and you don’t have to walk down a long hallway to get to your room. Similar to the Wyndham Bentley Brook, Vacation Village Berkshires has organized activities from family movie nights to arts and crafts activities for kids.

Suburbs 101 participates in affiliate programs including Amazon Associates Program and may earn from qualifying purchases.

things to do with kids berkshire

You May Also Be Interested In:

10 Things to Do in Stowe with Kids this Summer

Kid Friendly Mystic, CT: Hotels, Restaurants, Things to Do

Connecticut Beachfront Hotels for a Weekend Getaway

Need a Real Estate Agent for your vacation home in the Berkshires?

Suburbs 101 has a free service to connect you with local real estate agents. Check it out!

About Suburbs 101

Suburbs 101 is an online lifestyle guide for the New York Suburbs of Westchester County, Long Island, Fairfield County and Northern New Jersey.  Get the inside scoop on what it’s really like to live in the New York suburbs through our interviews with local suburbanites and features on Food, Fashion, Home, Travel, and Local Events. Be sure to Follow Us on InstagramLike Us on Facebook and subscribe to our Monthly Newsletter.

Scroll to Top