The Berkshires Family Vacation Fun in beautiful Western Massachusetts!

The Berkshires can be an ideal destination for a family vacation. And my friend Laura has lived most of her life in this scenic area of New England. I’ve asked Laura to provide her favorite destinations and attractions in the Berkshires for my visitors…

The Berkshires located in the beautiful hills of Western Massachusetts are most known for their cultural activities such as Tanglewood and Shakespeare and Company.

Coming to the Berkshires with your family can be a fun summer vacation filled with outdoor activities such as hiking, canoeing, swimming, fishing, as well as exploring cultural activities with your children.

Let’s explore some of the best family fun that can be found from North to South Berkshire County.

Pittsfield 4th of July Parade:

This annual tradition has been a part of the Berkshires since the 1800’s but didn’t become the spectacle it is until the 1970’s when a group of citizen volunteers took over the preparation.

USA Today calls the Pittsfield parade “among the best in the country.”

Every year has a different lineup but you can always count on numerous marching bands, shriners on pimped out go carts, large balloon animals, drum corps, horses, fire trucks, etc with the Air Force Blue Angels doing a fly over during the parade.

The parade starts at 10 am on July 4th, plan on getting a spot early along the route, which starts on South Street and continues straight up North Street. Fireworks that evening throughout Berkshire County including over Pittsfield’s Wahconah Park.

The Berkshire Scenic Railway:

The Berkshire Scenic Railway main station located in Lenox, with stations located in Lee and Stockbridge.

This classic train is a diesel locomotive pulling several passenger coaches through some of the most beautiful rural scenes in the Berkshires. The ride takes approximately 90 minutes from Lenox to Stockbridge and back.

Passengers can go one way and visit downtown Stockbridge, which is a short walk from the train station. There is also an option of getting off at the Lee station which has a trolley stop available for exploring downtown Lee and the Prime Outlets shopping area.

Narration is provided on board by your conductor, pointing out various spots of interest and offering history of the trains and their importance to the history of the area.

Catamount Adventure Park:

The Catamount Adventure Park in Egremont, is a newly opened rope course modeled after popular European adventure parks, which have bridges, rope and zip lines, that course through the tree tops from platform to platform!

Courses are designed for every skill level – from beginner to advance. The area advertises its use for ages 8 through adult, with the more advanced courses requiring adult supervision if your under a specific age.

The Catamount Adventure Park is also home to Catamount Ski Area, the scenic views from treetop and mountain top are worth the price of admission.

Berkshires Family Vacation Amusement Activities:

Pontoosuc Lake BeachPitch n PuttThunder AlleyBakers Golf Center located on the Pittsfield/Lanesboro line offers a multitude of choices for family fun!

There is a miniature golf course and driving range with a go cart course next door. There is also an 18 hole Par 3 golf course which is a perfect beginner course for kids to learn the basics of golf. If your looking for a day filled with fun activities for kids, this is the place.

Start your day across the street at The Donut Man or at Rita Marie’s for breakfast, head over to play 18 holes of golf with the kids. Then enjoy lunch at several small restaurants located within walking distance or take a picnic over to the public access beach on Pontoosuc Lake.

When you’ve done some swimming and want more to do, wander over to Wet n Wild Rentals for a jet ski or paddle boat rental.

Later in the afternoon, check out Thunder Alley go carts or the Bakers Mini Golf Course to wind down your day. Go home, collapse and get ready for the next day’s adventures!

Jiminy Peak Adventure Park:

Jiminy Peak Adventure Park located in Hancock, also the home of Jiminy Peak Ski Resort and the Zephyr wind turbine, has a family adventure park that includes an alpine slide, a mountain coaster, rope adventure area, rock climbing wall, giant swing, scenic chair lift rides, and a giant spider web slide just to name some of the activities!

An entire day can be spent doing any or all of these activities, but if you want to stretch it out for several days, the resort offers several options for lodging. A hotel, condos and timeshares are available for lodging throughout the year.

Walking and Hiking on a Berkshires Family Vacation:

Inexpensive Family Fun-Hiking in any of the Berkshires State Forests is an inexpensive family outing. Most State Forests have free parking at trailheads to begin your hike along with detailed maps that point out areas of interest along the way such as scenic vistas, waterfalls and gorges.

The Appalachian Trail or “AT” as most folks call it, has 90 miles that run through Berkshire County with numerous spots to hop on or off for a day hike.

Some popular day hike entry points are Race Brook Falls in Sheffield, Benedict Pond in Monterey, Jacobs Trail off Rt 20 in Lee, Washington Mt Road in Washington, Ashuwillticook Rail Trail, Mt Greylock Reservation, and Clarksburg State Forest.

Several of these day hikes, including the one from Benedict Pond in Monterey, will lead hikers to lean-to shelters for overnight camping if desired. There is a cabin available on first come, first serve basis at Upper Goose Pond in Lee for hikers on the AT near Lee and Tyringham.

Messing About on the Water:

Kayaking is a great family outing and the Berkshires have numerous lakes, ponds and rivers for this activity. You can bring your own or rent from several locations, such as Arcadian Shops, Lenox or Berkshire Outfitters in Adams.

Zoar Outdoors in Charlemont offers white water rafting on the Deerfield River.

A favorite kayak trip is down the Housatonic River, leaving from Canoe Meadows or New Lenox Road in Lenox and going downriver to Woods Pond. Many different species of wildlife can be seen on this stretch, from the occasional bald eagle to otters, beavers, deer and coyote.

In the summertime there are concerts performed at Windsor Lake with free parking and admission for the family. Food is available but families are welcome to bring a picnic basket and a blanket and enjoy fresh live music.

This area of Massachusetts has so much to offer for any type of vacation but especially for families.