Guides

The Berkshires is definitely a good place to live or visit….if you are an adult or young child. I have lived here for over 20 years and have raised 3 daughters who are now teenagers and young adults. While we agree this part of the state is very pretty and has been a safe place for them to grow up, we also agree that once they hit their teen years, there stopped being much for them to do. If you are planning a trip with teens to any of the beautiful towns that make up the Berkshires, I hope you find this guide helpful in finding places to go or things for them to do.

If you have a teenager who enjoys being outdoors, here are some local spots you won’t want to miss.

Laurel Lake in Lee and Lenox was always one of my daughters’ favorite places to go swimming. There is a trail teens can take from the back of the Lenox side of the lake that will lead them to a rope swing that many locals love to jump off of.

Lake Garfield in Tyringham is a gorgeous but small lake that my daughters all love to go to. It is very family friendly, but there is a dock that teens can swim out to and hang out in the sun away from smaller children.

Onota Lake in Pittsfield is also another popular spot for teens. There is a boat rental place as well there where teens can rent kayaks or canoes for the day to get space from younger siblings. My daughters have loved doing this and rentals are very cheap.

Green River in Great Barrington is extremely popular with local teens. There are multiple access points, but if your teen wants to find where the locals go, the trail off of Pumpkin Hollow Road is the one to use. Here they can walk down a short path to the river bank and spend hours floating in the lazy current.

There is no dearth of great hiking trails either. Kennedy Park in Lenox has miles of wooded trails that my daughters have loved taking our dogs on hikes on. October Mountain is another popular destination for teens who can drive because there are so many pull offs with beautiful views. October Mountain spans multiple towns, but is primarily accessed in Lee, Becket and Lenox. Pittsfield State Forest is very popular with teens who like to go mountain biking, so if you have an adrenaline junkie for a teen in tow, be sure to point them in this direction. Beartown State Forest in Great Barrington, Monterey, Lee, and Tyringham offers almost 200 acres of recreational space and is home to Benedict Pond, a popular meeting point for local teens.

The Lee Athletic Field always has some local teens playing basketball or tennis, using the skatepark or just hanging out in the pavilion. If your teen wants to make some new friends, I would definitely recommend having them spend an afternoon here. An added bonus is the Starbucks across the street or the sushi restaurant, Burmese Bowl, which is right next to the park.

If you have a teen who seeks adventure, then I recommend having them check out the ropes course at Bousquet Mountain in Pittsfield, or Ramblewild Adventure Park in Lanesborough. Ramblewild has been voted the best in the Berkshires for 9 years in a row and offers different levels of thrill seeking. Bousquet’s course is smaller but has suited my daughters just fine.

Bakers Golf in Lanesborough offers both a driving range and mini golf. Teens can practice their swing with a bucket of balls, or play the 19 hole mini golf course. Bakers also has Glow Ball mini golf experiences at night that teens love to play.

A longstanding popular meeting spot for local teens is The Cove bowling alley in Great Barrington. It tends to be crowded, especially at night, with local teens who want something to do for a few hours. This venue is a great place for your teen to meet people their age.

Great Barrington, in general, is a fun town for teens. There are a multitude of coffee houses, restaurants, and great shops for retail therapy. There are lots of places to sit and people watch, and during the summer months your teen might catch one of the popular Berkshire Busk street performances.

If your teen enjoys crafts or whimsy, then point them in the direction of Witchslapped in Pittsfield. This funky mystical shop offers different walk-in workshops where one can access a huge room of art supplies for craft making. They also offer Paint and Sips and tarot readings.

Mass MoCa in North Adams is a museum of contemporary visual and performing arts. They have incredible exhibits, pop up performances and a popular outside music scene where teens can meet up. My own kids have loved going there so I strongly recommend putting this on your own teen’s radar.

If you have a teen who is interested in chasing ghosts and haunted happenings, then here are two bonafide haunted places in Berkshire County. The Hoosac Tunnel in North Adams tops this list. Nicknamed The Bloody Pit, the Hoosac is a 5 mile railway through the Hoosac Mountain range. Back in the 1800s when construction began, almost 200 men died when fumes caused an explosion. The man who was responsible for causing the blast walked away unharmed, but a year later his body was found in the tunnel. It is believed that the ghosts of the men who died sought revenge, and today there continues to be reports of muffled cries, and lantern light coming from the tunnel. Mt. Greylock's Bellows Pipe Trail is another local haunted spot that your teen might want to explore. Legend claims that the ghost of a Civil War soldier from North Adams, Old Coot, can be seen going up the mountain on the Bellows Pipe trail.

I hope this guide helps your teen find some fun in the sun or excitement while visiting the Berkshires. This list is not exhaustive, but covers the most popular things that local teens enjoy doing around here in the summer.