Visit Like a Local

A list of not-to-miss gems to help you plan a perfect day in the Berkshires

Sometimes our most memorable travel experiences happen by happenstance, such as an amazing boutique tucked into an alleyway we discover as we walk by, or a trailhead for a lesser-known hiking spot when we take a wrong turn. One way to increase the probability of finding that Instagram-worthy experience is to ask a resident: Where do you like to go? What do you enjoy doing? And in the Berkshires, there’s no shortage of answers.

Here are 9 responses from residents showcasing a few of their favorite Berkshire things to inspire your next Western MA adventure…

Stroll the Ashuwillticook Rail Trail

Take a walk with your pup on the Ashuwillticook Rail Trail or rollerblade through multiple towns on the paved trail that winds through woods and flanks Cheshire Reservoir. Helpful tip, if you rollerblade from Adams to Pittsfield, when you return towards Adams you will be on a slight downhill decline, making the second half of your ride smooth sailing! After you’ve worked up an appetite, get take-out from Chee’s Chinese Cuisine. – Amanda

Go Skiing or Tune In at Tanglewood

In winter I love waking up to a bluebird day after a new snowfall and hopping into the car for a day of skiing, then as the day wanes meeting friends in Lenox for a tasty cocktail and tapas. In the summer we are all about Tanglewood – but before we pack up the perfect picnic and twinkle lights, you can find us swimming and paddleboarding in one of our many lakes. – Lindsey

Dance in Dalton

I really enjoy live music at the Dalton American Legion. – Kristen

Hike Greylock Glen

My favorite spot in the Berkshires is the Greylock Glen. Nothing is more relaxing than hiking with the dog while taking in the gorgeous 4-season views of Mt. Greylock. In winter, a crisp, snowy day with snowshoes is hard to beat! We also love spending Saturday afternoons at Bright Ideas Brewing, followed by a casual dinner at The Barn Kitchen & Bar at The Williams Inn, or maybe some Indian food from Spice Root. I’m also a big fan of golf and there are many courses to choose from. – Jonathan

Catch a Ball Game

A Pittsfield Suns game at Wahconah Park is my all time favorite way to spend a Berkshire afternoon. Afterwards, we enjoy getting a locally-brewed craft beer or grabbing a bite at one of North Street’s many great bars and restaurants. – Kevin

Savor the Day in North Adams

I adore a Saturday morning with my kids, taking in the City of North Adams. We start off at the North Adams Farmers Market where we pick out some superb produce, the kids play in the toy section while I make the rounds, grabbing bagels, lunch, and some sweet treats. From there we walk over to Berkshire Emporium for some Shire Donuts, juice boxes for the kids and an iced dirty chai for Dad. – Ben

Enjoy a Waterfall and Wine

One spot we really enjoy is the Cascade Trail. Although it’s not very long, it’s quiet, beautiful in the way the light filters in, and it leads to a peaceful, refreshing, and almost unexpected waterfall. Afterward, we often venture over to Balderdash Cellars in Richmond, truly my favorite Berkshires stop! – Cathleen

Meditate at the Lake

I love a quiet day spent at Cheshire Lake. It’s one of the most beautiful and serene places in the Berkshires to take a walk or sit and enjoy the view. It is also my favorite spot to kayak. – Christine

Picnic at The Mount

I always tell people to go have a picnic at The Mount. Tour the house (which is totally haunted), see the gardens and pet cemetery, and then relax on the stunning lawn with sandwiches from Guido’s Fresh Market Place – it’s especially gorgeous in summer but it’s worth a trip all year long. I also really love tooling around southern Berkshires – there are so many cute shops, bakeries, and coffee houses. – Elizabeth

Find more inspiration for where to play and stay in the Berkshires.

Funded, in part, by the Massachusetts Office of Travel & Tourism

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