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5 things you must do in the Berkshires this fall

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5 Things you must do in the Berkshires this Fall

How many of you are James Taylor fans? If you are you know the verse in Sweet Baby James that talks about the Berkshires in winter. I have wanted to visit the magical sounding Berkshires since I first heard that song in high school.

Well it turns out the Berkshires are just as magical as I’d hoped, but my favorite time to visit is in the fall.

Hancock Shaker Village view-0869

The Berkshires are a rural area in the southwest corner of Massachusetts. They are famous for outdoor activities, leaf peeping and being the summer home of the Boston Symphony Orchestra.

Here are the things you can’t miss when your travel with your kids to the Berkshires.

5 Best Things you must do in the Berkshires this fall:

Hancock Shaker Village

You and your kids will take a step back in time to the 1800’s and live the life of a Shaker. The Shakers were a religious group founded in England in the 1700s. They traveled to America to escape religious persecution.

Hancock Shaker Village round barn-0859

The spread out across the Northeast and formed communities based on farming, communal living, and equality. They also believed in celibacy and lived together as brothers and sisters. This belief and the advent of the industrial revolution lead to the dying out of the Shakers here in Hancock, Massachusetts.

Hancock Shaker Village tree-0862

In addition to viewing the buildings at Hancock Shaker Village they have interactive programs geared for kids.

We watched their beehives be extracted into honey. The kids were able to play with the chickens that hung around the round barn. My youngest helped take a goat for a walk.

Hancock Shaker Village goat-0880

There is a discovery barn with kids activities. My kids enjoyed the dress ups, weaving, and the games.

Plan on 2-3 hours.

Hancock Shaker Village cow-0872Hancock Shaker Village animals-0883Hancock Shaker Village (1 of 1)


Downtown Stockbridge

You may know Stockbridge from this famous Norman Rockwell painting.


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Although there has been some modernizing of this charming town, the main landmarks are still there. You can visit the Red Lion Inn for a meal or to stay overnight.

The beginning of December every year, the town of Stockbridge recreates Rockwell’s famous painting. They bring in old cars and dress the business as they did in the painting. If you can get there, you will be enchanted. Check out details here

Plan on 30 minutes to an hour to walk around Stockbridge

Norman Rockwell museum

This is an art museum a kid will love. Norman Rockwell is best known for his illustrations in the Saturday Evening Post. His art captures small town America in all its peculiarities. His art is humorous, touching and sentimental.  He is also a great artist for kids to understand, as many of his paintings feature kids in funny situations.
This photo of Norman Rockwell Museum is courtesy of TripAdvisor

In addition to the gallery of Norman Rockwell museum, there is a kids activity room in the basement.

Plan on 1-2 hours

Fall festival

The Berkshire fall harvest festival takes place the beginning of October every year.


It is held at the Berkshire botanic gardens and has booths with food and handicrafts. It features demonstrations like cheese making, weaving, and farming. There is a hay maze for the kids to play in.

My kids really loved the wish tree, where you could write down your wish and tie it to a tree.


Plan on 3-4 hours

The Mount

This was the home of the famous writer Edith Wharton.  There is a tour of her home, but really the best part of this tour is the extensive gardens. Even in the fall, they are beautiful.

garden at The Mount in Lenox Massachussetts

Although this may not be your kids favorite stop, they do a good job of making it child friendly. There is a scavenger hunt provided for the kids during the home tour, and the gardens are large, and the kids have lots of free space to run.

kitchen at the Mount

In October, there are also ghost tours available at the Mount.

formal garden at The Mountformal garden at The Mount 2

Plan on 2-3 hours. More if you want to hike on their trails.

Good Eats:

Bistro Box

If you love unique flavors combined with good old fashioned food, this is a must stop. We happened upon this place a number of years ago, and were so thrilled with the food, we have been back half a dozen times. The number one thing you want to order is the fries!

bistro box friesbistro box food

They have 3 different gourmet fries and it’s hard to pick but I think my favorite are the parmesan truffle fries. Also delicious is the box burger, which pairs garlic aioli with tomato bacon jam. You can eat your food in the area behind the kitchen and play games too!

bistro box seating


If you want more day trip ideas from Boston? Check out my best day trips from Boston post.

Want more ideas for things to do in the Berkshires? Click here.

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Hancock Shaker Village is a must visit in The Berkshires. Fun for the entire family with farm animals, demonstrations, and music. #theberkshires #familytravel


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