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.

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.

What to do in the Berkshires in the 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.

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.

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.

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

Plan on 2-3 hours.

 

Downtown Stockbridge

You may know Stockbridge from this famous Norman Rockwell painting.

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

The Berkshire 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.

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.

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

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

The Berkshires Fall Foliage Drive

Don’t miss one of the best attractions that the Berkshires has to offer in the Fall…the stunning fall foliage! One of the reasons we love the Berkshires in the fall is because we get to drive up Route 8 from Connecticut to Massachusetts. This is my favorite spot for fall leaf peeping in our part of New England. Of course the drive down Route 8 is just as beautiful as the ride up, so if you happen to be planning a visit, make sure to make this part of your trip.

Route 8 runs through charming New England towns and follows the flow of the Connecticut River. Due to its proximity to the water, the leaves change the most vibrant shades of orange and almost fluorescent pink. If you have always wanted to see New England fall foliage, this one won’t disappoint.

Where to Eat in The Berkshires

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!

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!

Where to Stay in The Berkshires

The Seven Hills Inn

This inn is in Lenox, Massachusetts and has 57 guest rooms. The rooms are simple and elegant and the hotel feels sumptuous while being moderately priced. You can play chess on the lawn with the oversized board, go for a bike ride, or sit by the indoor fireplace and enjoy the piano. You will feel like you have won the lottery while smugly knowing you have budget to spare.

For booking information click here.

 

Want to combine your long weekend to another charming fall destination? Visit nearby Saratoga Springs New York!

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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