Day Trip to the Berkshires, Massachusetts

On a weekend that our kids were away in August, we decided to escape the heat of the Boston area and take a day trip to the Berkshires in Western Massachusetts. After learning that this area was supposed to be at least 10° F cooler than anywhere else we were considering, we knew that we had picked the right destination!

The Berkshires themselves are the hilly area in western Massachusetts near the border with upstate New York, about 2.5 hours west of Boston.

There is a lot to do in the Berkshires, but in the end we decided to focus on scouting out the area so that we could figure out where we might want to bring our kids on a return trip.

Our itinerary included a scenic drive along the Mohawk Trail, a stop at the “Bridge of Flowers”, an exploration of Williamstown that included a visit to the Clark Art Institute, a drive through Lenox, a stop along a lake, and strolls through the downtowns of Stockbridge and Great Barrington. What a lovely day!

The Mohawk Trail

If you are driving between Boston and Williamstown, your best route will put you on at least 42 miles of the scenic Mohawk Trail (see driving tour 2), although there are quite a few other options if you want to explore this area more.

The Mohawk Trail was originally used long before the Europeans arrived in America, but once they did arrive it provided a handy way to visit various settlements and was eventually widened, and slightly shifted in certain places, to allow for wagon travel.

Bridge of Flowers

While we would have liked to explore the Mohawk Trail more, all we really made time for was a stop at the “Bridge of Flowers” in the town of Shelburne Falls.

Great choice! The town was small, but cute, and the bridge had an amazing assortment of flowers in full bloom! Even if you only stop for 10-15 minutes, you are sure to be delighted!


One surprise was after passing the Cold River, we saw a sign that welcomed us to Florida! No, not the state, but just a town with the same name. Another town that seemed oddly out of place for Massachusetts, but not so much for Florida, was the town of Orange.

Mohawk Trail State Forest

If we ever drive this way again, I am interested in venturing into the Mohawk Trail State Forest and exploring that area in more detail.


Our first lengthy stop was in Williamstown, home of Williams College. We spent some time exploring the college campus, the farmers market, the downtown, and then visited the Clark Art Institute.

The Clark Art Institute

The Clark Art Institute is amazing, well worth a visit, and could be considered a travel destination all of its own!

Given that Williamstown has a population of less than 8,000 people, we weren’t expecting much. That said, we were quite surprised on seeing walls with Monets and various French Impressionists. Not just those, but well-known 19th century American painters like Winslow Homer and such.

It turns out that a wealthy family from New York was looking for a location to publicly display their previously private art collection. Since they had ties to Williams College, this ended up being where the Clark Art Institute was founded.

On the day of our visit, the museum had “Images of Norway” on display as their special exhibit. Lovely!

In addition to the abundance of beautiful paintings, there are also plenty of decorative arts and sculptures. For some reason I was highly amused by this “Wind Rabbit.”

Behind the museum is a fairly extensive (and manicured) network of trails. If the idea of hiking entices you, but you are a bit nervous about the abundance of moderate and difficult trails in the area, these could be a happy compromise.

Destination: The Clark Art Institute

Location: 225 South Street Williamstown, MA 01267

Hours: Daily 10-5 in July and August. Closed on Mondays September-June.

Cost: $20 for adults, free for 0-17 and those with a valid student ID

Note that this art museum is mostly classical European art. If you are looking for modern or contemporary art, consider visiting the Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams instead.


If you want to listen to a Boston Pops summer performance at the Tanglewood, visit Edith Wharton’s home at the Mount, or watch a performance of Shakespeare & Company, Lenox is a great town to visit. Since we had no plans to do any of these things, we simply contented ourselves with a driving tour of the town.

Pontoosuc Lake

On our way to Stockbridge, we spotted a cute lake and pulled into a parking lot to explore it a bit further. It turns out that it was Pontoosuc Lake in Pittsfield.


Our next stop was the quaint, but cute town of Stockbridge. Think Norman Rockwell. The downtown area is only about 2 blocks long, so make sure you get out and enjoy the charm.

We saw there were some public bathrooms at the Town Hall, and while we were walking to them, we noted a lovely path that is maintained by the Laurel Hill Association. We walked on it for a bit until the bugs became mildly annoying, then decided to turn back.

Great Barrington

The last stop in the Berkshires was the town of Great Barrington.

Compared to all of the other towns we visited, this one felt much larger and more like a place that real people live. The downtown is quite extensive with plenty of shops and restaurants (slightly more practical than the others), as well as plenty of beautiful old buildings. If you are looking for a more lively place to base your time in the Berkshires, either here or in Williamstown would be great options!


On our way back to Boston, we decided to take a dinner detour into Amherst, a super cute college town in central Massachusetts.

Since we didn’t want anything elaborate, we decided to try Crazy Noodles, an Asian noodle house that has a strong Thai theme to the menu. Yum! Both the Drunken Noodles and the Yellow Curry Noodles were delicious!

If you are looking for a delightful road trip destination for your next vacation, consider the Berkshires!

Keep reading our travel blog to hear about more New England adventures:


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