Massachusetts’s Small Towns Shine on This Charming Day Trip

We start our driving journey out in Western Mass in the historic town of North Adams. Located on the Hoosic River, this was once a mill town. Today, North Adams is a fantastic day-trip destination with shops, restaurants, and hiking options like the trails at Natural Bridge State Park. North Adams is also home to MASS MoCA, one of the largest contemporary art and performing arts centers in the U.S. 

Of all the small towns in Massachusetts, Shelburne Falls has to be among the most unique. First of all, the village is listed as a National Register Historic District, and you will find numerous preserved historic buildings here. A second point of interest is its set of 50 glacial potholes in the riverbed of the Deerfield River that runs through town. 

These geological wonders range in size from 6 inches to 39 feet in diameter. While in town, you must also see the famous Bridge of Flowers, a 1908 trolley bridge that is now a pedestrian bridge with a garden. It’s open seasonally, so keep that in mind during your visit to Shelburne Falls.

Set in Franklin County, Greenfield is the county seat and is a larger town than the others on this road trip. Park on Main Street, where myriad shopping and dining options await. You can also wander along the Downtown Greenfield Abolitionist & Underground Railroad Art Walk. Poet’s Seat Trail is another point of interest in Greenfield and is located at Rocky Mountain Park.

If you want to grab a bite to eat while in town, check out the delicious Italian cuisine at Village Pizza.

Our last stop on this delightful day trip is the town of Northfield, home to fewer than 2,800 people. In this picturesque town, you can have a tasting at Cameron’s Winery & Cidery, get some fresh air at Great Falls Discovery Center, and try the brews at The Brewery at Four Star Farms.

Now that we’ve explored some of the most charming small towns in Massachusetts on this day trip driving tour, you’ll probably need some rest. Sure, you can head home—but what’s the fun in that?

If you have the time and would like to extend your day trip into an overnight getaway, a stay in the Minimalist Forest Retreat is a great idea. Set on 20 acres of private forest, you’ll enjoy solitude as you reconnect with nature.