Massachusetts' Most Picturesque Drive Is This Historic Byway With Serene Forests And Majestic Bridges

In autumn, lots of travelers head to New England destinations like the Berkshire Mountains to see fall foliage — according to the Old Farmer's Almanac and its predictions for 2025, the region will see peak colors in mid-October. The coming weeks are also an ideal time to hit the road for a scenic trip on the Mohawk Trail, one of Massachusetts' most picturesque drives. 

Named by Thrillist as the state's most beautiful highway in 2024, the historic route was once a footpath used by Native American hunters and fishers, and later by European settlers and traders. It begins near the Massachusetts-New York border (just over an hour's drive from Albany International Airport) and extends east for 63 miles to Millers Falls on the Connecticut River, leading road-trippers through the quiet forests of the Berkshire Hills and across the pretty covered bridges of the Connecticut Valley. 

The road is dotted with quaint shops, country inns, interesting museums, and traditional diners, so it's a pleasure to take breaks along the way. From a cultural perspective, two must-see stops on the journey are the Susan B. Anthony Birthplace Museum ($10 admission) and the Quaker Meeting House (open to the public on select Sundays), both located in Adams, Massachusetts. The former was the one-time home of the country's most famous suffragist, and the latter, dating back to 1782, is a pioneer-built landmark on the National Register of Historic Places. 

The Mohawk Trail also features natural attractions worth pulling over for. In the historic and serene village of Shelburne Falls, the Bridge of Flowers — an old trolley bridge built in 1908 — spans the Deerfield River and comes alive with colorful flowers from April to October. There's no admission fee, and visitors are welcome to admire the bridge 24 hours a day. Nearby, discover "glacial potholes" formed by whirlpools at Salmon Falls, once a Native American dwelling. Like the Bridge of Flowers, it's free to walk around. Before getting back on the road, stop into Shelburne Falls Coffee Roasters for a pick-me-up, or go to Hager's Farm Market, where you can buy local apples and other produce from fifth-generation farmers.

Other highlights along the Mohawk Trail include photogenic covered bridges, including Bissell Covered Bridge in Charlemont and Arthur A. Smith Bridge in Colrain, and historic New England-style houses in Deerfield, a charming town in the breathtaking Pioneer Valley. While in the area, stop into the Old Deerfield Country Store, a traditional shop specializing in local crafts.

Go for lunch at Wagon Wheel Restaurant in Gill, where you'll have the one-of-a-kind experience of dining in a country drive-in restaurant, or feast on homemade seafood chowder at Boston Sea Foods in North Adams. Lodgings along the route include the elegant Centennial House Bed & Breakfast, set on an early-19th-century estate in Northfield, or the Deerfield Inn, a restored inn that dates back to 1884.