SECTION 1

The journey officially commences and concludes at the summit of Mount Wachusett in Princeton, MA. Although it is a toll road, the ride to the top is well worth the fee. The day wraps up at the summit of Sugarloaf Mountain in Deerfield, MA. This route takes you through quaint New England villages and lovely parks, such as Barre Falls Dam State Park, Wendell State Forest, and ultimately ends at the Sugarloaf Mountain Observation Tower. You’ll find various lodging options in Deerfield and nearby Greenfield, as well as a few Airbnb locations along the way.

SECTION 2

From Sugarloaf Mountain to Mount Greylock in Adams, MA, the route meanders through the picturesque backroads of Western MA, with stops at Glendale Falls, the Bridge of Flowers, and Mass Audubon’s High Ledges Wildlife Sanctuary, among other spots to discover. The journey concludes at the summit of Mount Greylock, where you can explore the Veterans War Memorial Tower. There are ample lodging options in Williamstown and North Adams, including the Bascom Lodge atop the mountain.

SECTION 3

The path from Mount Greylock to Poet’s Seat Tower in Greenfield, MA, heads northeast from Adams, MA, briefly dipping into Southern Vermont. On this leg, you’ll cross the Vermont border twice. Excellent dining options include Readsboro General Store, Berkshire Pizza, Jack’s Hot Dog Stand, and ZA Hot Slice Pizza, as well as Blueberry Haus Ice Cream. The route culminates in Greenfield at Poet’s Seat Tower, which overlooks the vibrant little city to the west. Lodging can be found in Greenfield, Erving, and Bernardston, MA.

SECTION 4

The final stretch from Poet’s Seat Tower back to Mount Wachusett in Princeton, MA, completes the 550-mile loop, returning you to your starting point in Central MA. Before reaching Mount Wachusett, you’ll traverse some of the finest dirt roads in northern Central MA. For those looking to challenge their skills, Falls Road in Royalton offers an opportunity to ride into NH for a brief moment. However, be prepared, as Falls Road is quite challenging, featuring rocky terrain, steep descents, a water crossing at the bottom, and another steep ascent!