We updated this post with info for the current fall season.
When will the fall colors arrive? When will they peak? Is it going to be a good season? Where can I find a map of fall foliage? ( You can find one for Massachusetts right here!And here’s one for the state of New York!)
We commonly hear these phrases in the Berkshires and Upper Hudson Valley, where leaf peeping is a sport and the hunt for rare maples is as serious as the quest for the best apple cider doughnuts.
Autumn vistas of blazing foliage, many featuring bright-red barns and white-steepled churches, have launched a thousand New England and New York State Instagram posts. When it comes to leaf peeping, however, nothing beats the Berkshires and Upper Hudson Valley.
These three foliage routes feature back roads, small towns, and crimson colors, making Western Massachusetts the ultimate fall destination.
The fall breeze blows more than the leaves. The year-round appeal of the Berkshires and Upper Hudson Valley is a pull factor for homeowners looking to downsize or home buyers shopping for the ultimate second home retreat.
If you’re looking at real estate in the Berkshires and Upper Hudson Valley, we’d love to work with you. Add one of these fall foliage routes to your schedule as you look at homes for sale this fall.
The Mohawk Trail on Route 2 in Massachusetts
Once a Native American trade route, the Mohawk Trail along Route 2 in Massachusetts travels through the northern Berkshires from Greenfield to North Adams. Come October, the historic, 37-mile road is a leaf peeper’s paradise of autumn colors, from sugar-maple reds to honey-locust yellows.
And the seasonal indulgences don’t end with the leaves. Farm stands, hayrides, farm-to-table restaurants, and pick-your-own orchards fare all part of the Route 2 experience. Points of interest on the Mohawk Trail include Shelburne Falls, home of the Bridge of Flowers, and Mass MoCA, in North Adams. For lunch or dinner, head to PUBLIC Eat + Drink in North Adams, known for its farm-to-table menu offerings and creative craft beer program.

Great Barrington to North Adams on Route 7 in Massachusetts
U.S. Route 7 runs from southern Connecticut to northern Vermont, extending 54 miles through western Berkshire County and passing through towns such as Great Barrington, Lenox, and Pittsfield. Along the route you’ll see storybook farms, rolling hills, and so many scenic panoramas you’ll having a hard time keeping your eyes on the road.
Points of interest on Route 7 include the Berkshire Scenic Railway Museum, which is located in Lenox and the perfect fall detour for families, and the Norman Rockwell Museum in Stockbridge. Hilltop Orchard & Furnace Brook Winery in Richmond features numerous fall events, including hayrides, live music, full-moon walks, and pick-your-own apples. It also produces 15 award-winning wines.
In the Berkshires, all fall foliage trails lead to food. For lunch, stop at the Red Lion Inn, famously painted by Norman Rockwell, or Patrick’s Pub, located in Pittsfield’s main square and home of the “Best Wings in the Berkshires.”
Take a quick detour off Route 7 to reach our Great Barrington office and our West Stockbridge location! We’d love to see you.
The Summit of Mount Greylock
At 3,491 feet, Mount Greylock is the highest point in Massachusetts. On a clear day you can see more than 90 miles away. You can drive to the summit of Mount Greylock from North Adams, Lanesboro, and Williamstown.
Mount Greylock was the first state park designated by Massachusetts 1898. It’s been an inspiration for literary legends, including Nathanial Hawthorne, J.K. Rowling, and Herman Melville. In fact, Melville’s description of the “white whale” is believed to come from seeing Mount Greylock covered in snow.
No visit to the Mount Greylock region is complete without a stop at Bascom Lodge. The rustic mountain lodge was built in the 1930s and has vistas of four states and five mountain ranges. In the fall, Bascom Lodge offers a nightly prix-fixe dinner at its “windows of the world” cafe.
The Taconic State Parkway through Columbia County in New York
The Taconic State Parkway extends north and south through the middle of Columbia County. Its winding, sometimes hilly route features scenic views of highlands and mountains that show off fall foliage to perfection.
Some of the towns on the route are Taghkanic, Claverack, Ghent, and Chatham.
“Berkshire Vista” by Ogden Gigli is licensed under CC BY-ND 2.0
“Autumn Trees – Lenox” by MOTT is licensed under CC BY-ND 2.0
