Berkshires Fall Foliage Guide

The Berkshires boasts some of the best New England Fall foliage. Here are our top picks for panoramic Fall perfection! 

Photo of LFX Toole Wildlife Preserve

The locations listed below are our favorite places to view the Beautiful New England fall foliage right here in the Berkshires. Most views are accessible by car but a few require a hike.

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  • 1

    Falls Road, Town of Mount Washington, Massachusetts
    (413) 528-0330

    The highest waterfall in the State of Massachusetts features a series of cascades making it a spot to view during the fall. Please be careful around this fall as there is no swimming allowed and trails being slippery.

    Where: Follow US 7 South to MA 41 S in Egremont then follow Mt Washington Rd to Falls Rd. There is parking in New York and Massachusetts.

  • 2

    Cold River Road, Charlemont, Massachusetts
    (413) 339-5504

    Take a ride to the popular Hairpin Turn in North Adams/Clarksburg. This turn overlooks the city of North Adams and the beautiful Taconic Mountains. Be sure to also grab a bite to eat at the Golden Eagle Restaurant, located right at the turn. You can follow the Mohawk Trail if desired for more beautiful views of Massachusetts.

  • 3

    508 Canaan Road / Route 295, Richmond, Massachusetts 01254
    800-833-6274

    Our favorite orchard and winery, this spot is great for a day with the kids. Featuring apple picking, wine tasting, and hiking, Hilltop is the ultimate place for fall.

    Where: 508 Canaan Rd, Richmond, MA

  • 4

    2441-2599 Mohawk Trail, North Adams, Massachusetts 01247

    Three-mile ridgeline trail over cliffs to Spruce Hill is perfect for those hikers looking for a work-out. Views during the fall time are gorgeous.

    Where: Route 2, North Adams, MA

  • 5

    91 Pittsfield Rd., Lenox, Massachusetts

    This alluring park is perfect for those looking for an easy hike to view the fall leaves. Head to the top to take in the beautiful view and relax in the gazebo.

    Where: The best place to park your car and start your journey is at the Arcadian Shop. Be sure to go inside for information about Kennedy Park, they are very informative!

  • 6

    600 Stockbridge Rd., Great Barrington, Massachusetts
    413.298.3239

    Climb up this peak which gazes across the landscapes of Housatonic. View the Devil’s Pulpit and climb to the tallest point, 1,642 feet. Make sure to take a picture of the map, as there are different trails for all abilities.

    Where: Route 7, Great Barrington, MA

  • 7

    30 Rockwell Road, Lanesborough, Massachusetts
    (413) 499-4262

    Take a trip to the top of Mount Greylock for a spectacular view. The tallest peak in Massachusetts, 3,491 feet, yields views of the Green Mountains of Vermont and the Taconic Range. At the top is the Bascom Lodge and Veterans War Memorial Tower.

  • 8

    1041 Cascade St., Pittsfield, Massachusetts 01201
    (413) 442-8992

    This 11,000-acre forest is perfect for hiking, biking and driving. At the very top is Berry Pond and a beautiful outlook. Make sure to grab a map as there are many trails in this forest to explore! There is also a fee, $5 for MA residents and $10 for Non-MA residents for those who park.

    Where: Off Churchill street in Pittsfield, 1041 Cascade Street.

  • 9

    41 Railroad St, Cheshire, Massachusetts 01225

    Explore this 4-mile hiking loop which features a fantastic view of Hoosac Lake (or Cheshire Reservoir) and the town of Cheshire. You can even see the tower of Mount Greylock!

    Where: Furnace Hill Road, Cheshire, just off Route 8. Please park your car at the nearby Ashuwillticook Bike Path and walk to the trailhead. Parking is not available at the trailhead.

  • 10

    1289 Richmond Mountain Rd, West Stockbridge, Massachusetts 01254

    This overlook is perfect for those wanting an overlook and a hike. The overlook is a short drive from our hotel and features the beautiful mountains and Stockbridge Bowl. There are also hiking trails for those looking for adventure.

    Where: Michael H. Walsh Trail, Richmond, MA