Astronomical fall begins on Monday, September 22. Meaning, the official start to fall is under one week away. Before we know it, New England will turn into a painting of red, gold, and orange landscapes.

Northern New England— like Maine, Vermont, and New Hampshire experience a turn in leaves earlier in the season, around early October into the middle of the month—just in time for Indigenous People’s/Columbus Day weekend. Massachusetts and Connecticut will experience peak slightly later in the season, around Halloween and even into early November.

This route prioritizes areas of New England where the foliage begins to change a bit earlier in the season. Here is the perfect 7-stop round-trip loop to take from Boston for an idyllic fall foliage road trip, according to Helene Sula, a leading travel guide and blogger:

  • Boston, Massachusetts (Explore the Public Garden, Commonwealth Avenue Mall, Charles River Esplanade, and Arnold Arboretum)
  • Kancamagus Highway, New Hampshire (Enjoy the scenic drive)
  • White Mountains, New Hampshire (Hike Franconia Notch)
  • Stowe, Vermont (Take the Gondola at Stowe Mountain for incredible views at the summit)
  • Woodstock, Vermont (Explore Vermont’s covered bridges and local waterfalls)
  • Manchester, Vermont (Enjoy dazzling mountain views and grab some maple syrup)
  • The Berkshires, Massachusetts (Visit the historic and charming towns of Lenox and Stockbridge)
  • Back to Boston

Peak foliage for this loop, with the exception of Boston, is expected around October 11, all weather dependent. Find more detailed info on state-by-state peak estimates. The entire road trip is about 600 miles total, or 11 hours straight of driving, but you can break it up with stays in awesome getaways like this chalet in the New Hampshire clouds or Outbound Stowe!

Find the 7-stop journey in map form below. Halloween enthusiasts can pay a visit to Salem, Massachusetts just a stone’s throw from Boston!





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