Dream Design

The five shades of fall

  • Forest in autumn with colourful foliage
Boston – Jackson – Stowe – Woodstock – Lenox – Washington

The five shades
of fall

Chase the autumn hues down winding highways, up trail-cut mountains and through charming towns caught in a time-warp in arguably America’s most colourful region.

Travelling along the spectrum from yellow and orange to red, brown and purple, the cornucopia of all things historic – Boston – is the point of origin before the road trip leads to the White Mountain National Forest, where biking and kayaking take up some time.

It’s then onto two of Vermont’s shining stars, Stowe and Woodstock, for a side of historic architecture with your hikes. The scenic Route 7 is the thoroughfare to Lenox, the summer home of the Boston Symphony Orchestra, before finishing up in Washington, Connecticut to slow it down with guided tours of restored farmhouses and a nearby vineyard.

Farmhouse with cows in Woodstock in autumn
White church in Stowe at autumn time
Covred bridge in the White Mountain Forest during autumn
Itinerary essentials
  • 11
    NIGHTS
IDEAL TIME
  • Sep - Oct
    IDEAL
WHEN TO GO
  • 7hrs 40min
    LHR - BOS
FLIGHT TIME
  • Outdoorsy
    COUPLES
IDEAL FOR
Get in touch your way…
We customise every trip to you and our quotes are bespoke. We’re here to offer advice, recommendations and answer your questions.
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