You'll travel through some of the Berkshires' most celebrated towns—recognized nationally by publications such as Forbes and Smithsonian—as scenic roads wind through fiery reds and golden canopies.
Thoughtful stops invite you to stretch your legs, capture photos, and breathe in the crisp autumn air, as well as experience some of the region’s most iconic museums and living history sites.
Day 1:
- Photo ops include: The Mount, Edith Wharton's House, Stockbridge Bowl, Taconic Mountains, Monterey, Williamstown, Richmond, Bartholomew's Cobble
- Time to stroll and shop in Great Barrington, voted #1 Small Town in America by Smithsonian Magazine
- Entrance to two museums: The Norman Rockwell Museum, and The Bidwell House Museum & Gardens, with 90 minutes to enjoy at each
- Gourmet lunch and dinner, provided
Day 2:
- Photo ops include: Hancock Shaker Village, Mount Greylock Visitor's Center, Green Mountains, Mohawk Trail, stunning hairpin turn, Williamstown, Greylock Glen, North Adams Cemetery, Mount Greylock Summit & the Veterans War Memorial Tower
- Entrance to The Clark Art Institute with 90 minutes to enjoy
- Time to stroll and shop on Spring Street in the indelible city of Williamstown, home of Williams College, the top liberal arts college in the nation
- Gourmet lunch and dinner, provided
Ticket price:
$1299/per person
(6 person maximum)
Dates Available:
September 26-27, 2026
October 3-4, 2026
October 11-12, 2026
October 19-20, 2026
Custom dates can be curated for your party.
Location & Time:
8:00 AM Departure
8:00 PM Return Time
Most guests depart from our office location in Lenox. Transportation from select lodging partners may be available based on availability and location.
