Discover Worldly Beauty with These Peak Foliage Tours

A Berkshire Tapestry: Two Days of Art, Autumn, and Awe

Get ready for an immersive, two-day Berkshire County experience designed for those who want it all—culture, cuisine, countryside, and connection. From the gentle hills of South County, charming towns voted #1 small town in America by Smithsonian Magazine, to the sweeping vistas of the northern Green Mountains, this all-inclusive tour delivers the full spectrum of Berkshire County beauty and culture at its most spectacular time of the year. 

Along the way, you’ll enjoy private, curated access to two of the region’s most iconic museums and a living history site where the past comes vividly to life. You'll have a chance to experience Great Barrington, voted Top 10 Towns in America by Forbes. Scenic drives will wind you through fiery reds and golden canopies, with thoughtful stops for short walks, photo moments, and a breath of crisp autumn air.  Between cultural landmarks, you'll savor exceptional meals and local flavors, all planned and prepared with care.

This is not a tour—it’s a tapestry. Each moment is designed to surprise, delight, and root you more deeply in the land and stories that define this extraordinary region. 

Day 1:

• Boutique transportation from Lilac Park in Lenox Town Center
• 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, including one alcoholic drink, and gratuity for each meal

Day 2:

• Boutique transportation from Lilac Park in Lenox Town Center
• 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
• Gourmet lunch and dinner, including one alcoholic beverage and gratuity for each meal
• Spring Street, Williamstown, for a brief shopping spree and photos

Dates & Details

All-inclusive ticket price:

$998/person 

Date to Choose From: 

September 20-21, 2025

October 11-12, 2025.

Location & Time:

Guests will be picked up and dropped off daily in Lenox Town Center (Main Street & Sunset Avenue) at 8:30 AM and 8:30 PM.

**Please note: This tour does not include overnight hotel accommodations.**

One Full Day. A Dozen Moments You'll Talk About for Years.

Unlike standard sightseeing tours, this is an immersive, slow-travel experience with premium touches and personal stories woven in. It combines museums, historic sites, gardens, cuisine, and breathtaking golden landscapes into one seamless itinerary.
 

 Includes: 

Boutique-style transportation, entrance to the world-renowned Norman Rockwell Museum and The Sterling and Francine Clark Art Institute, with visits to local heritage sites and photo opportunities of Stockbridge Bowl, The Mount (Edith Wharton’s estate), Mount Greylock Summit, and the Veteran's War Memorial Tower. 

You'll enjoy curated photo opportunities, gourmet lunch and dinner, and a chance to stretch your legs in some of New England’s most charming towns. 

After dinner, we'll take a scenic ride at dusk around the Hancock Shaker Village and through the Taconic Mountain Range. 

All-inclusive ticket price:

$499/person 

Dates: 

September 27, 2025

October 4, 2025

October 18, 2025

October 25, 2025

Location & Time:

Guests will be picked up and dropped off in Lenox Town Center 

(Main Street & Sunset Avenue) 

at 8:30 AM and 8:30 PM.

Short on time, but still want the magic? Our half-day excursions deliver the full flavor of fall in just six unforgettable hours. Choose a golden morning escape or a twilight-to-stars adventure—either way, you’ll glide along winding backroads ablaze with color, pause for postcard-worthy photo ops, and savor a gourmet meal in the majestic Berkshires. 

Dates:

Both Morning Foliage Tours and Afternoon Foliage Tours are available on the these dates, but at different times: 

September 5 - SOLD OUT

September 6 - SOLD OUT

September 12

September 14

September 26

September 28

October 3

October 5

October 10

October 13

October 17

October 19

October 24

October 26

Morning Foliage Tour

Includes: Boutique-style transportation, scenic drives, multiple curated stops for photos, and a gourmet lunch at a beloved local spot. 

Noteworthy views: Stockbridge Bowl, charming farms, The Clark Museum's architecture, the Green Mountains, Berkshire Hills along the Appalachian and Mohawk Trails, overlooks, lakes, Mount Greylock, and its iconic Veteran War Memorial Tower (the highest point in Massachusetts).

Location & Time:

Guests will be picked up and dropped off in Lenox Town Center 

(Main Street & Sunset Avenue) 

at 8:30AM and 2:30PM

All-inclusive ticket price:

$249/Per person

Afternoon Foliage Tour 

Includes: Boutique-style transportation, scenic drives, multiple curated stops for photos, and a gourmet dinner at a beloved local spot. 

Noteworthy views: Stockbridge Bowl, charming farms, The Clark Museum's architecture, the Green Mountains, Berkshire Hills along the Appalachian and Mohawk Trails, overlooks, lakes, Mount Greylock, and its iconic Veteran War Memorial Tower (the highest point in Massachusetts).

Location & Time:

Guests will be picked up and dropped off in Lenox Town Center 

(Main Street & Sunset Avenue) at 3:30PM and 9:30PM. 

All-inclusive ticket price:

$329/per person