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4 color-themed Berkshires trips you have to take this autumn

Posted on October 02, 2023Written by LocalIQ in partnership with 1Berkshire
Updated on September 11, 2025

Woman sitting at Olivia Overlook viewing the fall foliage and water below

When it comes to fall, there’s no place like the Berkshires. With so many things to do and see, planning your trip can be challenging if you’re only staying for a long weekend. Since the number one attraction this time of year is the fall foliage, why not plan a getaway based on your favorite fall color? Crimson, pumpkin, goldenrod and chestnut: Which shade will guide your next visit? Read on for four itineraries to help you decide what to do, what to eat and drink – and whom to bring.

aerial view of Norman Rockwell Museum grounds in fall with fall foliage, walking paths, green grass, and Rockwell's red studio building

Norman Rockwell Museum

Crimson:

This intense shade of red evokes emotions like love and passion. Picking apples, peeping maple leaves, and sipping local wine are all on your travel wish list. Couldn’t steal away for a romantic summer vacation? No problem. Snuggling up with your sweetie on a crisp autumn night is even better.

  • Who to bring: Your sweetheart
  • Where to stay: Book a cozy room at any of the dozens of B&Bs and iconic New England-style inns.
  • What to eat and drink: Sample red wines at family-owned Les Trois Emme Vineyard & Winery in New Marlborough, Balderdash Cellars in Richmond, or Hilltop Orchards, home of JMash Cidery and Furnace Brook Winery, also in Richmond, then grab a bottle to go and plan a sunset picnic.
  • What to do: Wander through MASS MoCA, the largest contemporary art museum in the U.S., located in North Adams. Red is not only the color of their striking logo, but also can be found in many exhibits currently on display, like Amy Yoes’ Hot Corners. Then pick a hike that you’ll both enjoy – try wandering the 1,000-plus acres of Greylock Glen in Adams and time it to see the rosy sunset, or how about exploring TurnPark Art Space in West Stockbridge to see the outdoor sculptures along with brilliance of the fall foliage. Craving adventure? Soar through the colorful treetops at Ramblewild. For more cultural enrichment, visit Norman Rockwell’s beautiful barn-red studio on the grounds of the Norman Rockwell Museum in Stockbridge.

Pumpkin:

The iconic fall color is a marriage of bold red and cheery yellow. It’s classic – never basic – the color of campfires and home-baked pies. This is your invitation to grab your besties and lean into all things pumpkin, from cozy spiced lattes to warm soups and homemade donuts.

Goldenrod:

A warmer shade of yellow, this happy color may also be a signal to yield or slow down. With the school year back in full swing, you’re craving some quality family time. The color of waning sunbeams and perfectly golden baked goods is sure to put a smile on anyone’s face. This hue is a core memory in the making.

Horse standing with head above white fence with fall foliage in the background

Berkshire Equestrian Center, credit Gabrielle K Murphy

Chestnut:

This bold and deep brown is a grounding color. Brown is all around us in fall, from acorns to mushrooms to forest soil. Use your autumn getaway as a chance to reconnect with yourself or loved ones. Find comfort in the rich abundance of nature.

  • Who to bring: Yourself
  • Where to stay: A hotel room with a big, comfy bed all for yourself.
  • What to eat and drink: Start your day with a cup of rich dark roast coffee that will warm you inside and out coupled with some freshly baked and lightly toasted pastries. Try Berkshire Mountain Bakery in Housatonic and Pittsfield, or Spring Street Market and Café in Williamstown. Aptly named Haven Café and Bakery in Lenox is open all day – so you can set your own schedule. For dessert, pop by Chocolate Springs Café, also in Lenox. Visit Maple Corner Farm in Granville or Ioka Valley Farm in Hancock to pick up maple syrup to take home – and a dozen donuts from Shire Donuts, too.
  • What to do: Take one day to relax and unwind. Sleep in, then take a guided hike with Housatonic Heritage Walks, and appreciate the satisfying crunch of the carpet of fallen leaves under your feet. Turn in early with a good book or your latest binge-watching obsession. Then you’ll be well-rested for a day full of all your favorite activities. Try a horseback adventure at Blue Rider Stables in South Egremont and admire the different colors of bay and chestnut horses. Browse at Susan Silver Antiques in Sheffield and admire the beautiful burnished wood tones of the heirloom furniture. Visit the Susan B. Anthony Birthplace Museum in Adams and tour the stately home of a powerful woman who paved the way for the 19th Amendment.

Come savor the colors of fall to the fullest in the Berkshires! We can not wait to welcome you.

Plan your own colorful Berkshire adventure this fall at berkshires.org.

Funded, in part, by the Massachusetts Office of Travel & Tourism

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