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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 January 05, 2024

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


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 Furnace Brook Winery at Hilltop Orchards, 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, and Kelli Rae Adams: Forever In Your Debt. 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 exploring the Kennedy Park in Lenox to see the brilliance of the fall foliage. For more cultural enrichment, visit Norman Rockwell’s beautiful barn-red studio on the grounds of the Norman Rockwell Museum in Stockbridge.


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.

  • Who to bring: Your best friends
  • Where to stay: Find a vacation rental big enough for your whole group so you can turn the weekend into one big slumber party where you can cozy up around a warm fireplace.
  • What to eat and drink: Try local microbrews at Bright Ideas Brewing in North Adams or Big Elm Brewing in Sheffield – don’t miss the Jack-O-Lion beer with pumpkin and yam! Or pick up a bottle of local small-batch spirits at Berkshire Mountain Distillers in Sheffield. Let each person pick a new tasty spot to eat each night. You certainly won’t run out of options!
  • What to do: For a low-key weekend, opt for an easy hike and a day of shopping for antiques or at the outlet malls. Want to lean into the fall theme? Time your trip for the Fall Foliage Parade in North Adams or book tickets for The Incredible Pumpkin Show at Naumkeagin Stockbridge to see – and savor– the real thing.
Couple walking through Hancock Shaker Village in the Fall

Hancock Shaker Village, credit Ogden Gigli


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.

  • Who to bring: The whole family
  • Where to stay: Make it a getaway from kids and parents alike by choosing a family-friendly resort like Berkshire Mountain Lodge in Pittsfield or Jiminy Peak Mountain Resort in Hancock.
  • What to eat and drink: All the seasonal treats. Hit up as many local orchards and farm stands as you can, sampling cider donuts and pumpkin-spiced treats. And don’t forget the local cider!
  • What to do: Bring your camera and pack coordinating outfits. You’ll want to remember this family trip. Make time for apple picking at Hilltop Orchards in Richmond. After all, what could be better than a tasty golden cider (and a cider donut) to really make everyone warm and fuzzy inside? Drive up to Bash Bish Falls State Park in Mt. Washington to gawk at the state’s highest single-drop waterfall and time it for the golden hour to create the perfectly lit ambiance.
Horse standing with head above white fence with fall foliage in the background

Berkshire Equestrian Center, credit Gabrielle K Murphy


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 Pleasant and Main Café General Store in Housatonic 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 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 Berkshire Camino, 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 appreciate the achievements of our predecessors while touring this stately home.

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

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

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