I lived in The Berkshires for 15 years. These are the fall foods stops worth planning a trip around
From cider donuts and pick-your-own orchards to longtime harvest festivals and local farm stores, these are the Berkshire stops I still think about when fall rolls around.
The Berkshires have long been a summer escape for people coming up from New York City and other parts of the Northeast. For me, they were home year-round. I spent 15 years living in North Adams, Pittsfield, and southern Berkshire County, enough Berkshire winters to really appreciate what summer and fall brought with them.
Fall usually announced itself through food. Once the nights got colder, apple season was well underway, farm stands had shifted to squash and root vegetables, and I started thinking about which orchards I wanted to get to before the season moved on.
This is also where I began writing about food. Over the years, I learned which orchards grew apples I couldn't find in stores, where to look for the first sweet corn, and which farmers' markets were as much about running into people I knew as buying dinner. Those are still some of the things I remember most about fall there.
Why fall is a good time to visit the Berkshires
Cars parked near brick buildings with small businesses in Downtown North Adams, Berkshire County, Massachusetts, USA - April 23, 2025. North Adams has become home for several new restaurants, contemporary art galleries and cultural organizations. In addition, once-shuttered area factories and mills have been rehabilitated as lofts for artists to live and work in.
(Barry Winiker via Getty Images)Foliage brings plenty of visitors to the Berkshires in September and October, but the farms are just as much a part of the season.
By then, apples, squash, and root vegetables are filling farm stands across the county. Restaurants start working more of that harvest into their menus too, so something you see at the market in the morning may turn up again at dinner.
Best orchards for fall in the Berkshires
A stack of donuts with a brown glaze. The donuts are piled on top of each other, creating a visually appealing and appetizing display
(Matveev_Aleksandr via Getty Images)Apple season is probably the most obvious place to begin, especially once cider donuts start drawing weekend crowds to Bartlett's Orchard and Hilltop Orchards in Richmond. Hilltop also makes hard cider and wine on site, which gives you another reason to linger after picking apples.
Farther north, Whitney's Farm Market & Garden Center in Cheshire has a bakery, deli, and farm market, making it an easy stop if you're traveling through that part of the county. The apples themselves matter just as much. Varieties that rarely turn up in supermarkets are available for relatively short stretches, and what you'll find changes as the season moves along.
Windy Hill Farm in Great Barrington offers pick-your-own apples, while Taft Farms turns the stop into more of an outing with its farm market and seasonal activities. Bartlett's also opens its orchard for pick-your-own during apple season.
These places are spread across the county, so don't try to cram them all into one day. Pick an orchard based on where you're staying and leave some room in the trunk.
Berkshire fall festivals worth planning around
Autumn foliage along Main street in Lenox Massachusetts.
(Peter Blottman Photography via Getty Images)By late September, apple season moves beyond the orchards and into downtown Lenox, where the Lenox Apple Squeeze takes over the village with food and artisan vendors, live music, and family activities. It's one of the area's longtime fall events and an easy way to build a weekend around more than just leaf-peeping.
October brings another Berkshire tradition at Berkshire Botanical Garden in Stockbridge. Its Harvest Festival has been around for generations and draws thousands of visitors for food, crafts, and family activities spread across the garden.
If you're planning a trip around one of those weekends, it also gives you a reason to spend more time in Lenox or Stockbridge rather than trying to cover the whole county at once.
Farm stores to visit in the Berkshires
One iconic Berkshire stop is High Lawn Farm in Lee, where the Farmstead Creamery sells cheese, butter, milk, ice cream, and other locally produced foods. You can eat an ice cream cone or cheese board outside while the farm's Jersey cows graze nearby.
In the northern Berkshires, Cricket Creek Farm in Williamstown offers a different kind of stop. Its self-service farm store runs on the honor system and carries the farm's cheeses, raw milk, beef, pork, and other local and regional foods. Depending on what is stocked that day, you might also find butter, honey, pasta, coffee, or ice cream.
Second Drop Farm in Lanesborough has changed since I first knew the area. Along with produce, berries, and flowers, it now has a farm store and coffee house where you can pick up local dairy, eggs, meat, honey, baked goods, and prepared food.
Maple season itself happens in spring, but syrup doesn't disappear once fall arrives. Bottles from Berkshire and nearby producers still turn up at farm stores and markets throughout the season.
Where to drink local cider, beer, and spirits
In North Adams, Berkshire Cider Project makes dry, sparkling cider from Berkshire-grown and foraged apples at Greylock WORKS. Its weekend tasting room offers flights, snacks, and bottles that aren't widely available elsewhere.
Mass MoCA visitors don't have to go far for beer. Bright Ideas Brewing is right on the museum campus, while Hot Plate Brewing Co. gives you a downtown taproom option in Pittsfield.
Greylock WORKS has also become more of a food-and-drink destination than it was when I first lived in North Adams. Forager Distillery operates its cocktail bar inside the former mill, Berkshire Cider Project is next door, and STATE Food + Drink is in the same complex. You could easily make an afternoon out of that one stop instead of driving from place to place.
Berkshire farmers' markets and restaurants to visit in fall
The Saturday farmers' market in Great Barrington typically runs into mid-November. At the same time, North Adams continues through the end of October, which gives you a longer window than you might expect if you're visiting later in the season.
I always liked markets for more than the shopping. Vendors know where their food is going, and conversations often turn into restaurant recommendations.
North Adams has several places where those local connections show up on the menu. Trail House Kitchen sources from local suppliers when possible, while Casita works with local farmers and purveyors for its Mexican cooking.
Farther south, Cantina 229 in New Marlborough changes its menu with the season and relies heavily on local ingredients. In Hancock, BLUEBiRD & CO. also sources from nearby farms and producers when possible.
Why I still think about fall in the Berkshires
Fall is still the season I connect most closely with becoming a food writer in the Berkshires. Living there taught me to notice how quickly things changed: an orchard could be crowded one weekend, and a few weeks later the apples I had been waiting for were finished for the year. After a while, you learned not to put off the things you wanted to eat until next weekend.
