Perfect 3 Day Itinerary for Fall Foliage - The Berkshires, Massachusetts

October 2024

Perfect 3 Day Itinerary for Fall Foliage – The Berkshires, Massachusetts

After an incredible summer of travel, I had not given much thought on how to spend my birthday trip. Since flights were still expensive and our time was limited to a four day span, I looked around at drive-able destinations. We had such a spectacular trip to the White Mountains in New Hampshire so I looked at other New England fall foliage areas and found the Berkshires in western Massachusetts with plenty of small towns to explore. I found a fall foliage tracker and first, could not believe this was a thing and second, was pleased to find that during the second weekend of October, we were in peak fall foliage – The Berkshires, here we come! Consider us leaf peepers for the weekend.

Know before you go

This trip is going to require a car both to reach the destination and for getting around. Nearby airports are a bit slim, the closest being Albany, NY about an hour drive away. There are trains and buses that you can also string together but all will still require you to have a car to get to the Berkshires.

Peak foliage changes each year but generally the time to visit for this event is early October. Keep an eye on this fall foliage tracker to help plan the right time so you do not get there too soon or miss it altogether. Peak foliage generally only spans two weeks so the window of opportunity is short.

Because the peak season is so short, expect it to be crowded. Book accommodations in advance as they do fill up and can get quite expensive. This is often an annual pilgrimage for people in the New England area. It is less crowded during the week than on weekends but if you are like us, we only had the weekend to work with. Start the days early helps cut out a big chunk of people sleeping in on vacation.

Where to stay?

There are several towns around this are you can establish as your home base. We picked staying near Pittsfield since it was central to the western Berkshires area we wanted to explore, and would say saying near Lenox is another good choice. This Airbnb is a loft unit on Bittersweet Farm – they even have a farm stand where you can purchase farm products such as produce, flowers, and eggs – and enjoy the animals on the farm like chickens, goats, and horses. We adored our stay here and it worked perfectly for our Berkshires itinerary and exploring areas north and south of Pittsfield.

What is there to do?

Drive to the Top of Mount Greylock

One of the most iconic locations along the Berkshires is Mount Greylock as it is the highest point in Massacheusetts. Standing at 3500 ft, on a clear day you can see a panoramic view 100 miles of five neighboring states. There are so many hiking trails in this state reserve to enjoy, including hiking all the way to the top of Mount Greylock. But what makes this peak so great is that you can actually drive to the top – there is a 16 mile Scenic Byway that is open from mid-May to November. I would have loved the opportunity to explore the many hiking trails at the Mount Greylock State Reservation but with limited time, we utilized a quicker way to get to the top – driving. That is certainly what makes visiting Mount Greylock very accessible. It is also a free activity which certainly attracts visitors as well.

Climb the Mountains

There are many hiking opportunities in the Berkshires of varying difficulty that all offer incredible views of the valley and all those beautiful trees. The Appalachian Trail runs right through this region so there are tons of trails in this area depending on what you want to see and do. One popular trail is the Hickey and Peeskawso Peak Trail which is not too difficult and has a great vista at the top. Our favorite was The Cobbles Trail and this one is not as well known but this short trail has such a great pay off – simply stunning at the peak. Want something that is closer to the ground? Go visit Mass Audubon Pleasant Valley Wildlife Sanctuary for a peaceful walk through the forest where you can still catch great fall foliage.

Go Farm Hopping

When leaf peeping in the New England region, apple cider donuts are an essential part of the fall foliage experience. On our most recent fall trip to the Berkshires in Massachusetts, chasing apple cider donuts also meant leading us to some of the best farms in the area. These farms pull out all the stops to attract visitors and practically hold mini fall festivals throughout the peak season.

In addition to finding the best apple cider donuts in the Berkshires, there are other farms that are certainly worth a visit. And these two farms are a must stop for a Berkshires itinerary. High Lawn Farm is where diary dreams come true where Jersey cows are producing the best milk, chocolate milk, and cheese. Then make time to swing by Baldwin Farms for their farm fresh food truck – these sandwiches are outrageously delicious.

And finally, if you time your trip right you can attend the annual Harvest Festival at the Berkshire Botanical Gardens which combines the best of all the above in one event.

Visit Local Museums and Historic Sites

The Berkshires is home to many museums that feature a variety of topics so if you are looking for a break in the day or escape from bad weather, explore one of the museum offerings in the area. MASS MoCA is very popular and focuses on contemporary art. The Norman Rockwell Museum showcases Rockwell’s work was regularly featured on the front cover of the The Saturday Evening Post starting in the early 1900s, then tackled current event paintings such as Four Freedoms and portraits of presidents. The Hancock Shaker Village is a preserved community that now exists as a museum that educates on the Shaker community and their modest but efficient lifestyle. Another option is to visit Naumkeag estate public garden and Gilded Age style historic home, and during the fall season features The Incredible Naumkeag Pumpkin Show.

Enjoy the Downtown Areas

The downtown areas of Lenox, Pitssfield, West Stockbridge, Stockbridge, Adams, and North Adams (to name a few!). Make sure to take some time to walk the downtown areas and enjoy the shops.

Where to eat?

There is a fun food scene in the Berkshires that offers a casual environment with tons of great dining.

Pittsfield	Lenox	Stockbridge / West Stockbridge	Adams / North Adams
Flo’s Diner Dottie’s Coffee Lounge Smokey Diva’s A Little Nibble Sibaritas Otto’s Kitchen & Comfort Berkshire Mountain Bakery Pizza Cafe	Cello Bistro Zinc High Lawn Farm Alta Ombra Brava	Baldwin Farms No. Six Depot Roastery & Cafe Stockbridge Coffee & Tea The Lost Lamb	Daily Grind Jack’s Hot Dog Stand PUBLIC eat+drink Bright Ideas Brewing Tunnel City Coffee

Itinerary

This itinerary makes for a great long weekend – the power of a three day weekend is strong and just by using one PTO day! Mix and match the days to make the trip that works for you. Many itineraries string this destinations with other nearby areas in New York, New Hampshire, Vermont, and Massachusetts to make the ultimate fall foliage road trip so if you have the time to extend, this is how to spend your time at the Berkshires.

Here is how to experience the best of the Berkshires in Massachusetts in three days!

Day	Time	Activity
Day 0	Evening	Arrive in The Berkshires
Day 1	Day	Hike or Walk of Choice – Hickey and Peeskawso Peak Trail – The Cobbles Trail – Mass Audubon Pleasant Valley Wildlife Sanctuary Farm Hopping – Taft Farm – Barlett’s Orchard Farm Market – Whitney’s Farm – High Lawn Farm
	Evening	Downtown Lenox
Day 2	Day	Drive to the top of Mount Greylock Downtown Adams and North Adams Downtown Stockbridge / West Stockbridge Get sandwiches at Baldwin Farms If offered during your visit: Harvest Festival at the Berkshire Botanical Gardens
	Evening	The Incredible Naumkeag Pumpkin Show
Day 3	Day	Museum of Choice: – Hancock Shaker Village – Norman Rockwell Museum
	Evening	Depart

Perfect 3 Day Itinerary for Fall Foliage – The Berkshires, Massachusetts

Know before you go

Where to stay?