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How to Spend a Fall Weekend in the Berkshires

How to Spend a Fall Weekend in the Berkshires

If you are looking for a fall weekend getaway, you have to check out the Berkshires. The Berkshires is located in western Massachusetts and this region is one of the best places to spend a fall weekend in New England. You’ll find cute towns, rustic farms, scenic landscapes, and all the beautiful fall foliage. To see the best fall colors, I recommend visiting in mid to late October. There are so many things to do in the Berkshires. In this travel guide, I will be sharing how you can spend a fall weekend in the Berkshires.

Best Things to do in the Berkshires


There are a bunch of great hiking trails in the Berkshires. I love doing hikes in the fall since that is one of the best ways to see beautiful fall foliage. A few great moderate hiking trails are Hickey and Peeskawso Peak Loop, Laura’s Tower Trail, and Ice Glen Trail.

If you are looking for an easy hike with amazing views, check out the Stony Ledge Trail. We parked and started the trail on Sperry Road and it was an easy two miles to the top. It takes about 50 minutes to complete.

Mount Greylock

If you want great fall views without the hike, you can drive to the top of Mount Greylock. At almost 3,500 feet in elevation, it is the highest point in Massachusetts. The summit is open from from mid-May to November 1st.

Norman Rockwell Museum

Fall Weekend in the Berkshires

The Berkshires is filled with so much art, culture, and history. One of the museums I highly recommend visiting is the The Norman Rockwell Museum. It is an art museum in Stockbridge and home to the world’s largest collection of original Norman Rockwell art. You will get to see the best of American illustration and learn more about the history of Norman Rockwell.

The museum is open from Thursday to Tuesday 10am-5pm. Tickets are $20 per person.


Fall Weekend in the Berkshires

Throughout the Berkshires, you find antiques, clothing boutiques, artisanal shops and more! Check out the cute downtown of Lenox and Stockbridge and spend an afternoon exploring all the shops.

Berkshire Botanical Garden

The Berkshire Botanical Garden is a beautiful 24 acre botanical garden located in Stockbridge. You will find over 3,000 species and varieties of herbaceous and woody plants. They also offer classes, workshops, lectures, exhibits and special events throughout the year.

The Berkshire Botanical Garden is open May 1st through October 31st from 10am to 4pm. Tickets are $18 per person.

Hilltop Orchards

Hilltop Orchards is a family run orchard with breathtaking fall views! You can explore their variety of hiking trails and explore their beautiful orchard. They offer cidery tours and cider and wine tastings. And you have to try their freshly made apple cider donuts!

Hancock Shaker Village

The Hancock Shaker Village is a living history museum that is committed to bringing the Shaker story to life. It is located in Pittsfield. You can tour around the village and explore the twenty historic buildings and gardens. The village also includes a Shaker Mercantile for handmade and artisanal goods and Seeds Market Cafe for dining. You can also explore the various hiking trails on the property.

Hancock Shaker Village is open from mid-April through late November. To have enough time for your visit, it is recommended to arrive between 11am through 3pm. Tickets are $20 per person.

Stockbridge Bowl

Fall Weekend in the Berkshires

Stockbridge Bowl is the largest lake in Stockbridge. In the summer, it is a perfect spot for swimming, but in the fall, it is such a beautiful spot to see fall foliage.

Best Restaurants in the Berkshires


This is a great cafe for coffee, breakfast, sandwiches and pastries! Their bear bowl is so yummy! It is steel cut oatmeal with bear butter and fresh berries.

Haven Cafe

This is a popular breakfast and lunch spot! I loved their pumpkin pancakes.


A casual spot that serves Neapolitan style pizza.

District Kitchen + Bar

This is a casual dinner spot that serves modern American food with craft beer, innovative cocktails and great wine.

51 Park Restaurant + Tavern

Tavern that services sandwiches, burgers, salads, and wood fired pizzas. They offer a wide selection of craft beers, wines, and signature cocktails.

Hope you enjoyed my post on how to spend a fall weekend in the Berkshires!

Looking for more fall weekend getaway ideas?
Check my blog post on the best fall vacations on the East Coast

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