This post is in partnership with Expedia Group. Thank you so much for your support of my brand partners!

Every single year I look forward to Fall so that I can plan an escape up North to enjoy the Fall colors. I’ve previously done so in the Hudson Valley and several times in the Catskills, but following the 2021 purchase of a cottage by a dear friend of mine on the border of Massachusetts’ The Berkshires region, I’ve fully fallen in love with this area.

Over dinner one night, my friend Carly and I decided to plan a rather impromptu trip to The Berkshires to get our fix of foliage and Fall fun. If you’re unfamiliar, the Berkshires is a rural region in the mountains of western Massachusetts dotted with villages and towns. There are so many charming corners to it and so much to do here. From hiking trails to performing arts and fall festivals, to a great farm to table food scene and even amazing museums, The Berkshires is a place to be sure you add to your travel bucket list.

Berkshires In The Fall Travel Guide

Best Time To Visit The Berkshires

I’ve enjoyed the Berkshires nearly every season at this point but I have to say Fall is my favorite. The area just glows with all the orange, yellow and red colors of the trees as they change and you’re greeted with beautiful yet crisp temperatures. 

Things To Do In Berkshires

Visit the Farm Stands

The Berkshires boasts so many great farm stands along the side of the road so be ready with some totes to fill with pumpkins and apple cider and apples. Windy Hill Farm in Great Barrington is of particular note.

Visit The Clark Art Institute

This museum is so special. Not only do they have a beautiful collection of Impressionist works from Degas, Renoir and Monet, the grounds the museum is situated on are also beautiful. Don’t miss climbing the hill to get beautiful sweeping views – particularly stunning in the Fall as the colors on the trees change. 

Drive

One of my favorite things to do in The Berkshires is to get lost on the windy roads. You’ll lose cell service often which makes for the perfect excuse to tune out and enjoy the beautiful scenery. In the Fall, if you time it right in October, your drives will be full of insane fall colors, scenic farms and barns and plenty of turn off spots to capture the foliage. 

If you’re coming from New York City, The Berkshires are the perfect road trip destination. At just about three hours north of the city, it is a gorgeous drive up to the region. 

Visit The Mount

The Mount is the former country summer home of Edith Wharton, who designed the house and its grounds and considered it her “first real home.” The estate is open to the public and is such fun to visit! It was declared a National Historic Landmark in 1971 and features gorgeous gardens and the house has so many rooms to marvel at. The Mount also hosts a variety of events throughout the year so it is worth looking up their event calendar to see if anything sparks your interest.

Explore the Towns

The Berkshires has so many cute towns to visit. Pop into each and get out of the car to walk and explore and see what darling bakeries they are to enjoy. Scout House in Great Barrington is definitely worth popping into. 

And don’t miss Charles H. Baldwin & Sons in West Stockbridge. It’s like stepping back into time and their homemade spices and extracts are amazing!

Go Antiquing

One of my favorite pastimes while in The Berkshires is to go to the many antique stores. I have found so, so many treasures over the past two years of my visiting the region.

Apple Pick

There’s no better Fall tradition than apple picking! The Berkshires is full of orchards that have pre-picked or all you to do pick your own. And eat apple donuts while you’re at the orchard, too – but of course!

Visit Mass MoCA

This museum is actually still on my bucket list but I’ve heard that The Massachusetts Museum of Contemporary Art is a must when in the area. This museum is in a converted Arnold Print Works factory building complex and is one of the largest centers for contemporary visual art and performing arts in the United States.

Hike

One of the best things to do in this mountainous region is hike. And if visiting in the Fall, hiking is a great free activity that will allow you to soak up the Fall foliage. One popular hike to try is Monument Mountain. You can scale the 1,642-foot summit of this popular peak and gaze across the splendor of the Housatonic River Valley.

Berkshire Fall Festivals

Did you know loads of towns in the Berkshires do Fall Festivals annually?

Naumkeag Pumpkin Show

Naumkeag is a former country estate in Stockbridge, Massachusetts and it is now a museum open to the public. Every October they put on a pumpkin show on the grounds with over 1500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds. It is a ticketed event so be sure to purchase tickets in advance.

Berkshire Botanical Garden Harvest Festival

In early October this festival highlights all things autumnal at the Berkshire Botanical Gardens. It features over 100 craft and food vendors plus family and farm activities.

Lenox Apple Squeeze

At the end of September to kick off apple season this festival in the town of Lenox goes all out with apples. Visit this festival to find visitors serving up apple pie, apple cake, apple muffins, apple sauce, apple cider, and cider donuts during the Lenox Apple Squeeze.

At this festival you can also hop on a wagon ride through town, take in street performers entertaining the crowds and of course enjoy live music, too.  

Berkshires Fall Foliage

The Berkshires shines during Fall thanks to the mountainsides being covered by the foliage as it turns. Early to Mid October is usually the best time to see the Fall Foliage in The Berkshires but you can always consult a foliage map before you plan your trip to see when the colors are predicted to be peak!

Where To Stay In The Berkshires This Fall

The Berkshires has been seeing a renaissance when it comes to hotels, resorts, renovated Airbnbs and vacation rentals so there is no shortage of spots from which to choose. The hardest part will be deciding which one looks the best for you!

Life House Hotel

After seeing press around its recent opening, we decided to book our one night stay at the newly opened Life House Hotel near the town of Lenox. A renovated motel, the property got a makeover and has a beautiful lobby and bar area called The Club Room where we enjoyed good drinks and a cozy, chic atmosphere. The rooms were to be expected but did feature really, really comfy beds and Le Labo toiletries which leveled up the former-motel-vibes.

The Constance

I love this hotel because it is steps away from downtown Lenox, Massachusetts. As someone who doesn’t love to drive, this is a great location to be in the heart of The Berkshires and close to so many of my recs. They have a cozy fireplace living room, a lovely breakfast spread and updated, comfy rooms that are well priced. 

33 Main

This upscale B&B is also located in the historical town of Lenox and it is in great walking distance to loads of places. I’ve not stayed here *yet*.

The Williams Inn

The Williams Inn is located in one of my favorite towns in The Berkshires, Williamstown. The upscale lodge is surrounded by the art and culture of the Berkshires region and is popular among families with kids who attend Williams College.

Tourists

This hotel was designed to be a riverside retreat inspired by the classic American roadside motor lodge, set on the banks of the Hoosic River. It features a cozy main lodge area and plenty of outdoor space as well as a well loved restaurant. 

Where To Eat In The Berkshires

There are so many great little spots to eat and drink in The Berkshires. Below are my favorites! If you have any I’ve not mentioned – please do tell me in the Comments.

Six Depot Roastery and Cafe

One of my favorite spots in the Berkshires! They roast their delicious coffee on site and picking up a bag is a perfect way to remember your trip once you’re back home. And don’t miss their sandwiches! So delicious. If you go on a weekend expect a line at this spot.

West Stockbridge Public Market

Just down the road from Six Depot is the hole in the wall Public Market where you can get excellent sandwiches. 

Rubi’s Coffee and Sandwiches

Carly found this spot for us in the town of Great Barrington and the grilled cheeses did not disappoint. There’s a whole grilled cheese menu! Needless to say I need to go back to try another one because they all sounded good. And right around the corner is their cheese shop, Rubiner’s if you’re staying in town and want to pick up some items for a great cheese board. 

Hilltop Orchards

Call me dramatic but the hot, fresh, made to order apple cider donuts at Hilltop are what Fall dreams are made of. They melt in your mouth! I love this spot’s homemade salsas and sauces, too and you can even do wine tasting here. And of course, pick all the apples your heart desires.

High Lawn Farm

My friends introduced me to this spot over the summer and when I realized it was a 10 minute drive from our hotel we booked it over there for a pre-dinner treat. This dairy farm makes some of the best ice cream I’ve ever had and has a great store where you can pick up pints, cheeses, jams and lots more. Absolutely worth the visit and be sure to say hi to all their cows on property while there. Not to mention they have a pumpkin patch and cute pumpkin display!

Haven Cafe

Grab a coffee and a sweet treat at this cute local spot. Or sit for breakfast and enjoy their buttermilk pancakes or delicious breakfast sandwiches. They have friendly staff, a great maple latte and a huge brunch menu if you visit on Saturday or Sunday!

The Prairie Whale

This fine dining spot is on my bucket list for a future trip. I’ve great things about the elevated, area-sourced American fare & cocktails served in a charming house with a hip, rustic feel.

The Club Car

This is the restaurant & bar located in the Life House Hotel. Based on the dessert we had I’m not sure I’d go out of my way for dinner here, but definitely a fun locale for a drink.

The Red Lion Inn

Located in the town of Stockbridge, this place came recommended from several of my Instagram followers. The Inn is right in the downtown and feels a bit like stepping back in time thanks to its old school dining room and cozy tavern. 

Tourists

Want to sip coffee or have a cozy meal in front of a fireplace? This is the place to do it! Located in the town of North Adams this boutique hotel (another former motel given an upgrade) has a beautiful great room to welcome guests and visitors alike.  We just sipped coffees here but the lunch menu looked great.

Bartlett House

While technically in New York state, I couldn’t do this guide without including a place I never miss when in The Berkshires area – Bartlett House. This building is a historic railroad hotel, restored in 2016 to house a kitchen, bakery, and cafe. Everything at Bartlett House is good – so it is no wonder you can expect a line out the door on any given weekend. The pastries, the coffee, the bread, the shrubs, the sandwiches – they are all delicious. And this spot also features a full width front porch for you to enjoy on a crisp Fall day.

What to Wear in The Berkshires in Fall

Curious on what to pack to wear while in The Berkshires in the Fall? It’s cozy and casual all the way. Think Barbour jacket and boots and jeans and cashmere sweaters and flannel. You can see what I packed on my most recent trip here.

Have you been to The Berkshires? If so, I’d love any recommendations for my next trip in the Comments section below!

You May Also Like:

• All My Travel Essentials.
• Casual Fall Outfit Ideas With Jeans.
• How I Reset After Traveling.

This post contains affiliate links. Should you purchase something from an affiliate link, I may earn commission, at no cost to you. Thank you for your support of my work!