4 Towns to Visit in The Berkshires in the Fall

The Berkshires, a magical place to visit, especially in the Fall was the perfect mini- getaway. Especially popular during leaf peeping season, these small charming towns attract visitors all year round. The Berkshires, located in Western Massachusetts is about a 3.5 to 4 hour drive from NYC which makes for a wonderful road trip. Create a "Fall" Playlist, hit the open road and take in the amazing sights of the leaves changing colors. For me, I blasted Top Country, opened the windows, drank an ice coffee and took in all the sights as I made my way across the state of Massachusetts after visiting a friend outside of Boston.  From Boston, you can make it to the Berkshires, in about 2 hours.

There is so much to see, do and eat in The Berkshires. I think between 3-4 days would be the best to see as much as possible without cramming everything in. I spent two days, staying in Great Barrington, which is one of the many small towns that make up the Berkshires. During my visit I only went to 4  quaint and charming towns but there a so many more places to check out.

Where to Stay

There are so many cute Bed & Breakfast or quaint Inn's throughout the area. You can also rent an Airbnb if that is more your style. Side note, as a Marriott Employee one of the greatest perks, is discounted hotel stays. I was able to get a room on the cheaper side at the Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires. Also, I noticed a Holiday Inn Express down the road, so you can also check them out. 

Here are some other places:

30 Main St.
Stockbridge, MA

Where every room tells a story, this charming, modern country inn is located right on the Main St, in Stokbridge, a town that looks like it came from a story book. If you don't have a chance to stay here, at least get drinks on the patio overlooking Main St!

40 Plunkett St.
Lenox, MA

With 57 stylish guest rooms spanning over three buildings each offers a distinctive style, that will leave you yearning for more exploring just on the Inn grounds. While I didn't stay there, check out Shelby of TravelFitLove post on her stay

55 Lee Road
Lenox, MA

Open to the public, if you are not staying here, you can still enjoy the grounds, and even catch some wonderful fall foliage off the entrance. Whether dining, playing golf, or just exploring you are in for a treat with the scenic backdrop. 

Where to Eat

8 Franklin St.
Lenox, MA

Haven, not Heaven, although that could be more fitting is the cutest little restaurant in Lenox, MA and I highly recommend getting in the line to wait for a seat. Even if you are just picking up pastries, you are waiting in the line, which is 100% worth it. You take a menu to view while in line and then order at the counter. The hostess will give you a number which you give at the counter, then find your seat. Your meal is brought to you. It moves much quicker than I would have thought. Larger parties may have a little more of a hard time, but for solo dining or party of two you're good. Just look at the Crab Benedict below. Why yes, it is on a fresh make croissant! 

282 Main St.
Great Barrington, MA

This All-Day Breakfast, Lunch and Dinner can be found on Main St, in Great Barrington. It was my first stop before checking into my hotel. I grabbed a corner seat at the bar and was immediately greeted by the friendliest staff. Crab Cake Benedict was my go-to, no surprise there with an ice coffee and I would be ready to set out to explore the town. 

From the old school movie theatre to cute cafe's and charming shops, there is something for everyone. Check out Rubiner's cheesemongers & grocers, SoCo Creamery, and One Mercantile to name a few. 

Two Locations; Housatonic & Pittsfield. 

Other than saying if you are a carboholic  like myself, you need to visit and try their delicious breads. If you are looking more for pizza, grab any of their Take & Bake Pizza. I bought a customer favorite, the Bread & Chocolate and it was out of this world. Kuddos to Richard Bourdon, owner and baker!

What to Do

9 Glendale Road
Stockbridge, MA

Dedicated to education and the appreciation for art this museum is a must see in The Berkshires. From current exhibits to collections and other events, there is something for everyone. 

Rt. 71
Great Barrington, MA

With three main trails to choose from, you can be as adventurous or as cautious as you would like, I chose the less strenuous and shortest distance. When visiting in the Fall it is great to see the Foliage, just be careful from the rain and dampness that could make it harder than normal. Even though I was hiking alone, I never felt alone as there are always groups of people around.

Explore the towns and do some shopping. You can support many local small-owned businesses which is something I am extremely passionate about as of late. If you don't purchase something, you can always share about them on social media, so maybe someone else can the next time they visit. 

5 West Stockbridge Road
Stockbridge, MA

Open year-round you can visit anytime; however I missed the gardens by one week. The Gardens are open May 1st through Oct 11th. Still it is a beautiful place to visit, clear you mind, and do wonders to your soul.

These are just a few things that I saw, ate and did on my two days on my New England Fall Foliage Road Trip. 

What is one place in The Berkshires you want to visit?



  1. What a beautiful looking place! I've actually never herd of it but our next road trip I'm putting it on the list of places to stop.

    Stephanie Vainer

    1. You have to and I promise you won't regret it. There is so much to do, see and eat.

  2. We love a good road trip and we've been wanting to do one through the Berkshires for a long time. Thanks for the tips and where to get the good food :) Pinning this for next Fall

    1. You will absolutely love it and Fall is the perfect season to go. The foliage alone is gorgeous.


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