Our Fall Road Trip & Things to Do in the Berkshires

A few weeks ago Will and I went on a road trip to the Berskshires, in western Massachusetts, for my birthday weekend. Just before my birthday, we celebrated Liam’s first birthday. So, it felt like an extra good time to celebrate getting through that first year of parenthood and have some time for just the two of us. I’m so grateful to my mom and aunt who watched Liam that weekend – it truly was the best gift! Our road trip into the Berkshires felt like a trip back in time. You know the time.. when people didn’t have phones attached to their bodies at all times. The Berkshires or “the shire” as locals call it, it is a place to come relax and enjoy nature. And while you can visit year round, going in the fall seemed like the perfect time since New England is known for their fall foliage. We spent a good part of our road trip taking it easy and relaxing, so I wasn’t surprised that we didn’t get to everything on my list of things to do in the Berkshires. Since I would like to go back eventually, and some of you shared some recommendations, I wanted to share all the details with you.

Before I dive in, the Berkshires refers to a region of western Massachusetts that is made up of several small towns that all have a lot of history and charm. Some of the towns include Lenox, Stockbridge, Lee and Great Barrington.

Our Fall Road Trip & Things to Do in the Berkshires - SCsScoop.com
Norman Rockwell’s studio in Stockbridge, Ma.

Getting to the Berkshires

Traveling from the DC area, it took us about 6.5 hours to get there. We did make a pit stop in NYC to spend the night there, which provided great contrast to the Berkshires! From NYC It is easy to escape the city or the business of your life in the Berkshires. Conveniently located off of the Mass Turnpike and not far from NYC the Berkshires is a great trip for nature and culture lovers.

By car, fom New York City to the Berkshires, you will follow the parkway to I-87 to I-90 East to Exit 2 Lee, Massachusetts. It will take you about 3 hours by car, but you will feel like you are entering a world world. It’s a beautiful drive!

From Boston, it is only a 2 hour drive west on the Mass Turnpike. The ride is a straight shot. If you want a more scenic drive to Western Massachusetts, you can take the Mohawk Trail (Route 2 and 2A). It will take you to iconic spots such as the Shelburne Falls Bridge of Flowers and the Hair Pin turn in North Adams.

Things to do in the Berkshires

Norman Rockwell Museum

Located in Stockbridge, Ma., the Norman Rockwell Museum is located on a beautiful estate and includes many of his iconic works of art. Norman Rockwell called the Berkshires home and derived much inspiration for his work. When you visit you will see why! The museum houses the world’s largest collection of Rockwell works and is open year round. I recommend getting tickets in advance if you are going during a busy season because they are known to sell out!

Visit the Charming Towns of the Berkshires

Peruse the shops and unique historic architecture that can only be found in the Berkshires. My favorite towns in the Berkshires are Lenox, Stockbridge, and Great Barrington. But, there are many more charming places that you will find along your road trip through the Berkshires that you will fall in love with. It’s the perfect place to drive down a winding road and see which charming town it takes you to.


Located near the main street in Stockbridge, Ma., Naumkeag is a former country estate and Gilded Age mansion. The vast gardens and the instagrammable pine tree-lined driveway brings you back in time. It is beautiful and in the fall they have an awesome jack-o’-lantern display!

Hike to the Highest Point in Massachusetts- Mount Greylock

If you enjoy the thrill of going to the highest peak, this hike is for you. Mount Greylock is the highest peak in Massachusetts at 3,489 feet. Located in the western part of Adams in Berkshire County this will definitely be the most challenging hike in Massachusetts. The 3-mile strenuous hike to the top with 1100 ft elevation gain is worth it for the views!

Hike Monument Mountain

This is where we hiked, not far from Housatonic, Ma. We did the Hickey and Peeskawso Peak Loop, which is about 2.5 miles and took us just under 2 hours (with breaks at the top). There are so many beautiful hiking trails in this area. Visit AllTrails.com to check out more.

High Lawn Dairy Farm & Shop

This local farm would be a great place to visit if you want to get a taste of the local flavor in more ways than one! Their creamery includes a selection of ice cream and cheese, and you can visit with their cows in the barn.


Located in Lenox, Ma., Tanglewood is the home of the Boston Symphony Orchestra. While it was not open for business when we visited it is known for its summer music events.

Hancock Shaker Village

Located in Hancock, Ma. the historic Hancock Shaker Village is an open-air museum as well as on the National Register of Historic Places. It was active from 1790 until 1960! At the height there were 300 Shakers living at Hancock Shaker Village, men and women lived separately, and they were highly regarded for their honest and industriousness. The Shaker Community was one of the longest religious movements in the United States.

Our Fall Road Trip & Things to Do in the Berkshires - SCsScoop.com - Hiking Monument Mountain
Our Fall Road Trip & Things to Do in the Berkshires - SCsScoop.com - Hiking Monument Mountain

My Hiking Outfit

This fleece pullover is very cozy and perfect for hiking in the fall or winter. I got my normal size but you could size up if you prefer a roomier fit. I paired it with my favorite everyday leggings and running sneakers.

Places to Stay

There are so many charming places to stay in the Berkshires, from Airbnbs to Bed and Breakfasts and quaint hotels. Below are a few of the places that caught my eye while researching the area. A lot of them sell out quickly during their busy seasons, so book them as soon as you can.

Seven Hills Inn

Set on 27 acres of lush lawns and stunning gardens, the Seven Hills Inn is a stylishly renovated year-round boutique hotel. It is located in Lenox, Ma.

Apple Tree Inn

This is where we stayed. It was a great, charming and affordable option, and one of the few places that still had a couple rooms open when we booked our trip! They have live music on Saturday nights and a fun bar in their main house.

Red Lion Inn

Located in Stockbridge, Ma. this historic inn has lots of charm and great reviews! They have a restaurant and a quaint tavern that both look amazing.

Places to Eat in the Berkshires

Berkshire Mountain Bakery

This place was recently featured on Netflix’s Cooked, season 4, and for good reason. Their baked goods are delicious. When we stopped by, it was clear it’s a place the locals go and love. Definitely worth visiting and grabbing some extra baked goods to bring home with you. You can also pick up take & bake pizza here – a perfect option if you are staying in a cabin or Airbnb.

Rubiner’s Cheese Mongers

We didn’t make it to this place, but it was highly recommended by a couple people. Their cheese selection looks amazing! Definitely a place I will visit next time.

GB Eats

Located in Great Barrington, Ma., we stopped at GB Eats after our hike and were not disappointed. I loved my burger and the American fare on their menu looks like it would please a wide range preferences. They are open for breakfast, lunch and dinner.

Haven Cafe Bakery

Located in Lenox, Ma. This bakery offers breakfast, lunch and a delicious brunch on the weekends.


This restaurant and wine bar in Lenox, Ma. was packed when we were visiting. Their Meditteranean menu and wine selection looks amazing, and I am guessing it was drawing a crowd for good reason. This would be a great option if you want to do a fancy dinner one night.

Related: 5-Day Road Trip Itinerary from Portland to San Francisco

I hope you enjoyed this travel guide for the Berkshires. If you go and visit any of these places, I would love to hear about it. And whether or not you go to the Berkshires, I hope this inspires you to check out a new place and create a road trip with memories of your own.



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