How to Spend a Perfect Fall Weekend in Pittsfield, Massachusetts in the Berkshires

There’s nothing I love more than hitting the road on a Friday afternoon for a weekend escape out of the city. And one of the best weekend getaways my husband and I took recently was to Pittsfield, Massachusetts, in the heart of the Berkshires.

While I have been to the Berkshires many times, this was the first time I spent the weekend in Pittsfield. I’m so glad I did because after a full weekend of exploring, I can say with complete confidence that this under-the-radar city in the Berkshires is about to take off.

Why?

Well, there are a few reasons I feel that Pittsfield, Massachusetts is about to show up on everyone’s must-visit list.

First, there’s the Berkshire Flyer. It’s an Amtrak train offering direct service from NYC to Pittsfield. The pilot program took place on weekends this past summer, and it was a rousing success. There’s now talk of running this route full-time plus Summer 2023 will be another opportunity to experience this route for yourself.

The second reason is that this historic mill town with a walkable Main Street has good bones. How do I know this? Let’s just say that with the amount of time I’ve spent over the years producing HGTV shows in small towns, I’ve come to recognize when a town has the right mix of charm, character, and history to make it a special place. And Pittsfield has all of these things.

Lastly, Pittsfield has an eclectic mix of restaurants, shops, and cultural offerings located in the heart of downtown, all just minutes away from scenic hiking trails, lakes, and of course, the majestic Berkshires mountains!

So, are you ready to hear more about Pittsfield, Massachusetts so you can plan a weekend getaway there?

Keep reading for all of my travel tips!

Where is Pittsfield, Massachusetts?

Pittsfield Massachusetts is located in the heart of the Berkshires, a beautiful, mountainous area in Western Massachusetts. In case you aren’t familiar with the region, the Berkshires are made of many small, charming towns like Great Barrington, Lenox, Stockbridge, and North Adams. (Read my Great Barrington travel guide for more info and travel tips.)

How Do You Get to Pittsfield?

The quickest way to get to Pittsfield is by car. From NYC, it’s 150 miles, approximately a 3-hour drive if the traffic isn’t bad. From Boston, it’s 137 miles and will take you about 2.5 hours to get there.

But the coolest way to travel to Pittsfield now is the Berkshire Flyer. The fact that this train even exists is a big deal! For years, there has been talk about adding additional train lines to connect NYC and Massachusetts and it’s exciting to see that it has finally happened. Plus, at $45 each way, it’s a very affordable option for transport.

One caveat is that right now, Amtrak is only offering seasonal weekend train service from NYC to Pittsfield, MA. This past summer (2022) was the pilot program, and they ran the train from July through September. It was such a success that there is now a push to make this train year-round. I hope this happens because it will open Pittsfield Massachusetts and the surrounding Berkshires up to so many more people.

Lastly, you can also get to Pittsfield by bus. Greyhound has daily trips but I don’t really recommend this option because you’ll be on the bus all day, connecting through Boston to get to Pittsfield. The better bus option is via Peter Pan, which has a daily departure from NYC to Pittsfield Friday through Sunday. Since bus options to the area are still limited, that’s why we are hopeful that in the future the Berkshire Flyer will become a year-round option.

Why You Should Visit Pittsfield, Massachusetts in the Fall

Visiting the Berkshires in the fall is magical. The leaves are golden-hued, the temperature is perfect for exploring, and the region is full of things to see and do. Add to the list charming towns, vibrant restaurants, and cozy cocktail bars, and you have everything you need to spend the perfect fall weekend out of the city.

For sure, one of the highlights of visiting Pittsfield during autumn is hiking because the changing color of the foliage is spectacular. There is a comprehensive guide to hiking trails in the area at the BNRC Berkshires Trails App and website. We did The Boulders hike which has various routes of different lengths. The weather was so spectacular, we ended up doing the 5-mile loop.

We happened to visit Pittsfield the weekend right before Halloween which was a good decision because the area has so many cool Halloween events that happen here annually. Definitely bookmark this post if you want to plan a trip to Pittsfield and the Berkshires next year during Halloween.

(Pro-Tip: Massachusetts is also home to Salem, one of the most famous towns to visit during Halloween, but having spent Halloween weekend there as well, I can tell you firsthand that you’ll have a much more enjoyable experience celebrating Halloween in Pittsfield, where you won’t be fighting massive crowds and waiting in extremely long lines to get in everywhere.)

Here’s a rundown of all of the Halloween-related activities we did in Pittsfield that I highly recommend!

• Haunted Hancock at Shaker Village: If you like ghost stories, you’ll love this evening tour full of haunted stories at Hancock’s Shaker Village.
• Halloween Parade in Downtown Pittsfield: The 2022 parade kicked off on Friday, Oct. 28 after a two-year hiatus due to Covid restrictions. Around 5,000 people lined Tyler Street to watch a procession of floats, schools, and other organizations dressed to the nine in their spookiest garb for the 76th annual parade. See parade photos here.
• The Incredible Naumkeag Pumpkin Show: Every year Naumkeag, one of the Berkshires’ original gilded-age estates, hosts a massive pumpkin show where you get to see over 1,000 carved pumpkins. This is a great activity for kids and adults alike. They also serve hot and cold alcoholic and non-alcoholic drinks, plus yummy fall treats like apple cider donuts.
• The Rocky Horror Picture Show at the Colonial Theater: I think I saw the Rocky Horror Picture Show over 10 times when I was in high school and college, but my husband, who grew up in India and Indonesia had no idea what this show was about, so of course, I had to take him! We were able to buy a bag of props at the theater, so we had everything we needed to fully enjoy the interactive show. And let’s just say, IYKYK!

In addition to Halloween-related activities, the Berkshires are also home to a number of Orchards and farms. If you like apple picking or wandering through pumpkin patches this time of year, you won’t be disappointed! Ioka Valley Farm is a short drive from Pittsfield and hosts fall festivities throughout the season.

Where to Stay in Pittsfield, Massachusetts:

• Hotel on North: A locally owned boutique hotel with exposed brick walls and lots of charm. Located right on North Street, Pittsfield’s main thoroughfare.
• Holiday Inn: Also locally owned, this hotel is a great option if you have kids. There’s an indoor swimming pool, a gym, and the popular 101 Restaurant and Bar. There’s also a rooftop deck with incredible views of the surrounding Berkshires.

Where to Eat and Drink in Pittsfield, Massachusetts:

• Methuselah Bar and Lounge – a great spot for craft cocktails, cheese boards, and eclectic eats including tacos and Bi Bim Bap. (The owner is Korean and she’s originally from NYC. We loved chatting with her and learning more about her story.)
• Lulu’s Tiny Grocery – A great spot for a quick but filling breakfast (we had the breakfast burritos) and specialty coffees.
• Marketplace Café – A very popular café in town with tons of healthy and delicious salads and sandwiches.
• District Kitchen and Bar – One of the happening spots in town, we loved the vibe and the food!
• Dottie’s Coffee Lounge – If you have time for a more leisurely breakfast/lunch, I highly recommend this place. And you cannot leave without buying a jar of Bear Butter. It is insanely good!
• Thistle and Mirth – Right next to District Kitchen and Bar, this local craft beer bar also serves up delicious Ramen. Check their website for weekly events including trivia and karaoke.
• Berkshire Palate – The restaurant is located at Hotel North, a great spot for lunch or dinner offering seasonal food in an elevated atmosphere.

Things To Do in and Near Pittsfield:

• Hike the Boulders Trail – As I mentioned above, this is a great local trail that isn’t too rigorous and has multiple options depending on how many miles you want to hike.
• Berkshire Museum – Right in the heart of downtown, it’s a museum of art, natural history, and ancient civilization.
• Ioka Valley Farm – a working farm started in 1936 that has a variety of locally grown products and hosts events throughout the year.
• Hancock Shaker Village – a living history museum that brings the story of the Shakers to life.
• The Colonial Theater – Situated right downtown on North Street, there’s always a good show at the Colonial Theater worth seeing. We saw the Rocky Horror Picture Show when we visited.
• Herman Melville’s Arrowhead – Run by the Berkshire County Historical Society, the grounds include the home where Herman Melville lived and wrote Moby Dick. Tours are about an hour long and are full of interesting facts about Herman Melville’s life.

Where to Shop in Pittsfield

• Witchslapped – This shop was especially fun to visit during Halloween weekend and has everything from tarot cards to crystals.
• Dory & Ginger – I wanted everything in this well-curated home goods store!
• Museum Facsimiles – Another shop with an amazing selection of home goods, artwork, and antiques.

Are you Ready for the Perfect Fall Weekend in Pittsfield, Massachusetts?

My husband and I had such a great fall weekend in Pittsfield, Massachusetts. We are already planning our next visit! Next, we want to come in the wintertime to enjoy everything that the season has to offer. Plus, we want to hit up Bousquet Mountain for skiing, snow tubing, and après ski drinks at Lift Bistro.

Now I’d love to hear from you! Have you been to the Berkshires, and if so, have you visited Pittsfield? If not, I hope you found this post helpful when you’re planning your next trip. As a New Yorker who loves to explore the region on weekends, I truly feel the Berkshires are about to have a big moment. And that definitely includes Pittsfield.

Happy travels!