Pittsfield, Massachusetts: A Guide to Your Weekend Getaway

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If you live in the Northeast, you’ve likely heard of the Berkshires before. But have you heard of the charming, and culture-packed city of Pittsfield, Massachusetts? Nestled smack in the middle of Berkshire County, the city of Pittsfield offers everything you need for a weekend escape from New York City. Whether you’re looking for gourmet farm-to-table dining, boutique hotels, endless hiking trails, or world-class theater, Pittsfield offers it all just a short train right away from NYC. 

Not only is Pittsfield a great destination for a weekend getaway, but it is also the perfect base for exploring the broader Berkshire area, as it sits just between “North County” and “South County”. A stay in Pittsfield allows you to quickly access both the northern cities of Williamstown and North Adams, as well as the popular southern cities of Great Barrington and West Stockbridge. 

I was invited by the town of Pittsfield to come experience everything the city has to offer, and experience the inaugural train journey from NYC to Berkshire County.

mural in pittsfield by jesse tobin mccauley local artist
Mural by local artist Jesse Tobin McCauley

Getting to Pittsfield via The Berkshire Flyer

After 51 years, train service has resumed, this time powered by Amtrak, to offer direct access from New York City to the Berkshires by train. The Berkshire Flyer, which launched on July 8th, is a pilot program for the summer to test the demand for this route. The current schedule offers 1 round trip service per week, departing from the new Mohyian Penn Station in NYC at 3:15 on Fridays, and returning from Pittsfield, MA on Sundays departing at 3pm. 

The train, which makes a number of stops including Yonkers, Poughkeepsie, Hudson, and Albany, takes 4 hours. Previous to the launch of the new route, the easiest way to get to the Berkshires from NYC by public transportation was to take the Metro North to Wassaic, followed by a bus. Having direct train access from NYC encourages a new wave of tourism to Pittsfield and the broader Berkshire county.  During my trip, I had the opportunity to sit down with Berkshire County Senator Adam Hinds who shared that the city is taking a number of actions to making visit Pittsfield even more accessible to New York tourists, including new shuttles services and an Enterprise car rental outpost directly next to the main train station. 

new berkshire flyer train service
berkshire flyer at sunset

Best Time of Year to Visit Pittsfield, Massachusetts

Pittsfield offers round-year activities for its guests, where you’re looking to explore the hiking trails or the ski trails. Visiting in July, we were welcomed with perfect summer weather. However, there is plenty to see and do in the winter months as well!

Best Things to do in Pittsfield, Massachusetts 

The city of Pittsfield has something to offer for any type of traveler. Whether you’re looking for gourmet farm-to-table dining, boutique hotels, endless hiking trails, or world-class theater, Pittsfield offers it all just a short train right away from NYC. 

Attend a show at the theater – either at Barrington Stage Company or the Colonial Theater 

Pittsfield is a city full of artists, and that talent shines through at the performances put on at both the Barrington Stage Company and Colonial Theater. With tickets as low as $59, a night at the theater should absolutely be added to your Pittsfield travel itinerary. 

I had the opportunity to see Ain’t Misbehaving during my recent visit to Pittsfield and it was fantastic!

Visit the historic home of Herman Melville 

I’m sure you’ve heard of the classic American novel Moby Dick. But did you know that Melville wrote this classic novel while living in the Berkshires? While in Pittsfield, stop by the historic home of Herman Melville for a flash back in time. 

 historic home of Herman Melville 
 historic home of Herman Melville 

Enjoy a luxury stay at boutique hotel, Hotel on North 

My stay at the boutique hotel of Hotel on North was easily a highlight of my trip to Pittsfield. From the unbelievably attentive staff to the attention to detail in all of the decor and design, the team at Hotel on North will make sure that your stay is perfect. Not to mention, it is conveniently located just a 2 minute walk from the train station. 

What was once an old department store, Hotel on North now offers 45 charming and unique rooms for its guests, since it opened as a hotel 7 years ago. 

hotel on north pittsfield massachusetts

With rooms starting around $160 in the winter months and $200 in the summer months, Hotel on North is an affordable slice of paradise for New York City tourists. Looking to splurge? Book yourself a stay in the Library Suite. The suite, which is appropriately named, is filled with hundreds of books, perfect for a real-life Belle moment. 

hotel on north library suite
hotel on north library suite

Go for a hike in Pittsfield State Forest (or the Boulders)

One of the best things to do in Pittsfield is enjoy the many hiking trails that fill the city, including Pittsfield State Forest. With over 30 miles of trails, you could spend your entire vacation here! But if you’re looking for a quick afternoon experience, I recommend checking out Berry Pond, the highest body of water in Massachusetts. The pond can be reached by car or foot. If you’re looking to camp, make sure to reserve a campsite ahead of time. Rates start at $17.00/night for a tent-only site. 

The BNRC Berkshire Trails app is a comprehensive guide to hiking trails in state forests, parks & nonprofit land preserves.

 Pittsfield State Forest
 Pittsfield State Forest

Unfamiliar with the trails and looking for some additional guidance? Mindy from Berkshire Camino offers guided walks and hiking tours throughout Pittsfield and the greater Berkshire county. Mindy’s hiking tours are inspired by her experience hiking the Camino de Santiago in Spain. Her tours are so much more than just a walk through the woods, as she brings in beautiful elements of mindfulness and meditation into all of her guided tours. 

Tours start at $50 and are suitable for all fitness levels. 

Head to the slopes at nearby Bousquet Mountain or Jiminy Peak 

Pittsfield and the Berkshires are not just a summer destination. Come in the winter to enjoy great skiing at nearby mountains of Bousquet Mountain and Jiminy Peak. Bousquet Mountain is less than 10 minutes away by car from the heart of Pittsfield, while Jiminy Peak, which is located in Hancock, can be reached in 20 minutes by car. 

Visit Hancock Shaker Village 

Hancock Shaker Village is a landmark destination of 750 acres, 20 historic Shaker buildings and over 22,000 Shaker artifacts. On the National Historic Register, it is the most comprehensively interpreted Shaker site in the world and the oldest working farm in the nation.

Pictured below is one of the rotating art exhibits.

Visit Hancock Shaker Village 
Visit Hancock Shaker Village 

Take a stroll down North St 

North St is Pittsfield’s charming main road. You’ll find restaurants, shops. and hotels dotting the picturesque city street. Make sure to stop in Dory & Ginger (pictured below) for the cutest gifts and home goods.

north st
dory and ginger

Visit the Pittsfield Farmers Market

The Pittsfield Farmers Market runs weekly on Saturdays, from May to October. Local fruits and veggies are provided by Roots Rising, whose mission is to empower youth and build community through food and farming. On select weekends you’ll also find tons of local vendors, from clothing to aromatherapy essentials like Kenzie’s Essentials.

Where to eat in Pittsfield, Massachusetts 

There is no shortage of great dining options in Pittsfield. Below are just a few of my favorites that I tried!

District Kitchen & Bar  

Our meal at District Kitchen & Bar was hands down the best meal that we ate while in Pittsfield. Serving contemporary American cuisine, it is one of the best dining options in town. The restaurant was established just a few years after its sister restaurant in North Adams, Public. You’ll find a few of the same classic menu items, including the Mac & Cheese, PEI Mussels, and appropriately named Public Salad.

While the restaurant doesn’t take any reservations, you can add yourself to the waitlist on their website, where you’ll also be given estimated wait time.

District Kitchen & Bar  
District Kitchen & Bar  

The Marketplace 

A more casual farm-to-table eatery, The Marketplace is a great option for picnic lunches while in Pittsfield. Planning a hike? Swing by The Marketplace ahead of time to grab one of their delicious sandwiches or salads. I got the Stockbridge Bowl with grilled chicken and it was delicious and super filling.

Do yourself a favor and order the lemon bar for a real treat. They are big enough to share, but delicious enough to enjoy all on your own.

The Marketplace pittsfield
The Marketplace at berry pond

Berkshire Palate 

The Berkshire Palate is attached to the Hotel on Room, making it a great stop for any guests of the hotel. The food is delicious, and the beer selection is great! The kitchen is typically open until around 9pm, with the bar serving drinks until 10pm.

Dottie’s Coffee Lounge 

Dottie’s is a Pittsfield breakfast classic. A local favorite, Dottie’s provides food and drinks locally sourced for a sustainable community. Dottie’s runs a program called Berkshire Oats, where each oatmeal purchased provides one for someone in need in the community. Locals rave about their famous Bear Butter.

Dottie’s Coffee Lounge  pittsfield massachusetts
Dottie’s Coffee Lounge  pittsfield massachusetts

Methuselah Bar & Lounge

Methuselah Bar & Lounge is a great option if you’re looking for a drink in Pittsfield, Massachusetts. This charming locale serves organic wines & craft beer paired with local New American fare. While I wasn’t super impressed by the food, the cocktails were incredible. I particularly enjoyed the Paper Plane.

 Methuselah Bar & Lounge
Methuselah Bar & Lounge pittsfield

Mission 

A tapas-style restaurant in the heart of Downtown Pittsfield, Mission is a great option for pre-theater food if you are attending a show at the Barrington Stage Company.

Thistle & Mirth 

Although I didn’t have a chance to stop at Thistle & Mirth myself, it is affectionately claimed as the local bar for a weekend night out in Pittsfield, Massachusetts. Stop by and let me know what you think!

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Taylor Taverna
Taylor Taverna

Taylor is a NYC-based solo traveler and travel blogger. Taylor shares travel tips and itineraries from the 70 countries she’s visited around the world.

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