A travel guide to Pittsfield, Massachusetts

Pittsfield, Massachusetts, is a charming town nestled in the heart of the Berkshires. With its rich history, vibrant arts scene, and stunning natural beauty, Pittsfield has something to offer everyone.

Getting There To Pittsfield

Pittsfield is easily accessible by car, located about 2.5 hours from Boston, 3 hours from New York City, and 1 hour from Albany, NY. The nearest major airport is Albany International Airport, which is about 45 minutes away by car.

Where to Stay

Hotel on North

Located in the heart of Pittsfield’s historic downtown, Hotel on North is a beautifully renovated 19th-century building that offers guests a unique blend of old-world charm and modern amenities. From the moment I walked into the lobby, I was struck by the hotel’s elegant decor, warm lighting, and welcoming staff.

My room was spacious, bright, and beautifully decorated with a cozy bed, plush linens, and a luxurious bathroom. But what really set Hotel on North apart was the attention to detail and central location, you can’t beat the tall ceilings and the beautiful hardwood floors. However the true show stopper is the library suite – where you can sleep amongst hundreds of books.

One of the highlights of my stay was the hotel’s on-site restaurant, Berkshire Palate. The restaurant serves delicious farm-to-table cuisine using locally-sourced ingredients. I enjoyed a fantastic lunch there, accompanied by a local beer from their impressive selection. The atmosphere was lively and convivial, with friendly staff and a bustling open kitchen.

Aside from the hotel’s amenities, Pittsfield itself has a lot to offer. The town is home to a vibrant arts scene, with several galleries and museums, including the Berkshire Museum and the Norman Rockwell Museum. The hotel’s central location made it easy to explore the town’s attractions and historic sites, such as the Colonial Theatre and the Arrowhead estate.

My stay at Hotel North in Pittsfield, MA was an unforgettable experience. The hotel’s combination of classic charm, modern amenities, and impeccable service made me feel right at home. And with its prime location in the heart of Pittsfield’s vibrant downtown, Hotel North is the perfect base for exploring all that this beautiful town has to offer.

What to See and Do:

Berkshire Museum – This museum features a variety of exhibits on art, science, and history. Don’t miss the “Objects and Their Stories” exhibit, which showcases some of the museum’s most interesting artifacts. This a great option if you are traveling with kids!

Colonial Theatre – This historic theater hosts a variety of shows and events throughout the year, including plays, concerts, and comedy shows.

The Mount – This historic home and gardens was once the residence of author Edith Wharton. Visitors can tour the home and gardens, as well as attend special events and performances.

Tanglewood – This world-renowned music venue is the summer home of the Boston Symphony Orchestra. Visitors can attend concerts and performances throughout the summer season.

Housatonic River Walk – This scenic trail follows the Housatonic River through downtown Pittsfield. It’s a great way to enjoy the natural beauty of the area and get some exercise.

Ski at Bousquet Mountain – this recently renovated community ski mountain is the perfect place to get a few runs in before dining at their amazing pub overlooking the slopes. They also offer night skiing!

Take a Brewery Tour at Hot Plate – this women owned brewery is the perfect place to gather with friends over a board game.

Take a tour of Arrowhead– the historic home of Herman Melville, author of Moby Dick. Tour the grounds of this stunning estate and even peer out the infamous view of Mount Greylock from Herman Melville’s desk. This was quite possibly my favorite part of our visit to Pittsfield. Our tour guide, Jana, was enthusiastic and welcoming. She gave us such a fantastic glimpse of the history of the estate and Herman’s life.

looking for more getaway ideas? Check my suggestions for Massachusetts getaways here.

Where to Eat during your travel to Pittsfield

Berkshire Palate – This on-site restaurant at Hotel North serves delicious farm-to-table cuisine using locally-sourced ingredients.

Dottie’s Coffee Lounge – This cozy cafe serves coffee, tea, and light bites in a relaxed atmosphere. Don’t miss the freshly baked pastries!

Mission – This trendy restaurant features a variety of small plates, as well as a full bar with creative cocktails.

Methuselah Bar and Lounge – This stylish bar features craft cocktails and live music in a chic setting. It also has an amazing late night scene, as it is open until 2 am.

District – this community staple is the perfect place for a cozy meal that packs a punch. With locally sourced ingredients and menu that reflects, its the perfect place to grab dinner. We also recommend the incredible cocktail list – we went the Maple Old Fashioned.

Misty Moon – This retro dinner is heavy on the coffee and charm. Sit amongst retro relics as you enjoy the best diner food in town.

Pittsfield is a charming town with plenty to see and do. I was definitely surprised, as this place often gets passed over. Whether you’re interested in history, art, or outdoor activities, there’s something for everyone in Pittsfield.