Things to do in Pittsfield MA: A Fun 3-Day Guide

Things to do in Pittsfield MA

If you are looking for things to do in Pittsfield MA, you’ve come to the right place!

We recently went on a girls’ trip to Pittsfield MA inspired by the book The House in The Pines by Ana Reyes. Our trip was generously covered by the city of Pittsfield.

Below, we will share some of our favorite restaurants, where we stayed, and things to do in Pittsfield MA, and the surrounding area – which is only a short ride away from our home in Philly.

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Hotel on North

Where to Stay in Pittsfield Massachusetts

If you are looking for where to stay in Pittsfield, chances are you’ve already come across the Hotel on North.

I’m sure there are other hotels and AirBNBs in the area, but this hotel fit our bill perfectly. It was centrally located to all our activities, had free parking on site, and was newly renovated.

The rooms at Hotel on North are spacious, with high ceilings due to the fact that it’s a converted warehouse. Our room was located on the 2nd floor right off of a gorgeous sitting area complete with ceiling lights.

The lobby of this boutique hotel is a welcome oasis with plush leather chairs and a 24/7 tea and coffee bar – a big perk for the caffeine obsessed.

The hotel is situated in the center of town within walking distance of quite a few restaurants and the various theatres the Berkshires are well known for – but more on those later.


Where to Eat: Pittsfield MA Restaurants

There are many restaurant options in downtown Pittsfield. Coffee bars, diners, nicer restaurants, and grab-and-go locations are scattered up and down North Street. There are also quite a few bars in the area – including one off the hotel lobby – if you are hoping for a nightcap.

Now let’s get into some of our favorite Pittsfield MA restaurants and bars.


Breakfast and Lunch Restaurants in Pittsfield MA

Dottie’s Coffee Lounge is breakfast heaven. It serves up freshly baked goodies, eggs, yogurt, lattes, oatmeal, and so on. You name it, it’s on the menu. I’m a coffee snob and I was craving their lavender latte every morning.

We also enjoyed Sunday brunch at the Proprietor’s Lodge. It’s served buffet style and features omelets, bagels with fixings, fresh fruit, a carving station, biscuits, and gravy, and tons of dessert goodies. They also do mimosas and bloody mary flights. And the view at the lodge is gorgeous. It looks right over Pontoosuc Lake with trees and mountains in the distance.

For lunch, try Marketplace Cafe which makes fresh sandwiches, salads, and paninis with unique ingredients. You can eat it in-store or even better, take it with you on a hike.


Dinner Restaurants in Pittsfield MA

Let’s start with our favorite meal – Sibarita’s. This Italian eatery is absolutely delicious! We relished every morsel as we sampled many different menu bites. You can’t go wrong with any of the pasta dishes on the menu.

District Kitchen was another highlight. My carne asada tacos were a dream and Jackie adored her salmon. The locals come back again and again for their burgers – so if that’s your jam, it’s worth ordering. Their cocktail menu is also a delight – Jackie had a sparkly pink lavender gin drink that was as yummy as it was gorgeous.

We also enjoyed Methuselah – a full-service bar with lighter bites. The food was delightful and the drinks were perfection, but be advised – with only one chef, the wait for your food can be a little long. Fine for a regular night out, but not ideal for a meal before the theater. We felt rushed which was more a timing issue on our end than theirs. I’d recommend this on a night you can relax.

Things to Do in Things to do in Pittsfield MA

Pittsfield Massachusetts is in the middle of the Berkshires, making it a fun locale year-round. There are so many things to do in Pittsfield MA, and the surrounding areas, so I put together a guide for an ideal first visit.

Edith Warton

3-Day Itinerary w/ Pittsfield MA Restaurants

Day 1 – Arrival

  • On your drive into town, stop into the nearby town of Lenox to walk the grounds of Edith Warton’s Estate “The Manor.” You can tour the actual manor house for $20 – or simply enjoy the wooded trails and lush gardens for free.
  • Check into the Hotel on North.
  • Grab dinner and a nightcap at Methuselah
Hiking 2

Day 2 – Explore Pittsfield

  • Enjoy breakfast at Dottie’s Coffee Lounge
  • Stop by Marketplace Cafe to grab food for a picnic lunch.
  • Head to Berry Pond for gorgeous views and a fun hike through the Berkshires. Or bring a chair or blanket and a good book to read while enjoying lunch.
  • If you want to unwind, head over to Balderdash Cellar, a local winery for house-made wines, frozen cocktails, and live music.
  • Grab an early dinner at District Kitchen + Pub
  • Head to a Berkshire Theatre Group show at The Colonial or to the Barrington Stage for a production put on by the Barrington Stage Company.
Shaker Village

Day 3 – Herman Melville’s House and the Shaker Village

  • Head to Brunch at Proprietor’s Lodge
  • Take a tour of Herman Melville’s home, Arrowhead, where he wrote Moby Dick.
  • Make your way to the Shaker Village (you can grab lunch on-site) to see the animals, stroll through the farm garden, and learn about the history of this former religious settlement.
  • Eat dinner at Sibarita’s.
Museum Facsimilie

Departure Day

  • Check out from the hotel.
  • Before you head home, check out Dory & Ginger in the hotel lobby for all kinds of giftware and stop by Museum Facsimiles to see the gorgeous book spine artwork crafted by the owner. I bought 3 art pieces there!

So that is our list of things to do in Pittsfield MA. Would you head to this vacation spot?

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