Babymoon in the Berkshires: Top Things To Do In Pittsfield, MA

There are not many things that I love more than a great weekend road trip from NYC. Recently I learned about a small city in the Berkshires that is the perfect destination for a weekend trip from NYC: Pittsfield, MA.

Pittsfield is a small city located in the heart of the Berkshires, less than three hours driving distance from New York City. While it is a very popular summer destination, it is fantastic to visit year-round: whether you want to see the changing leaves in the fall, go skiing and snow tubing in the winter, or enjoy hikes and fresh air in the spring.

This winter I was invited to visit Pittsfield, MA and decided to turn the trip into a mini-babymoon. It is the perfect destination for a weekend babymoon near NYC, with a ton of fun activities to do and great restaurants to try (many with fantastic mocktails options- cheers!).

Below is a guide of the top places to stay, things to do, and places to eat when visiting Pittsfield, MA for a weekend getaway or babymoon.

*Please note that this post may contain affiliate links and any sales made through such links will reward me a small commission – at no extra cost to you.

Where to Stay in Pittsfield, MA

There are two hotels to choose from in downtown Pittsfield, MA.

Holiday Inn & Suites Pittsfield

Holiday Inn & Suites Pittsfield is a great budget-friendly hotel option. This hotel is located walking distance to many restaurants and theaters in Pittsfield. Their rooms offer beautiful views of downtown Pittsfield and the mountains. They also have an indoor pool, making this a great choice for families or if you are pregnant and want to enjoy some pool time.

Book your stay at Holiday Inn Pittsfield here.

Hotel On North

Hotel On North is a boutique hotel located in the heart of downtown Pittsfield. From their unique library suite and premier fireplace rooms to their boutique shop and craft restaurant, this hotel is oozing with character and charm.

Book your stay at Hotel On North here.

Things to Do in Pittsfield, MA

Go Shopping

Downtown Pittsfield has a lot of cute shops perfect for finding unique souvenirs and local goods. One of my favorites was Museum Facsimiles which has a variety of artwork, home items, and novelty gifts. Witch Slapped and Dory & Ginger are two other boutique shops you should be sure to peruse.

Go Skiing/Snowboarding/Snow Tubing (Winter)

Pittsfield is home to Bousquet Mountain which has over 20 trails, a terrain park, and also offers snow tubing. They have a really cozy ski lodge equipped with a fireplace and high quality food and drink items perfect for apres-ski.

Enjoy a Spa Day at Blu Salon

If you prefer to avoid the slopes (especially if you are in town for your babymoon like me), then enjoying a spa day is a must-do alternative activity in Pittsfield, MA.

In addition to being a full hair and nail salon, Blu Salon also offers a variety of services and treatments including massages, facials, infrared sauna, and waxing. Be sure to book your mani/pedi with Haylee and upgrade to the “classic pedicure” which comes with a foot scrub, mask, and hot rock massage. Blu Salon uses high quality products infused with essential oils rotating by season.

Enjoy Water Activities (Summer)

If you visit Pittsfield in the summer, there are a variety of activities to enjoy on the water such as boating, kayaking, paddle boarding, and water skiing. Head to LovePittsfield for more recommendations of things to do in Pittsfield, MA during the summer.

Go Hiking

Located in the heart of the Berkshires, Pittsfield is the perfect destination if you love to hike. There are a lot of hiking options, including The Boulders, Canoe Meadows Wildlife Sanctuary, Mahanna Cobble Reserve Trailhead, Pittsfield State Forest, and Springside Park.

Visit Herman Melville’s Arrowhead

Herman Melville’s Arrowhead is the historic home of Herman Melville, author of Moby-Dick. They offer tours (check their website for a current tour schedule) where you can take in the same views that Herman Melville enjoyed from the actual desk where he wrote Moby-Dick. It was so interesting to learn about Melville’s life which was filled with travel and adventures plus a pinch of scandal. Be sure to put this at the top of your list of things to do in Pittsfield, MA.

See a Theater Performance

Pittsfield, MA is a must-visit town for theater/arts lovers. There are several theaters and stage companies in town offering multiple shows every week. While I was in town I saw a comedy show at The Colonial Theater and a new play festival from Barrington Stage Company.

Visit Berkshire Museum

Opened in 1903, Berkshire Museum has three floors of exhibitions related to art, science, and history. It is perfect for visitors of all ages, with unique programming for children/families as well as adults.

Where to Eat and Drink in Pittsfield, MA

101 Restaurant and Bar

101 Restaurant and Bar is a family-owned restaurant offering a modern, southern-inspired menu. In addition to the food listed on their menu, their staff is very accommodating and can prepare other items if you have any dietary restrictions/preferences. 101 Restaurant prepared several fantastic vegan options for me (I absolutely loved their cauliflower steak), as well as made me a killer mocktail. Be sure to try their french fries which are some of the best french fries I have tried (they use a secret ingredient to make them extra crispy and flavorful- ask about it when you visit).

*Cauliflower Steak at 101 Restaurant and Bar*

Thrive “A Fresh Cuisine Diner”

Thrive is located in a train car diner that was bought and renovated four years ago. They offer a high quality, plant-based, organic menu with a ton of comfort food options. I loved their buffalo tofu nuggets and cashew curry tempeh sandwich.

Dottie’s Coffee Lounge

Dottie’s Coffee Lounge is a must-visit in downtown Pittsfield. They offer expertly crafted coffee and espresso drinks as well as a large variety of breakfast and lunch items. Be sure to try their breakfast burrito with bacon, sausage, or tempeh bacon, and their homemade soup of the day. While you there, you can peruse their gallery of art by local artists as well as visit their small boutique curated with specialty items (and don’t forget to buy a jar of their Bear Butter Almond Butter to take home with you).

Trattoria Rustica

Trattoria Rustica is an authentic Italian restaurant with a head chef hailing from Pompeii, Italy. Stepping into this restaurant will make you feel like you have been transported to Italy, with traditional art and homemade decor inspired by the ancient city of Pompeii.

They offer fantastic cocktail/mocktail options, a large wine menu, and a variety of appetizers, entrees, pastas, and desserts using high-quality local ingredients.

Misty Moonlight Diner

Misty Moonlight Diner is a classic American diner that will make you feel like you have stepped back in time to the 1950’s. From their bright red counter stools and checkered floors to their walls lined with memorabilia (including a custom Harley Davidson), every detail in this diner looks like it came straight out of a movie set.

If you enjoy reading, be sure to pick up a copy of “The House in The Pines” by Ana Reyes before visiting Pittsfield. A significant scene in this book takes place at an unnamed diner that is most likely Misty Moonlight. Reading the first few pages of the book will add an additional element of fun to visiting this diner!

Lift Bistropub

Yes- one of the top restaurants on my list of places to eat in Pittsfield, MA is located at a ski lodge! If you are a skier, you know that typical ski lodge food is overpriced and underwhelming. However, Lift Bistropub at Bousquet Mountain offers an incredible menu at a great price if you are looking for an elevated apres-ski meal. Be sure to try their winter greens salad and brussel sprouts, and enjoy sitting by their cozy fireplace.

Hot Plate Brewing

Hot Plate Brewing is a latina/women-owned brewpub that opened in downtown Pittsfield in 2023. Co-founder Sarah Real started brewing on hot plates in her small Brooklyn apartment (where the name “Hot Plate Brewing” comes from), and recently moved to their 7-barrel brewhouse and taproom in Pittsfield.

In addition to beer, Hot Plate Brewing also offers wine, cider, hard seltzers, and non-alcoholic drinks (their non-alcoholic beer options were perfect to enjoy during my babymoon!).