Guest content and photo from Traveling Teacher Girl

Located in the heart of the Berkshires, Pittsfield is the perfect destination for a weekend babymoon. Whether you are hoping to spend your babymoon food tasting and mocktail tasting, getting pampered at a spa, or enjoying the local theater and arts scene, there is something in Pittsfield for every type of soon-to-be parent.

Pittsfield is a great babymoon destination any time of year: in the fall and spring, you can enjoy a variety of beautiful hiking trails. In the summer you relax on lakeside beaches. And, in the winter, you can enjoy the cozy vibes found at most downtown spots.

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

Take A Literary Break

Herman Melville’s Arrowhead is the historic home of Herman Melville, author of Moby-Dick. They offer public and private 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 Moby-Dick was written. Delve into the fascinating life of this literary legend, filled with travel, adventure, and a hint of scandal.

Go Shopping

Downtown Pittsfield has a variety of charming stores perfect for finding local goods and unique souvenirs. Don’t miss out on Museum Facsimiles, a favorite for its selection of distinctive artwork, home items, and adorable baby items. Dory & Ginger and Witch Slapped are two other boutique shops that you should be sure to peruse.

Get The Spa Treatment

Blu Salon is the perfect spot to enjoy a spa day during your Pittsfield babymoon. Blu Salon is a hair and nail salon that also offers prenatal massages, facials, and waxing. Be sure to book a mani/pedi and upgrade to the “classic pedicure” which comes with a foot scrub, mask, and hot rock massage- trust me, your tired feet will thank you!

Spend A Night At The Theater

Pittsfield, MA is a must-visit town for theater and arts lovers. There are several theaters and stage companies in town offering multiple shows almost every week. While I was in town, I saw a comedy show at The Colonial Theater, which is a beautifully designed theater that is over 100 years old. I also saw a new play festival as part of the town’s 10×10 Arts festival, at Barrington Stage Company which has multiple venues and stages downtown.

Visit Dottie’s Coffee Lounge

While in Pittsfield, a visit to Dottie’s Coffee Lounge is a must. This quaint spot offers an impressive selection of expertly crafted coffee and espresso drinks, as well as a diverse menu of breakfast and lunch items. Don’t leave without trying their breakfast burrito with your choice of bacon, sausage, or tempeh bacon, and be sure to sample their savory homemade soup of the day. While you’re there, take a moment to peruse their gallery of locally sourced art. And if you’re looking for a delicious souvenir, don’t forget to grab a jar of Bear Butter Almond Butter to enjoy at home.

Enjoy Dinner and Mocktails at 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 had (they use a secret ingredient to make them extra crispy and flavorful- ask about it when you visit).

Have a Romantic Meal at Trattoria Rustica

Transport yourself to Italy with a visit to Trattoria Rustica, an authentic Italian restaurant featuring a head chef straight from Pompeii, Italy. From the moment you walk through the door, you’ll be immersed in traditional art and handmade decor inspired by the ancient city. Their dishes are made with high-quality local ingredients and include a variety of appetizers, entrees, pastas, and desserts.

This visit was the perfect trip to turn into a mini-babymoon weekend away given the destination’s close driving proximity to NYC, plus all of the fun indoor and outdoor activities to experience and tons of great restaurants to try (many with fantastic mocktails options- cheers!).