By Maria Ottomanelli and Doreen Wong
This trip was reported from a 2022 visit. Hotel branding, restaurant menus, attraction hours, event schedules and transportation service can change, so check current details before traveling.
Whether you live in the Berkshires or are planning a visit, Pittsfield offers scenery, hiking, culture, food and outdoor activities. Our adventurous group traveled from New York and New Jersey by Amtrak, rolling along the Hudson River Valley before arriving at the Joseph Scelsi Intermodal Transportation Center in downtown Pittsfield.
Travelers planning another Northeast escape may also enjoy our Mystic, Connecticut weekend getaway.
Where we stayed in Pittsfield
The Holiday Inn & Suites in Pittsfield, MA is the tallest building in Berkshire County. The top floor hosts receptions, meetings, and presentations. It has an amazing panoramic view, especially during sunset. At an evening reception there, we were greeted by Susan who gave us an interesting overview of the landmarks and attractions of the Berkshires. The sample of food: Brussels sprouts and smoked apples, pork belly and hoe cakes, cheddar jalapeño hush puppies, & mini pulled pork sandwiches, certainly enticed us to dine at 101 Restaurant & Bar on the second floor. It is a family-run business and has created an original, southern-inspired menu for everyone’s palate. We enjoyed tasting delicious beet blue salad with shrimp and salmon, Caesar salad, and a fried chicken sandwich.
Pittsfield Farmers Market
The Pittsfield Farmers Market is a program of Roots Rising, whose mission is to empower youth and build community through food and farming. It was the first teen-run farmers market in the region. During our 2022 visit, the market ran Saturdays at Pittsfield Common, 100 First Street; travelers should check the current market schedule before visiting. We enjoyed the live music that was playing while strolling through the farmers market. There were fresh seasonal fruits and vegetables. We spoke to some vendors and discovered unique products, including handmade petits choux & confiserie from Les Petits Choux Bakery and barking good biscuits from Roxie’s Bakery. Support local farmers and bakers by shopping here.
Berkshire Camino guided hiking
Each Berkshire Camino guided hike is designed to take an individual or a group of hikers on a journey exploring the beautiful landscape, history, and culture, and letting go of anything that is worrisome. Our expert guide, Mindy Miraglia, intrigued us with her knowledge of the history, culture, and spirit of the Berkshires. We walked with intention, curiosity, and mindfulness at the Boulders. The Green Trail (1.4 miles) offered a longer hike than the Healthy Heart Loop, while still maintaining an easy difficulty level. It intersected with the Red Trail which was a longer hike.
We were in touch with the natural environment and bewildered by the chirping of sparrows, Daddy Long Legs, and two majestic trees connected by their roots. There were fallen trees which reminded us of the life cycle and the nonfiction book, Log Hotel, by Anne Schreiber. We had moments of silence and self-reflection and gained a deeper appreciation of the serene nature.
This is absolutely a destination, educational, and spiritual experience. Above all, Mindy with Berkshire Camino will help you plan a hike, one that is safe and engaging. So, you can just show up.
Things to do in Pittsfield and the Berkshires
After this invigorating hike, we were transported to Pittsfield State Forest for a tasty picnic lunch from Marketplace Cafe. We had fresh Naked Granny salads, assorted sandwiches, refreshing Joe’s iced tea, scrumptious desserts overlooking Berry Pond, the highest natural body of water in MA. It was definitely the highlight of our exciting trip!
Since we had some leisure time in the afternoon, some of us cooled off in the Holiday Inn & Suites pool. Splish, splash, here comes Piper…
Others explored the local area. If you want a unique shopping experience, visit Museum Outlets which has an eclectic mix of merchandise such as custom frames, distinctive wall art, home decor, jewelry, and women’s accessories. You can also shop online to your heart’s content at https://museumoutlets.com/. Try Brooklyn’s Best if you’re in the mood for Italian cuisine and shop at Maria’s European Delights Delicatessen.
District Kitchen & Bar
We had a fabulous dinner at District Kitchen and Bar. It is certainly a must-try when in Pittsfield, MA. You can relax and have a drink at the bar or have a sit-down dinner. We loved the pan-seared duck breast and the pan-roasted salmon. We enjoyed the cheese board with added daily charcuterie. This popular restaurant has New York vibes and also offers a nice selection of flatbreads and burgers.
Barrington Stage Company
The Barrington Stage Company is a venue that you will truly enjoy if you are a theater-goer. We watched an entertaining performance of A Little Night Music. The story had romantic twists and turns for a mature audience. This was definitely a Broadway-quality production!
Dottie’s Coffee Lounge
During our 2022 visit, Dottie’s was a popular community breakfast stop with indoor and outdoor seating, coffee, tea and fresh food. Live-music schedules and hours can change, so check the current information before visiting. We loved the avocado toast and Bear Bowl which included steel-cut oats with fresh berries. The matcha iced latte was the perfect complement to a hearty breakfast!
Herman Melville’s Arrowhead
Herman Melville was an American novelist, short story writer, and poet of the American Renaissance period. Arrowhead is the Pittsfield house where Herman Melville lived. Today, it is a historic house museum that has tours and shares the history of Herman Melville’s life. It was interesting to learn about his life and how his passion for writing began.
Hancock Shaker Village
We visited the historic working farm and landmark destination. It was the home to the Shaker community and continues to preserve its history. The farm has livestock and vegetables. You can leisurely tour the various houses on the property and the art exhibitions that are displayed for public viewing. Why not enjoy some goat yoga on the beautiful farm? Check the website for special events and exhibitions.
Bousquet Mountain
Bousquet Mountain was operating as more than a ski resort during our visit, with warm-weather activities as well as winter recreation. The property had undergone renovations around that period. Seasonal programming, dining and operating schedules can change, so check Bousquet Mountain’s current information before planning a visit. During our trip, its dining options included LIFT Bistro Pub and a Sunday brunch selection.
A weekend worth repeating
Now it was time to head back to the Berkshire Flyer for our trip back to NY. We will miss you, Pittsfield! What we loved most about Pittsfield is that it felt like a home away from home. Once you’ve visited Pittsfield, you will want to return to experience the different seasons, explore all the activities, and enjoy the beauty of the Berkshires.
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