Pittsfield, Massachusetts for the Weekend

aerial image of the Berkshires

by Maria Ottomanelli and Doreen Wong

Whether you live in the Berkshires or are planning to visit, there are numerous attractions here for everyone.  The Berkshires is known for its spectacular scenery, hiking trails, cultural events, delicious food, and outdoor fun.  Our adventurous group from New York and New Jersey traveled from Penn Station to the Joseph Scelsi Intermodal Transportation Center, located in downtown Pittsfield, MA.  The four-hour Amtrak train ride was punctual and scenic, rolling along the Hudson River valley.  But here we were finally in Pittsfield, the heart of the Berkshires, and our adventures truly began! 

Hotel Accommodations

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.

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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’s the first teen-run farmers market in the region.  It runs every Saturday (rain or shine) from May 14th to Oct 8th from 9 am to 1 pm, Pittsfield Common, 100 First Street.  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.

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Transportation and Tour Guide

Berkshire Camino

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.

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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!

image of Berry Pond in Pittsfield, MA in the Berkshires

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…  

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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.

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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!

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Dottie’s Coffee Lounge  

This is the breakfast place everybody loves and knows in the community.  It has indoor seating with live music on Sundays at 10 am, outdoor seating, a great selection of fancy teas and coffees, and fresh food.  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!

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Herman Melville’s Arrowhead  

Herman Melville was an American novelist,  short story writer, and poet of the American Renaissance period.  Arrowhead is the house that Herman Melville lived in located in Pittsfield, MA.  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.

image of Herman Melville's Arrowhead in Pittsfield, MA in the Berkshires

Hancock Shaker Village

We visited the oldest working farm in the nation and a 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.

image of Hancock Shaker Village in Pittsfield, MA in the Berkshires

Bousquet Mountain

Bousquet Mountain is a year-round destination and not only a ski resort.  It’s open year-round and was recently fully renovated.  It’s a great destination for music and movies in the summer months.   Also, make sure you visit the restaurant, LIFT Bistorpub, for refreshing drinks and delicious food. The Sunday brunch has a selection of baked goods.

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Now it was time to head back to the Berkshires 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.  

image of streetview in Pittsfield, MA in the Berkshires