The Top 5 Reasons to Visit Pittsfield, Massachusetts Now
BY 5 REASONS TO VISIT® EDITORIAL STAFF
December 2021 • 3 minute read
Situated within the heart of the Berkshires in Massachusetts, Pittsfield offers a laidback city atmosphere inspired by its local roots. The Berkshires are a special place, filled with artists, artisans, and purveyors who thrive on originality. Deep, historic roots can be traced to this region, and yet it’s laced with a refreshingly modern vibe in its dining, culture, design, and industry.
1. THE SHOPPING
With a plethora of shopping selections scattered along Pittsfield’s historic downtown streets, welcome to Dory & Ginger, where the motto is “Live and Give.” Offering a fabulous selection of treasures for your home and lifestyle—Dory & Ginger also has the perfect gift for that special someone or that occasion that begs for something unique.
Located next to the Hotel on North, come in and share a laugh, enjoy the atmosphere, and soak in the aesthetic of the best boutique in Pittsfield, Massachusetts.
2. THE ART
Artscape is an energetic, volunteer-led committee responsible for public art throughout various downtown locations in Pittsfield, Massachusetts. One of their most visible contributions are the beautifully painted electrical boxes. Artscape has helped bring a unique type of art, which includes street murals and painted pianos to the Berkshires.
Enjoy indoor and storefront art shows, murals, outdoor sculpture and nineteen of Artscape’s Pittsfield Paintboxes at First Fridays Artswalk. Click here for a map of all indoor and outdoor locations, including hours for the indoor shows.
3. THE COCKTAILS & CUISINE
Tucked away in a historic, 19th-century building, the restaurant at Hotel on North is a Berkshires favorite for eclectic, farm-to-table cuisine and hand-crafted libations that are both seasonally influenced and well balanced. For your artisanal cocktail fix, we recommend trying the Berkshire Mountain Luxury—concocted with Berkshire Mountain Distillers Ragged Rum, Luxardo Mascherino, fresh grapefruit and fresh-squeezed lime.
Highlighting contemporary American dishes and feel good bites—favorite ala carte dishes to indulge on at Berkshire Palate include delectable Pan Seared Roast Duck with curried acorn squash.
This exciting dining experience constantly strives to bring together and showcase the local purveyors and producers in and around the Berkshires.
4. THE GARDENS
Located on the flanks of Springside Park, Hebert Arboretum is a living tree library. Encompassing 231 acres within Pittsfield, Massachusetts, the park is a unique sanctuary for plant and animal life. Diverse habitats of rolling hills, meadows, woodlands, streams, marshes and ponds are home for over 50 species of native trees, 338 species of plant life, and a tremendous wildflower variety of over 135 species.
Landscaped gardens include the colorful and nectar-filled butterfly and hummingbird gardens, Master Gardener demonstration gardens, a peaceful Memory Garden, and the Vincent J. Hebert Lilac Walk—all of this amid a backdrop of fields, forest and beautiful Berkshire views. The park is host to a “migration funnel” where migrating songbirds come in the spring and fall for sanctuary and rest.
5. THE ARCHITECTURE
Built in the 1780s by Captain David Bush, Arrowhead, also known as the Herman Melville House, is a historic house museum in Pittsfield, Massachusetts. Arrowhead was the home of American author Herman Melville during his most productive years, 1850–1863. Here, Melville wrote some of his major work: the novels Moby-Dick, Pierre (dedicated to nearby Mount Greylock), The Confidence-Man, and Israel Potter; The Piazza Tales (a short story collection named for Arrowhead's porch); and magazine stories such as “I and My Chimney.”
The wood frame and clapboard house consists of a simple rectangular structure with five window bays across and two deep, with a large central chimney. The Berkshire County Historical Society acquired the house and has restored most of the house to Melville's period. It is open to the public during warmer months and has been designated a National Historic Landmark and is listed on the National Register of Historic Places.
WHERE TO STAY IN PITTSFIELD, MASSACHUSETTS



