22 Best Things To Do In Pittsfield, Massachusetts

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Looking for the best things to do in Pittsfield, Massachusetts? We have you covered with this blog post! Located in the heart of the Berkshires, this vibrant city offers a plethora of exciting activities and attractions that cater to all interests and ages. From scenic outdoor adventures to cultural experiences and mouthwatering culinary delights, Pittsfield has something to enchant every visitor. 

Whether you’re a nature lover seeking tranquil lakes and breathtaking hiking trails or an art enthusiast yearning for world-class museums and theaters, this guide has got you covered. Get ready to explore the 21 best things to do in Pittsfield, and discover why this charming city is a must-visit destination for travelers seeking an unforgettable experience in The Berkshires.

1. Learn about the fascinating history of the Hancock Shaker Village

Hancock Shaker Village in Pittsfield, Massachusetts

Hancock Shaker Village in Pittsfield, Massachusetts, is a captivating living history museum that offers a fascinating glimpse into the Shaker community’s rich heritage. Founded in 1783, this well-preserved village served as a thriving Shaker community for over 200 years. Today, the site stands as a testament to the Shaker way of life, showcasing authentic Shaker architecture, artifacts, and craftsmanship. 

Visitors can immerse themselves in the village’s serene ambiance, exploring historic buildings, lush gardens, and peaceful pastures that once bustled with the industrious activities of the Shaker people. Engaging demonstrations of traditional Shaker crafts, such as woodworking and weaving, provide a unique opportunity to witness the community’s legacy in action. Whether you’re strolling through the tranquil landscapes or participating in interactive exhibits, Hancock Shaker Village offers an enriching experience that honors the Shaker’s dedication to simplicity, innovation, and spirituality. Tickets are required to enter the village, so be sure to purchase them online or at the ticket counter.

Learn more at hancockshakervillage.org 

Location Directions: HERE

2. Explore Herman Melville’s Arrowhead

Herman Melville's Arrowhead in Pittsfield, Massachusetts

Herman Melville’s Arrowhead is a historic treasure that provides a fascinating insight into the life and work of the renowned American author, Herman Melville. This charming farmhouse, built in the 1780s, served as Melville’s home from 1850 to 1863, during which he penned his masterpiece, “Moby-Dick.” Today, Arrowhead stands as a living museum, offering visitors an immersive experience of the world of Melville and the 19th-century Berkshire farming community. 

Guided tours take visitors through the rooms where Melville crafted his literary masterpieces, providing a glimpse of the writer’s personal life and creative process. The surrounding landscape, including the picturesque fields and woods, echoes the natural settings that once inspired Melville’s literary endeavors. There are wonderful trails throughout the property which are great for hiking year-round. From exploring the author’s study to admiring the scenic views that inspired him, a visit to Herman Melville’s Arrowhead is a captivating journey back in time and a celebration of one of America’s greatest literary figures.

Location Directions: HERE

3. Admire the displays at the Berkshire Museum

Berkshire Museum in Pittsfield, Massachusetts
“The Berkshire Museum – Pittsfield” by Massachusetts Office of Travel & Tourism is licensed under CC BY-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd/2.0/

The Berkshire Museum in Pittsfield, Massachusetts, is a cultural gem that offers a diverse and enriching experience for visitors of all ages. Established in 1903 by Zenas Crane, this dynamic museum showcases a remarkable collection of art, science, and history exhibits, celebrating the region’s rich cultural heritage. Crane was inspired by famed institutions including the American Museum of Natural History, the Smithsonian, and the Metropolitan Museum of Art. He took the best aspects of all these museums to create the Berkshire Museum. From awe-inspiring paintings and sculptures to engaging interactive displays on natural history and science, The Berkshire Museum caters to diverse interests and curiosities. 

Its innovative approach to blending art and science creates an immersive and thought-provoking atmosphere, making it a favorite destination for families, students, and art enthusiasts alike. The museum also hosts rotating exhibitions, engaging events, summer camps for kids, and other educational programs. A visit to The Berkshire Museum promises an unforgettable journey through art, history, and the wonders of the world, making it a must-visit destination in Pittsfield, Massachusetts.

Location Directions: HERE

4. Hike, relax, camp, and swim at Pittsfield State Forest

Pittsfield State Forest in Pittsfield, Massachusetts

Pittsfield State Forest in Pittsfield, Massachusetts, is a nature lover’s paradise that offers a plethora of outdoor activities amidst breathtaking scenery. This expansive forest is a haven for hikers, with an extensive network of well-maintained trails winding through its lush landscapes, providing opportunities for both leisurely strolls and challenging treks. For those seeking a tranquil camping experience, the forest offers several picturesque campsites nestled amidst the serene woodlands. One of the highlights of the forest is the enchanting Lulu Cascade waterfall, a hidden gem that cascades gracefully through the forest, creating a mesmerizing spectacle. Adventurous souls can discover a natural swimming hole, offering a refreshing retreat on warm summer days. Whether you’re hiking to witness the beauty of the Lulu Cascade or indulging in camping and swimming adventures, Pittsfield State Forest promises an invigorating escape into the wonders of nature.

Location Directions: HERE

5. Make a stop at Balance Rock State Park

Balance Rock State Park in Pittsfield, Massachusetts

Balance Rock State Par, is a unique and fascinating natural wonder that captivates visitors with its awe-inspiring geological formation. The park’s centerpiece is the iconic Balance Rock, a massive boulder precariously balanced atop a ledge, seemingly defying gravity. This geological marvel stands as a testament to the forces of nature that shaped the landscape over millennia. 

As visitors approach the park, they are greeted by the striking sight of Balance Rock, drawing them closer to witness this extraordinary sight up close. The park offers a short, scenic trail leading to the rock, allowing visitors to explore the surrounding woodlands and appreciate the beauty of The Berkshires. Balance Rock State Park serves as a testament to the enduring power of nature and provides a serene setting for contemplation and appreciation of the Earth’s geological wonders. Be sure to add this spot to your Pittsfield trip itinerary!

Location Directions: HERE

6. Enjoy some local brews at the Wandering Star Craft Brewery

Wandering Star Craft Brewery in Pittsfield, Massachusetts, is a haven for craft beer enthusiasts seeking an exceptional brewing experience. Founded by a passionate team of beer aficionados, this brewery is dedicated to crafting high-quality and innovative brews that delight the palate. With a commitment to using locally sourced ingredients and traditional brewing techniques, Wandering Star produces a diverse selection of artisanal beers that cater to all tastes. The brewery has a 15-barrel production and some of its top-rated brews are Thunderbolt IPA, Loopy Juice IPA, and Bert’s Disqualified Imperial Stout. 

The brewery’s taproom provides a warm and welcoming atmosphere for visitors to sample a wide range of handcrafted beers, from classic ales and lagers to unique and experimental brews. There is also a great beer garden which is open during the summer months. This microbrewery also self-distributes kegs and cans throughout Berkshire County. Whether you’re a seasoned beer connoisseur or just curious to explore the world of craft brewing, a visit to Wandering Star Craft Brewery promises a memorable and flavorful journey through the art of beer making in the heart of Pittsfield, Massachusetts. 

Follow Wandering Star Craft Brewery on Facebook to stay up-to-date: facebook.com/p/Wandering-Star-Craft-Brewery

Location Directions: HERE

7. Get tickets for a show at the iconic Colonial Theatre

Colonial Theatre in Pittsfield, Massachusetts
“Colonial Theatre, Pittsfield, MA” by Massachusetts Office of Travel & Tourism is licensed under CC BY-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd/2.0/

The Colonial Theatre in Pittsfield, Massachusetts, is a historic and beloved cultural landmark that has been entertaining audiences for over a century. Built-in 1903, this grand theater boasts stunning Colonial Revival architecture, transporting visitors back to the golden age of live entertainment. Throughout its illustrious history, the Colonial Theatre has hosted a wide array of performances, from Broadway productions and musicals to concerts, comedy shows, and film screenings. 

Today, the theater is run by The Berkshire Theatre Group and it continues to showcase a diverse and vibrant lineup of performances, attracting both local and touring acts to its hallowed stage. Renovated and restored to its former glory, the Colonial Theatre offers a captivating and immersive experience for theater enthusiasts and patrons alike. Whether you’re attending a dazzling musical, a thought-provoking play, or a lively concert, a visit to the Colonial Theatre promises an unforgettable and magical journey into the world of performing arts in Pittsfield, Massachusetts.

Learn more at berkshiretheatregroup.org

Location Directions: HERE

8. Savor some local flavors at Roasted Garlic

Roasted Garlic, a delightful restaurant in Pittsfield, is a culinary gem that delights food enthusiasts with its delectable offerings. Known for its warm and inviting ambiance, the restaurant offers a welcoming retreat for diners seeking a memorable dining experience. Roasted Garlic is known for its wood-fired pizza, delicious soups, savory sandwiches, and fresh salads. Oh yeah, their homemade desserts are amazing too! Everything is made in-house and sourced locally whenever possible. This is some of the most creative and fresh food you will find in The Berkshires.

Check out the menu and learn more at theroastedgarlic.com

Location Directions: HERE

9. Enjoy boating, fishing, and swimming at Lake Onota

Lake Onota in Pittsfield, Massachusetts
“Onota Lake, August 2014” by gigi_nyc is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/2.0/

Onota Lake, in the heart of Pittsfield, is a picturesque and serene destination that beckons both locals and visitors alike. This beautiful freshwater lake offers a tranquil retreat for nature enthusiasts and outdoor adventurers seeking respite from the hustle and bustle of daily life. Surrounded by lush greenery and rolling hills, Onota Lake provides a stunning backdrop for various recreational activities both in the water and onshore. The best way to visit the lack is by going to the 153-acre park known as Burbank Park. There is a public boat launch which is perfect for those seeking to do some boating, kayaking, or paddleboarding. On the shore, visitors can enjoy a swimming beach with lifeguards on duty during the summer, picnic tables, charcoal grills, a fishing pier, and a restroom. A public walking path also goes around the lake. Whether you’re seeking a peaceful day by the water or embarking on an exciting aquatic adventure, Onota Lake presents an idyllic escape that celebrates the beauty of nature right in the heart of Pittsfield.

Location Directions: HERE

10. Shop like a local at Pittsfield Farmers Market

Pittsfield Farmers Market in Pittsfield, Massachusetts
“Pittsfield Farmers Market, photo credit Faith Gagliardi, photo courtesy of the Berkshire Visitors Bureau” by Massachusetts Office of Travel & Tourism is licensed under CC BY-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd/2.0/

Pittsfield Farmers Market is a vibrant and bustling community hub that celebrates the best of local produce, artisanal goods, and friendly camaraderie. Held in the heart of downtown, this beloved market is a weekly summer gathering place where farmers, artisans, and food purveyors come together to showcase their finest offerings. One super great aspect of this market is that it is organized and run by Roots Rising which is a nonprofit organization. Their mission is to empower youth and build community through food and farming.

Visitors can peruse an array of fresh fruits and vegetables, locally sourced meats, homemade baked goods, and handcrafted products, all brimming with the flavors and charm of The Berkshires. Beyond the delectable treats, the market often buzzes with live music, cooking demonstrations, and activities for all ages, fostering a lively and welcoming atmosphere. A visit to the Pittsfield Farmers Market not only supports local growers and producers but also allows visitors to connect with the community’s agricultural heritage while savoring the authentic tastes of the region.

Learn more about the farmers market and when it is being held at farmersmarketpittsfield.org   

Location Directions: HERE

11. Enjoy a play from the Barrington Stage Company

Barrington Stage Company in Pittsfield, Massachusetts
“A Crossing a Dance Musical” by Massachusetts Office of Travel & Tourism is licensed under CC BY-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd/2.0/

The Barrington Stage Company in Pittsfield, Massachusetts, is a dynamic and acclaimed theater company that has become a cultural cornerstone of The Berkshires. Founded in 1995, this award-winning company has earned a reputation for producing top-notch theatrical performances that captivate and inspire audiences. Housed in the historic Boyd-Quinson Mainstage, as well as the St. Germain Stage, the Barrington Stage Company showcases a diverse repertoire of plays and musicals, ranging from classic works to contemporary pieces. 

It has been successful since it started operating in fact. During its first year, Barrington Stage Company achieved the honor of winning the Elliot Norton/Boston Theatre Critics Award for its outstanding performance of The Diary of Anne Frank. By its third year, the company’s success soared even higher as it claimed two more Elliot Norton/Boston Theatre Critics Awards and four Outer Critics Awards for its remarkable production of Cabaret. The show’s success was so immense that it transferred to Boston for an extended run at the renowned Hasty Pudding Theatre, solidifying BSC’s reputation as a premier theater company.

With a commitment to promoting new talent and fostering artistic innovation, the theater has remained a breeding ground for emerging playwrights, actors, and directors. Throughout the year, theater enthusiasts flock to the Barrington Stage Company to witness captivating performances that touch on a myriad of emotions and subjects. The company’s dedication to excellence in storytelling and entertainment has made it a cherished institution in Pittsfield, attracting both locals and visitors to experience the magic of live theater at its finest. There truly is nothing quite like the Barrington Stage Company!

Learn about upcoming performances and purchase tickets at barringtonstageco.org

Location Directions: HERE

12. Shop in downtown Pittsfield

Downtown Pittsfield, Massachusetts, offers a charming and vibrant shopping experience for locals and visitors alike. Strolling through the picturesque streets, you’ll find a delightful mix of boutiques, specialty shops, and local artisans, each offering a unique array of treasures waiting to be discovered. From trendy fashion boutiques to antique stores brimming with hidden gems, the diverse selection ensures that shoppers of all tastes and preferences will find something to delight them. The friendly and welcoming atmosphere adds to the charm of the shopping district, making it a pleasure to explore the shops and interact with the local shopkeepers. Whether you’re searching for one-of-a-kind gifts, locally crafted souvenirs, or the latest fashion trends, downtown Pittsfield has something to offer every shopper, making it a must-visit destination for retail therapy in The Berkshires.

13. Savor wines (and views) at Balderdash Cellars

Balderdash Cellars on the Pittsfield/Richmond town line is a charming and inviting winery that offers wine lovers the chance to savor the fruits of meticulous craftsmanship. Located in the picturesque Berkshires, this family-owned and operated winery is dedicated to producing exceptional small-batch wines that reflect the region’s unique terroir. With a passion for sustainability and innovation, Balderdash Cellars showcases an array of thoughtfully crafted wines, from crisp whites to robust reds, each carefully nurtured from vine to bottle. They offer several different varieties of white, red, and rose wines.  

The winery’s tasting room provides an intimate and welcoming space for visitors to sample their handcrafted creations while soaking in the breathtaking views of the surrounding vineyards and mountains. Throughout the year, the winery brings in many live music acts. There are also often local food vendors on the weekends. With a commitment to excellence and warm hospitality, Balderdash Cellars offers a delightful and memorable wine-tasting experience that celebrates the beauty and flavors of The Berkshires. Not able to make it to the winery? Bottles are stocked at several wine shops nearby.

Learn more about the winery and upcoming events at balderdashcellars.com

Location Directions: HERE

14. Re-charge at Dottie’s Coffee Lounge

Dottie’s Coffee Lounge in Pittsfield, Massachusetts, is a beloved and bustling coffee haven that captures the hearts of locals and visitors alike. Renowned for its expertly crafted coffee, this charming lounge boasts a warm and welcoming atmosphere, where friendly baristas greet you with a smile as they skillfully prepare your favorite brew. Not a fan of coffee? No worries! There are great matcha green tea, chai, turmeric, and lavender lattes.

Beyond the exceptional coffee offerings, Dottie’s delights with its fabulous organic and locally sourced food, making it a favorite spot for nourishing and delicious meals. Some of the highlights include breakfast burritos, egg sandwiches, and waffles. For lunch, there are great salads, sandwiches, and soups. The homemade baked goods tempt the taste buds with their mouthwatering flavors, complementing the coffee experience perfectly. There are also plenty of vegan options on the menu!

For a delightful Sunday treat, jazz enthusiasts gather for the captivating jazz brunch, creating an enchanting ambiance that pairs beautifully with the delectable offerings. With a commitment to quality and community, Dottie’s Coffee Lounge is a cherished gathering spot where the art of coffee, food, and music come together to create a truly memorable experience.

Learn more at dottiescoffeelounge.com

Location Directions: HERE

15. Go skiing, snowboarding, or tubing at Bousquet Mountain Ski Area

Bousquet Mountain Ski Area in Pittsfield, Massachusetts
“Bousquet Ski Resort & Summer Family Fun Center – Pittsfield” by Massachusetts Office of Travel & Tourism is licensed under CC BY-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd/2.0/

Bousquet Mountain Ski Area in Pittsfield is a beloved winter wonderland that beckons snow enthusiasts with its exhilarating slopes and picturesque scenery. Nestled in the heart of The Berkshires, this family-friendly ski area offers a perfect blend of adventure and relaxation for skiers and snowboarders of all levels. With its well-groomed trails and state-of-the-art snowmaking, Bousquet ensures optimal snow conditions throughout the season, creating a haven for winter sports enthusiasts. 

Beyond the slopes, the ski area provides a variety of amenities and services, including ski lessons, equipment rentals, and a cozy lodge to warm up and unwind after a day on the mountain. Located on the lodge’s 2nd floor, you’ll find LIFT Bistropub, a delightful full-service bar and restaurant offering a diverse culinary experience. Whether you’re craving a quick snack or a hearty dinner with delectable desserts, LIFT has something to satisfy every palate. Their menu boasts an array of options, including soups, salads, flatbreads, and daily specials, perfectly complemented by a selection of cocktails, wines, and locally brewed beers. A true gem for visitors year-round, LIFT promises a one-of-a-kind dining adventure, with both indoor and outdoor seating options. Take in the stunning mountain views from the comfort of the 2nd-floor deck or relish the cozy ambiance of the indoor bar and restaurant area. Be sure to check out their website to learn more about events at LIFT happening throughout the year.  Whether you’re a seasoned skier seeking thrills on challenging runs or a beginner eager to learn, Bousquet Mountain Ski Area promises an unforgettable and fun-filled winter experience for all ages.

Learn more at bousquetmountain.com/  

Location Directions: HERE

16. Walk the grounds of the historic Pittsfield Cemetery

Pittsfield Cemetery in Pittsfield, Massachusetts
“Pittsfield Cemetery, MA:” by IslesPunkFan is licensed under CC BY-NC 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc/2.0/

Established in 1850, the Pittsfield Cemetery serves as a final resting place for countless individuals who have shaped the city’s rich history. The cemetery was initially established in 1850 to accommodate the city’s burgeoning population and the full capacity of its primary burying ground at North and East Streets. While its beginnings were modest and unadorned in 1850, the next century saw the addition of several captivating features. In 1885, Thomas Allen, Jr., generously donated funds for the Allen Memorial Arch and Main Gate, creating a grand entrance to the grounds. Another striking memorial dedicated to Allen believed to be the world’s largest red granite piece, can be found elsewhere in the cemetery. In 1900, a chapel was devotedly inaugurated, and during the 1930s, the Superintendent’s Cottage and a Maintenance Garage were added. As the cemetery expanded during the 1910s, the prestigious Olmsted Brothers landscape firm was enlisted to expertly plan the layout of new sections within the cemetery.

As visitors stroll through the hallowed grounds, they are met with elegant tombstones, ornate mausoleums, and poignant memorials that pay tribute to the lives and legacies of those laid to rest here. Beyond its somber beauty, the cemetery also serves as a repository of local heritage, preserving the stories of notable figures, veterans, and generations of Pittsfield residents. It was even listed on the National Register of Historic Places on March 13, 2007, due to its historical significance and its great artistic value. A visit to the Pittsfield Cemetery is not just an exploration of history, but a contemplative experience that honors the past and celebrates the enduring spirit of this vibrant city. 

Location Directions: HERE

17. Shop fresh produce and handcraft provisions at Guido’s Fresh Marketplace

Guido’s Fresh Marketplace in Pittsfield is a culinary haven that truly celebrates the essence of local flavors and community spirit. This family-owned and operated market has a commitment to supporting local producers. Guido’s proudly stocks a wide array of locally sourced products, bringing the best of the region to its shelves. Beyond their extensive selection of fresh produce, artisanal cheeses, and gourmet delights, Guido’s also offers a delightful array of to-go foods that cater to every palate. Their handcrafted sandwiches, made with the finest ingredients, are perfect for a quick and delicious meal on the go. For those with a taste for the exotic, their sushi selection promises to delight with its authenticity and flavor. And when it comes to the ultimate comfort food, Guido’s freshly baked pizzas, prepared with care and creativity, are sure to satisfy any craving. Guido’s Fresh Marketplace stands as a true culinary destination, where locals and visitors alike can indulge in the finest products and indulge in delectable to-go options that exemplify the best of Berkshire’s flavors.

Learn more about Guido’s Fresh Marketplace at guidosfreshmarketplace.com 

Location Directions: HERE

18. Carb up at Berkshire Mountain Bakery

Berkshire Mountain Bakery in Pittsfield, Massachusetts
“Berkshire Mountain Bakery” by Leslee_atFlickr is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/2.0/

Nestled in the charming village of Housatonic in Pittsfield, Massachusetts, the Berkshire Mountain Bakery stands as a beacon of artisanal baking excellence. With a rich history and dedication to the craft, this bakery has become a beloved destination for locals and visitors seeking the finest bread and baked goods in the region. The aroma of freshly baked loaves fills the air as customers step into the inviting space, showcasing a delightful array of bread varieties, from hearty whole-grain loaves to crusty baguettes. Some customer favorites include Sunny Flax (Naturally leavened with sourdough with flax and sunflower seeds inside), Bread & Chocolate (Dark Callebaut chocolate chunks are folded into a white boule), and Spelt Raisin (Naturally leavened sourdough with organic spelt flour, raisins, and cinnamon). Along with over a dozen different types of bread, the bakery produces awesome cookies and pizza crusts. 

Each bite is a testament to the bakery’s commitment to using high-quality, locally sourced ingredients and traditional baking methods that result in exceptional taste and texture. The bakery’s warm ambiance and friendly staff create an inviting atmosphere that makes every visit a memorable experience. For those seeking the art of artisanal baking in the heart of Housatonic, the Berkshire Mountain Bakery is a must-visit destination that captures the essence of the region’s culinary heritage.

Along with their flagship bakery in Housatonic, they also run Berkshire Mountain Bakery Pizza Cafe on Elm Street in Pittsfield. This shop offers freshly baked breads along with handcrafted pizzas, salads, and sandwiches. Additionally, Bakerhsire Mountain Bakery breads are stocked at a number of local markets and offered at many local restaurants and cafes.

Learn more about the bakery at berkshiremountainbakery.com

Location Directions: HERE

19. Hike up to Mahanna Cobble

Mahanna Cobble in Pittsfield, Massachusetts
“IMG_4132 P” by Ani Od Chai is licensed under CC BY-NC 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc/2.0/

Hiking up to Mahanna Cobble in Pittsfield is an exhilarating outdoor adventure that offers breathtaking views and a connection with nature. The Cobble, situated on the northern summit of Lenox Mountain, forms part of the long and scenic ridge stretching from Olivia’s Overlook to the Bousquet Ski Area in Pittsfield. Locally known as “Cobbles,” this geological formation consists of exposed bedrock perched high on the ridge, providing evidence of ancient tectonic movements that shifted underlying rock layers.

The moderately challenging trail to the Cobble winds through lush forests and rocky terrain. It is an out-and-back trail which is 3 miles long. It features 780 feet of elevation gain and it is typically completed in around 2 hours. The first 10 minutes of the trail are the most strenougs, it then gradually inclines to the summit. The trailhead is located at the Bousquet Mountain Ski Area. 

Whether seeking solitude in nature or simply yearning for a refreshing escape, hiking Mahanna Cobble promises an unforgettable experience that showcases the beauty and serenity of The Berkshires.

Learn more about the Mahana Cobble and get trail information at bnrc.org/trails-and-maps/mahanna-cobble/

Location Directions: HERE

20. Stroll around Wild Acres Park

Wild Acres Park in Pittsfield, Massachusetts
“2029-10-13 Morning Dog Walk (13)” by Paul-W is licensed under CC BY-NC-SA 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-sa/2.0/

Wild Acres Park is a great little park located adjacent to Pittfield’s Airport. The park is a hidden gem offering a tranquil oasis for nature enthusiasts and outdoor lovers. The highlight is the Wild Acres Park Loop Trail. This trail is just under a mile long and features less than 100 feet of elevation gain. This makes it a perfect trail for people of all ages and abilities. The trail circles a lovely little pond that is home to great wildlife. Bird watchers are sure to love this location. Additionally, on the southern edge of the pond, visitors can enjoy the Wild Acres Observation Tower. This steel tower gives visitors an elevated view of the park and the surrounding area. Wild Acres Park provides a refreshing escape from the bustle of city life and a chance to bask in the beauty of Pittsfield’s natural surroundings.

Location Directions: HERE

21. Enjoy some fun at Pontoosuc Lake

Pontoosuc Lake in Pittsfield, Massachusetts
“Pontoosuc Lake – Pittsfield” by Massachusetts Office of Travel & Tourism is licensed under CC BY-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nd/2.0/

Pontoosuc Lake, located between the city of Pittsfield and the town of Lanesboro, is a stunning natural gem that beckons locals and visitors alike to embrace its tranquil beauty. This 511-acre lake offers a host of recreational opportunities, from boating and fishing to picnicking and hiking along its scenic shores. With its clear blue waters reflecting the surrounding mountains, Pontoosuc Lake provides the perfect setting for outdoor enthusiasts to connect with nature and bask in the serenity of their surroundings. Families can enjoy fun-filled days by the water’s edge, while nature lovers can explore the diverse flora and fauna that call the lake home. 

One of the best places to enjoy the lake is by visiting Pontoosuc Lake Park. This public park is set on the southern shore of the lake in the city of Pittsfield. The park is home to a large parking lot, boat ramp, beach, and walking trails. Whether seeking relaxation or adventure, Pontoosuc Lake promises an unforgettable experience in the heart of Pittsfield’s natural splendor.

Location Directions: HERE

22. Locate the beautiful Shaker Brook Falls

Shaker Brook Falls in Pittsfield, Massachusetts

Shaker Brook Falls, also referred to as the Cascades on Shaker Brook, is a picturesque 7-foot waterfall situated near Hancock Shaker Village in Hancock, Massachusetts. You can easily access it via a short walk from a well-marked parking lot along the U.S. Route. Begin your journey on the Shaker Trail, covering about 0.3 miles until you reach Shaker Brook. Continue for another 0.2 miles along the trail beside the brook, where you’ll find the waterfall marked by an informative sign. This waterfall is notable for flowing through a historic stone dam from the 1810s. While not large in size, it typically has a strong flow and provides a tranquil spot for relaxation and photography.

Officially, the waterfall is situated within the Pittsfield State Forest, spanning 11,000 acres and managed by the Massachusetts Department of Conservation and Recreation (DCR). The Hancock Shaker Brook Village team maintains the Shaker Trail, offering information about the historical structures along the route, including dams, bridges, reservoirs, mills, and homes. It’s advisable to check in with the village’s front desk before starting your hike for updated information and a safe hiking experience.

Learn more at goxplr.com/places/shaker-brook-falls

Location Directions: HERE


As you bid farewell to Pittsfield, Massachusetts, you’ll undoubtedly carry cherished memories of an enriching and diverse adventure. From the captivating cultural attractions to the picturesque outdoor landscapes, Pittsfield’s allure leaves a lasting impression on every visitor. Whether you’re an art lover, a nature enthusiast, a foodie, or someone seeking a relaxing getaway, Pittsfield caters to your desires with open arms. The 21 best things to do in Pittsfield have shown that this city is a treasure trove of experiences waiting to be explored. So, pack your bags, head to Pittsfield, and immerse yourself in the delights this charming Berkshire destination has to offer. From hiking the scenic trails to savoring local flavors and indulging in cultural treats, Pittsfield promises an unforgettable journey that will leave you longing to return.

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Tom Riley

Hi! I'm Tom. I am the creator of GoXplr. I started this website with a focus on helping people explore better and explore more. I am based in New England and obsessed with traveling. Here at GoXplr, you will find expert blog posts and also maps containing all of the best places to explore. These blogs and maps have taken thousands of hours to complete. I hope you enjoy this resource and it inspires you to get out and explore!

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