15 Best Things to Do in Pittsfield, MA

Pittsfield, MA
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Explore the vibrant city of Pittsfield with its lively artistic community, scenic outdoor spaces, and exciting exploration opportunities.

A trip to the city of Pittsfield will truly delight the young and the young at heart with its diverse offerings in the arts, outdoor recreation, history, and more.

Stroll through the downtown, unwind in Pittsfield's picturesque natural areas, go skiing in the winter, and many more!

The city of Pittsfield has a lot to offer to keep your weekend getaway brimming with exciting activities.

If you're planning a trip to this charming city, here are the 15 best things to do on your trip to Pittsfield, Massachusetts:

Experience the Shaker Life at Hancock Shaker Village

Scenic View of Hancock Shaker Village
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If you're looking for something interesting and educational to do on your trip to Pittsfield, make sure to spend a day at the Hancock Shaker Village.

Explore all 750 beautiful acres that house the oldest working farm in Berkshire, where you'll marvel at the innovative engineering and architecture of the Shaker community.

Spend a day experiencing the Shaker life in this living history museum with many activities to do!

Scenic View of Hancock Shaker Village
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Check out thousands of Shaker artifacts and household items on display in the village’s 20 authentic, historic buildings.

Experience the farm and gardens of the Shaker community, including its herb gardens, heirloom vegetable gardens, and heritage livestock.

Scenic View of Hancock Shaker Village
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Test your crafty hands in The Discovery Barn, where you can try to spin wool, create a Shaker chair, or weave a loom.

Immerse deeper into the Shaker culture by trying on the Shaker-style clothing and take a portrait of you in your Shaker look.

Scenic View of Hancock Shaker Village
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Shop and Dine at Downtown Pittsfield

View of Downtown Pittsfield
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A trip to Pittsfield wouldn't be complete without strolling through the cultural district of the town.

Downtown Pittsfield is the spot for all your shopping and dining needs.

Scour through shops offering an expansive selection of items to take home as a souvenir, and you'll also be supporting local businesses with your purchase.

View of Downtown Pittsfield
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After your stroll, you can stop by for some grubs in the selection of restaurants that offer whatever you're in the mood for.

Experience more of Pittsfield by spending an afternoon at Downtown Pittsfield and getting acquainted with the town’s tight-knit community.

View of Downtown Pittsfield
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Learn About History, Culture, and Sciences at Berkshire Museum

Front View of  Berkshire Museum
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Delight your interest in discoveries on tour at the Berkshire Museum.

The Berkshire Museum is a must-stop if you're looking for a fun, educational experience on your trip to Pittsfield.

Stroll through the museum showcasing an expansive collection of fine arts, historical artifacts, and natural science specimens that offers thought-provoking experiences for visitors of all ages.

Aerial View of  Berkshire Museum
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You can engage in hands-on exhibits, delve deeper into natural sciences, and uncover the region’s rich history.

A trip to the Berkshire Museum makes for an educational yet fun indoor exploration experience, so make sure to stop by and don't forget to bring your curiosity with you!

Front View of  Berkshire Museum
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Catch Live Performances at the Barrington Stage Company

The Barrington Stage Company is a must-stop if you enjoy watching live performances by talented artists.

This award-winning theatre is home to top-notch musicals, great classics, comedies, dramas, and thought-provoking new performances.

Support the artistic scene of the community of Pittsfield by reserving a seat for a show that you’re interested in!

Check out their website to get updated on their show schedules and reserve a seat to the show you're eyeing.

The fantastic performances will surely delight audiences of all ages, so make sure to stop by to watch live performances of the talented locals in Pittsfield.

Visit the Home of Herman Melville at Arrowhead

Home of Herman Melville at Arrowhead
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A visit to the Arrowhead should definitely be on your list of destinations in Pittsfield for the history buffs and book lovers out there.

Located along Holmes Road is the charming 18th-century yellow house surrounded by lush greeneries.

This historical museum was once the home of the famous American author Herman Melville where he created his literary pieces.

Home of Herman Melville at Arrowhead
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You can tour inside the home of Herman Melville and learn about the fascinating life of the famous American author.

Look out the window from Herman Melville's desk and experience the inspiring scenery that became part of the author's artistic endeavors.

A trip to the Arrowhead will inspire you with stories tied with the area and delight you with the charm of the quaint house.

Paddle Your Way Through Lake Onota

View of Lake Onota
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Escape the hustle and bustle of your daily cares in this tranquil nature respite nestled in the City of Pittsfield.

Lake Onota is the ideal spot to enjoy a relaxed time away from the busy city; this sprawling 617-acre lake offers plenty of recreational water activities that will truly delight all ages.

You can paddle your way through the calm waters of the lake in a kayak or a canoe, cast your lines to reel in some fresh catch from the lake, or go for a dip to cool off from the warm weather.

View of Lake Onota
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Pack some snacks and set up a BBQ to spend an amusing picnic date with the breathtaking view of Lake Onota.

Don't forget to catch the sunset at Lake Onota to be fascinated a the golden colors reflected in the calm waters and highlight the charming view of the mountain.

Make great memories on a day spent in Lake Onota and get lost in the breathtaking beauty of nature surrounding the area.

Hike the Trails of Pittsfield State Forest

Experience the perfect outdoor adventure on this 11,000-acre wooded state park in Pittsfield.

The Pittsfield State Forest is the ideal destination for adventure seekers and outdoor junkies.

Keep your worries away in this nature respite where you'll enjoy the sound of cascading streams and birds chirping from a distance on your exploration at Pittsfield State Forest.

View of Pittsfield State Forest
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You can hike the state park trails to enjoy the calming ambiance of the woods up to the Berry Pond, where you can go for a dip after a tiring hike.

Amp up your outdoor adventure by pitching your tent and camping out at the state park to enjoy the sight of starry skies during the night.

The Pittsfield State Forest should definitely be on your list of destinations, so you don't miss out on a chance to immerse yourself in nature with exciting adventures.

Spend the Skiing Season at Bousquet Mountain

Nothing beats experiencing thrilling adventures on a winter wonderland, so make sure to spend your winter skiing at the Bosquet Mountain.

Bosquet Mountain is a wintertime gem treasured by the locals and home to fun family experiences from its establishment in 1932.

This ski resort features a 750 ski slope up to the northern summit with two double lifts and carpet lifts.

Ski your way down the hill of the mountain.

Whether you're a beginner or you're just trying to satisfy your ski fix, the Bosquet Mountain has got you covered!

You can go skiing, snowboarding, and snow tubing in the winter, or enroll yourself in their snowsports lessons and programs.

If you visit Bosquet Mountain in the summer, you can still enjoy plenty of activities when the snow is gone.

You can wade their pools, enjoy six waterslides, play in their 9-hole disc golf course, or get an adrenaline rush from their zipline during the summer.

Bosquet Mountain is the perfect spot to visit for outdoor adventure opportunities with the family, whatever season of the year it is.

Explore the Flora and Fauna at Canoe Meadows Wildlife Sanctuary

View of Canoe Meadows Wildlife Sanctuary
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If you're looking for a serene place to take a peaceful walk and get lost in the beauty of nature, then head out for an adventure at the Canoe Meadows Wildlife Sanctuary.

Hike through the paved walking trails that wind through the sanctuary's scenic woods, fields, marshes, and wetlands.

You can meet a variety of wildlife along your hike, like the warblers, turtles, ospreys, otters, and bears at different times of the year.

Don't forget to stop by and check out the native flora of Pittsfield to delve deeper into your nature explorations.

The Canoe Meadows Wildlife Sanctuary is a nature respite among the suburbia where you can go on an escapade to get away from your daily stresses.

Catch Live Performances in Colonial Theatre

Historic Walls of the Colonial Theatre
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If you're looking for more destinations to appreciate the artistic community of Pittsfield, then make sure to reserve a seat at the Colonial Theatre.

You'll be delighted with the charming fusion of historic architecture from its establishment in 1903 and enthralling live performances at the Colonial Theatre.

This historic theatre offers 760-seat space, surrounded by the intricate details of the opulent place.

The Colonial Theatre is an abode to artists and theatre fanatics with its range of shows from musicals to comedies.

Go Fishing at Pontoosuc Lake

View of Pontoosuc Lake
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If your definition of a perfect day is with a fishing rod at hand on the perfect fishing weather, then head out to Pontoosuc Lake on your trip to Pittsfield.

This scenic lake borders the City of Pittsfield and the Town of Lanesborough with its sprawling waters.

The Pontoosuc Lake is the perfect spot to cast your line to reel in the fresh catch, go paddling to explore the calm waters and enjoy the scenic view of the natural area.

This hidden gem in Pittsfield is a must-visit if you're looking for a serene place to escape the hustle and bustle of the busy city.

View of Pontoosuc Lake
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Tee Off at the Berkshire Hills Country Club

The Berkshire Hills Country Club is the perfect place to spend a tee time on the ideal golfing weather and enjoy the serene sight of the surrounding natural area.

The Berkshire Hills Country Club features well-maintained fairways and pristine greens with some elevation changes and water hazards for a bit of challenge.

Whether you’re a pro golf player or a beginner, you'll surely enjoy some of the funky holes blended for some fun and challenge in the course.

After your tee time, make sure to stop by in their clubhouse to get some grubs and cool off with cold drinks.

A trip to Berkshire Hills Country Club is a must-visit on your trip to Pittsfield to get active.

Other Things to Do Nearby

Meet the Beavers at Pleasant Valley Wildlife Sanctuary

View of Pleasant Valley Wildlife Sanctuary
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Head out for a 15-minute drive to this charming sanctuary to take a relaxing nature walk and meet the beavers, the most visible wildlife resident in the sanctuary.

The Pleasant Valley Wildlife Sanctuary offers sprawling 1,000 lush acres that consist of forests, meadows, and wetlands.

View of Pleasant Valley Wildlife Sanctuary
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Whether you're looking to go on a leisurely walk or go for a bit of challenge, there is a 7-mile paved trail that includes three popular loops for varying skill levels.

You'll surely enjoy the relaxing sights and sounds of nature as you venture into the forests.

View of Pleasant Valley Wildlife Sanctuary
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Sip and Swirl Berkshire's Finest Wines at Balderdash Cellars

Nothing beats spending a relaxed time at a winery tasting a selection of fine wines with the beautiful sight of nature, so don't forget to stop by at Balderdash Cellars.

A 10-minute drive from Pittsfield leads to this charming winery in Richmond that offers a selection of fine wines.

Whether you're looking for something sweet and rounded, something fruity, or oaky, the Balderdash Cellar has got something to offer to match all different palates.

Aside from wine tasting, you'll also enjoy the rustic atmosphere of the winery with its panoramic view of the lake and the mountains with the occasional live music performances.

A trip to the Balderdash Cellars is the perfect side trip when visiting Pittsfield to unwind and enjoy the taste of Berkshire’s wines.

Learn About the Railway History of Berkshire at Berkshire Scenic Railway Museum

View of  Berkshire Scenic Railway Museum
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For the railway buffs out there, you shouldn't miss out on an interesting day exploring railway history at the Berkshire Scenic Railway Museum.

Just 15 minutes' drive away from the city of Pittsfield is this quaint museum featuring the railroading history in the Berkshire Hills.

The museum houses an expansive collection of train equipment, artifacts, restoration projects, and archives about the railroading heritage of the area.

You can also go on a train ride that will take you through the scenic Hoosac Valley with seasonal themes to amp up your railroad experience.

Final Thoughts

Pittsfield is the ideal destination for weekend getaways filled with outdoor adventure and relaxing nature escapades.

Don’t forget to reference this list if you’re planning a trip to the charming city of Pittsfield soon!