Things To Do In Pittsfield

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Skyline Country Club is a semi-private club that welcomes golfers with sweeping views of the Berkshire mountains and glimmering waters that intersect the grounds. Elevation changes and blind tee shots are frequent throughout the 6,075-yard course, as seen on the 4th hole, which rewards precise tee shots of roughly 110–165 yards with an easy 110-yard shot to the green. The par 5 12th, the course's most difficult hole, forces players to drive onto a tight fairway along the straight 490-yard layout that ends with a false front, a greenside slope that often tricks golfers and sends balls rolling back toward the player like an industrial-grade pop-a-shot. After finishing the course with two consecutive par 4's, golfers can retire to the Club's pub for drinks and eats on the open-air deck, which offers views of the surrounding landscape.

Course at a Glance:

  • 18-hole, par 71 course
  • Total length of 6,075 yards from the back tees
  • Three sets of tees per hole
405 S Main St
Lanesboro,
MA
US

His breath puffing visibly in the freezing air, Paul Tawczynski ventures out onto the ice with fishing gear in tow. He leads groups of all ages and fishing experience out onto frozen bodies of water during ice-fishing expeditions. He teaches fishing teams how to drill holes through the up to 30 inches of ice supporting them and how to set up lines to catch the slow-drifting winter fish. Paul will also lead groups on bass-fishing trips during warmer weather.

119 Park Street
Great Barrington,
MA
US

Home to 20 historic Shaker buildings, the current Hancock Shaker Village is an open-air relic of the Hancock Shaker community, originally founded in the 1780s and once boasting more than 300 residents and 3,000 acres. Learn the laudable history of Shaker craftsmanship, architecture, and agricultural techniques with a self-guided tour of the 20-acre grounds, which includes open access to original structures such as the famous 1826 round stone barn, the 1830 brick dwelling, and the 1940 laser-tag amphitheater. Artifacts such as early Shaker washing machines, drying racks, and furniture populate many of the buildings and guests can watch on-site artisans demonstrate Shaker crafts, listen to guides discuss Shaker worship and work customs, or dedicate the rest of their lives to manufacturing Shaker-style textiles.

1843 W Housatonic St
Pittsfield,
MA
US

In 1936, Robert and Dorothy Leab drove their 13 head of cattle over Brodie Mountain and into Ioka Valley, where they broke ground on their new home. Despite the poor quality of the farm’s soil, their hard work gradually resulted in bountiful harvests. Decades later, the third generation of the Leab family still tills the land, planting assorted crops and opening the farm to visitors for year-round activities.

Each season brings new life to the farm, from the pastel buds and new shoots of spring to summer’s vibrant strawberries, which are grown on raised beds so visitors can pick their own pints. Kids frolic in Uncle Don’s Barnyard all summer, petting tame rabbits and llamas and whooshing down a 40-foot pipeline slide. Fall festival activities include hayrides and pumpkin picking, and during the winter, snow-covered Christmas trees can be carted home to add holiday cheer or provide a new project for the family’s pet beaver. Maple season stretches from February to April in the sugar house, occupied by 5,000 taps and two boilers. The farm churns out deep maple syrup that is served over pancakes and waffles in the Calf-A, a calf barn converted into a café. The farm’s cattle herds are pasture-raised during warm months, with their diet supplemented by the farm’s own corn, before becoming hormone-free, all natural beef.

3475 Route 43
Hancock,
MA
US

Nearly a century ago, the Hippodrome opened as a combination movie palace and vaudeville theater, spending more than 70 years hosting big names such as Bob Hope and Frank Sinatra. Following a double-decade period of slow business and bad hairstyles, the Hippodrome closed down in 1990. Now, however, after an exhaustive restoration project that reanimated the theater’s chandelier-lit arches, the mural above the proscenium stage, and the grand-theater boxes that hearken back to opera’s heyday, the Hippodrome reopens to the delight of Baltimore’s cultural landscape.

27 East Housatonic
Pittsfield,
Massachusetts
US

In the summer of 1850, a moderately successful writer brought his young wife, Lizzie, and their baby, Malcolm, to the town where his father grew up, Berkshire. Seduced by its picturesque countryside, the writer impulsively bought a farm, which would become the family’s home for the next 13 years and the place where he penned a novel that would change the face of American literature: Moby-Dick.

Today, the Berkshire Historical Society maintains the farmhouse where Melville sharpened his quills, gazed out the library window, and drank in the view of Mount Greylock, whose statuesque peak supposedly inspired the elusive white whale that taught Ahab to use his nose as a blowhole. The house was old even then, as it was originally built in the Georgian style back in 1780, acquiring Federal-style details in the 1840s. Careful preservation allows visitors to wander through Melville’s study and gaze upon the fireplace featured in his short story I and My Chimney. They can also observe the piazza that makes an appearance in The Piazza Tales, and see the restored barn where Melville and Nathaniel Hawthorne whiled away the hours with deep literary conversation and video games.

In addition to pondering the rooms where Melville lived his days, visitors peruse furniture, portraits, and clothing from the Berkshire Historical Society’s collection of artifacts and enjoy exhibits and events such as plays. Those who make appointments in advance can also immerse themselves in the manuscripts, atlases, oral-history tapes, and photographs that populate the Margaret H. Hall Library and Archives.

780 Holmes Rd
Pittsfield,
MA
US