Street Festivals

The City of Pittsfield is host to many street festivals and special events that take place each season of the year. The City features a flourishing year round monthly visual arts event, First Fridays Artswalk, in Pittsfield's Upstreet Cultural District in the heart of the Berkshires of western Massachusetts.  On the first Friday of every month, participating businesses simultaneously unveil new exhibits of paintings, photographs and other works from local and regional artists. A free guided walking tour with co-founder Mary McGinnis is also offered. 

In collaboration with Barrington Stage Company, the City of Pittsfield presents the 10×10 Upstreet Arts Festival in February.  The festival features art shows, theater, dance, spoken word and musical exhibitions in downtown Pittsfield’s Upstreet Cultural District.  From May through October the streets come alive with musicians, artists, activities, sidewalk dining, and much more with the City’s popular 3rd.Thursdays downtown street festivals. Lift Ev'ry Voice: Celebrating African-American Culture & Heritage in the Berkshires is a biennial month-long countywide festival that celebrates the rich traditions of African-American community, arts and culture, history and heritage found within Berkshire County and across the nation that takes place in June. 

Pittsfield is also the home of the famous Pittsfield Fourth of July Parade; one of the biggest in all of New England. The annual summer Polish Picnic has been a favorite community event for nearly 50 years.  Plan to enjoy live polka music and dine on an extensive array of Polish food and drink.  The GATHER-IN, Berkshire County’s only traditionally African-American community festival, has been a neighborhood tradition in Pittsfield for over 40 years. It features a basketball tournament, traditional home-cooked food, children’s activities, live music, entertainment, dancing, face painting, magicians, vendors, pony rides and much more. Inspired by the craft, craze and creativity of the hula hoop, Pittsfield City Hoopla is held annually in the gorgeous public gardens of Springside Park. In August, the annual Word X Word Festival celebrates the transformative power of words—written, spoken, and sung; to engage diverse groups in cutting-edge, live performances as both audiences and participants.  The first weekend in June the annual Berkshire International Film Festival is held in both Pittsfield and Great Barrington, highlighting the best in independent films and the latest in independent features, documentaries, shorts, and family films; along with lively panel discussions and special events focusing on filmmakers and talented artists from both sides of the camera.  The City of Pittsfield also hosts the annual Pittsfield Ethnic Fair in August, honoring the many cultures that make up the Berkshires and beyond. The Ethnic Fair features dozens of international food and craft vendors as well as traditional music and dance performances. Also in August, at the St. George Greek Orthodox Church on Bradford Street, you will find the Berkshire Greek Fest.  This is a two-day event that highlights the best of Greek traditions, music, dances and delicious food.

The Festival of Sharing Roots, hosted by St. Joseph Parish, is an annual community event in September that features multicultural food, entertainment, crafts and much more.  The Discover Tyler Street festival is an annual event hosted by the Tyler Street Business Group, to bring more awareness to the many businesses along Tyler Street and to aid in the revitalization of the Morningside district.  The event features live music and entertainment, food, activities for kids and information booths. In October enjoy Berktoberfest, a non-profit event with proceeds to benefit Berkshire Brewing Heritage and the Pittsfield City Jazz Festival which offers an array of regionally-based jazz musicians in venues from the majestic Colonial Theatre to downtown restaurants. And every year, in celebration of the holiday season, the Berkshire Museum presents the Festival of Trees featuring more than a hundred twinkling holiday trees, decked in colorful ornaments, arranged throughout the museum’s galleries from mid-November through the New Year.

For more information please visit the Discover Pittsfield website.