10 Best Festivals and Events in Boston

Boston’s Irish American community comes out in force each March for a St. Patrick’s Day parade that frequently attracts over a million green-clad revelers. Held each year on the Sunday closest to March 17, the event features colorful floats, live music, marching bands, and dancers, all making their way through South Boston on a route that typically begins at Broadway Station.

High-spirited crowds get into the party spirit at the many Irish bars and pubs in South Boston, raising a glass to the patron saint of Ireland in one of the country’s liveliest St. Patrick’s Day celebrations. It’s wise to arrive early for the best views of the parades themselves, and to keep an eye on any weather conditions that might impact on the parade route.

First held in 1981, Boston Harborfest has grown over the decades to become one of the most vibrant Independence Day events in the United States. Expect spectacular fireworks, live music, historical reenactments, children’s entertainment, and walking tours in an annual festival that spans several days leading up to July 4.

It’s free to attend many of the events, which take place at locations across Boston’s historic downtown and along the waterfront. Hungry visitors should be sure to try the bowls of traditional chowder handed out to the crowds as part of a tradition that has become known as Chowderfest.

Expect dazzling pyrotechnics, live music, and a family-friendly atmosphere at First Night. The mammoth New Year’s Eve party has been entertaining Boston residents since 1975, making it one of the best-established events of its kind in the country.

Free to attend, First Night is an alcohol-free event with an emphasis on fun, family-friendly celebrations. Events typically take place on and around Copley Square in the Back Bay neighborhood. Partiers can expect daytime events and early evening fireworks for younger children as well as late-night music and fireworks on the stroke of midnight for those old enough to stay up late. The party attracts upwards of 1 million revelers, so arrive early to secure a good spot for the festivities.

Boston prides itself on being a musical city, and Boston Calling Music Festival is one of the biggest events on the city’s cultural calendar. The annual 3-day event attracts some of the biggest names from across the worlds of pop, rock, and hip hop, with past headliners including Foo Fighters, Alanis Morissette, The National, and Metallica.

The event, which is held each year over the Memorial Day weekend in late May, sees Harvard Athletic Complex host food and drink stalls, art installations, a giant Ferris wheel, and acts from across the musical map performing on multiple stages. After starting out at Boston City Hall Plaza in 2013, Boston Calling moved to its current outdoor location in 2017, catering to the ever-growing crowds who wanted to attend.

Founded in 1989 by former Boston Harbor Hotel executive chef Daniel Bruce, Boston Wine & Food Festival is the longest-running wine festival in the US. Bruce, who headed up the hotel’s kitchen for 32 years before stepping down in 2021, remains at the helm of an event that attracts some of the world’s best winemakers each year to showcase their best bottles over 12 weeks of lunches, dinners, seminars, and tastings from January onwards.

Foodies and wine lovers will be in their element at the event, which offers advice on perfect pairings as well as an opportunity to sample dishes and drinks that have put this Rowe Wharf hotel firmly on the international culinary and viticultural map.

Held annually since 1970, Boston’s Chinatown August Moon Festival is a celebration of Chinese culture in the city as well as an important Asian festivity offering thanks for a successful harvest. The mid-August celebrations are a day-long feast of traditional music, dancing, arts, and crafts, held in the streets surrounding Chinatown Gate.

Sometimes known as the Mid-Autumn Festival, the origins of the August Moon Festival go back over 3,000 years and today a key part of the celebrations in Boston are the displays of traditional folk dancing, lion dancing, martial arts, and calligraphy. There’s plenty of opportunity to sample Chinese food and drink, and revelers should be sure to try the sweet pastry ‘mooncakes,’ an integral part of the festivities.

Billed as the world’s largest 2-day rowing race, the Head of the Charles Regatta is held in late October and attracts huge crowds to see talented teams of athletes race along the Charles River against a gorgeous backdrop of autumn foliage.

The 3-mile race was first held in 1965, and today thousands of top rowers from across the world head here to put their skills to the test. It’s free to watch the competition from the riverbanks, and a large-scale fitness expo might even encourage onlookers to take up the sport themselves. For those who prefer a relaxed day, there’s ample opportunity to try local food and with a river view at the Reunion Village hospitality tent.

Delicious food, lively music and dancing, and a taste of Greek culture are on the menu at the annual Woburn Greek Festival. Organized by the Annunciation Greek Orthodox Church of Woburn, the festival runs over several days each June. It attracts huge numbers of families, foodies, and festival lovers to the scenic suburb, which lies some 9 miles north of downtown Boston.

Family-friendly and free to attend, the festival takes place at the church itself and offers a chance to try treats like loukoumades (Greek donuts) and savory gyros (pita bread typically stuffed with meat, potatoes, and salad). Greek drinks flow freely at the festival’s tavern, and revelers are encouraged to try traditional Greek dance steps accompanied by live bands.

A multi-day, multi-venue event taking place on and around Boston Common each July, Outside the Box Festival brings together musicians, dancers, actors, magicians, and street performers in a free-to-attend event.

Founded in 2015 by Boston arts enthusiast and philanthropist Ted Cutler, the inaugural 6-day event sees over 70 performances take place on Boston Common, the oldest public park in the US. The aim of the event is to promote a love of the arts, and a series of events aimed at young people offers a chance for emerging artists and performers to hone their skills.