From the first signs of spring each May, the state of Massachusetts kicks off its much-anticipated warm season with a festival just about every weekend. Most of the big ones take place in Boston, but travelers can also expect special events around Cape Cod and in the historic towns of Pioneer Valley and the Berkshires. Massachusetts holidays also include large-scale American events like Independence Day and an epic New Year's celebration.

St Patrick’s Day Parade

Boston, with its deep Irish heritage, held the first St Paddy’s Day parade in 1737 and is still going strong every March. It’s one of America’s top destinations for the green occasion, featuring a colorful float parade and lots of amazing food. Starting at Broadway, the parade runs to Andrew Square and is easily the highlight. But after, the party really gets going at virtually every bar in the city and is in full party mode for a few days afterward.


The six-block area around Harvard Square in Cambridge, Massachusetts turns into a street carnival each spring for the very popular Mayfair celebration. Three stages are set up to feature live music, while a host of street performers, clowns, and other entertainment wander the streets keeping everyone in good spirits. It’s a superb day for kids, but the overall party atmosphere makes it just as fun for adults. The food is excellent and an arts and crafts fair has 200 stalls of creative work from around the world.

Berklee Bean Town Jazz Festival

Every September as the summer draws to a close, Boston gears up for fall with a superb jazz festival. Held outdoors along Columbus Avenue, the event sees three stages set up with top musicians from around the country. It’s free and backed up with tasty food vendors, craft stalls, and a special family fun zone where parents and kids can hang out together.

The Big E

The largest fair in the northeastern United States takes place in Springfield, Massachusetts. This classic state fair is held at the city’s Eastern States Exposition, usually around the end of September or early October, and features everything you’d expect from a true Americana get together. There are carnival rides, livestock shows, concerts, games, a circus, food, and fun. With 17 days of events, it’s hard to go wrong with the Big E.

Martha’s Vineyard Food & Wine Festival

Each October, this lovely island takes a week off to indulge itself in great food and wine. Every village in Martha’s Vineyard participates in their own way and the emphasis is on regional and local fare. You can enjoy wine tastings, cooking classes, samples, and other special events centered around everything gourmet.

Head of the Charles Regatta

The largest rowing race on the planet takes place in Massachusetts, and is a spectacle well worth a trip to Boston in October. An international regatta, the team with the best time wins the title “Head of the Charles River”, which is a big accolade. With so many teams competing in waves of three mile races, it is really something to see.