Massachusetts knows how to throw a festival, and these are the kind you plan a whole year around.
Think massive crowds, live music echoing through the air, food stands working nonstop, and traditions that have been drawing people in for decades.
Some celebrate history in loud and unexpected ways, others take over streets with music, parades, or food that you will still be thinking about weeks later.
These festivals happen at different times of year, but they all have one thing in common: they turn an ordinary weekend into something unforgettable.
Keep reading to discover ten Massachusetts festivals that deserve a permanent spot on your calendar.
1. Salem Haunted Happenings (Salem)
Time of year: October
Salem Haunted Happenings takes over historic Salem, with festivities on Essex Street, at Salem Common, and across the downtown area.
It’s famous for embracing the 1692 Salem Witch Trials, and you can expect a parade, outdoor concerts, street performers, pop-up markets, and ghost tours.
The whole city gets in on it, and you’ll see thousands in full Halloween costumes, tarot readers, and museums like the Witch House offering special exhibits.
Fun fact: This event runs throughout the entire month of October, draws over a million people, and is one of the biggest Halloween celebrations in the country.
2. Boston Calling Music Festival (Boston)
Time of year: June
Boston Calling Music Festival is held at the Harvard Athletic Complex, just across the Charles River from downtown Boston.
This three-day event brings in huge names like T-Pain and Avril Lavigne, with multiple stages across the fields and nonstop sets from afternoon to night.
You can expect a packed schedule of rock, pop, hip hop, and indie artists, plus food vendors with lobster rolls, fried chicken sandwiches, and other local favorites.
With open-air views and 40,000+ fans each day, Boston Calling feels like the ultimate summer highlight in the state.
3. Lowell Folk Festival (Lowell)
Time of year: Late July
Lowell Folk Festival fills downtown Lowell with stages set up along Market Street, Boarding House Park, and St. Anne’s Churchyard.
It’s a three-day celebration of traditional music and dance, with folk bands, fiddlers, blues players, and cultural groups from around the world.
Between performances, you can wander around, explore activities, and grab food from dozens of stalls serving things like Greek fries and Vietnamese spring rolls.
Since it started in 1987, Lowell Folk has grown into one of the biggest free folk festivals in the country, now drawing more than 150,000 people each year.
4. Tanglewood (Lenox and Stockbridge)
Time of year: July-August
Tanglewood brings the Boston Symphony Orchestra to the Berkshires each summer for a full season of live concerts.
Events take place between Lenox and Stockbridge, with performances inside the Koussevitzky Music Shed and on the surrounding lawn.
You’ll hear everything from classical masterpieces and orchestral pops to film score tributes and popular artists in a scenic outdoor setting.
Dating back to 1937 and welcoming more than 350,000 visitors every season, it’s one of Massachusetts’ most iconic summer music traditions.
5. King Richard’s Faire (Carver)
Time of year: September to October
King Richard’s Faire is set on an 80-acre wooded site in Carver, right off Route 58.
This is New England’s largest Renaissance faire, famous for jousting, fire-breathing acts, mud-beggar shows, and costumed performers roaming the grounds.
You can also spend the day browsing shops for leather goods and swords, eating giant turkey legs, and sipping mead while listening to live music.
Started in 1982, King Richard’s Faire pulls in tens of thousands of people every season and feels like stepping straight into a medieval village for the day.
6. Whaling City Festival (New Bedford)
Time of year: Mid-July
Whaling City Festival takes place in New Bedford at Buttonwood Park.
It’s a long-running event featuring a carnival with rides, food booths, games, local bands, and family-friendly entertainment.
There’s more than enough to fill a full day, with activities happening all around the park.
With roots going back to the 1970s, the festival now draws over 150,000 people each year and turns New Bedford into a nonstop summer party by the harbor.
7. Gloucester Schooner Festival (Gloucester)
Time of year: Late August
Gloucester Schooner Festival is held on Gloucester Harbor every Labor Day weekend, with events centered along the waterfront.
This one is popular for its dramatic schooner races, where massive wooden sailing ships with towering sails compete at full speed.
All weekend long, you can watch the scheduled action, step aboard docked schooners, and soak up the fun atmosphere.
First held in 1985, this festival honors America’s oldest seaport and gives you a front row seat to one of the most exciting sailing events in New England.
8. Wellfleet OysterFest (Wellfleet)
Time of year: Mid-October
Wellfleet OysterFest fills Main Street in Wellfleet for two days, shutting down the road and turning the town into a full-on seafood celebration.
It’s best known for tons of freshly shucked Wellfleet oysters served by local harvesters, along with food and drink tents, a road race, and live music.
If you want the full experience, you can watch the oyster shucking contest, browse arts and crafts booths, and take in the community spirit around town.
What began in 2001 now draws more than 20,000 people in a single weekend, making it one of the most delicious fall festivals in the state.
9. North Quabbin Garlic & Arts Festival (Orange)
Time of year: Late September
The North Quabbin Garlic and Arts Festival is hosted at Forster’s Farm in Orange, surrounded by rolling fields and scenic views.
This is a two-day celebration of all things garlic, with local growers, garlic snacks, and plenty of fall flavor in the air.
You can also check out 120 booths, catch live music on multiple stages, watch cooking demos, and let kids loose in hands-on craft areas.
It’s been a local favorite since 1999, turning into a tradition that brings together thousands for food, art, and community.
10. Johnny Appleseed Festival (Leominster)
Time of year: September
Johnny Appleseed Festival takes place in downtown Leominster, with events spread along the streets.
The festival celebrates the city’s connection to John Chapman, better known as Johnny Appleseed, who was born here in 1774.
You can expect plenty of local food and drink, live music, and craft and vendor booths, plus the festival’s “World’s Best Apple Crisp” topped with vanilla ice cream.
With kids’ activities, community spirit, and a focus on local history, the Johnny Appleseed Festival is a fun way to kick off fall in the state.
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