Columbus Day weekend in Boston might be a Bostonian’s favorite two weeks of the year, not just because of our long weekend, but also because the region’s weather is indisputably pleasant—a terribly rare circumstance for New England. So, we’ve rounded up our favorite activities to get out there and enjoy the splendid crisp autumn air that coincides with this mid-October holiday weekend and honor the Indigenous People of our land!
When is Columbus Day weekend?
Columbus Day falls on Monday, October 14, 2024. Columbus Day Weekend thus begins on Friday, October 11, and runs through Monday, October 14.
Indigenous People’s/Columbus Day Weekend in Boston events:
We’ve rounded up some of the most exciting events to do in Boston and beyond this upcoming holiday weekend!
1. Go on a spooktacular outdoor mystery picnic
Columbus Day weekend is just about one week before Boston slowly reaches peak foliage. Enjoy an outdoor picnic (mystery edition) and scavenger hunt hybrid to unlock the destination of your picnic in a bed of vibrant leaves.
2. Have a shucking good time at an oceanfront oyster festival on the Vineyard
The inaugural Oceans & Oysters festival debuts at The Winnetu Oceanside Resort this year, recently ranked the best resort in New England. Enjoy a splendid waterfront clambake, shucking class and more in this can’t-miss event! Oceans & Oysters is all-weekend from October 11-14, guests can opt for tickets to an individual event or try the package deal!
3. Enjoy a fall flannel jam festival in Marshfield and on the island of Nantucket
Levitate’s annual Fall Flannel Jam music festival aligns perfectly with Columbus Day weekend. The festival begins in Marshfield, Massachusetts on October 12 before it heads to Nantucket on October 14. Sport your best flannel and get ready to rock!
Check out The Winnetu’s dual-island adventure to enjoy Oceans & Oysters on the Vineyard and sail over to Nantucket for Levitate the next day!
4. Get spooked at this massive haunted festival in the city
Enjoy some local frills and thrills with the ongoing Wicked Haunt Fest—Boston’s first large-scale Halloween festival! Held outdoors in Charlestown, the festival offers family-friendly fun like pumpkin painting and trick-or-treating in addition to 3 scary haunted houses.
5. Go on a New England fall foliage road trip
Mid-October is some of the best time to enjoy fall foliage in New England! The northern part of the region peaks from late September, while the rest of the region follows, with Connecticut and the islands turning in early November. Check out some of our fall foliage guides below for an idyllic day trip or overnight voyage!
6. Enjoy a FREE performance with the Wampanoag Nation Singers and Dancers
Hailing from the tribal communities of Mashpee, Cape Cod and Aquinnah on Martha’s Vineyard, Wampanoag Nation performers will sing and dance in a free one-hour performance! Enjoy the traditional eastern dances and songs at the Concord Museum. Registration is encouraged, for the event on Monday, October 14 from 10-11 AM.
7. Visit the Topsfield Fair
Celebrating 206 years as the “oldest country fair in America,” the Topsfield Fair traditionally falls around Columbus Day weekend. The fair takes place on more than 60,000-square-feet of grounds with 300+ vendors, rides, parades, and more!
Happy long weekend, Boston!