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From Trick-or-Treating to Pumpkin-Painting, Here’s Where to Have a Classic Halloween in Boston

With the picturesque New England fall in the backdrop, Boston-area families have always enjoyed Halloween festivities in and around the city—but this year, with PruBoo returning to Prudential Center for its 30th anniversary, celebrating spooky season is even more exciting.

PruBoo, a highly-anticipated annual event designed for children and families, not only coalesces all things Halloween into one day, but kicks those classics up a notch. On Sunday, October 27th from 11 am to 1 pm, the event will celebrate its 30th year and treat attendees (both new and returning) to a vibrant, festive atmosphere full of performances, costumes, activities, candy and more. So get your monster masks, witch hats, superhero capes, princess crowns and other creative costumes out and head to this (free!) event—and when you get there, here’s what to expect.

At the Event

During the event, trick-or-treating, activities and entertainment will be taking place all throughout Prudential Center, so lace up those walking shoes and get ready to explore! And before you get started collecting all those goodies and treats, stop by one of the event’s welcome tables, where a $5 donation to the event’s charitable partner, Boston Children’s Hospital, earns you a Prudential Center trick-or-treat bag (and benefits a good cause while you’re at it). 

Perhaps the most classic and beloved of all spooky season traditions, families can kick off the PruBoo excitement by trick-or-treating through the over forty stores and restaurants participating in the event. And while you’re enjoying those treats (and sneaking a piece or two of candy from your child’s bag), there are activities to fully embrace the Halloween spirit. Kids will love to express their artistic sides with a classic pumpkin-decorating experience, and they can further transform into their favorite characters and costumes by getting their faces painted on-site. There’s seasonal entertainment to enjoy, too: Magic shows by Robert Clarke will take place at 11:30am and 12:30pm, and you won’t want to miss a musical performance by Vanessa Trien and the Jumping Monkeys at noon.  

When you’re stopping by PruBoo’s many participating retailers, don’t miss Dick’s House of Sport, where you can show off your costumes and celebrate all things Halloween with a trick-or-treat scavenger hunt, games, music and more. For an even more immersive Halloween experience, don’t miss View Boston’s ticket promotion, which scores you a free youth ticket for every adult ticket purchased between 10 am and 2 pm. With those tickets, you’ll gain access to Prudential Tower’s 52nd floor, where you will be greeted by some of your favorite characters including a winged American hero, princesses, the Sanderson Sisters and more (and some beautiful views, too). 

These experiences capture all the whimsy, joy and wonder that characterizes Halloween for children—and allow the whole family to enjoy the best spooky season in one place. 

PruBoo will be taking place On Sunday, October 27th from 11 am to 1 pm. To learn more about all the fun of the 30th anniversary event, click here.