Halloween Happenings :: Trick-or-Treating in Boston Neighborhoods

trick or treating - Boston Moms BlogFrom Beacon Hill to Brookline and beyond, there are so many amazing Boston-area neighborhoods that are perfect for your traditional trick-or-treating — the kind that brings neighbors together by the dozens, by the hundreds, or sometimes even by the thousands, for one spooky night. If you’re looking for that perfect spot to stroll around on a chilly October 31 evening, these areas in Boston boast the best trick-or-treating around, residential style:

Beacon Hill

There’s something haunting about Beacon Hill’s leaning townhouses, cobbled lanes, and wrought iron. It’s the perfect setting for a traditional All Hallows’ Eve. Wind your way up the hill through the narrow passageways, and you’ll be rewarded with plenty of serious treats. (These folks on the hill don’t skimp.) Pinckney and Mount Vernon are especially prime streets.

Back Bay

Another grande-dame neighborhood, the Back Bay offers almost as much charm as Beacon Hill, minus the hike up the hill and the narrow sidewalks and the crowds. Plus, the Back Bay’s straightforward grid layout allows you to rest assured you won’t skip a Snickers. Be sure to hit Marlborough and Dartmouth Streets, and while you and your little ones are in the area, check out the annual Halloween party at the Clarendon Street playground.

Charlestown

An authentic old neighborhood with some recent Hollywood film cred, Charlestown offers spooky sites along with your trick-or-treat. The Mystic River never seems as mystical as on Halloween night, and the USS Constitution looks like an old ghost ship on a foggy October evening. If you like your fright with a side of fun, make your way to Monument Square for Charlestown’s annual parade.

Brookline

Family-friendly Brookline offers prime trick-or-treating throughout its neighborhoods, but we think the best can be found in densely populated North Brookline. Coolidge Corner residents rave about the annual revelry on Beals Street, while Brookline Village folks stay loyal to bustling Brooks Street. Both are often closed to traffic. Some years, Brookline Village also treats the younger set to an afternoon parade from Netherlands Road to the Puppet Showplace Theatre.

Cambridge

Another neighborhood known for big charm and even bigger candy bars, Brattle Street is lined with beautiful homes where friendly folks meet you at their doorsteps. It’s the perfect street to canvas with your kids in tow, ending at Harvard Square for more Halloween festivities. (Just go on the early side, before the square gets too rowdy.)

Of course, there are still other great hoods for haunting: Southie, Brighton, and the North End come to mind. And further afield, there’s always Salem for a ghoulish good time.


This post was originally published in 2015 and has been updated for 2022.

A Maine native, Jessie migrated down the coast to Boston after college, and it’s been home ever since. In this great city, Jessie met her husband, graduated law school, played in numerous basketball leagues, worked as a marketing writer, ran the marathon, lived through several home renovations, and wrote many beginnings of many books. But of all these great adventures, she most loves the one she’s on now: on-the-go-mom to three energetic and hilarious daughters. Jessie, her husband, and their trio of little ladies live in Brookline.

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