The Top Streets for Trick-or-Treating in Boston

Here’s where to go on Halloween for a car-free, huge-candy, kid-happy evening.

Halloween is just about here, and chances are, you’ve got the costumes down pat, but… do you know where you’ll be going? Because not to state the obvious, but your odds of having a car-free, full-sized-candy-bar night—the kind that, by the way, can exhaust a kid no matter how sugared his bloodstream—hinge on hitting up the right streets in the right neighborhoods. Or did you think you’d just step out your front door and go from there?

If you’re not in prime candyland territory already, never fear. We anticipated this need and took the opportunity to canvas our editors and scan the web for the best spots in town for your costumed kids and their pillowcase/jack-o’-lantern bucket. Below, find out exactly where you need go. —Reporting by Becca Fox and Meara Hamidiani

Pickney and Mount Vernon Streets, Beacon Hill

Resoundingly popular among Boston staffers, Beacon Hill has a lot to offer; not only is the atmosphere spot-on with the wrought iron, cobblestones, and seriously all-out decoration, but two of the big streets—Pickney and Mount Vernon—will be closed to traffic, keeping revelers safe. Plus, rumor has it that John Kerry dishes out full-size candy bars from his Louisburg Square house.

Brattle Street, Cambridge

Kind of like Beacon Hill in a way, Brattle Street is heavy on ambience and big houses—meaning enthusiastic families handing out serious treats (or as one of our staffers phrased it: “That’s where all the rich peeps are livin’! And you know they’re gonna be handing out full-sized Reese’s Cups and none of that Tootsie Roll crap!”). There’s also a big bonus by way of the Harvard Square end, where spots like candy-heaven-palace-extraordinaire Hidden Sweets have been known to hand out goods of their own to costumed passersby.

Beals Street and North Brookline Neighborhood, Brookline

Brookline is yet another perfect Halloween-ing area loaded with large homes and little traffic along the side streets, especially in North Brookline and on Beals Street—the latter of which is often closed to traffic for trick-or-treaters and “crazy busy with little angels and devils.” Plus, when the kids can’t take the walking anymore (or more likely, the attending parents can’t), there’s Puppet Showplace Theatre’s Spooky Story Slam, open to trick-or-treaters who find themselves in Brookline Village.

Marlborough, Dartmouth, and Clarendon Streets, Back Bay

If you haven’t yet figured out it’s best to leave your car at home on Halloween, then trust us: it is—because the Back Bay’s also wholeheartedly joined the movement to shut down several of its streets to keep roaming families all the safer. Stretches of Marlborough, Dartmouth, and Clarendon will all be thick with trick-or-treaters gathering their dues from the well-to-do homes of the area (well-to-do meaning a strong chance for generously-sized candies). And, to top off the tradition, the Clarendon Street Playground hosts an annual party with free food, sweets, and activities like hayrides around the neighborhood.

Hanover Street and Beyond, North End

The North End has a high walk score, low crime rates, really creepy graveyards, and a heck of a lot of neighborhood-friendly businesses that’ll be ready and waiting to hand over goodies to passersby (look for the sign that participating spots will post in their windows). One quick word of advice to parents though: bring a map. North End streets can be cornfield-maze-esque, especially in the evenings, and we all know what can happen in a cornfield maze in Massachusetts.

Melville Avenue, Dorchester

And the winner for most-surprisingly awesome trick-or-treating spot is: Melville Ave. in Dorchester, yes, Dorchester. It’s a safe, quiet, tucked-away Victorian sort of neighborhood whose residents do not necessarily advertise their role in the Halloween tradition, but who are nonetheless more than ready to jump into action to treat the long lines of trick-or-treaters who appear at their doors each year.

East and West Broadway Streets, Southie

You won’t find the sort of sprawling massive homes here that guarantee a full-size Snickers bar a la Beacon Hill, but you will find a wealth of neighborliness, open doors, and bowls of candy along the stretch of homes and businesses that line East and West Broadway. Word of advice though, don’t do the Whitey Bulger costume here, OK?

* Note, this post has been updated to reflect the fact that while North End businesses that participate in trick-or-treating are marked with signs, most residences there do not open their doors to trick-or-treaters. Many thanks to our commenter for pointing this out!

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  • Jesse

    a word about Northend Halloween. Most residents DO NOT open doors to trick or treaters unless they are expecting friends or family members. There are enough Halloween activities in the Northend… the NEWMA trick or treat event (the signs in the store windows) … an event on the Prado … a parade on Saturday and party at one of the religious societies and a haunted house and Halloween party on Friday Oct 28 at the Nazarro community center… that most parents do not take the kids around door to door (except the ones who go to Beacon Hill or the burbs).