10 Ways to Celebrate Halloween in Boston

Here's where to scare up a good time
October 29, 2015
by Scott Kearnan

1. Take a bar crawl in the Seaport. Even if you're not dressed like a zombie, you'll probably be staggering like one by the end of "Halloween on the Harbor," a spirits-centric crawl between bars and restaurants in the Seaport. On Friday, October 30, you'll check in at TAMO Bistro + Bar at 7 PM — then hop on dedicated Duck boats running a constant circuit between nearby participants like The Barking Crab, Temazcal Tequila Cantina, and Jerry Remy's Sports Bar and Grill, all offering special cocktails, apps, costume prizes and more. It's $5 to use the boats (which will benefit Friends of the Fort Point Channel), or free to walk — but bring some extra cash, because individual restaurants may choose to set their own covers. 

2. Hit a food truck festival at City Hall Plaza. BuyMaster, the Boston-based startup behind an app that pinpoints discounts and deals based on a user's location, will host a "Truck 'r Treat" festival on City Hall Plaza from 11:30 AM to 3:30 PM on Saturday, October 31. Before you head out to Halloween soirees, fuel up from a number of food trucks, including ice cream sandwich slingers Frozen Hoagies, BBQ experts M&M Ribs, and Middle Eastern cuisine-focused Chubby Chickpea. A lineup of live bands will take the stage every half-hour, and you'll also find local vendors, games, costume contests, raffles and more. Entry is free with the BuyMaster app, or $3 in advance (here); $5 at the gate. 

3. Travel back in time at Canary SquareIf you're the type to break out Day-Glo leggings and lace gloves for your Halloween costume,  you may want to fly by Canary Square. On Saturday, October 31 the Jamaica Plain restaurant will resurrect "Love Night," a cult favorite '80s-skewing dance party that once popped up at Common Ground, Canary's then-sibling bar in Allston. You'll dance to music spanning from Phil Collins to The Misfits, imbibe $10 themed cocktails and nosh on a bar menu (deviled eggs, anyone?) served from 10 PM on; come earlier for the full dinner experience. Plus: costume prizes throughout the night. 

4. Sup Samhain-style at Beat BrasserieBelieve it or not, Halloween was not founded as a Pagan holiday dedicated to the act of dressing like a slutty nurse — or a slutty cat, or a slutty cauliflower, whatever. Enjoy an edible history lesson at Harvard Square's Beat Brasserie through Saturday, October 31. During each dinner service chef Ignacio Lopez is offering a supplementary Samhain menu inspired by foods that were traditionally associated with the Celtic festival. For instance, you'll find fadge (an Irish potato cake) with roasted apples and butter. (Traditionally a ring was baked into the cake; it was believed whoever found it would be married within the year.) Also on the agenda: colcannon (an Irish dish of mashed potatoes and cabbage), applecake, barmbrack (a raisin bread) and more. 

5. Dive into a "Monsters of the Sea" dinner at Bambara (pictured). Tales of mysterious sea monsters once terrified generations of ocean travelers. (Hence all those "THERE BE MONSTERS" scrawlings on early maps.) Luckily, human guests will be the ones doing the devouring at Bambara's special Halloween dinner dedicated to seafood. The four-course feast ($40) features spicy pumpkin soup with lobster; grilled octopus with blood orange salad; "Boo-illabaisse" of monkfish, skate, eel, sunfish and more; and the sweet finish of jellyfish-inspired panna cotta. Plus you can wrap your tentacles around brandy and cordial pairings for an additional $15.

6. Trick or treat at the Townsman cake table. For the next installment of its monthly (last Saturdays; 11 AM-2 PM) brunch, chef Matt Jennings' Townsman will get into the spirit of the season with a Halloween-themed "#caketable", a massive spread of pastries so good, you'll wish you could toss a few in your pillowcase. Plus there will be themed a la carte items like pumpkin waffles with cinnamon whipped cream and Skull Punch served in glass skull-shaped bowls. The best part: You'll still have time for a disco nap before hitting the town for some Saturday Night Fever-style festivities. 

7. Shake your bones at Naco TacoThe funky Central Square taco joint (pictured) is getting an early start on Day of the Dead celebrations with its October 31 "Dancing Fiesta" to kick off Dia de Los Muertos. Starting at 9 PM you'll find food and drink specials — $2 tacos, $3 beers, $5 sangria — plus groovy music and a costume contest, so don your most impressive candy skull makeup job. 

8. Earn an "eternal discount" at Moonshine 152Things that live forever: zombies, vampires, and 10% off discounts at this hot South Boston spot. That is, if you stop by during October 31's extended brunch (11 AM-3 PM) or dinner (5:30 PM-1:30 AM), when chef Asia Mei will put out a few special items, like spiked apple cider — and give costumed guests a Moonshine VIP Card that entitles them to "an eternal 10% discount" on food. Now please, stop looking at our neck. 

9. Get tea and a tarot reading at L'EspalierHope a new job, a new love, or an old dream is in the cards? Here's your chance to ask. On Saturday, October 31 and Sunday, November 1 the high-end Back Bay French will put a spooky spin on its weekend Tea Tastings (1:30-2:45 PM) with tea sommelier Cynthia Gold, bringing in someone to read tarot cards for future-minded guests. It's $50 per person, and also includes all the typical tea and pastries. 

10. Get tossed in the Clink with Beetlejuice. The clever Tim Burton-directed Michael Keaton movie Beetlejuice serves as the inspiration for a Halloween dinner and party at Clink, the restaurant inside The Liberty Hotel (the former Charles Street Jail). Here's the deal: Spend $50 on food and drink, which includes options like oysters with "beet juice mignonette," and — for an additional $50 — you can purchase a ticket to the otherwise sold-out "Beetlejuice" costume party, which starts at 8 PM.