Boston's Ultimate Guide to Halloween

By Scott Kearnan  |  October 22, 2013

You want to: leave the meat-eating to the werewolves.

So: Head to UpStairs on the Square for a Halloween-themed, vegan prix fixe with creative selections like the Full Moon Squash Soup and Pasta from the Black Lagoon, tofu-stuffed ravioli with black quinoa and smoked black trumpet mushrooms. The four-course feast is $49 ($72 with wine pairings) and will also be available on Friday, November 1, and Saturday, November 2. While you're there, stop by the restaurant's Monday Club Bar to perform your finest rendition of "Thriller" during Scary-Oke at 9:30 PM. (The bar will also have a separate meat-inclusive prix fixe for $40, plus the restaurant's full menu.) 

You want to: wear your drink. 

So: Hit the bars with your most offensive pick-up line: we guarantee you'll be on the receiving end of a vodka-soda shower in no time. Alternatively, check out The Hawthorne's concept for its Halloween party on October 31: "Come As Your Favorite Cocktail." Yes, the idea is to wear a costume inspired by your favorite drink. Are you a Manhattan? (Or a sexy Manhattan?) Are you a Sidecar? (Or a sexy Sidecar?) Are you wondering, how the heck am I going to dress like a cocktail? (We are too.) Give it your best shot (heh-heh), and if you bomb the costume contest, don't worry. There are still drinks to be had, apples to bob for, and black-and-white horror movies to watch in the Stone Room. Red Sox DJ TJ Connelly will spin tunes too. Tickets are $25 here.

You want to: look evil, do good. 

So: Don your devil costume but indulge your angelic side by heading over to Wahlburgers on Friday, October 25. From 9 PM to 1 AM, the burger-centric restaurant from chef Paul Wahlberg (brother to Mark and Donnie) will host the Wahl-O-Ween Bash to benefit Remember Betty, a breast cancer nonprofit founded by New Kids on the Block member Danny Wood, in honor of his mother. The $30 tickets (available here) will raise funds for breast cancer awareness. Appetizers and a sundae dessert bar are part of the package, as well as dancing to DJ tunes and a costume contest. Win/win. 

You want to: imagine what would happen if the grand finale of Pretty in Pink involved Molly Ringwald eating someone's brain. 

So: Buzz over to The Beehive on October 31 for an '80s-themed Zombie Prom. From 5:30 PM to 1 AM, servers decked out in full Night of the Living Dead makeup will deliver Halloween-y dinner specials (plus the regular menu offerings) from new chef Marc Orfaly. And at 9 PM, a Reagan Era-inspired cover band will take the stage to dole out sonic offerings from Michael Jackson, Cyndi Lauper, Billy Idol and other iconic stars. Reservations are recommended. (Prefer something a little less gory? Milton's Abby Park is hosting an '80s-themed costume party on Wednesday, October 30, sans zombie stuff.) 

You want to: have a family-friendly dinner.

So: Treat the kids (or yourself, whatever) to a pre-trick-or-treat pizza buffet that Bella Luna is laying out on Halloween (4:30-6:30 PM) as an early-bird option before the little ones go door-knocking. The restaurant's Spooktacular Children's Carnival ($5 kids; $7 adults) will also host games and activities, and you can always reserve a seat for the main dinner hours if you want to treat yourself (because, sorry, you're too old for that Casper-looking bedsheet).

You want to: sleep in, celebrate later. 

So: Hit the hay early (Halloween on a work night can be a drag) and save yourself for the weekend, when chef JJ Gonson's gourmet locavore biz Cuisine en Locale will host its next ONCE (One Night Culinary Event) dinner on Saturday, November 2. Called "Muertos III: A Day of the Dead Fiesta," it will offer a night of farm-to-table "MassMex" cuisine, including Taza chocolate chicken mole, tomatillo Stillman pork verde, custom-made corn ice cream from Toscanini’s and more. There will also be beer tastings from Somerville's Slumbrew, cocktails from boutique bartending service Booze Époque, and music and performances from party band Mariachi Mexico Lindo and "SteamCrunk" act Walter Sickert & the Army of Broken Toys. Tickets are $35-$50 here