The Boston area is embracing the Halloween season with a mix of indulgent dining, festive cocktails, and family-friendly events. From themed parties for adults to creative ways for kids to offload their candy haul, the region is offering unforgettable experiences all month long.
Upscale Thrills: Themed Drinks and Dining at Sugar Factory Boston
Sugar Factory Boston is transforming indulgence into a spooky celebration, offering a limited-time Halloween Menu now through November 2. Guests can enjoy over-the-top treats and creative, holiday-inspired cocktails at this festive location.
A Menu of Monster Mashups
The restaurant is marking National Pasta Day on October 17 with a chilling special: Spooky Skull Penne Alfredo, featuring creamy Alfredo and a “blood-red” sauce, topped with ghostly garlic crostini. For National Frankenstein Friday on October 31, diners can dare to devour the Frankenstein Burger, a massive creation featuring double Angus patties, a Nashville Mozzarella block, caramelized onions, and chipotle mayo. Sugar Factory also celebrates National Chicken & Waffles Day on October 20 with its classic vanilla bean waffle and buttermilk fried chicken options.
Day of the Dead Celebration and Candy Collection at Margaritas
Margaritas Mexican Restaurant is honoring the traditional Mexican holiday, Día de los Muertos, on Saturday, November 1, with a family-friendly event focused on festive traditions and giving back.
Calavera Facepainting and Treats for Troops
Families who dine at participating Margaritas locations can receive complimentary calavera (sugar skull) facepainting, getting into the spirit of the holiday. In a post-Halloween twist, Margaritas is partnering with the Treats for Troops program: children who donate their sealed Halloween sweets will receive a free kids’ entrée, with options like tacos, fajitas, and burritos, plus a side and ice cream treat. The collected candy is donated to military families and veterans.
Seasonal Sanguine Cocktails
For adults, the restaurant is stirring up a limited-time cocktail special through November 2. The Tequila Transfusion is a sinister blend of Tequileño blanco, triple sec, and a mix of blood orange, passionfruit, and pomegranate purees, served in a “blood bag” style. A nonalcoholic version, the Monster’s Blood mocktail, is also available.
Andover’s Stylish Soiree: Music and Costumes at 34 Park
34 Park in Andover is launching a celebratory series of weekend events throughout October and an adults-only costume party to ring in November.
34 DARK Fall Music Series
Every Saturday in October, starting at 8:00 p.m., the restaurant hosts the “34 DARK” Fall Music Series, featuring live performances from local artists like Lou Antonucci and Bella Perrota, alongside craft cocktails.
Trick or Treat and Costume Contest
Families are invited to visit 34 Park between October 25 and October 31: kids in costume will receive a special Halloween goody bag. The spooky festivities culminate on Saturday, November 1, with the Halloween Costume Party, a 21+ event featuring live music by Steve Haiddaichuk, specialty cocktails, and prizes awarded for the Best Costume and Best Couples Costume.
Gifford House Inn: October Halloweekend Events
Seasonal Entertainment and Unique Social Events
The Gifford House Inn is hosting a week of specialized entertainment and social gatherings from October 24th through November 1st, catering to both local patrons and visitors. The calendar is packed with unique opportunities, including a one-night-only solo performance by Marti Gould Cummings on October 24th, a renowned drag artist and activist. The Halloween theme is further celebrated with a special edition of The Paige and Peter Show sketch comedy on October 27th, and a major Masquerade Ball on October 30th featuring a red carpet, DJ, and costume contests, with discounted entry for community residents. Additionally, the inn will screen Halloween-themed movies as double features in The Yard, encouraging guests to gather around a fire pit with drinks. Creative and active pursuits are also available, such as guided figure drawing sessions on Tuesdays and line dancing classes for all skill levels on Wednesdays. The week concludes with the launch of a new afternoon dance and social event called The Big Wiggle on November 1st.
