Shop ’til you drop! Check back as this list may be updated!
Back Bay
Christmas Craft Fair at Old South Church
When: December 3, 10am – 4pm
Where: Gordon Chapel in Old South Church
Highlights: New England-based artists and live music
Cambridge
Harvard Square Holiday Fairs 2022
When: Fridays, Saturdays, and Sundays on Dec 9-11, Dec 16-18, Dec 19-22
Where: 33 Dunster Street, Cambridge
Highlights: An assortment of rotating vendors, so make sure you stop back in!
Winter Market
When: Saturday, December 3 – Sunday, December 4, 2022, from 11 AM-4 PM
Where: 1350 Kendall Street, Cambridge, MA, 02142
Highlights: Local vendors, ice skating and ice sculptures
Dorchester
Holiday Sip + Shop at Boston Harbor Distillery
When: Sunday, December 18th from 2pm-6pm
Where: Boston Harbor Distillery
Highlights: Enjoy a day of shopping, music, food, and craft cocktails
Holiday Sip + Shop at Landmark Public House
When: Thursday, December 8th 6pm-9pm
Tables set up inside and out featuring local vendors. Apple cider and specialty cocktails, plus Santa will be making an appearance.
Sip and Shop at Tavolo
When: Sunday, December 4th from 3-6pm
Where: Tavolo Restaurant
Highlights: Seasonal cocktails, local vendors and an appearance from Ms. Harlow Havoc Claus!
Holiday Pop-Up Market
When: Saturday, November 27th at 3pm
Where: Ashmont MBTA Plaza
Highlights: Celebrate with local vendors and live music
Downtown
Downtown Boston Holiday Market
When: Nov 25—Dec 17, Fridays and Saturdays
Where: Downtown Crossing
Highlights: Keep your eyes peeled for carolers and other performers!
Holly Gay Market
When: Sunday, December 11th
Where: Royale NightClub
Highlights: 90+ LGBTQ+ vendors, special drag performances.
Fenway
Boston Women’s Market Holiday Shop
When: December 10th
Where: Time Out Market Boston
Highlights: Features a selection of women-founded businesses/vendors
Fenway Flea Winter Market
When: Weekends Throughout December, Saturday & Sunday from 12pm-5pm
Where: Time Out Market
Highlights: Local vendors, food and drink from Time Out Market and Ice skating.
The North End
Boston Women’s Market Holiday Shop
When: November 13th – December 18th
Where: Hub Hall
Highlights: Features a selection of women-founded businesses/vendors
Holiday Creator Market
When: Starting November 25th
Where: Boston Public Market
Highlights: BPM’s year-round vendors plus many, many more!
Somerville
The Somerville Flea Holiday Markets
When: TBD
Where: 191 Highland Ave. Somerville MA, 02143
Rococo’s Holiday Affair and Makers Market
When: Saturday, Nov 26th
Where: Bow Market, Union Square
Highlights: Local makers, fire pits, hot chocolate and specialty cocktails.
South Boston/Seaport
Snowport Holiday Market
When: November 11th – January 2nd
Where: 100 Seaport Boulevard
Highlights: 120 + vendors, holidays activities, and a tree market
South Boston Holiday Stroll
When: Thursday, Dec.1 from 4-6 p.m
Where: Local businesses and restaurants in South Boston
Highlights: Santa on an antique fire truck, followed by a Classic Cadillac convertible with up-and-coming pop singers Carly Underwood and Tyler Levs of MusicBall Entertainment. More than 50 participating businesses will be offering incredible savings on Dec. 1; look for the big red bow on their storefronts.
Laboure Christmas Shoppe
When: Monday – Friday – 10am-6pm (until inventory runs out)
Where: Laboure Center
Get ready to deck the halls with the help of the Laboure Christmas Shoppe, featuring holiday decorations, Christmas decor, candles, tree trimmings, gifts, and more
Harpoon Holiday Market
When: December 3rd from 12pm-5pm
Where: Harpoon Brewery
Highlights: Boston Women’s Market and lots of Harpoon Beer
Winter Market at Castle Island Taproom
When: December 11th 12pm-4pm
Where: Castle Island Brewing Co.
Highlights: Unique local businesses and lots of beer
The Broadway Sip + Shop
When: Wednesday, December 14th 6pm-9pm
Where: The Broadway
Highlights: Eat, drink, + be merry while you shop local vendors!
4th Annual Holiday Bazaar
When December 4th and December 11th – 12pm-4pm
Where: Grand Ten Distilling
Highlights: Craft Cocktails and Local Vendors.
South End
Bazaar Mezzanna
When: December 10th 11am- 3pm
Where: Bar Mezzana
Highlights: Local Vendors and brunch!
SoWa Winter Festival
When: Starting November 5th
Where: SoWa Power Station
Highlights: 100+ vendors, live music, specialty cocktails
Roxbury
Black Legacy Marketplace
When: Every Saturday from November 26-December 24 from 1 PM- 5 PM
Where: 2136 Washington Street, Roxbury, MA 02119
Highlights: 50 talented local Black artisans and artists, three floors of holiday cheer, and live entertainment.
Reagan is a Food & Drink Photographer, Social Media Content Creator and a sometimes-blogger based in Boston, MA. Self proclaimed foodie passionate about photography, travel and her Frenchie Flyp.
