Boston in December: Your 2025 events Guide
Boston feels especially charming in December - part cozy, part celebratory, and full of local events that make the month feel a little brighter. Whether you're hunting for gifts, looking for a festive night out, or craving a community-driven gathering, here’s your curated guide to what’s happening around the city.
Holiday Markets & Festive Shopping
December 5th, 2025 • Holiday art fair from 12-6pm. Music starts at 7:30pm
Daily Brew Coffee House & Lounge. 412 North Falmouth Highway, North Falmouth, MA 02556
The Daily Brew Coffee House turns into a holiday destination with its annual art fair, bringing together local artists and handmade pieces perfect for gifting. It’s the kind of place where you can sip something warm, browse thoughtfully made work, and ease into the spirit of the season.
Once the fair winds down, the energy shifts into Barn Night with The Lounge at the Brew, offering an even cozier atmosphere. Get your tickets here.
December 6th, 2025 • 5pm-8pm
116 Pleasant St. Eastworks Suite
This night market gathers a wide range of artists and vintage sellers under one roof, offering everything from ceramics to skateboards. It’s a great way to discover one-of-a-kind pieces while supporting independent creators.
The mix of arts, collectibles, and handmade goods makes it easy to find something special for someone on your list - or just enjoy browsing while soaking in the lively community atmosphere.
December 7th, 2025 • 12:30-5pm
Cambridge Community Center, 5 Callender St
Holiday Hassle brings together 85+ small businesses, creating a bustling mix of art, flea finds, and live music. With artists onsite and café treats available, it’s the perfect place to spend an unhurried winter afternoon.
The scale of the market means there’s constantly something new to stumble across, whether that’s a handmade gift, a vintage treasure, or a local creator you haven’t discovered yet. It’s festive, low-pressure, and super fun to explore!
December 7th, 2025 • 2-6pm
39 South Main Street, Ipswich, MA 01938
This handmade celebration invites you into an afternoon filled with craft-driven cheer - from paper chains to block-printed cards and other holiday projects. It’s playful and delightfully nostalgic, offering a slower way to connect with the season.
The focus on making rather than buying gives the event a refreshing feel, making it a great pick if you love hands-on creating or want a break from busy December routines. Get your tickets here!
Food, Drinks & Seasonal Dining
December 4th, 2025 • 7-11pm
La Fabrica Central, 450 Massachusetts Avenue
Junebug’s holiday party brings together biodynamic wines, oysters, and music by CJ for an early-December celebration that feels both lively and intimate. It’s a great choice for anyone wanting festive energy without large-crowd chaos.
With a focus on wines from biodynamic icons, the evening highlights unique pours in a setting that feels welcoming and relaxed. Pair that with oysters and good music, and it becomes a perfect midweek treat.
December 9th, 2025 • 6-9pm
170 W Broadway, Boston, MA 02127
This edition of Fox & Knife’s wine dinner series features black truffles and Northern Italian wine - a pairing made for colder nights. It’s a thoughtful, seasonal experience that leans into rich winter flavors.
Held at Bar Volpe, the dinner offers an intimate and atmospheric setting, making it ideal for a special night out, a date, or simply treating yourself to something memorable during the holiday stretch.
Neighborhood Celebrations & Cultural Events
December 4th, 2025 • 4-7pm
Brookline Booksmith, 279 Harvard Street, Coolidge Corner
Brookline Booksmith takes part in the neighborhood-wide First Light celebration, opening its doors for an evening of festive treats, live music, wine, and welcoming activities. It’s a chance to explore the shop in a more social, celebratory setting.
Wandering around town during First Light is part of the charm - there’s a sense of discovery as you move between stops, meet neighbors, and enjoy small pockets of holiday cheer. It’s one of the city’s sweetest early-December traditions.
Music & Nightlife
December 5th, 2025 • From 7pm
Cantab Lounge, 738 Massachusetts Ave, Cambridge
Cantab Lounge hosts a full lineup featuring Emily Irving, Wooll, and Miss Bones for just $10 - an incredible value for a night packed with live music. The venue’s intimate setting makes the performances feel close, energetic, and personal.
Whether you’re already a fan of the artists or just looking for a fun night out, the mix of acts keeps the evening moving and creates an easy, no-fuss way to enjoy local music during a busy month.
Make sure to get your ticket now!
December 12th, 2025 • 9-11pm
Ripple Cafe, 1906 Dorchester Ave
Ripple Café hosts a Coffee & Mimosas mixer with Haul and Vibe, offering a dedicated space for Black & Brown queer women to gather, connect, and celebrate. With a DJ, food, and drinks, it’s designed to feel uplifting and welcoming.
The event blends community, music, and conversation in a way that feels joyful without being overwhelming - the kind of gathering where people actually meet, talk, and stay awhile.
Secure your spot here.
December 13th, 2025 • From 9:30pm
nathálie Wine Bar186 Brookline Ave., Boston
nathalie Wine Bar’s Holiday Ho-Down features DJ L’Duke, a festive “show-ho-ho” by Spice, and a guest bartender behind the bar. It’s a playful, spirited December night that leans into holiday fun without taking itself too seriously.
Expect a lively crowd, good beats, and a creative twist on the usual holiday party. It’s an easy pick if you’re craving something celebratory and a little cheeky as the month winds down.
Get it locked in!
Ready to plan your December? Whether you’re browsing markets, settling in for a wine dinner, or dancing the night away, Boston has a full calendar of festive options. Save your favorites, bring your people, and make the most of the month.
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