Frigid Nights & Festive Lights

A freezing weekend ahead, but the neighborhood refuses to slow down: Union Square’s Jingle Festival spreads markets across every corner, Crystal Ballroom hosts 50+ makers, artist studios open their doors for a three-floor holiday showcase, and Bow Market adds its Green & Jolly sustainable faire to the mix. It’s the rare weekend where festivals, fairs, and creative pop-ups overlap so much you can build an entire day around browsing, sipping, skating, and thawing out between stops.

December 04, 2025

LAST SECOND THURSDAY PLANS

Holiday Wine Party @ June Bug, Somerville – First Crush takes over June Bug for a holiday wine party with natural pours from Kermit Lynch producers, unlimited oysters and pizza, a welcome pour, DJ Knina Mixtapes on the decks and a raffle of standout bottles all night — meet new people and learn about wine..p.s. only a couple of tickets left | $85, 7–11pm

WEEKEND SPOTLIGHT

Union Square goes full holiday mode with markets tucked everywhere — artist studios, maker galleries, vintage vendors, and curated pop-ups threaded throughout the neighborhood. Sip something warm, browse one-of-a-kind gifts, follow the Festivus Trail, snap Elfie selfies, and loop through every corner of the Square for the full Jingle experience from afternoon to early evening

Friday, December 5th

Coffee Tasting at Ten @ Counter Culture Coffee, Somerville – A mellow Friday morning coffee tasting where you sample fresh brews, learn how each roast is sourced and made, and chat with other coffee-curious locals over beautifully brewed cups | FREE, 10–11am

Yes and Everything: Live Arts Night @ Life Drawing Boston, Somerville – A late-night mashup of open-mic chaos and curated acts — comedians, jugglers, magicians, drag performers, and wild interdisciplinary artists — all packed into Joy Street for a costumed, anything-goes creative hang | $20, 8–10:30pm

Rock Bottom Improv Comedy @ The Rockwell, Somerville – If you need a chaotic holiday laugh with a packed room and performers who’ll turn your suggestions into wild improv mayhem, this Friday show brings the energy and the crowd | $15–20, 9–10pm

THE STOOP’S PICK’S

Kendall Square’s outdoor rink reopens Saturday with smooth new ice, open public skating, and plenty of room to loop around with friends as winter officially arrives in the neighborhood — be on the lookout for changes due to weather (IG: @canal.district.kendall)

A packed two-floor holiday market in Davis Square with 50+ artisan, maker, and vintage vendors, printed art, ceramics, standout vintage fashion, and handcrafted gifts, plus a full bar and expanded mezzanine space to explore

Saturday, December 6th

  

Ice Rink Opening @ Canal District Kendall, Cambridge – The Kendall Square rink opens for the season this Saturday, bringing back outdoor skating vibes, winter energy, and a chance to be among the first to glide on freshly made ice — please make sure to check for weather updates for potential opening delays | FREE, 11am-9pm

Small Mart Holiday Market @ Crystal Ballroom, Somerville – One of the city’s most beloved indie markets takes over the Crystal Ballroom and Somerville Theatre mezzanine with 50+ artists and vintage curators, a full bar, and endless handcrafted treasures to hunt for | FREE, 11am–4pm

Indoor Holiday Movie: The Polar Express @ CambridgeSide, Cambridge – Kick off your Saturday with a warm indoor crowd, early festivities, and a midday screening of The Polar Express that turns CambridgeSide into a cozy holiday hang for families, friends, and anyone craving a little seasonal nostalgia | FREE, 11am–2pm

Brewery Tour & Tasting @ Lamplighter Broadway, Cambridge – If you’ve ever wanted the inside scoop on how Lamplighter brews its favorites, this monthly tour gives you early pours, production-floor access, and a beer school diploma to frame in your living room | $34, 1–2pm

Honky Tonk Dancing w/ The Talking Hearts @ Arts at the Armory, Somerville – With a 30-minute two-step lesson, a six-piece ensemble, witty originals, classic country covers, and bright pedal steel, this holiday show turns the Armory into a Southern-style dance night you can jump right into | $30 in advance, $35 at the door, 7–9pm

Sunday, December 7th

  

Boston Café Bikers Ride @ Circus Cooperative Cafe, Cambridge – A chill December ride led by the Boston Café Bikers community, starting at the Aquarium and cruising to Circus Cooperative Café with group safety tips, winter gear guidance, and a friendly bunch that proves biking Boston in cold weather is actually doable — technically this starts at the aquarium in Boston but ends in Central | FREE, 10am-12pm

Somerville Flea Holiday Market @ Arts at the Armory, Somerville – Explore two packed floors of curated vintage pieces, handmade items, and artisan goods at the 13th annual holiday market, where local makers bring out their best for festive gift shopping | FREE, 10am–4pm

Paint & Sip Brunch @ Boston Figure Arts Center, Somerville – If you’ve wanted a low-stakes creative morning, this brunch session pairs mimosas with a relaxed Bob-Ross-style painting lesson where you follow along, add a twist, and leave with your own finished piece | $45, 11am–1pm

Artist Studios Holiday Market @ Artists Studio, Somerville– One of Somerville’s biggest holiday markets takes over all three floors with art, vintage pieces, handmade gifts, music, snacks, and open studios that let you explore the whole creative building | FREE, 12–6pm

Intro to Watercolors @ The Foundry, Cambridge – A beginner-friendly workshop where you learn watercolor basics, sketch your own reference image, and explore techniques for building color, light, and shadow as you paint your own house portrait | $45–56, 1–3pm

Cornhole Bar Tab Tourney @ CambridgeSide, Cambridge – A casual Sunday cornhole tournament where you’re paired up on-site, play through pool rounds, and compete for a $50 bar tab while catching NFL games on the TVs | FREE for Volo Pass (New members can use promo code for $10/mo), 1–3pm

Union Square Jingle Festival: Shop, Sip & Mingle @ Union Square, Somerville – The Square turns into a full holiday playground for one afternoon: markets, music, inflatables, characters, contests, and endless spots to sip, browse, and stroll with friends while supporting local makers | FREE, 1–6pm

Painting & Crafts @ The School of Painting, Somerville – If you want a quieter holiday shop-stop, this micro market mixes local art, handmade goods, and a watercolor table where you can craft your own card on the spot | FREE, 1–6pm

Green & Jolly Holiday Faire @ Bow Market, Somerville – Bow’s upstairs space flips into a sustainable holiday marketplace with unique handmade goods, recycled-paper gift wrapping, and local makers selling one-of-a-kind pieces you won’t find anywhere else | FREE, 2–6pm

Speed Dating (Ages 32–44) @ Theory Bar & Lounge, Cambridge – If the apps feel stale, this in-person mixer lines up real first dates, gives you a drink on arrival, and moves you through a quick, fun rotation where you can actually talk, connect, and get your matches the next day | $43, 6–8pm

COMING UP NEXT WEEK

Rebel Rebel and Nibble Kitchen join forces for a holiday night celebrating Guatemalan cuisine through wine pairings, featuring Chef Benita’s tamales de puerco and chuchitos served with seasonal reds chosen by the Rebel Rebel team. Order your plate from Nibble, stroll it over to Rebel, and enjoy a warm, communal tasting experience built around storytelling, tradition, and slow sips