Friday, December 12th 

Free Coffee Tasting @ Counter Culture Coffee, Boston – This weekly event is a ritual for true coffee lovers, giving you access to sample fresh micro-lot selections while communing with experts over beautifully brewed cups in their training center | FREE, 10am–11am

Somerville Illuminations Walk @ City-Wide, Somerville – Grab the interactive map and take a self-guided tour of the most creative holiday light displays across the city, giving you the best excuse to pile into a car and find the houses everyone is posting about | FREE, 4:30pm

Holiday Night Market @ First Street Market (FSM), Cambridge – Get to FSM for the second of their night markets, featuring 20+ local vendors and an open bar serving cocktails and cocoa, all paired with live music, making this the best way to kick off your weekend shopping | FREE, 5–10pm

Saturday, December 13th

Computer Science Weekend @ Museum of Science, Cambridge – This is the ultimate weekend for STEM fans, letting you connect with local roboticists and computer scientists while getting hands-on with activities and demonstrations, including a dedicated segment from Boston Dynamics that you absolutely have to see live | $33, 10am–4pm

Winter Market 2025 @ Canal District, Kendall Sq, Cambridge – This two-day festival is the move for finding genuinely cool gifts this weekend, packing the area with 30+ artisan vendors, free arts and crafts stations, plus professional figure skating performances and gourmet hot cocoa from Tuck's Truffles that you'll be seeing all over Instagram | FREE, 11am–6pm

Escape to Elephantine Bike Ride @ Cambridgeport Bluebikes Station, Cambridge – Join the Boston Cafe Bikers for a relaxed, conversational mid-day social ride that pushes through the chilly weather, rewarding your effort with a full warm-up—think incredible pastries and hot coffee at the destination, Elephantine | FREE, 11am

Somerville Art Fair @ Upstairs at Bow Market, Somerville – Head upstairs for the absolute last chance to shop directly from the nine most exciting artists in the SAF series, ensuring you find meaningful holiday gifts while supporting local creative small businesses | FREE, 12–4pm

Clothing Swap + Fashion Show @ The Loov, Somerville – Life Drawing Boston is hosting a killer event where you can redo your entire wardrobe for just $10 at this massive clothing swap, which culminates in a real fashion show—runway, red carpet, and photographer included—where you can walk in your new thrifted look | $10, 2pm swap (6pm party)

Somerville Illuminations Bike Tour @ Somerville High School (Reavis Field), Somerville – Get moving and get festive by joining this fun, family-friendly 60-minute ride that highlights all the beautiful, resident-created light displays—it's the best way to see the city sparkle after sunset | FREE, 5:45–8pm

Hubbub Comedy @ Lamplighter CX, Cambridge – Lamplighter's Cambridge Crossing location hosts a killer lineup of Boston's best comics, where you can submit your deepest secrets or burning questions for them to answer live onstage between flowing beer taps and big laughs | $15, 7:30–10pm

Sunday, December 14th

Community Sketching @ Harvard Art Museums, Cambridge – A museum outing with a twist - grab your graphite and a sketchpad for a rare chance to draw from a live model inside the stunning Calderwood Courtyard, with expert tips from Life Drawing Boston to seriously level up your skills in three quick 30-minute sessions | FREE (registration required), 11am–1pm

Holiday Caroling @ Bow Market, Somerville – Round up a crew or fly solo for a casual hour of festive volunteering, where you’ll be handed a song sheet and a drink ticket just for showing up and adding your voice to the holiday soundtrack in the courtyard — oh, and no experience needed | FREE, 12-2pm

Dungeons & Dragons @ Aeronaut Brewery, Somerville – Have you ever wanted to try Dunegeons & Dragons? Get into the Strangers Things season and level up your Sunday by diving into an epic D&D one-shot led by a professional Dungeon Master — plus two drinks tickets included | $50, 1–5pm

Gingerbread House Decorating @ Aeronaut Brewery, Somerville – Your Sunday just got a lot more festive: secure a spot to build your winter wonderland gingerbread house (four sessions available) while sipping on brewery-fresh beer, with your ticket including one full kit—but hurry, there’s only a few tickets left with | $23, 2–8pm

Cambridge Singles Night @ Theory Bar & Lounge, Cambridge – Secure a seat for this fast-paced, high-value night of dating (ages 28–39) and your first drink is on the house if you arrive by 6:15 PM, giving you a safe and easy way to meet like-minded people in person and enjoy a fun evening out | $43, 6–8pm

Home Alone Movie Night @ Lamplighter Brewing, Cambridge – Lamplighter is turning their taproom into a private cinema for a cozy screening of Home Alone, offering three ridiculously named, themed drink specials and late-night slices from Controne to make your Sunday night memorable | FREE, 6–8pm