Monday, September 29th

Comedy Dating Show @ Aeronaut Brewing, Somerville – Want some last minute Monday night plans? Four single comedians head on blindfolded dates live on stage while the audience heckles and helps steer the chaos. Improv and reality dating show; it’s messy, hilarious, and with a side of romance. Want to be a contestant? CLICK HERE | $25, doors 7pm / show 7:30pm–9pm

Tuesday, September 30th 

AI Collages @ MIT Museum, Cambridge – Ever wondered how the textures and patterns inside AI’s “brain” look? This hands-on workshop turns neural network visuals into paper collages, helping you peek inside the AI black box while getting creative. Hosted as part of Boston AI Week | FREE, 2:30pm–4:30pm

Free Salsa Class @ Magazine Beach, Cambridge – Learn the basics of Cuban salsa in a friendly, no-pressure setting. In Rueda de Casino, dancers form a circle and move together as the “caller” cues each step — it’s social, energetic, and a fun way to join the community | FREE, 6pm-7pm

Wednesday, October 1st

Live Music Wednesdays @ The Sea Hag, Cambridge – After years without a steady scene, live music is back in Harvard Square. The Sea Hag is kicking off a weekly Wednesday series, starting with guitarist Barrett Anderson joined by Paul Loranger on bass and Joey Pafumi on drums. Settle in during dinner hours for blues and roots played by some of Boston’s most seasoned musicians | FREE, 6:30–9pm

Survivor Watch Party @ Lamplighter CX, Cambridge – Settle in for an evening of blindsides, alliances, and Survivor chaos on the big screen. Lamplighter keeps things fun with themed beer flights, bingo, and a prize wheel so the competition doesn’t stop when the episode ends | First come, first serve, 21+, 8–9:30pm

Thursday, October 2nd

Crazzy Tacos Launch Pop-Up @ Lamplighter CX, Cambridge – After a string of pop-ups, Crazzy Tacos is launching and celebrating their debut with Lamplighter. Expect their greatest hits — chicken, al pastor, and Impossible vegan tacos — served fresh in the upstairs taproom, perfect with a Lamplighter pint | FREE to attend, 5pm-9pm

The Goonies Movie Night @ Urban Park Roof Garden, Cambridge (rescheduled from 9/25 rainout) – Grab your blanket and snacks for free outdoor movie screening of The Goonies (one of my all time favorites) at Urban Park’s roof garden. Movie starts at 6pm, weather permitting. No tickets needed;alcoholic drinks are not allowed | FREE, 6pm-8pm

Blues Union Dance Night @ Dance Union (16 Bow St), Somerville – Learn, move, and groove at this weekly blues social. No partner necessary, just bring comfortable shoes and a willingness to move | sliding scale $10–$25, 7pm–11pm

Friday, October 3rd

Lo-Fi Friday @ Lamplighter CX, Cambridge – Need a little calm to start the day? The back taproom transforms into a quiet zone every Friday morning, with Pepita coffee, ambient music, and plenty of space to read, work, or just recharge. Minimal talking preferred. Think of it as your weekly slice of peace | FREE, 8am–2pm

Taylor Swift Album Release Party @ Remnant Brewing, Somerville – Come scream-sing with Remnant and celebrate Taylor’s new album drop—sing along to old favorites, then listen through The Life of a Showgirl in full. Doors at 9 PM, 21+ only, first 30 Swifties get a party bag. Entry is free, but space is limited. Show up early to secure your spot | FREE, 9pm–Midnight

Saturday, October 4th

Somerville 5K Road Race (393 Highland Ave) @ Davis Square, Somerville – Now in its 30th year, this annual run/walk courses through the heart of Davis Square to benefit the Somerville Homeless Coalition. Choose to run, jog, or stroll — everyone’s welcome. Early registrants even get a free tee; fundraisers hitting $250+ may register for free | $35 (adults), $30 (kids), 9–11am

Outdoor Fall Party @ Kendall/MIT Open Space, Cambridge – Grab a blanket (or a chair) and settle into an autumn picnic with live music, crafts, free popcorn, cotton candy, lawn games, and a chance to learn local history with History Cambridge, hosted byt MIT Open Space | FREE, 2–5pm

Rebel’s 7th Birthday Bash @ Bow Market, Somerville – After seven years of wine, community, and doing things a little loud, Rebel’s throwing a party you won’t forget. Expect BTG wine pours, a Champagne ice luge (yes, really), smashburgers by Gray’s Hall, and caviar aplenty. Ticket includes either a caviar bump or one ice-luge round — your call | $15, 2pm–11:30pm

Sunday, October 5th

Brewery Yoga @ Lamplighter CX, Cambridge – Stretch, breathe, and ease into your Sunday in the upstairs taproom with a gentle yoga flow (all levels welcome). After class, you’re invited to hang, sip, or linger. Each ticket includes 1 hour yoga class + 1 beer token | $32, 12:30–1:30pm

The Jam Improv Night @ Union Comedy (593 Somerville Ave), Somerville – A free, off-the-cuff improv jam where anyone — from first-timers to seasoned performers — can throw their name in the bucket and hop on stage, or just sit back and watch the chaos unfold. Expect surprise sets from local indie teams before the audience joins in for scenes and montages | FREE, 5pm

Speed Dating (Ages 30–42) @ Theory Bar & Lounge, Cambridge – Trade swipes for real conversations at this Kendall Square speed dating night. You’ll get a welcome drink (beer, wine, soda, or cocktail), up to 14 five-minute mini dates, and your matches delivered within 24 hours. The night kicks off with a short happy hour, then rolls into quick rounds guided by the hosts | $48, 21+, 6–8pm

Sunday Sessions Open Mic Jam @ The Cantab, Cambridge – Calling all musicians: bring your band or hop in with the house crew for a night of pop, rock, and R&B jams. It’s an open mic with a full band setup, plenty of energy, and the chance to play your favorites on stage | $5 (FREE with student ID), 21+, 8pm–12am