Tuesday, October 21st

Halloween Square Dance @ Warehouse XI, Somerville – This month’s Somerville Square Dance gets a spooky twist with live string band music by Lillian & The Buds, a costume contest, and a beginner-friendly vibes so don’t sweat if it’s your first time. Show up ready to stomp and spin | $10–20, 7pm–11pm

Movie Trivia Night @ Crystal Ballroom, Somerville – Every 3rd Tuesday, cinephiles pack the Crystal Ballroom for a trivia night hosted by the crew from The Brattle and Somerville Theatre. Form a team of up to six (or join a new crew!) for prizes, guest rounds, and plenty of beer, pizza, and popcorn | FREE, 7pm–9pm

Wednesday, October 22nd 

Movie Night (Jennifer’s Body) @ Bow Market, Somerville – A night of drag, murder, and mayhem hosted by Tara Dikhof, featuring a screening of the cult classic Jennifer’s Body. Expect costume contests, prizes, and plenty of campy chaos upstairs at Bow Market | $10, 6pm–10pm

Thursday, October 23rd

Halloween at the Museum @ Harvard Museum of Natural History, Cambridge – The Harvard Museums open late for a free Halloween night filled with eerie exhibits, spooky specimens, and themed activities. Trick-or-treat through the galleries, spot “zombie” fruit flies, explore the Sea Monsters exhibit, and grab a drink while you wander with friends or on a date | FREE, 5pm–9pm

Rewind, Record, PLAY! @ Crystal Ballroom, Somerville – A one-night-only cocktail bash celebrating the Somerville Museum’s 100th anniversary with century-spanning music, live emcees, and time-traveling exhibits. Sip, dance, and mingle through 100 years of Somerville history reimagined for the future | $100 (I’m just the messenger, don’t kill me), 5:30pm–8:30pm

Stitch and Screen: Pride & Prejudice Craft Night @ Kendall/MIT Open Space, Cambridge – Bring your knitting, stitching, or doodles and settle in for a cozy screening of Pride & Prejudice in collaboration with the PKG Public Service Center and the MIT Women’s League. The lights stay softly on so you can craft and connect while the film plays | FREE, 6pm–8pm

Discovery After Dark @ Kendall/MIT Open Space, Cambridge – An after-hours science party where curiosity meets nightlife. Step inside the Broad Discovery Center for an interactive outbreak simulation, glowing exhibits, and a DJ-backed dance floor surrounded by innovation and light | FREE, 6pm–8pm

Friday, October 24th

Inmanween @ Inman Square, Cambridge – Inman Square turns into a neighborhood block party with Halloween crafts, live ghost stories, and a family movie to close out the night. Wander shop to shop for sweets, then stick around for stories in Vellucci Plaza and a screening at Naveo Credit Union | FREE, 3pm–7pm

Movie Night (Halloweentown) @ Assembly Row, Somerville – Watch Halloweentown on the big screen during Hallo-Weekend on The Lawn, complete with free popcorn, candy, and drinks from The Lawn Bar. Bring a blanket or your own snacks, and settle in for a community movie night | FREE, 7pm-9pm

Saturday, October 25th

The Big Squash Pumpkin Festival @ First Street Market, Cambridge – First Street Market’s annual pumpkin fest returns with cooking demos, kids’ storytelling, indoor games, and a pumpkin decorating station. Sip hot cider, shop local produce, and celebrate fall with farm-fresh flavors and cozy community vibes. If pumpkin spice bevvies are religion this time of year this ones for you | $15, 11am–2pm

Fall Vintage Mega Market & Scavenger Hunt @ Cambridge Crossing, Cambridge – Vintage is trending and Found Boston takes over the streets of Cambridge Crossing with 80+ vintage and sustainable vendors, a beer garden, live DJ, and a citywide scavenger hunt with prizes—including a $500 grand prize. Spend the afternoon digging for vintage gems, local finds, and hidden clues across the Commons | FREE, 12pm–5pm

4th Annual Makers’ Market @ Somerville Community Growing Center, Somerville – A neighborhood favorite returns with a curated secondhand sale and a makers’ market featuring local artists and crafters. Shop vintage finds, handmade goods, and fall treasures while supporting the Growing Center’s community programs | FREE, 12pm–5pm

Howl-O-Ween Yappy Hour @ The Lawn Bar, Assembly Row, Somerville – A dog-friendly Halloween social where pups (and their humans) can mix, mingle, and show off their costumes for a chance to win prizes from local favorites like Splash & Dash, Muse Paintbar, and Pet Wants Cambridge. Expect tail-wagging treats, photo ops, and a chill Saturday hang by The Lawn Bar | FREE, 1pm–3pm

Take the Fear Out of Dating @ The Green Room, Cambridge – A hands-on workshop for singles led by dating coach Caitlyn Hana dive into what’s really holding you back from dating. Candid talks, breakout exercises, and real-world tips you can use right away to kick off cuffing season | FREE, 2pm-3:30pm

Halloween Block Party & Pet Spooktacular @ Chuckie Harris Park, Somerville – Pups take center stage at East Somerville’s annual Halloween bash, complete with a pet costume contest, prizes, and plenty of treats for furry friends. Stick around for live music, raffles, and local vendors while the four-legged crowd steals the show; I’m going to try and make this one myself| FREE, 3pm–6pm

Urban Park Beer Garden @ Kendall Square, Cambridge – Sip Lamplighter brews for the last pop-up beer garden of the year at Urban Park rooftop. A $5 donation gets you a beer token, with proceeds going to local charities—great beer, good weather, and a cause worth raising a glass to | $5, 4:30pm–9pm

Sunday, October 26th

Spooky Science Sunday @ Museum of Science, Cambridge – A full day of Halloween fun at the Museum of Science with family-friendly experiments, design challenges, and live presentations. Come in costume for a dance party with DJ Ooch, hands-on activities across the exhibit halls, and a chance to celebrate science with a spooky twist | FREE with museum admission, 9am–4pm

Halloween Flea Market @ Davis Square, Somerville – The Somerville Flea goes full Halloween with vintage vendors, local makers, DJs, and spooky tunes in Davis Square. Bring your costume, grab some candy, and browse handmade goods, vinyl, and farm stand finds with a festive crowd | FREE, 10am–4pm

Halloween Movie Night (Hocus Pocus & IT) @ Lamplighter Brewing, Cambridge – Settle in for a pint (or two) at Lamplighter’s Broadway taproom for a Halloween double feature pairing Hocus Pocus at 5pm with IT at 7pm. — first-come seating, so show up early and grab a table | FREE, 5pm–9:30pm