REMINDER

Now with Halloween in the rearview, the holiday season is in full swing and that includes The Stoop’s list of curated social events. The more I’ve been doing this, the more resources I’ve been able to find draw events from. That means more vintage markets, more festivals, more block parties, more bangers.

As promised, there’ll be two drops: one for Mon–Thurs (today’s) and another on Thursday for Fri–Sun. More events, less scrolling, and more reasons to get out, stay warm, and conquer the short winter days!

Monday, November 3rd

Jeopardy! Bar League Trivia @ Lamplighter Brewing CX, Cambridge – Test your trivia chops in the official Jeopardy! Bar League, a live two-hour quiz where teams compete through smartphone buzzers across real Jeopardy, Double, and Final rounds. Grab a pint, channel your inner Trebek, and play for bragging rights | FREE, 7pm–9pm

Pitch-A-Friend Boston @ Aeronaut Brewing, Somerville – Ever wished your friends could sell your best qualities for you? At this live matchmaking night, they actually do as they pitch their single pals in quick slides inside Aeronaut’s buzzing taproom. Grab a beer, cheer them on, and stick around to mingle after. Pitch submissions are full but you can still attend and get on the on the waitlist | FREE, 7:30pm

Figure Drawing Class @ Still Life Studios, Cambridge – A full-day figure drawing class focused on speed, gesture, and flow, helping you refine your style through structured practice and guided exercises. All materials provided, or bring your own canvas for a personal touch | $10–$25, 7:30pm-8:30pm

Tuesday, November 4th

Cocktail/Mocktail Class @ Kendall Center (Pioneer Room), Cambridge – Mix, shake, and sip your way through a cocktail class led by Boston Beverage Catering, where you’ll learn tips for crafting signature drinks just in time to show your off your skills during the holidays. 21+ only, registration required | FREE, 5:30pm–6:30pm

Honky Tonk Music + Dance @ The Burren, Somerville – Grab your boots and two-step into a night of country charm with The Talking Hearts, blending pedal steel, mandolin, and harmony-rich originals that channel Loretta Lynn and Buck Owens. A quick dance lesson kicks things off before the band takes over | $25 at door, $20 in advance, 6:30pm

Fiber Arts Night @ Still Life Studios, Cambridge – A cozy, come-as-you-are evening of sewing, knitting, crocheting, and mending led by Avu Studio. Bring your own project or learn the basics in a short beginner knitting class at 6:30pm. Tools and materials are available to borrow, and all experience levels are welcome | $5–15, 6:30pm–8:30pm

Geeks Who Drink Trivia Night @ The Smoke Shop BBQ, Somerville – Test your random knowledge and claim bragging rights at this weekly pub quiz that pairs brainy banter with barbecue and beers. Bring a team or join one on the spot—winners walk away with prizes (and glory) | FREE, 7pm–9pm

Code for Boston: Hybrid Hack Night @ CIC, Cambridge – Part community meetup, part hackathon, this open civic-tech night brings together coders, designers, and curious locals to build tools for public good. Join in person (or Zoom) to connect with project teams, swap ideas, and get hands-on with real city challenges. Great way to network if you’re considering an industry pivot | FREE, 7pm–9:30pm

Songwriter Showcase @ The Cantab Lounge, Cambridge – The Cantab turns the spotlight on local songwriters for a night of open mic sets and original music, starting with sign-ups at 8 and a showcase that kicks off soon after. If you’re looking for your big break or just want a cozy bar vibe, raw talent, and plenty of heart | FREE, 8pm–10pm

Wednesday, November 5th

Line Dancing Wednesdays @ McCarthy’s, Somerville – Lace up your boots and head upstairs for a high-energy night of classic line dances and country hits led by LDQ. No experience needed—just follow the moves, join the rhythm, and let loose with the crowd | Free, 8:30–11:30pm

Figure Drawing Class @ Still Life Studios, Cambridge – A full-day figure drawing class focused on speed, gesture, and flow, helping you refine your style through structured practice and guided exercises. All materials provided, or bring your own canvas for a personal touch | $10–25, 7:30pm-8:30pm

Thursday, November 6th

Guided Night Bike Ride: Daylight Savings Edition @ Assembly Row, Somerville – A group ride hosted by Assembly Connect to help cyclists get comfortable biking after dark. Learn safety tips for night riding, cruise an easy route with fellow riders, and grab a free bike light to take home | FREE, 5pm–6pm

Cornhole Singles Mixer @ CanalSide Galleria, Cambridge – A social cornhole night made for singles, mixing light competition with easy conversation by the water. Teams rotate every few minutes to keep things fresh, and after the games wrap, everyone heads to the bar for beers, wine, and a bit of post-match mingling. Volo members even score a free drink ticket | $11, 6pm–7pm

Singles Social Night (21-35) @ Upstairs at Bow, Somerville – A mixer for singles aged 21–35 hosted by the Thursday App, turning Bow’s upstairs bar into a buzzing spot for conversation, music, and maybe a spark or two. Your first drink’s included, so come solo or with friends and see where the night takes you | $25, 7pm–11pm

Comedy & DJ Night: After Work Thursdays @ McCarthy’s, Somerville – A free after-work social for Boston’s millennial crowd that kicks off with stand-up from Joe Fenti (@FentiFriedChicken), a Boston Comedy Festival semi-finalist, before DJ Ronny spins upstairs for a relaxed mix of music, drinks, and new connections | FREE, 8:30pm–10:30pm

Late Night DJ @ McCarthy’s, Somerville – Upstairs turns into a full-on dance floor with a rotating lineup of DJs spinning throwbacks, remixes, and party tracks till close. Grab a drink, find your spot, and let the night get loud | FREE, 10:30pm–2am