Drink & Doodle @ Aeronaut Brewery, Somerville – Grab a drink and a pen for a relaxed evening of creativity where it doesn’t matter if your art is stick-figures or abstract—you’ll find good company, cold pints, and uninhibited doodling | Free, 7pm-9pm

U.S. Steinholding State Qualifier @ Aeronaut Brewing, Somerville – Raise your stein and see if you’ve got the grip & endurance to compete in this qualifier event, where winners go on to represent Massachusetts in the State Finals at Jack’s Abby; cheers and hefting encouraged | Free, 7 pm–9 pm

Theater in the Open Bar(d) @ Bow Market in Somerville – Grab a pint and let Shakespeare get rowdy: the audience votes on the play, actors read straight from cue scrolls, and scenes unfold with tavern-style unpredictability | Pay-what-you-will, doors 6pm, show 7pm

Sips & Small Bites Cooking @ Nibble Kitchen Inside Bow Market, Somerville – Immerse yourself in Laotian flavors as Chef Vekonda leads a hands-on evening of savory bites paired with sips; just 9 seats | $65 per person, 6pm-830pm

Dirty Water Fitness @ MIT Open Space, 292 Main St, Cambridge – Sweat through a high-energy, full-body bootcamp that blends strength, cardio, and core with just bodyweight—totally beginner-friendly and designed to move at your pace, outdoors or indoors if the weather flips; bring water and comfy clothes | Free, 6pm–7pm

Cook it Up with Chef Joe Gatto @ Urban Park Roof Garden, Cambridge – Chef Joe Gatto returns with culinary tips & tricks in an hour-long cooking demo on the Roof Garden kitchen, where complimentary sips and skyline views sweeten every slice, spots fill up fast make sure to register | Free, 6pm-7pm

Fluff Fest Night Market @ Bow Market, Somerville– The 20th anniversary of Somerville’s sweetest tradition kicks off with a marketplace buzzing with Fluff-inspired food and drink specials, exclusive merch drops, live art, and local makers celebrating the gooey treat under Bow Market’s lights | Free, 4pm–9pm

Pickleball 101 @ Urban Park Roof Garden, Kendall Center, Cambridge – New players welcome to learn the basics of pickleball in every half-hour slot from 4-8 PM, with PKL instructors on hand, BBQ from Pig Beach available for munchies, and no experience needed, registration details being finalized continue checking the link below | Free, 4pm-8pm

Taste of Canal District Kendall @ Canal District Kendall (314 Main st), Cambridge – Get a first taste of Kendall’s newest neighborhood with bites from local eateries, live music, and community vibes—wander, sample & soak up the evening in Termeer Square | Free, 5pm-7pm

3D Printing 101 (Main) @ Cambridge Public Library (The Hive) – Dive into hands-on design using Prusa 3D printers and Tinkercad, earn your certification for future Hive use, and prep first by completing Hive Safety Training | Free, 9:30 am–11:00 am

Jonathan van Halem Comedy Show – The Rockwell (255 Elm St, Somerville) – Brooklyn-based comedian & writer from The Tonight Show Starring Jimmy Fallon, Jonathan mixes sharp observations with absurdist wit, treating the everyday like material for laughter—expect viral clips, off-beat rants, and punchlines that sneak up on you; 21+ show | $15–$20, 9pm

Danehy Park Family Day @ Danehy Park, Cambridge – Cambridge’s vast 55-acre greenscape turns into a riot of amusement rides, arts & crafts, roving performers, music, giveaways, and good-natured family chaos—picnics and lawn chairs welcome; free shuttle service across the city | Free, 11am–3 pm

Yoga in the Park @ Assembly Row (Baxter Park), Somerville – Stretch along the Mystic with a free riverfront yoga flow by YogaSix, sponsored by Mass General Brigham, where you provide the mat & water, move mindfully under open sky, and start the week with calm | Free, 9am–10am

Aeronaut Oktoberfest @ Aeronaut Brewing, Somerville – Raise a stein at Somerville’s favorite beer fest with German-inspired brews, live polka from Maestro’s Men, festive fare from Mimi’s Chuka Diner (hello schnitzel, brats & laugenbrezels), stein-holding & costume contests, and VIP perks for those who want to go big | VIP $30 / General $10, 12pm-8pm

Craft & Cookies @ Urban Park Roof Garden, Kendall Center, Cambridge – Gather for an afternoon of creativity with the Community Art Center: all ages welcome to decorate cookies and dive into hands-on art under the sky with everything supplied, no experience needed | Free, 1pm-2:30pm

Central Square Night Market is Back @ University Park (65 Sidney St, Cambridge) – University Park transforms into a starlit festival of food trucks, a buzzing beer garden, live performances, games & photo-worthy installations—fun for all ages & totally free to attend | Free, 5pm-10pm

Boston Café Bikers Ride @ Harvard Square → Green Haus Café, Cambridge – A 4.4-mile Sunday spin with friends, family & fellow riders, rolling from Harvard Square to Green Haus Café with stops at local bakeries and plenty of community vibes—everyone welcome | Free, 11am

Cambridge Science Carnival @ Kendall/MIT Open Space, Cambridge – A full-day family-friendly explosion of science fun: interactive STEM booths, mad-science demos, local innovators showcasing projects, hands-on experiments for kids and adults, plus food trucks and music to keep the energy high | Free (suggested donation), 12pm-4pm

Aeronaut Oktoberfest @ Aeronaut Brewing, Somerville (cont’d) – Raise a stein at Somerville’s favorite beer fest with German-inspired brews, live polka from Maestro’s Men, festive fare from Mimi’s Chuka Diner (hello schnitzel, brats & laugenbrezels), stein-holding & costume contests, and VIP perks for those who want to go big | VIP $30 / General $10, 12pm-8pm

Candlelight Flow Yoga @ Bow Market (Upstairs at Bow), Somerville – A slow-flow yoga session under candlelight and a disco ball, guided by Zola of Be Easy Meditation, set to modern R&B and ending with a dreamy shavasana; bring your own mat | 2-for-$25 classpack code, 7:30 pm–8:30 pm

Good Will Hunting Movie Night @ Lamplighter Brewing (284 Broadway), Cambridge – Grab a pint & settle in for Boston-flavored storytelling, iconic performances & a projector playing Good Will Hunting, with popcorn & beers to round out your movie-night ritual | RSVP encouraged but not required, 8pm-10pm