Weekend Picks – October 16th

3.6 min readBy Published On: October 15th, 2026Categories: See and Do0 Comments on Weekend Picks – October 16th

Visit the Golden Thread

East Boston’s newest art exhibit, The Golden Thread, is celebrating the stories of the city. The arches will be located at the Golden Stairs, Lewis Mall, Border Street, Central Square, and the Mary Ellen Welch Greenway. Learn more here! 

ICA College Night

This Friday, join the ICA for College Night! Head to the Seaport for a night of live performance and DJ sets by Boston-based student artists, creative art-making, and stunning harbor views. Take home a goodie bag with treats and discounts to Boston favorites, including Salt + Straw, Life Alive, Mike & Patty’s, and more.

Live Mariachi at La Hacienda

Stop by La Hacienda’s beautiful patio on Friday night for live mariachi music, paired with delicious homestyle El Salvadoran and Mexican food. Open until 2am every day, it’s a great late-night hang whether you’re grabbing dinner or just stopping in for drinks.  Check out our recent visit to La Hacienda here.

Sweater Weather Takes over City Hall Plaza

Sweater Weather Fest, the first film festival to be held on Boston City Hall Plaza, will take place Saturday, Oct. 17, 2026, from 2 p.m. until 11 p.m. Free and open to all ages, the outdoor festival will feature industry panels, film screenings, DJs, local food and vendors, and activities connecting attendees with Massachusetts’ film and television community. The evening will close with the final two episodes of Apple TV’s “Widow’s Bay,” projected onto the festival’s giant 60-foot screen on the plaza. Filmed in Massachusetts, including Gloucester and Rockport, the horror-comedy series recently won 14 Emmy Awards, including outstanding comedy series, becoming the most awarded first-season comedy in Emmy history. Get all the details here.

Olivia Rodrigo Unraveled Experience at The Tall Ship

The Tall Ship has a packed lineup this weekend! Starting off strong with a B/Spoke fitness takeover and then La Rockola: Fiesta de las flores, the rest of the weekend will be an Olivia Rodrigo experience. 

Boston Book Festival

The Boston Book Festival is taking over Copley Square this weekend! The free main festival happens Saturday, October 17th—plus a ticketed preview event on Friday night! Browse 80 events featuring over 200 amazing authors. Build your ideal day with keynotes, creative workshops, guided walking tours, and tons of fun activities while discovering top literary talents! Check out the complete event lineup here!

Noche de Catrinas Mexican Celebration in Eastie

Celebrate Mexican culture and traditions at the Noche de Catrinas Mexican Celebration on Saturday, October 17th, from 5:30pm–11pm at the Veronica Robles Cultural Center, 282 Meridian Street! This free event will feature live music, dance performances, traditional art, and delicious Mexican food and drinks available for purchase. A fun night of culture, community, and celebration! Get all the details here.

Annual Harvest Festival at Belle Isle Marsh

This Sunday, October 18, 2026, at 1:00 PM, join the community for a family-friendly outdoor autumn festival featuring live music, pumpkin decorating, a reptile showcase, and guided nature walks hosted by the Friends of Belle Isle Marsh. More info here!

Boston Women’s Market at Suffolk Downs: Makers at the Yard

This Sunday, Oct 18, 11:00 AM head to the Yard for fun, local makers, food, music, and beer! More info here!

Sweater Weather Fest at City Hall Plaza

The first-ever Sweater Weather Fest takes over City Hall Plaza on Saturday, October 17th, from 2pm–11pm! This FREE festival features live DJs, film screenings, local food vendors, industry panels, and plenty of fall fun! Plus, the evening wraps up with a screening of the final two episodes of Apple TV’s Widow’s Bay on a giant outdoor screen. Bring a blanket, grab some cider doughnuts, and enjoy a fun fall day in Boston! You can learn more and RSVP here.

Live Music at Cisco Fenway

Cold beers and live music? Sounds like a good weekend! Cisco Brewing Fenway has a rotating live music lineup every weekend. See who’s playing here.

SPORTS!

Patriots vs. Jets– Sunday, October 18th at 1pm.

Bruins vs. Ducks – Friday, October 16th at 10pm.

Bruins vs. Kings – Saturday, October 17th at 9pm.

Celtics vs. 76ers – Friday, October 16th at 7pm.

MLB Playoff Schedule

Here are  7 Places to Watch in the Neighborhood! 

Check back! This list may be updated! 

Have a fun-filled weekend! Thank you to our Caught in Southie readers and Neighborhood Partners for supporting our local neighborhood media efforts!

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