Weekend Picks – October 16th

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

Sweet Treats at Sweet Teez

Sweet Teez has officially been open for 4 months! Stop by this weekend and pick up something sweet while supporting this small business! 

Weekend Fun at Blend

Blend has a packed weekend lined up. Kick things off Friday, October 16th at 6:30pm with a double feature of Carrie and Psycho; then stick around for Friday Feels: Supernature at 10pm, a disco dance party hosted by drag queens Bossi Boots, Dottie Ave, and Splash O Cran with music by Brian Derrick, 21+ and no cover. Saturday, October 17th at 10pm, keep the party going with Mayhem Saturdays featuring DJ Tyler James, also 21+ with no cover.

Help Clean Up Moakley Park

Show Moakley Park some love! Join Boston Harbor Now, South Boston en Acción, Boston Parks and Recreation, and Boston Cares for a community cleanup on Saturday, October 17th, from 9:30am–11:30am. It’s a great way to give back, enjoy some fresh air, and help keep our neighborhood looking its best! Get all the details here.

Live Music at McGonagle’s

Enjoy live music at McGonagle’s on Friday it’s Jinty McGrath and Mo Jurphy on Saturday! Stop by for dinner and stick around for the entertainment!

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!

Dorchester Fields Corner Community Clean Up

Help keep the neighborhood clean and beautiful! On Saturday, October 18th at 11am, meet at ADSL at 1565 Dot Ave for a neighborhood cleanup! Kindly bring gloves and a trash bag!

Pumpkin Carving at the Lower Mills Library

Get into the Halloween spirit! The Friends of the Lower Mills Branch are hosting their annual pumpkin carving event on Saturday, October 17th! Kids can carve, paint, and decorate their own pumpkins to bring home. Registration is required, and supplies are limited, so don’t wait! Find the event and register through the Boston Public Library.

Weekend Fun at Yellow Door

Spend your weekend at Yellow Door featuring tacos, margaritas, weekend brunch (Saturday + Sunday) and $1 oysters on Sunday!

Cabo Verde Night at Gillette Stadium

This Saturday, October 17, the New England Revolution are hosting Cabo Verde Night when they host Chicago Fire FC in Major League soccer action. Fans are invited to join the Revolution at Gillette Stadium as they celebrate the music, culture, traditions, and community of Cabo Verde. Prior to the match, the Revolution Fan Zone (open at 5:00 p.m.) will feature live musical and cultural performances, along with local community organizations. Discounted tickets here!

Flutie 5K Monster Mash Dash

Calling all little ghosts and goblins! Get ready for some Halloween fun at the Flutie 5K Monster Mash Dash on Sunday, October 18th, from 10am–12pm at McConnell Park in Dorchester! Read more 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.

Savin Hill Halloween Parade

The 17th annual Savin Hill Little Kids Halloween parade returns to McConnell Playground this Sunday, October 18th! Children are invited to line up in their costumes starting at 3pm, with the parade kicking off at 3:15pm. Enjoy plenty of fall fun and activities for the whole family. The event is free and open to all. Don’t forget to bring your candy bag!

Book a Yurt

It’s almost yurt season in Dorchester! The Bowery Bar is bringing back its popular outdoor winter village, and online reservations are officially open! The four cozy yurts are decked out with twinkle lights, heaters, fluffy blankets, and plenty of winter charm. Add in creative cocktails and delicious food, and you’ve got the perfect spot for a girls’ night, date night, birthday celebration, or just a fun night out with friends!  You can learn more 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

If you’re watching the game this weekend, check out our list of 10 places to catch the action in Dot, or check out 12 of our favorites in South Boston!

Check back! This list may be updated! 

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

 

 

 

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