Outdoor Movie Night

You’re killin’ me smalls! This Friday, 5:30PM, at the Bremen Street Park Amphitheater, you can watch The Sandlot! It’s free and there’s popcorn! More here!

Blessing of the Animals

Bring your four-legged friends to Sacred Heart Parish for a special Blessing of the Animals on Saturday, October 3 at 4:45pm. The blessing, held in honor of St. Francis of Assisi, will take place in the church parking lot and all pets are welcome — just make sure they’re safely leashed or in a carrier.

Crush Pizza

A local favorite! Homemade sourdough, wraps to die for, and pizza that will make you feel like you’re back in Italy! Learn more here!

ICA First Fridays: Pumpkin Patch

This Friday, October 2nd, join the ICA for a country fair-themed evening featuring line dancing, specialty drinks, and music. Strap on your boots and flannel! Tickets here!

Treat Yourself The Blue Caboose

Check out the iconic blue train car on the Greenway for some delicious ice cream and coffee; serving Lionheart donuts all weekend! Learn more on their Instagram.

The Tall Ship Oktoberfest

October 3, 2026, starting at 1:00 PM. The 6th annual event features over 40 local craft beers, German food specials, and live music by Kier Byrnes & The Kettle Burners. Tickets here!

Fall Fest (Taylor’s Version) at the Lawn on D

Calling all Swifties! Fall Fest (Taylor’s Version) is taking over The Lawn on D on Saturday, October 3. Dress in your favorite era and enjoy an afternoon of Taylor Swift fun from 12pm–5pm, including bracelet-making, face-painting, and a live Taylor Swift tribute by Anna Daley Young from 2pm–5pm. Admission is free, with food and drinks available for purchase. Plus, Ear-piercing with Nurse Cassandra @thisnursetravels2u and shopping with COSMO CAPRI @shopcosmocapri. You can learn more here!

Spice Things Up

SpicetoberFest is back on Saturday, October 3rd from 11am–6pm, bringing plenty of heat to Boston! This fall festival celebrates all things spicy with local food vendors, chefs, hot sauce makers, urban farmers, craft beverages, entertainment, and more. Come hungry, try something new, and see just how much heat you can handle! 🌶️🔥 Get tickets and learn more about SpicetoberFest.

SPORTS

Patriots vs. Bills – Sunday, October 4th at 1pm.

Bruins vs. Jets – Friday, October 2nd at 8pm.

Bruins vs. Wild – Saturday, October 3rd at 8pm.

MLB Playoffs 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!