THANK YOU for visiting the DDSB event page. We are excited to bring lots of family-friendly events to the community and surrounding area. 

Please contact us with any questions!

  • Movies on Main

    Constitution Square

    Click here for Movie Details: Encanto  Free entry & water Bring your blankets and chairs for a movie under the stars Candy Drinks and popcorn for sale by Exquisite Events […]

  • Splash Into Summer

    Downtown South Boston

    DDSB presents the first Splash into Summer on Thursday evening, June 2, 2022 from 5pm-8pm. Enjoy supper, spirits, and beverages at local restaurants. After you enjoy your food and drinks […]

  • July 4th Celebration

    Downtown South Boston

    Happy 4th of July at Constitution Square!

  • Movies on Main

    Constitution Square

    Movies on Main is back with Spider-Man: No Way Home on August 5 at 8:30pm.

  • Cruz-In

    Downtown South Boston

    Thanks to our great sponsors!   All cars, trucks, and bikes welcome! Main Street is closed for this event. There will be door prizes, delicious food, and some fantastic cars […]

  • Halloween Extravaganza

    Fun at the Farmer's Market! This is a HUGE Halloween Extravaganza! FREE food and drinks, activities and games for all ages, costume and pumpkin carving contests, trail of treats, and […]

  • Small Business Saturday

    Celebrate all small businesses on this very special day! Help them keep the doors open and support the community and all who live here!

  • ‘Engage with Downtown’ on Valentine’s Day

    This year's them for downtown South Boston is "Engage with Downtown"!   And what better day than Valentine's Day to "Engage with Downtown" - visit the shops and see all […]

  • Engage with Downtown

    The theme this year for downtown South Boston is "Engage with Downtown"! And what better day to do it than Valentine's Day?!?  Visit the shops and see all of the […]

  • Shamrock the Block

    Shamrock the Block is back! Watch for details!

  • Spring Fling

    IT'S BACK!!! SPRING FLING!!!   Watch for details!

  • All for Mom

    May is all about mom and Mother's Day - and downtown is celebrating. What better way to "Engage with Downtown" than to shop for mom!?! And there are some surprises […]

  • Wednesday at the Market

    Every Wednesday through September the Downtown South Boston Farmers Market is open with live entertainment, food trucks, activities, and plenty of vendors. Visit the Facebook page to find out what's […]

  • Dads and Dudes

    June is Father's Day and there are lots of dads and dudes out there to celebrate. Some have children, and some may not have children, but dudes have dogs, horses, […]

  • Dog Days of Summer

    It may be hot and muggy, but that's not stopping us from celebrating all of our special little pups and dogs! Get ready for a fun time with your furry […]

  • South Boston Harvest Festival

    The South Boston Harvest Festival has become a favorite with kids, parents, singles, and everyone! Enjoy the attractions, entertainment, activities, and food that are fun for all ages! Come out […]

  • Small Business Saturday

    Join us as we celebrate Small Business Saturday in a big way! Help our local businesses keep the doors open - and watch for the fun happening on this annual […]

  • Christmas Parade

    Floats, bands, music, horses, dancing, and more! Don't miss this historic event on Main Street!