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!

Events Search and Views Navigation

Event Views Navigation

Today

  • 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 coming for this special event so check back often!

  • 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 happening this week! It's family fun entertainment all summer long!   EVERY WEDNESDAY - MAY THROUGH SEPTEMBER FROM 3PM - 7PM

  • 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, and more - we're celebrating all the dads and dudes no matter who or what they take care of! Watch for details!

  • 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 friends! ENTER OUR DOG DAYS OF SUMMER CONTEST TO WIN $100!!! Visit our Facebook page for details beginning Saturday, August 12, 2023!

  • 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 and enjoy South Boston’s favorite place to celebrate the season! *Sponsored by Destination Downtown South Boston, Inc. Click here for more details.

  • 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 celebration of our local businesses!

  • Christmas Parade

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

  • Downtown South Boston Farmers Market Season Opening

    Join us for the 2024 Season Opening of the Downtown South Boston Farmers Market! It's going to be a grand event with old and new vendors - and kids will enjoy POP Club and shamrock painting too. They'll get a $5 voucher to spend at the market. There will be FREE seeds and plants, lots […]

  • Annual Spring Fling

    The sidewalks downtown will be lined with vendors offering crafts, jewelry, clothing, woodworking projects, customized items, and more. And the Downtown South Boston Farmers Market will be open and celebrating Spring Fling with lots of vendors too! Mark the date and plan to spend the day. Restaurants and coffee shops will be open - and […]

  • July 4th Celebration

    Downtown South Boston

    July 4th celebration with activities, food, music, and more!

  • Annual Harvest Festival

    Mark the date now for all of the fun in downtown South Boston, VA! Activities, vendors, food trucks, ice cream, music, entertainment on multiple stages, fireworks, and loads of fun!

  • Downtown South Boston Christmas Open House

    The Annual Christmas Open House is the perfect time to explore downtown South Boston, VA. Shops will have their doors wide open with lots of gift ideas, food, and fun. And there's a contest with a great prize so check back for more details!

  • Small Business Saturday

    Shop Small...Shop Local Saturday is Small Business Saturday - help our locally owned downtown businesses stay alive!

  • South Boston Christmas Parade

    The Annual South Boston Christmas Parade is happening again and it's going to be spectacular!!!

  • Spring Open House

    Enjoy fun in downtown South Boston as we welcome spring! Shops will be open for business and you can enter to win a prize with every purchase you make!!! And the fun continues at Factory Street Brewing in the afternoon so plan to come early and stay late!