Destination Downtown South Boston

10/14/2026

NEW DATE FOR THE CRUZ-IN!

REV UP YOUR ENGINES AND GET READY FOR THE DOWNTOWN SOUTH BOSTON CRUZ-IN!

The weekend weather didn't dampen our spirits and the Cruz-In has a new date!

Sunday, October 18th from 3-6pm the cars, trucks, and motorcycles will line up on Main Street! We're counting on a beautiful day for an awesome Cruz-In so mark your calendars now.

Join the fun with antique vehicles, music on the street thanks to Ernelle Bellamy of Big Fade Entertainment, and a great time with friends.

THANKS TO OUR SPONSORS!

Hitachi Energy South Boston
Terry of South Boston
J.E. Burton Construction Company
IperionX
H&R Block South Boston

And also thanks to:

Old Dominion Electric Cooperative
Yancey Wholesale Supply
Francisco, Bowen & Trent, PLLC
CSUSA MidAtlantic

10/14/2026

Exciting things are blooming in Downtown South Boston! 🌻 Destination Downtown South Boston has been awarded a $50,000 Downtown Investment Grant for Petals on Main. We’re looking forward to bringing more color, greenery, and beauty to our downtown!

Read the article below to learn more!

Destination Downtown South Boston was awarded $50,000 through the Virginia Department of Housing and Community Development’s Downtown Investment Grant program for Petals on Main, a downtown beautification initiative designed to

10/13/2026

SAVE THE DATE!

The Downtown South Boston Farmers Market is getting ready for the amazing Halloween Extravaganza that you don't want to miss. It's happening Saturday, October 31, 2026 from 8am-1pm and there will be plenty to do, see, and taste!

Seasoned with Grace will have some seasonal favorites along with some scary new treats! And don't miss the Pumpkin Bounce House and the Halloween Costume Contest (contest begins at 11am). Kids can trick-or-treat around the market as vendors hand out treats too - NO TRICKS!

POP Club members will taste a concoction of Apple Juice Elixir and they can Pin the Spider on the Web. And kids get $5 to spend at the market on healthy food just for participating in POP Club.

Be sure to bring your phone or camera for the Halloween Photo Set-up!

It's going to be a scary fun time so mark your calendars now!

10/11/2026

REV UP YOUR ENGINES AND GET READY FOR THE DOWNTOWN SOUTH BOSTON CRUZ-IN!

The weekend weather didn't dampen our spirits and the Cruz-In has a new date! Sunday, October 18th from 3-6pm the cars, trucks, and motorcycles will line up on Main Street! We're counting on a beautiful day for an awesome Cruz-In so mark your calendars now.

Join the fun with antique vehicles, music on the street thanks to Ernelle Bellamy of Big Fade Entertainment, and a great time with friends.

Tinkers Car Club South Boston Virginia and Old School Car Club in conjunction with DDSB are sponsoring the event.

And thanks to Terry of South Boston, Hitachi Energy South Boston, J.E. Burton Construction Company, IperionX, and H&R Block South Boston for being our top sponsors.

10/10/2026

Due to the weather, today’s Downtown South Boston Cruz-In has been canceled. The rain date of Sunday, October 11, is also expected to bring unfavorable weather conditions, so we’ll be working to determine a new date soon.

Stay tuned for an update, and thank you for understanding! We look forward to seeing everyone soon!

10/09/2026

The Downtown South Boston Cruz-In is TOMORROW! 🏎️🏁

Come out October 10th from 3pm-6pm and enjoy an afternoon of cool cars, great music, delicious food, and fun!

Stroll along Main Street, check out all the rides, and stop by our downtown businesses while you’re here. Seasoned with Grace and Country Gals will be onsite with delicious food and drinks, so come hungry!

🚧 Parking & Traffic Notice: Parking on Main Street will close after 2pm. Main Street (Route 501) will be closed from Johnston Street to Constitution Square.

Bring your friends and family, enjoy the cars and music, grab something good to eat, and spend the afternoon downtown!

10/08/2026

Destination Downtown South Boston (DDSB) is pleased to announce that we have been awarded $50,000 through the Virginia Department of Housing and Community Development’s (DHCD) Downtown Investment Grant program to support Petals on Main, a downtown beautification initiative focused on adding color, greenery, and visual interest throughout downtown South Boston.

The award was announced by Governor Abigail Spanberger as part of more than $615,000 in Downtown Investment and Community Vitality Grant awards supporting community development projects across Virginia. DDSB was one of 10 organizations selected to receive a Downtown Investment Grant, with the $50,000 Petals on Main award representing one of the largest awards through the program.

This funding will support the continued development of Petals on Main, including additional flowers, flower baskets, planters, and decorative banners throughout the downtown district. Our goal is to create a more vibrant and welcoming environment for residents, businesses, and visitors while continuing to enhance the overall appearance of downtown South Boston.

We are incredibly grateful to the Virginia Department of Housing and Community Development for their investment in South Boston and their support of revitalization efforts.

A special thank you goes to the Town of South Boston Public Works Department for helping maintain the flowers throughout the season. Their hard work plays an important role in keeping downtown looking its best.

We are excited for what this funding will make possible and look forward to continuing to invest in the beauty and vibrancy of South Boston!🌸

09/28/2026

Mark your calendars for the annual Sentara Halifax drive-thru event and get your flu shot. You'll be ready for flu season - no appointment needed and it's FREE!

It's Saturday, October 10th from 8am-12noon at the Downtown South Boston Farmers Market. Don't miss it!