• Welcome to Downtown South Boston, VA

    A Main Street America™ Accredited Town

  • Support Small Business

    Downtown South Boston, VA

  • Where People and Fun Come Together

    Downtown South Boston, VA

“A healthy, viable downtown is crucial to the economic
health and civic pride of the entire community”

~ National Trust for Historic Preservation

Shamrock the Block!

March 1 – 24, 2023

It’s time for the Downtown South Boston annual “SHAMROCK THE BLOCK”! Use your imagination and create your St. Patrick’s Day entry to be entered into a contest to win up to $150 to spend at downtown shops and businesses. Prize categories:
  1. Ages 3-10 ($50 prize)
  2. Ages 11-18 ($100)
  3. Ages 19+ ($150)
Use your imagination! Sparkly green fields of clover, drawings or paintings, rainbow flower pots, dancing leprechauns, a brightly decorated cake, and pots of gold are just the beginning! And yes – we accept your creative videos too! So get started. We start accepting submissions March 12th.

  • Deliver submissions to the DDSB Office at 432 Main Street Monday-Friday or to Wister’s at 435 Main Street Tuesday-Saturday beginning March 12th and no later than 3pm on March 24th.
  • Photos will be posted on our Facebook page for voting on March 27th and a winner will be announced April 1st.
  • So, help us “Shamrock the Block” downtown with your creations!
Wishing you a wee bit ‘o luck!”


Downtown South Boston Spring Fling

Saturday, April 29, 2023

“Engage with Downtown” during Spring Fling and enter the contest to win $1,000!

The Downtown South Boston Spring Fling is back on Saturday, April 29, 2023 from 10am-3pm. Downtown shops have their doors wide open and vendors are lining the sidewalks with crafts, jewelry, personal care items, handmade wreaths, flowers, home decor, food, drinks, and so much more! This event is held on the sidewalks and the streets remain open.

There will be a $1,000 prize giveaway this year. When you make a purchase at one of the locally owned shops downtown during Spring Fling, you can enter the contest to win $1,000 which can be spent at downtown shops. (Purchases must be made at a locally owned downtown shop and excludes vendor purchases on the sidewalk).

The variety of products, crafts, and art is impressive. So far, there are vendors bringing home décor, original art, personal care items, wood crafts, candles and melts, jewelry and accessories, soaps and lotions, door hangers, hair accessories, clothing, books, and more.”

This year festival visitors will enjoy food trucks making it easy to enjoy the day and grab lunch or snacks on the sidewalk, or by visiting one of the Main Street coffee shops or restaurants. The Sunset Slush Cool Bus is joining Spring Fling for a special treat.

The local fire and police departments are participating again this year and kids will enjoy a close-up look at a fire engine and police cruiser. Police officers and firemen will also provide information on fire safety and staying safe and are available to interact with kids in a friendly atmosphere.

If you’re interested in registering as a vendor, be sure and register early. (There are a limited number of spaces for tents.)

Thanks to Hitachi for being our Title Sponsor for 2023 Spring Fling!

Downtown South Boston Business Directory

If you’re looking for a downtown business, you’ve come to the right place. All downtown South Boston businesses are included in our online Business Directory. You can search by name, category (type of business), or view the alphabetical listing. If you don’t see a business you’re looking for, please contact us and let us know. Thank you for supporting our downtown businesses and helping them grow and thrive in our community.

Downtown South Boston Farmers Market

The Downtown South Boston Farmers Market is home to many local farmers, bakers, and artisans. You can find homegrown vegetables, baked goods, plants and flowers, handmade gifts and home decor, and so much more. The Market is open seasonally and during other times of the year.

Visit the Facebook page to see  weekly updates on what’s available and see all of their events. Click the link below to learn more or to download applications for Daily or Annual participation in the Market. Shop small and shop local!


It’s a great place in a spacious outdoor space with covered stage for your events.


As a Main Street America Accredited program, Destination Downtown South Boston is a recognized leading program among the national network of more than 1,200 neighborhoods and communities who share both a commitment to creating high-quality places and to building stronger communities through preservation-based economic development. All Main Street America™ Accredited programs meet a set of National Accreditation Standards of Performance as outlined by Main Street America.

Celebrate Your Veterans

Celebrate and honor your Veterans with a street banner. The initial cost per banner is $225 for the production, hardware, installation, and removal of the banner. If you apply to install a previously displayed banner that is still in good condition, the cost of installation and removal of the banner is $50.00. The banner will be displayed from June 30 to Veterans Day of each year (display schedule is tentative and could change each year). Click the button for more information.