Williamsburg's 2nd Sundays Art & Music Festival, the free monthly street fair that typically fills North Boundary Street with artisans, musicians and food trucks, remains planned for Oct. 11, 2026, despite rain in the forecast. The event is expected to bring crowds browsing handmade goods and catching live performances.
The organizer's own website, 2nd Sundays Williamsburg, listed the Oct. 11 event from 11 a.m. to 4 p.m. Merchants' Square has listed the recurring monthly festival's hours as running from 11 a.m. to 5 p.m., so visitors checking different sources may see different times for the event.
A Free Street Fair Built Around Six Blocks of Art
When it's running, the festival spreads across six blocks of downtown Williamsburg along North Boundary Street, organizers say on the 2nd Sundays Williamsburg site, with one key gathering point in front of the Williamsburg Community Building at 401 North Boundary Street. Admission is free, and the event is open to all ages along with well-behaved pets, according to the same organizer listing.
Vendor counts vary slightly depending on the source. Williamsburg Families describes the festival as drawing more than 190 vendors alongside six blocks of live music, food trucks and performing arts, while the organizer's own site describes roughly 200 unique artisans, musicians, street performers, food vendors, food and dessert trucks, and a beer or beverage garden. Either way, it's a sizable footprint for a monthly neighborhood event.
A Decade of Growth From One Stage to Four
The festival wasn't always this big. It started as a small neighborhood art show before evolving into a street festival in 2010, according to a historical report from Williamsburg Yorktown Daily. That first iteration featured just 20 artists and a single performance stage covering half a block downtown, the outlet reported, and it has since grown to cover four blocks with four performance stages. The same report noted at least 10 performances each month from musicians, magicians, jugglers, hula hoop performers and mimes.
Under a normal schedule, the festival runs on the second Sunday of every month from March through December, according to Merchants' Square. A Williamsburg Yorktown Daily report on an earlier season described the festival running from March 8 through Dec. 13 that year, illustrating how consistent the monthly cadence has been over time.
The festival also maintains a social media following, with its Facebook page showing nearly 15,000 followers and thousands marked as having attended past events. The festival remained planned for Oct. 11, 2026.
