The Social Event Of The Year and World’s Largest Wine Walk is Back! The Ventura Winter Wine Walk & Holiday Street Fair will once again return to beautiful Downtown Ventura on Saturday, December 2, 2017! The Most Magical day in Ventura will kick off with the Holiday Street Fair starting from 12pm-8pm on the 400 and 500 blocks of Main Street with vendors and live entertainment. Shop artists, crafters, non-profit organizations, commercial and food vendors. The street fair and entertainment is FREE and open to the public starting at Noon!