Overview The Wine and Chocolate Run is an evening 5K through Jacksonville's historic San Marco neighborhood that finishes in a party on San Marco Square, where every runner of legal drinking age gets two pours of red, white or bubbly and there is chocolate from Peterbrooke. 1st Place Sports, the Jacksonville running store that runs a year-round calendar of the city's road races, puts it on, and it counts as a race in the store's Jacksonville Grand Prix, the season-long, age-graded points series. The race supports the beautification of San Marco Square. On site The start is on San Marco Boulevard at the east end of the square, with the gun at 5 p.m. The course runs through the historic neighborhood, and the party afterward is held in the square: pours are tied to the race bib, and the wine cannot leave the square. Awards start at 6. The top three men and women overall take prize money, the first male and female masters finishers take a cash award, and custom plaques go three deep in each of 16 age divisions. Every entrant gets a moisture-wicking race shirt, and packets are picked up at 1st Place Sports stores in the two days before the race or at the square from 3:30 on race day.