CT Main Street Keystone Award
Sponsored by

New Haven Grand Prix: A Twilight Bike Race & Street Festival in Downtown New Haven

Recipient: CT Cycling Advancement Program; Town Green District
Partners: City of New Haven; Taste of New Haven

Opportunities & Challenges

  • Already a home to a vibrant downtown filled with food, culture, and entertainment, New Haven is also home to a growing bike culture. With an award-winning Complete Streets Plan, the City recognizes bikers as commuters.
  • The Connecticut Cycling Advancement Program’s (CT CAP) mission is to ensure that Connecticut’s youth and their families have access and exposure to an organized state-wide youth cycling league. Bike racing is a high-end sport that requires resources. CT CAP is dedicated to investing in youth participation statewide – no matter an individual’s financial status..
  • Since 2015, Aidan Charles of CT CAP and Win Davis of New Haven’s Town Green (Special Services) District have collaborated to bring this tailor-made event to downtown New Haven.


  • CT CAP and Town Green District work closely to ensure that the bike-centered activities and the dining, strolling and entertainment in downtown complement each other. CT CAP contracted with “Taste of New Haven” to bring in food trucks for the Apizza & Eats Feast, complete with live music and a beer garden on College Street. The energy and components of the event are unique, and set downtown apart from other places in the City.
  • Numerous city departments collaborate to ensure the event is successful. The City Parks, Departments of Public Works, Health, Economic Development, and Police are all excellent partners. All major streets in downtown are closed for the event – a Friday night in September – which attracts 15,000 spectators.
  • The races run a rectangular route from Chapel and Temple to High Street up to Elm, then back down Chapel. There are three races: an under-18 race, which runs 20 laps around the rectangle; a professional women’s race, also 20 laps; and a 40-lap (or approximately 48-50 mile) professional men’s race.
  • CT CAP begins the event with a kids race, which features kids from nearby suburbs racing alongside those from the local urban neighborhoods.
  • To ensure that downtown restaurants benefit, Town Green District works with sponsors to encourage their attendees to support local bars and restaurants throughout the evening. The Apizza & Eats Feast is placed away from bars & restaurants, with entertainment strategically located – including “Slide the City”; a 1,000 ft slip & slide. Town Green District has secured free slots in the Apizza & Eats Feast for all downtown restaurants directly impacted by the race route.


  • CT CAP invests well over $100,000 into the event. Town Green invests approximately $5,000 into the Crossroads Festival, street closing costs, and staff time.