Ride: Day Rides

Riders who would like to take part in the event, but cannot make the full weekend commitment, may ride any one-day, two-day combination, or the 9-mile route on Sunday in Greenwich. We will keep you well fed and well supported. One day riders can add overnight accommodations during registration.

Day One – Friday, June 23rd

Participants who ride our Day One will join us at the Start Line at Boston College in Newton, MA on Friday for a 104 mile ride to the University of Connecticut. Day One is a gorgeous ride through the back roads of Massachusetts and into Connecticut's 'Quiet Corner'.

  • Rider Check-in opens at 5:00am at Boston College in Newton, MA
  • There is a mandatory route overview at 5:45am
  • Ride Out is at 6:00am sharp
  • We finish with an all-day barbeque and dinner at UCONN
  • Transportation is available from UCONN back to the Start Line in Newton
  • See the Day 1 route here

Day Two – Saturday, June 24th

Day Two is 91.6 miles of cycling through everything Connecticut has to offer. Starting with wooded back-country in Mansfield, we cycle to Lyme and take the ferry over the Connecticut River. From there we enjoy winding coastal roads, before taking to some city streets - passing Yale and arriving at the University of New Haven. Saturday night is one of the most powerful nights of the weekend. We hand out some awards and then open the microphone to anyone who wants to share his or her "Why I Trek" story.

  • Rider Check-in opens at 6:30am at UCONN
  • There is a mandatory route overview at 7:20am
  • Ride Out is at 7:30am
  • We finish with a barbeque lunch/dinner at the University of New Haven
  • We apologize, but transportation is not available
  • See the Day 2 route here

Day Three – Sunday, June 25th

Day Three is 79.4 miles and features our most challenging route of the weekend. A beautiful ride beginning in New Haven, the route consists of wooded back roads and steeper hills all the way through southwest Connecticut into Westchester County, NY. The day's 4th rest stop is at mile 70 and located at the top of John Street. Riders can climb John St. once or more and then grab some pizza and cheer others up the hill. All riders will leave the top of John St. at 2pm for the final 9 miles including a spectacular ride down Greenwich Ave and a picturesque finish at Roger Sherman Baldwin Park.

  • Rider Check-in opens at 5:00am. Cyclists who don't want to make the early morning drive to New Haven may join us at our Saturday evening overnight. Check in is before 6pm on Saturday evening. (Please make sure to specify if you need overnight accommodations when registering)
  • We finish in Greenwich, CT with a police escort down Greenwich Ave
  • Parking is available at the finish line and in Greenwich
  • Transportation is not provided, but it's an easy Metro North train ride. The Metro North Line runs from our finish in Greenwich, CT, to New Haven.
  • See the Day 3 route here

Greenwich Sgt. Roger Petrone 9-Mile Ride – Sunday, June 25th

New in 2014, the Greenwich Sgt. Roger Petrone 9-Mile Ride offers riders a less challenging way to participate in the event. The ride starts at the Greenwich Audubon Society and finishes at Roger Sherman Baldwin Park in Greenwich, CT.

  • Rider Check-in opens at 12:00pm. Park your car at the Audubon Society
  • The ride starts at 2pm and we finish in Greenwich, CT with a police escort down Greenwich Ave
  • Transportation is not provided
  • See the Greenwich Sgt. Roger Petrone 9-Mile Ride route here