Spring on the North Fork means more than blue skies and new blooms — it’s also the time that local roads fill up with runners and walkers ready to get moving after a long winter. From festive 5Ks to vineyard runs and even a beginner-friendly triathlon, May offers a full calendar of events for runners and walkers of all levels. Put on your running shoes and join the community for fundraising, fitness and fun.
This race starts at 9 a.m. on Saturday, May 2 at the Greenport Fire Department and kicks off Greenport’s month-long Cherry Blossom Festival — a celebration with various events taking place as over 300 cherry trees bloom throughout Greenport.
The cost for the race is $30 if you signed up before April 11, $35 for signup between April 12-May 1 and $40 on the day of the race. American Beech is offering a special brunch add-on for $25 for participants, perfect for celebrating after the race. Run for the Petals benefits the Greenport Business Improvement District and Greenport’s Village Tree Committee.
This long-standing race raises funds for the Greenport Fire Department and is scheduled for Saturday, May 9 at 9 a.m. this year — the 20th annual race. The cost for the 5K run/walk is $30 for adults, $15 for students with advance registration and $35 for adults and $15 for students for signup on race day. The untimed John May Mile race costs $10 for adults and $7 for ages 14 and under/ages 55 and over. The family-friendly events feature a barbecue lunch, raffles and more.
“Celebrating the 20th anniversary of the John May Mile and 5K is incredibly meaningful for all of us at Peconic Landing,” says Robert J. Syron, President and CEO of the not-for-profit Peconic Landing. “For two decades, this event has brought the community together in support of the Greenport Fire Department and the dedicated volunteers who show up every day to protect and serve the North Fork. Now more than ever, we must continue to rally behind them to ensure they have the resources they need to respond when it matters most.”
Since its inception in 2005, the annual John May Mile and 5K has raised more than $400,570 to support local first responders. The most recent event in 2025 contributed a total of $28,570, helping to purchase and maintain rescue equipment vital to keeping fire department volunteers safe during response efforts.
Pindar Vineyards partners with The New York Cancer Foundation for their 7th annual Memorial Day race on Sunday, May 24, rain or shine. The race, a relatively flat course through the vineyards, starts at 9 a.m., with the 1-mile walk stepping off at 9:05 a.m. The cost for the 5K is $47; for the 1-mile walk $32; with a 10% discount per event for signing up for another Pindar race this year.
The after party features live music, food trucks, a complimentary glass of Pindar wine for participants (a full wine bar and tasting options are also available) and puppies for adoption from Pawsitive Possibilities. Participants receive a race t-shirt and a Run the Vineyards stemless wine glass.
On Saturday, May 30, the second annual Harbor Hustle kicks off at 9 a.m. rain or shine through Greenport Village, ending at the high school with post-race refreshments. The cost is $30 for adults, $15 for students who sign up before May 16, $35 for adults, $15 for students who sign up between May 15-29, and $40 for adults, $15 for students on the day of the race.
“The race is a great community event that brings together runners, families and supporters of our school,” says Brian Toussaint, Greenport High School’s athletic director. “Proceeds from the race go directly toward supporting Greenport’s student-athletes,” Toussaint says, with the Booster Club helping to fund team needs, special initiatives and events such as Greenport’s end of the year awards celebration.
Mighty North Fork Triathlon | Cedar Beach County Park, 3690 Cedar Beach Road, Southold, liparks.com
One of the best courses for a first-time triathlete, this race kicks off early on Sunday, May 31 at 6:50 a.m. at Cedar Beach, with the approximate finish time at 9 a.m. and an awards ceremony at 9:10 a.m. The race includes a 500-meter swim in Peconic Bay, a mostly flat 7-mile bike ride and a scenic 3.5-mile run.
To sign up as an individual costs $160 for adults, $110 for ages 14-18; as a relay team $210 for adults and $155 for ages 14-18; for the bike/run segments or for aquabike (swim/bike segments) $155, with price increases after May 24.
