5K races near Pleasantville

The Sugar Loaf 5K is a morning road race in the historic hamlet of Sugar Loaf, located in New York’s Hudson Valley. This is a local 5K designed for a broad range of participants; walkers and beginners can complete the distance, while regular runners will find enough gentle climbing to make it a worthwhile effort. The course follows country roads through the hamlet, with Sugar Loaf Mountain visible overhead. The terrain features a mix of flat sections and mild hills. The Sugar Loaf Community Foundation organizes the event, with proceeds benefiting infrastructure improvements within the hamlet. Following the race, participants and observers can explore the hamlet’s artisan shops, galleries, and restaurants, which are situated near the race venue.

The Gemstone Sparkle Sprint 5K is a fall trail race in Wilton, Connecticut, starting from Quiet Lake Lane. It is a nonprofit running event with a 5K option for runners and walkers, plus a shorter accessible Sparkle Stroller run/walk of 0.75 miles. The event is hosted with Prospector Theater, CT Run Co., and Brooks, and it supports the Prospectors’ work creating meaningful jobs for people with disabilities. The race is returning for its third edition, and the setup points to a family-friendly morning with food, spectators, sponsorship options, and room for both trail runners and people who want a shorter accessible route.

The Happy Jack 5K begins and ends at Germonds Park in West Nyack, New York. This is an officially timed out-and-back 5K suitable for runners and walkers. It is held annually in memory of John Thomas “Happy Jack” Doyle. The race series also includes a virtual 5K and a kids’ fun run prior to the main event. The course follows local roads surrounding Germonds Park, with traffic control provided by the Clarkstown Police Department. Funds raised benefit The Happy Jack Fund, which provides yearly scholarships to high school students who have lost a sibling and offers support to families experiencing the loss of a child. All participants, kids and adults, receive medals. The first 200 main-event registrants will get race shirts. Teams are encouraged, and trophies will be awarded to the five largest teams based on registration.

Purple flair and finisher medals are part of the annual fall Miles for Migraine - New York City event. This timed 5K and 2-mile walk is organized by the Miles for Migraine nonprofit. It serves as a New York City walk/run for migraine and headache awareness, functioning as a fundraiser for treatment, research, patient support, and specialist training. The event has taken place in major city parks such as Flushing Meadows and Randall's Island Park. The day includes a professionally timed 5K, an untimed walk, and a festival area with speakers and sponsors. Funds raised support local headache centers and training programs, including those at Montefiore, Mt. Sinai, and a headache fellowship program at Weill Cornell.

The Harrington Park Fall Spectacular is a fall race morning based at Harrington Park School in Harrington Park, New Jersey. Its main event is a USATF-certified 5K run/walk on a relatively flat route through town, with a one-mile fun run and a kiddie dash for shorter-distance runners. The 5K starts later in the morning after the kids' events, and it is open to all ages. The 5K has water stations at miles 1 and 2, and results are posted with both chip time and gun time, with awards decided by gun time. Strollers are allowed, but bicycles, scooters, rollerblades, and dogs are not. The Harrington Park Road Runners Association, a 501(c)(3) nonprofit, organizes the event, and race-day extras include professional pre-race stretching, a live DJ, and an indoor awards ceremony in the school gymnasium.

Faith in Children - 5K Run/Walk is a 5K run or walk held at 20 Randalls Island Park in New York City. An international virtual option is available for those unable to attend in person. The race generates funds for Faith in Children programs that aid the physical, mental, and emotional health of individuals and families. It is designed for a mixed group, not just runners: adults, teens, children, walkers, and dogs are welcome, including the Kids and Dogs Run Too! segment. The in-person event focuses on simplicity and family, offering same-day bib and shirt pickup. Medals are provided for adults, teens, and children, along with race bandanas, bibs, and medals for dogs. Kids and dogs also receive goodie bags. All participants get refreshments and snacks and are entered into a free raffle. Proceeds support Mindfulness Education, Community-based Outreach, and Nourished Bellies initiatives across the United States, Canada, Brazil, Malawi, Madagascar, and Congo. Specific projects include food deliveries in Harlem and Toronto, food baskets in Pernambuco, clean water initiatives near Ambovombe, mindfulness programs in Long Beach and at Dzaleka Refugee Camp, and yoga for children and teens at Orphanage City of Love.

The Ridgefield Road Fest begins at the Boys & Girls Club of Ridgefield in Ridgefield, Connecticut, offering three road-race options: a half marathon, a 7-miler, and a 5K. This October running event features distances of 21.1 km, 11.3 km, and 5.0 km. The course provides runners a choice between a half-marathon effort, a middle-distance road race, or a shorter 5K. The Iris Fund benefits from the 5K, and the series is celebrating its 50th anniversary, adding local history to the event.

The Brookfield Halloween 5K begins and ends at the Brookfield Municipal Center on Pocono Road in Brookfield, Connecticut. This October running event includes a USATF-certified, chip-timed 5K and a short Kids Fun Run, suitable for runners aiming for a measured time and families seeking a Halloween activity. The 5K course, certified as CT06013JHP, accommodates walkers, strollers, and leashed dogs, contributing to a diverse field. The Kids Fun Run is a 0.23-mile loop within the park. Costumes are encouraged, with awards for the best dressed. All participants get short-sleeve T-shirts, and age-group awards are presented for runners from 8-and-under to 70-plus.