3360 Middle Cheshire Rd, Canandaigua NY
Saturday, September 5th, 2026
Join us in Canandaigua for a late-summer tradition that’s been bringing runners, walkers, families and the community together for over 23 years. Formerly known as the Crosswinds 5K, the Crosswinds Run Series now offers multiple race-day options designed for all ages and abilities: whether you’re chasing a PR, enjoying a scenic walk or supporting a great local cause.
Our iconic, USA Track & Field-certified course is as fun as it is challenging, perfect for walkers, first-time racers and competitive runners alike. You’ll enjoy:
Introduced to the series last year and back by popular demand, the 10K builds on the tradition of the 5K’s hills with a longer, more demanding route for seasoned runners looking for a rewarding challenge. Key details include:
A half-mile course entirely on the event campus, perfect for young runners (preschool through 5th grade). It’s a safe, energetic, and memorable way for kids to experience race day. Every child receives:
The Crosswinds Run Series is more than a finish line, it’s a movement with a mission. All proceeds benefit The Spot, a local organization providing free school supplies, clothing, food, and shoes to students in need across the Canandaigua and Victor School districts. Key accomplishments include:
Whether you’re here to tackle the hills, cheer from the sidelines, or support local kids in a meaningful way, the Crosswinds Run Series offers something for everyone.
Join us and be part of a tradition that truly gives back!
Date: 2026-09-05
Location: 3360 Middle Cheshire Rd, Canandaigua, NY
To register, visit: Crosswinds Run Series Registration.
Race-day essentials
Light, simple picks for a fast effort.


SHOKZ OpenRun Bone Conduction Open-Ear Bluetooth Sport Headphones, Running Workout Bundle with Waterproof Carrying Case & Sweat Headband, IP67 Sweat Resistant, 8H Playtime, Mic, Black
$129.95

Garmin Forerunner 55, GPS Running Watch with Daily Suggested Workouts, Up to 2 Weeks of Battery Life, Black - 010-02562-00
$164.99

goodr A Unicorn's Calamity Polarized Sunglasses, Medium Sized (OG), Black Solid Frames with Black Non-Reflective Glare Reducing Lenses, UV400 Protection, No Slip, No Bounce
$30.00

Nathan Peak Running Hydration Waist Pack Belt w/Speed Draw Flask Water Bottle, 18oz/535 ml Push/Pull Race Cap, Expandable Zippered Stretch Pocket
$44.00
Train for this race
Run clubs in Canandaigua, NY host weekly group runs — a great way to prep for race day.