Entry to the Crosswinds Run Series costs between free and $45, depending on the distance you choose. The September 5, 2026 event in Canandaigua, New York offers three racing options: a 1K, 5K, and 10K. The race starts at 8:30 AM from 3360 Middle Cheshire Road. This setup allows runners at different levels to participate on the same day, making it accessible whether you're training for a longer distance or running a shorter effort. Consider your fitness level and race goals when selecting your distance, then plan your travel and accommodation accordingly for the early morning start time.
From the Race Organizer
Welcome to the Crosswinds Run Series! 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. 5K Run/Walk 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 an exhilarating downhill first mile through the City of Canandaigua, followed by the well-known climb up West Lake Road, and finish strong on the rolling hills of Ferris Hills. 10K Run 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. This USATF-certified course has a 90-minute time limit, after which roads will reopen to traffic. Kids Fun Run 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: Race t-shirt Finisher’s medal Access to a fun post-race snack table More Than a Race 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. Thanks to runners, walkers, volunteers and business sponsors, last year’s event raised $13,400 for The Spot. With the continued growth of the Run Series, our goal is simple: make an even bigger impact in 2026. Are You Ready to Commit? 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!
Hotels Near This Race
Find accommodation close to the start line in Canandaigua, NY. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
RaceHotelFinder earns a small commission when you book through links on this page, at no extra cost to you. Results are sorted by distance from the race venue.
Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.
Race Travel Insurance
Don't forget travel insurance for September 5.
You've trained for months and booked a trip to Canandaigua, NY.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is Crosswinds Run Series 2026 — Canandaigua, NY?
Crosswinds Run Series 2026 — Canandaigua, NY takes place on September 5, 2026. The race is held in Canandaigua, New York.
Where is Crosswinds Run Series 2026 — Canandaigua, NY held?
Crosswinds Run Series 2026 — Canandaigua, NY is held at 3360 Middle Cheshire Rd in Canandaigua, New York.
Where can I find hotels near Crosswinds Run Series 2026 — Canandaigua, NY?
RaceHotelFinder shows hotels sorted by distance from the race venue in Canandaigua. Use the map or list view on this page to compare options and book race weekend accommodation.
