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Trail Running Calendar near Canandaigua 2026-2027

Monthly updates for Canandaigua

Get new running races (and updates) in your inbox every month.

Explore the top trail runs near Canandaigua for 2026-2027! We've gathered 19 exciting races in the area. Check out our detailed list below to find your next local race.

January 2026
Jan
17
Sa

Mrs. Mccormick's Ice House Tonic

Trail Run 4 mi 8 mi 12 mi
Jan
31
Sa

Devil's Shadow Winter Trail Races

Trail Run 5 mi 25 km 50 km
February 2026
Feb
22
Su

Cabin Fever Trail Races

Trail Run 5 mi 10 mi
April 2026
Apr
4
Sa

Three Brothers Spiked Apple 5K

Trail Run 5 km
Apr
18
Sa

Muddy Sneaker 20K Trail Run

Trail Run 20 km
May 2026
May
3
Su

Medved Madness Trail Races

Trail Run 5 mi 13 mi
June 2026
Jun
6
Sa

Frost Town Trail Festival

Trail Run 10 km 25 km
Jun
28
Su

RHSC's Super Hear-O 5K

Trail Run 5 km
Jun
28
Su

Run the Vineyards - Sheldrake Point Winery 5K

Trail Run 5 km
July 2026
Jul
11
Sa

High Tor Trail Marathon

Trail Run 13 mi 26 mi
Jul
18
Sa

Keuka Outlet Trail Half Marathon

Trail Run 10 km Half Marathon
Jul
25
Sa

Webster Trail Classic

Trail Run 4 mi 10 mi
Jul
25-26
Sa - Su

The Mighty Mosquito Trail Race

Trail Run 5 mi 10 mi ... 99 mi 100 mi
August 2026
Aug
22
Sa

Twisted Branch Trail Run

Trail Run 100 km
September 2026
Sep
12
Sa

Ontario Summit Trail Races

Trail Run 5 mi 13 mi
Sep
13
Su

ROCovery Run/Walk & X-Challenge

Trail Run Obstacle Run 5 km 10 km
October 2026
Oct
16
Fr

Sunshine Camp Trail Mix & Beer Fest

Trail Run 5 km
Oct
16
Fr

Boos & Brews 5K (Rochester)

Trail Run 5 km
December 2026
Dec
12
Sa

0 Degree Winter Trail Festival

Trail Run 5 mi 10 mi 15 mi