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Trail Running Calendar near Roxbury 2026-2027

Monthly updates for Roxbury

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

Explore the top trail runs near Roxbury for 2026-2027! We've gathered 27 exciting races in the area. Check out our detailed list below to find your next local race.

March 2026
Mar
29
Su

Sleeping Giant Trail Runs

Trail Run 25 km 50 km
April 2026
Apr
12
Su

John Jay Community Trail Race

Trail Run 4 km 5 km
Apr
25
Sa

Lake Mohegan Women's Trail Race

Trail Run 5 km 10 km 4 hr
Apr
26
Su

Jack Bristol Lake Waramaug Ultra Races

Trail Run 50 km 50 mi 100 km
Apr
26
Su

Leatherman's Loop

Trail Run 10 km
May 2026
May
3
Su

The Blue 2 Blue Challenge

Trail Run 50 km
May
17
Su

Spring Run the Farm

Trail Run 5 mi
May
24
Su

Mine Hill Half Marathon

Trail Run Half Marathon
June 2026
Jun
4-7
Th - Su

Ironhike Endurance Series - Spring

Trail Run 15 mi 28 mi ... 100 mi 152 mi
Jun
7
Su

Run in the Park 5K

Trail Run 5 km
July 2026
Jul
5
Su

Red Wing Trail Challenge

Trail Run 15 km 30 km 60 km
Jul
11
Sa

The Revolution

Trail Run
August 2026
Aug
1
Sa

Ridge Reaper Trail Runs

Trail Run 25 km 50 km 50 mi
September 2026
Sep
13
Su

Macedonia Trail Race

Trail Run 12 km 25 km 50 km
Sep
20
Su

Where the Pavement Ends Double Loop

Trail Run 4 mi 8 mi
October 2026
Oct
1-4
Th - Su

IronHike Endurance Series

Trail Run 61 mi
Oct
3-4
Sa - Su

Iron Hike - Kuwohi Trail Marathon Plus Relay

Trail Run 28 mi
Oct
11
Su

Mohawk Mountain Race

Trail Run 5 km 10 km 13 mi 26 mi
Oct
25
Su

Run The Farm - Katonah

Trail Run 5 mi
Oct-Nov
31-1
Sa - Su

Fall Back Into The Trails Series

Trail Run 10 km 50 km 100 km