Wellesley close

Trail Running Calendar near Wellesley 2025-2026

Explore the top trail runs near Wellesley for 2025-2026! We've gathered 18 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
5
Sunday

Groton Town Forest Trail Races

Trail Run 3 mi 9 mi
Oct
5
Sunday

Houghton's Pond Trail Race

Trail Run 4 mi 7 mi
Oct
5
Sunday

Stairs4RTroops Gillette Stadium

Urban Trail
Oct
12
Sunday

Wayland / HFC Striders XC Festival

Trail Run 3 km 5 km
Oct
19
Sunday

Weir River Farm Trail Race

Trail Run 3 mi 6 mi 10 mi
Oct
25
Saturday

Womp Romp

Trail Run 10 mi 50 km
Oct
25
Saturday

Pumpkin Pacer 5k

Trail Run 5 km
Oct
26
Sunday

Powisset Farm Trail Run - Fall

Trail Run 2 mi 3 mi 6 mi 8 mi
Oct
26
Sunday

Run for the Hills - Harvard

Trail Run 5 km
November 2025
Nov
9
Sunday

Upton Half Marathon Trail Race

Trail Run 11 km Half Marathon
Nov
27
Thursday

Turkeywacker 5K

Trail Run 5 km
December 2025
Dec
6
Saturday

TARC Winter Classic

Trail Run 8 mi 32 mi 40 mi
Dec
13
Saturday

Mount Hood Nutcracker Challenge

Trail Run 2 mi 4 mi
February 2026
Feb
7-8
Sa - Su

Tarctic Frozen Yeti

Trail Run 15 mi 30 hr
April 2026
Apr
11
Saturday

Merrimack River Trail Race

Trail Run 10 mi
Apr
11
Saturday

Spring Fever 5K | 5M | 8H

Trail Run 5 km 5 mi 8 hr
Apr
25
Saturday

TARC Spring Classic

Trail Run 10 km Half Marathon Marathon 50 km
May 2026
May
30
Saturday

Wildcat 5K Trail Run-Walk-Wag

Trail Run 5 km
Articles
Top 10 Marathons in the Netherlands — The Ultimate Dutch Marathon Bucket List: 10 Unmissable Races
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series