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Trail Running Calendar near Wellesley 2025-2026

Explore the top trail runs near Wellesley for 2025-2026! We've gathered 19 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
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
2
Sunday

The Fall Trailblazer Ultra @ White Barn Farm

Trail Run 12 mi 24 mi 36 mi
Nov
2
Sunday

GFRC Busa Bushwhack Trail Races

Trail Run 5 mi 10 mi
Nov
9
Sunday

Upton Half Marathon Trail Race

Trail Run 11 km Half Marathon
Nov
27
Thursday

Turkeywacker 5K

Trail Run 5 km
Nov
27
Thursday

F.I.T. Turkey Trot Trail Race

Trail Run 5 km 5 mi
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
March 2026
Mar
21
Saturday

Tarc to Hale and Back

Trail Run 4 mi 6 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
August 2026
Aug
23
Sunday

Old Goat Track Club XC Classic

Trail Run 5 km
September 2026
Sep
5
Saturday

TARC Fall Classic

Trail Run 10 km Half Marathon ... 50 km 50 mi
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