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Trail Running Calendar near Fenway–Kenmore 2025-2026

Explore the top trail runs near Fenway–Kenmore for 2025-2026! We've gathered 92 exciting races in the area. Check out our detailed list below to find your next local race.

June 2025
Jun
21
Saturday

TARC Blue Hills Skyline Trail Run

Trail Run 12 km
Jun
22
Sunday

Cohasset Triathlon

Triathlon
Jun
26
Thursday

St. Peter's Fiesta 5K

5 km
Jun
28
Saturday

Hanover Day 5K

5 km
Jun
28
Saturday

Pioneers Run Crew Anniversary

10 km
Jun
29
Sunday

Summer Classic

5 km
July 2025
Jul
4
Friday

Bill Feeney 5K

5 km
Jul
13
Sunday

Narragansett Summer Running Festival

10 km 13 mi
Jul
19
Saturday

Miles for Migraine Massachusetts

2 mi 5 km
Jul
19
Saturday

12 Hours of Lawrence Woods

Backyard Ultra 12 hr
Jul
26
Saturday

Miles for Smiles - Lower Allston

5 km
August 2025
Aug
5
Tuesday

NCSL Fun Run 5K

5 km
Aug
7
Thursday

Beverly Homecoming 5K

5 km
Aug
10
Sunday

Sharon Triathlon

Triathlon
Aug
16
Saturday

Tarc Summer Classic

Trail Run 10 mi 50 km 40 mi
Aug
23
Saturday

Greenbelt's Vineyard Hill Trail Run

Trail Run 5 km 10 km
September 2025
Sep
1
Monday

Marshfield Run for the Hills

5 km
Sep
1
Monday

Walpole Labor Day Road Race

5 km 10 km
Sep
6
Saturday

Run to the Rock

5 km 10 km 13 mi
Sep
6
Saturday

HOOMPA Nickel 5 Miler Road Race

5 mi
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