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Triathlon Calendar near Middletown 2025-2026

Explore the top triathlons near Middletown for 2025-2026! We've gathered 39 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
Sep
6
Saturday

The Inferno 10k

Trail Run 5 km 10 km
Sep
6
Saturday

Lock 2 Lock Marathon

10 km 13 mi 26 mi
Sep
6
Saturday

Damascus Freedom 5k

5 km
Sep
20
Saturday

Run On The Rocks

10 mi 13 mi 20 mi
Sep
20
Saturday

The Final Countdown

Backyard Ultra
Sep
27
Saturday

Runnin' with the Dogs 5K

5 km
October 2025
Oct
4
Saturday

MoCo Cares Charity Race

5 km 10 km
Oct
4
Saturday

Freedom's Run

5 km 10 km 13 mi 26 mi
Oct
11
Saturday

Run the Vineyards Williams Gap

5 km
Oct
12
Sunday

Rick O'Donnell Memorial Ultra Challenge

Trail Run 5 mi 4 hr 8 hr
Oct
26
Sunday

Ghostly Grapes 10k at Two Twisted Posts

5 km 10 km
November 2025
Nov
2
Sunday

Friends 10K

5 km 10 km
Nov
8
Saturday

Stone Mill 50 Mile Run

Trail Run 50 mi
Nov
8
Saturday

Schaeffer Half Marathon and 10K Trail Run

Trail Run 10 km 13 mi
Nov
22
Saturday

Run Under the Lights

5 km
Nov
27
Thursday

Landsdowne Turkey Trot

5 km
Nov
30
Sunday

Henway Hard Cider Turkey Trot 10k

5 km 10 km
December 2025
Dec
27
Saturday

Summit Point Half

5 km 10 km 13 mi
May 2026
May
2-3
Sa - Su

Frederick Running Festival

5 km 13 mi
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