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Triathlon Calendar near Middletown 2025-2026

Explore the top triathlons near Middletown for 2025-2026! We've gathered 37 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
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
Sep
27
Saturday

The House That Beer Built 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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