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Trail Running Calendar near Great Diamond Island 2025-2026

Explore the top trail runs near Great Diamond Island for 2025-2026! We've gathered 46 exciting races in the area. Check out our detailed list below to find your next local race.

July 2025
Jul
26
Saturday

Casco Days Road Race

4 mi
Jul
26
Saturday

Peaks Island Road Race

5 mi
Jul
27
Sunday

Island Ripple Run

4 mi
August 2025
Aug
2
Saturday

Beach to Beacon 10k

10 km
Aug
2
Saturday

Rock the Boat 5K

5 km
Aug
3
Sunday

Blue Lobster 4-Miler

4 mi
Aug
8
Friday

Steady State Distance Festival

5 km
Aug
9
Saturday

Ruck for the Fallen

Obstacle Run 10 km
Aug
10
Sunday

Naples Community 5K

5 km
Aug
16
Saturday

Breakaway 5K

5 km
Aug
16
Saturday

Save a Stray 5K

5 km
Aug
18-24
Mo - Su

The Maine Event

Trail Run 8 mi 10 mi 15 mi 26 mi
Aug
23
Saturday

Firebird Trail Races

Trail Run 13 mi 26 mi 50 km
Aug
23
Saturday

Family Fun Run

5 km
Aug
30
Saturday

Last Man Standing Ultramarathon

Backyard Ultra 4 mi
Aug
30
Saturday

Tunnel to Towers 5K - Portland, ME

5 km
September 2025
Sep
6
Saturday

Cherry Hill Farm Ultra

Trail Run 10 km 25 km 50 km
Sep
7
Sunday

Lake Auburn Half Marathon

5 km 13 mi
Sep
20
Saturday

ACT Trail Fest

Trail Run 5 km 10 km 13 mi
Sep
20
Saturday

Autumn & Ales

5 km 10 km 13 mi
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