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Trail Running Calendar near Kennebunkport 2025-2026

Explore the top trail runs near Kennebunkport for 2025-2026! We've gathered 44 exciting races in the area. Check out our detailed list below to find your next local race.

May 2026
May
2
Saturday

Dash for the Derby

5 km
May
3
Sunday

Salty's 10K Double Nubble

5 km 10 km
May
3
Sunday

Wallis Sands Half Marathon

Half Marathon
May
16
Saturday

Fox Point 5 Miler

5 km 5 mi
May
23
Saturday

Pharos House 5K

5 km
June 2026
Jun
6
Saturday

Shipyard Old Port Half Marathon

5 km Half Marathon
Jun
7
Sunday

Maine Running Hall of Fame 5K

5 km
Jun
13
Saturday

Market Square Day 10K

10 km
Jun
13
Saturday

Otter Pond Trail Races

Trail Run 10 km
Jun
14
Sunday

Luv 2 Run Portland

5 km
Jun
18
Thursday

Gorham 4-Miler

4 mi
Jun
21
Sunday

Raccoon Run

5 km
Jun
27
Saturday

South Berwick Strawberry Run

3 mi 5 mi
July 2026
Jul
11
Saturday

Back Cove Backyard Ultra

Backyard Ultra 4 mi
Jul
12
Sunday

Windham Center 5K

5 km
August 2026
Aug
2
Sunday

Blue Lobster 4-Miler

4 mi
Aug
9
Sunday

Sabine Strong 3.3

3 mi
Aug
15
Saturday

Breakaway 5K

5 km
Aug
22
Saturday

Firebird Trail Races

Trail Run 13 mi Marathon 50 km
September 2026
Sep
12
Saturday

Pumpkinman Triathlon Festival

Triathlon
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