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Trail Running Calendar near Kennebunkport 2025-2026

Explore the top trail runs near Kennebunkport for 2025-2026! We've gathered 42 exciting races in the area. Check out our detailed list below to find your next local race.

November 2025
Nov
1
Saturday

Holistic Hustle

Trail Run 5 km 10 km
Nov
1
Saturday

Trot For Catholic Education 5K

5 km
Nov
1
Saturday

Mingle Jingle Run

5 km
Nov
2
Sunday

Henry's Crusade against Epilepsy

5 km
Nov
8
Saturday

Wells Veterans Day 5K

5 km
Nov
8
Saturday

Lyseth 5k Fun Run

5 km
Nov
9
Sunday

Kick Out Mesothelioma 5-Miler In Memory of John W. Griffin

2 mi 5 mi
Nov
16
Sunday

Turkey Trot Tune Up

4 mi
Nov
23
Sunday

Maine Track Club Turkey Trot

5 km
Nov
27
Thursday

Dover Turkey Trot

5 km
Nov
27
Thursday

Outfitters Turkey Trot

5 km
Nov
27
Thursday

Free Fall

5 km
Nov
27
Thursday

Savage Family Turkey Trot 5K (Run/Walk)

5 km
Nov
30
Sunday

Ugly Sweater 5K - Waterboro

5 km
December 2025
Dec
6
Saturday

Ugly Sweater 5K

5 km
Dec
20
Saturday

Seaside Santa Dash

5 km 10 km
January 2026
Jan
18
Sunday

Jimmy the Greek's Frozen 4-Miler

4 mi
April 2026
Apr
11
Saturday

Falmouth 4-Miler

4 mi
May 2026
May
2-3
Sa - Su

Maine Coast Marathon

5 mi 13 mi 26 mi
May
2
Saturday

Dash for the Derby

5 km
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