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Trail Running Calendar near Winthrop 2025-2026

Explore the top trail runs near Winthrop for 2025-2026! We've gathered 76 exciting races in the area. Check out our detailed list below to find your next local race.

May 2025
May
10
Saturday

Stride Along the Tide 5K

5 km
May
10
Saturday

Boston Marine Corps Honor Run

5 km
May
10
Saturday

Saint Catherine of Siena School 5K

5 km
May
11
Sunday

Melrose Run For Women

3 mi
May
11
Sunday

Moms' Run - Somerville

5 km
May
17
Saturday

Beach and Back Half Marathon

5 km 13 mi
May
17
Saturday

Barns & Blooms Half Marathon

13 mi
May
17
Saturday

Dash For Dane & Family Day

Trail Run 5 km
May
18
Sunday

Evan's Run

5 km
May
18
Sunday

Harpoon 5-Miler

5 mi
May
18
Sunday

New England Season Opener

Triathlon
May
18
Sunday

Great Bear Run

5 km
May
18
Sunday

Arlington Education Foundation 5K

5 km
May
18
Sunday

Mystic River Herring Run and Paddle

5 km 9 mi 12 mi
May
18
Sunday

Bluefin Blowout Family Fun 5K

5 km
May
18
Sunday

Newton South High School Lion's 5k

5 km
May
21-22
We - Th

4K Trail Run

Trail Run 4 km
May
24
Saturday

Health is Wealth Race

5 km
May
24
Saturday

The Team Hoyt Memorial

2 mi 5 mi
May
26
Monday

Powisset Farm Trail Run - Spring

Trail Run 3 mi 5 mi 8 mi
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