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Walking Events Calendar near Hillsboro 2026-2027

Monthly updates for Hillsboro

Get new walking events (and updates) in your inbox every month.

Explore the top walking events near Hillsboro for 2026-2027! We've gathered 40 great walks in the area. Check out our detailed list below to find your next local walk.

August 2026
Aug
8
Sa

Third Winchester Battlefield Half

Trail Run Walk
Aug
23
Su

Leopold's Preserve 5K & 10K

Trail Run Walk
September 2026
Sep
5
Sa

Kentlands/Lakelands 5K

Road Race Walk 5 km
Sep
7
Mo

Footprints of Hope 5K Run/Walk

Road Race Walk 5 km
Sep
7
Mo

Montgomery County Interfaith 5K

Road Race Walk
Sep
12
Sa

Pleasant Valley 5K Run/Walk / Aquathlon Challenge / Dog Swim

Road Race Walk Aquathlon Aquathlon Challenge - Swi... 150 m 5 km
Sep
12
Sa

Charity Dog Walk & Pool Pawty - Stephens City

Walk 2 mi
Sep
13
Su

Heeling House 5K

Road Race Walk
Sep
13
Su

Firefighters Foundation 10K

Road Race Walk 5 km 10 km
Sep
19
Sa

Poolesville Day 5K

Road Race Walk 3 mi
Sep
26
Sa

Runnin' with the Dogs 5K

Road Race Walk 5 km
Sep
26
Sa

Trails 4 Miles

Trail Run Walk
Sep
26
Sa

Freedom Futbol Club 5K

Road Race Walk
Sep
27
Su

Lovettsville 5K & 10K

Road Race Walk
October 2026
Oct
3
Sa

MoCo Cares Charity Race

Road Race Trail Run Walk
Oct
3
Sa

Fall Harvest 5k

Trail Run Walk
Oct
3
Sa

Pink and Blue 5K - Middletown

Road Race Walk 5 km
Oct
11
Su

Run for MWS 5K

Road Race Walk 5 km
Oct
24
Sa

Spring Mills Rotary Ready, Set, Glow 5K

Road Race Walk 5 km
Oct
24
Sa

Valor 5K

Road Race Walk 5 km
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