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Walking Events Calendar near Portland 2026-2027

Monthly updates for Portland

Get new running races (and updates) in your inbox every month.

Explore the top walking events near Portland for 2026-2027! We've gathered 43 great walks in the area. Check out our detailed list below to find your next local walk.

December 2026
Dec
5
Sa

Santa Made Me Do It

Road Race Walk 2 mi
The 2 Mile walk begins on the Bethlehem Town Green in front of Memorial Hall and follows the 5K course on rolling country roads, turning back at the one mile mark. Parking is at the Bethlehem Fair Grounds with shuttle buses to the Green, and the..
Dec
5
Sa

Jingle Bell Run - Connecticut

Road Race Walk 5 km
Walkers can join the 3.1 Miles course alongside the running races, starting at 370 Bassett Road, North Haven, CT. Walkers receive a shirt, jingle bells, and a medal.
May 2027
May
8
Sa

Path of Hope Run/Walk

Road Race Walk 5 km
Walkers can take part in the 5K in Hartford, following the first loop with the option to complete the second loop alongside the running race. Event offers live online results and free video and same day finish line photos for participants.
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