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Walking Events Calendar near San Mateo 2026-2027

Monthly updates for San Mateo

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

June 2027
Jun
26
Sa

Stars and Strides 10K Run/Walk

Road Race Walk 5 km 10 km
Walkers can choose 5 km or 10 km routes starting at Discovery Meadow in downtown San Jose, following park paths and open meadow terrain alongside the running races. Virtual walk options are offered with race items mailed to participants.
July 2027
Jul
4
Su

Alameda Parade R.A.C.E.

Road Race Walk 3 mi
Walkers follow a point to point 5K (3.1 Miles) on closed streets through Alameda from 1420 Park St to the Webster Farmers Market. A free post event shuttle returns walkers to the start while spectators gather for the parade.
October 2027
Oct
9
Sa

Ashland Cherryland 5K Fun Run

Road Race Walk 5 km
Walkers can take the 5K route starting at REACH Ashland Youth Center (16335 E. 14th Street, San Leandro) along streets through the Ashland community. The event includes a family festival with food and activities and provides a free T shirt, bib a..
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