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We found great results, but some are outside San Mateo. Showing results in neighboring cities.
Limit search to San Mateo.
#1 of 6 Outdoor Activities in San Mateo
Skirting the pristine Crystal Springs Reservoir and surrounded on both sides by lush and vibrant vegetation and trees, walking, running or biking this trail is a treat for all senses.
Park at either trail head and walk as far as you want along water views, trees and pastures, various wildlife and some historic structures.
#2 of 6 Outdoor Activities in San Mateo
Awesomely clean, accessible, large dog park with many trails right over the fence!
Their is a great dog park as well.
#3 of 6 Outdoor Activities in San Mateo
#4 of 6 Outdoor Activities in San Mateo

Fly Bay Area

San Carlos 4.2 mi away
#1 of 2 Outdoor Activities in San Carlos
#5 of 6 Outdoor Activities in San Mateo

Bay Area Ridge Riders

Belmont 2.0 mi away
#2 of 2 Outdoor Activities in Belmont
As a horse owner and regular rider, I am quite often disappointed with paid trail rides but love riding in new and different country.

Twin Pines Park

Belmont 2.9 mi away
#1 of 2 Outdoor Activities in Belmont

California Windsurfing

Foster City 2.6 mi away
#1 of 2 Outdoor Activities in Foster City

Crystal Springs Golf Club

Burlingame 3.8 mi away
#1 of 1 Outdoor Activities in Burlingame
#2 of 2 Outdoor Activities in San Carlos

Half Moon Bay Coastside Trail

Half Moon Bay 8.8 mi away
#1 of 31 Outdoor Activities in Half Moon Bay
It goes through several sections of terrain, little towns and parallels Highway 1. Easy walking and well kept walkways with occasional benches to enjoy the scenery a bit longer.
This is a wonderfully well manicured,wide paved trail winding through and around the Ritz Carlton golf course with beach access and gorgeous flora and scenery at each turn.
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