Walk on the Wise Side

A wise man once said, “Walk it off.” And San Francisco has just the place for a colorful walk via a 2.7-mile loop along Philosopher’s Way Trail in the 318-acre John McLaren Park (San Francisco’s second largest park, after Golden Gate). The path gently dips and ascends from eucalyptus trees to open vistas of SF’s gridded buildings and brightly painted homes, decorating the hills like a mosaic.

The trail is marked by granite arrows, with 14 informational plaques that include photos, facts, and thought-provoking quotes, all designed to highlight the ecology, geography, and history of southeast San Francisco. Benches also line the path, which alternates between dirt and paved alongside fields of clover and groves of thick-trunked oaks.

Though the elevation gain is only about 400 feet, there’s still a sensation of glory as the trail peaks at a bright baby-blue water tower soaring 80 feet high. You’ll also get excellent views of the Bay Bridge, Mount Davidson, and Sutro Tower. Walk past the Jerry Garcia Amphitheater and the relic of a playground as you round out the route back to the starting viewpoint.

BONUS COLOR: For an extra color boost, when you encounter a neon green bench at about 1.5 miles on the trail, follow the spur path left, and exit the park. Four blocks out, you’ll find a garden mosaic by artist Dana Albany. It’s an homage to the hummingbirds that adorn the bottle brush trees in the area, and the dairy cows that once grazed the Excelsior back in the 1800s.

Parking for the Philosopher’s Way Trailhead is located at the Overlook Parking Lot just beyond the intersection of Mansell St. and Visitacion Ave. in San Francisco. Directional markers lead the way, but early on, arrows point in two directions. One direction is for a shorter loop. For the 2.7-mile loop, keep left at the double arrows. We recommend having a map handy. The mural is located at 701 Excelsior Ave. at the corner of Vienna St. Dog-friendly!