Walk on the Wise Side

Walking the Philosopher's Way Trail in SF

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!

Trending Stories NorCal

View all Stories
  1. Redwoods Star Power

    Go on a 5-mile (round-trip) redwoods hike that starts from Chabot’s Moon Gate entrance and through Dr. Aurelia Reinhardt Redwood Regional Park, then visit the Chabot Space and Science Center for a rooftop telescope star viewing or a space

    View
  2. Bike to Aardvark Beach

    Two wheels, a fresh sea breeze, birds, and a beach stop: now that's a California bike ride. Pack a beach blanket and set out on this 16-mile out-and-back pedal along the San Francisco Bay to Aardvark Beach.

    View
  3. Cheers to Chimney

    If you’re looking for all that Point Reyes has to offer in spring, Chimney Rock is the place to be. The 1.75-mile (round-trip) hike to Chimney may be short, but it packs a visual punch, quadrupling the viewing thrills during spring.

    View
  4. Woman on Mesquite Flat Sand Dunes at Death Valley National Park

    Starry Night & Dark Sky Adventures

    You don’t have to stay out all that late to experience eminent stargazing at Death Valley National Park. The park's been given the highest ranking of darkness by the International Dark Sky Association. From ranger-led to self-guided adventures, here are a few amazing ways to witness the mesmerizing night sky at Death Valley.

    View

Trending Stories SoCal

View all Stories
  1. Garland in Bloom

    Carmel Valley is known for its quaint wineries and scenic hiking trails. Enjoy both on this 3.75-mile loop through Garland Ranch Regional Park.

    View
  2. Sponsored

    No Limits Family Trip: Reno Tahoe

    What if your next family getaway didn’t come with a set agenda—just the freedom to go where the day takes you? Find yourselves in Reno Tahoe, a land of no limits and plenty of outdoor bounty.

    View
  3. Can We Get a Whoop Whoop!

    City, mountain, and ocean views all in one hike? Whoop whoop! It’s no surprise the the Kenter Fire Road and Whoop-de-Doos Trail (a combo of fire road and singletrack) is a favorite among local mountain bikers and hikers alike.

    View
  4. Eat, Explore, Repeat: Point Reyes Station

    It’s small and laid-back, but Point Reyes Station is a standout gateway to Point Reyes National Seashore. Fresh food, cool culture, and an unfussy vibe are part of the draw.

    View