For centuries, Europe’s Tour du Mont Blanc and Camino de Santiago trails have welcomed hikers eager to traverse a singular path on this planet that abounds with both breathtaking nature and memorable doses of local culture. Here in the Bay Area, we are blessed with a bounty of beautiful routes to take, including the 400 miles (and counting) of the ongoing Ridge Trail project. And in 2017, it was even announced that San Francisco was the first city in the United States where every resident lives within a 10-minute walk from a park. But if you’re looking to take in a side of San Francisco that you’ve never seen before, nothing beats the unique experience of walking the newly formed Crosstown Trail.
Starting at the Sunrise Point fishing pier in the Candlestick Point State Recreation Area, the dirt paths that define the majority of the Crosstown Trail collectively cover an elevation gain of over 2,000 feet and temperature fluctuations of up to 30 degrees, but it’s unquestionably worth the effort. Beyond the views and secret staircases, you’ll also pass countless gardens, the site of America’s first fireworks factory in Glen Park, and, depending on the season, a cornucopia of wildflowers blooming on the Philosopher’s Way Trail in McLaren Park.
This 17-mile route connecting hidden swathes of nature with underappreciated neighborhoods across the city happened when Bob Siegel, stimulated by the vision of Craig Dawson and Peter Brastow to establish a diagonal trail across San Francisco, connected existing trails and scenic routes.
It didn’t happen overnight. Forged over the course of five years via a devoted coalition of nonprofits and like-minded organizations, the Crosstown Trail debuted to the public in 2019 and surged in popularity following the implementation of Covid-19 lockdown precautions the following year. Today, interested hikers can tackle the terrain on their own via downloaded maps or a smartphone app. For real-time guidance, join up in June and October for one of the complimentary tours offered by a tight-knit crew of exceptionally knowledgeable guides (details found on crosstowntrail.org).
The success of the Crosstown Trail — and subsequently, the rise of a reverse diagonal path through SF dubbed the Double Cross Trail — has already inspired similar efforts in Seattle’s Olmsted Trail and Boston’s Walking City Trail and has seen Siegel featured in a New York Times profile on the subject. In celebration of this wonderful achievement and all it offers, here’s a handy guide to making the most of your time on the most unique trail in all of San Francisco.
Feature photo courtesy of San Francisco Travel Association, by Seth Warren.
Section One
Candlestick Point, Visitacion Valley, McLaren Park
Ever since the San Francisco 49ers pulled up stakes and moved to Santa Clara in 2014, the Candlestick Park State Recreation Area has grown quite lonely. That’s why the Crosstown Trail starts at the Sunrise Point Pier, where you’re likely to encounter locals fishing and dog walkers enjoying nature. The first neighborhood you’ll hit, called Little Hollywood, has a fun celeb history, and then you’ll end up on Leland Avenue where you’ll see interesting storefronts and one of the sweetest coffee shops in the city as you make your way to what founder Bob Siegel hails as “the Lombard of walking paths”: Visitacion Valley Greenway. Enjoy the sights of urban gardens — including the largest geranium in the world and a giant hummingbird mural by artist Cameron “Camer1” Moberg — as you push on to McLaren Park, where wildflowers abound each spring.
FOOD SHOUTOUT
Need some energy to fuel your journey? Swing by Mission Blue Coffee at 144 Leland Ave for delicious espresso and a delightful selection of Crosstown Trail swag like t-shirts and caps for purchase.
HIGHLIGHTS
- Take a selfie at 294 Tocoloma Ave., where Tinseltown stars like Mae West once populated the neighborhood during its heyday as “Little Hollywood.”
- Created in 2013 by Exploratorium staff artists Peter Richards and Susan Schwartzenberg, the Philosopher’s Way is the only path built for philosophers (there are 14 plaques, along the 2.7-mile trail) in the United States.
Section Two
Glen Park Greenway, Glen Canyon Park, Laguna Honda Trail
You may forget you’re still in San Francisco as you enter the second section of the Crosstown Trail. Lush green spaces headline this segment, which winds through 60 acres of restored natural habitat in Glen Canyon Park. Other highlights include street art by Amos Goldbaum before the Bernal Cut Bridge and in Glen Park and a glimpse of the aptly named “Bedpan Alley” — today the remnants of a dump site once utilized by the Laguna Honda Hospital. Be sure not to miss the site of America’s first dynamite factory and the Glen Park Canyon trail named for the Gum Tree Girls: the group of 1960s activists who successfully prevented the construction of a freeway through the canyon.
FOOD SHOUTOUT
Grab Crosstown Trail merch or your next favorite read at jazz bookstore Bird & Beckett (653 Chenery St) — and come back in the evenings to hear some sultry tunes. You can also replenish your caffeine quotient at Higher Grounds (691 Chenery St) or Bello Coffee & Tea (2885 Diamond St).
HIGHLIGHTS
- Be sure to take the time to soak in the Burnside Mural (created by Elaine Chu and Marina Perez-Wong) and Burnside Tiled Stairs (by Colette Crutcher and Aileen Barr).
- Read the plaque commemorating the country’s first dynamite factory at the entrance to Glen Park.
Section Three
Golden Gate Heights Park, Grandview Park, Tiled Stairways
Meander through Forest Hill, developed in 1912. While the “exclusivity” intent of the original developers was a bit shady, today the only shade you’ll find is from mature trees that line the manicured streets. See why San Francisco’s secret staircases are the stuff of legend as you discover a wealth of murals. While it’s best to prepare for some exertion, the rich rewards of your efforts include both a selection of staggering staircase art and a slew of immaculate views of the San Francisco cityscape.
FOOD SHOUTOUT
If you’re feeling ready for a cocktail after completing three sections of the Crosstown Trail, head two blocks over to The Sage & the Drifter (1368 Irving St) or, for more filling sustenance, go an equally short distance to your right and get a tasty sandwich at Irving Subs (1298 12th Ave).
HIGHLIGHTS
- Steps, steps and more steps: from the majestic staircases of Forest Hill to the Instagram-famous Sunset tiled stairs, your heart will be happy with this portion of the trail.
- City planners were very thoughtful when they created Grandview Park, which does indeed have a grand view.
Section Four
Blue Heron Lake, Rose Garden, Park Presidio Boulevard
Even the familiar, if spacious, confines of Golden Gate Park share a new side courtesy of the Crosstown Trail. Skipping many of the landmark site’s most notable attractions, you’ll instead enjoy a stroll across Blue Heron Lake’s stone bridge en route to a date with the park’s radiant Rose Garden. As you pass by the boathouse, you’ll also have a chance to admire one of the only statues in GGP dedicated to a woman: a work created for the Panama-Pacific International Exposition in 1914 in tribute to the pioneer women of the Oregon and California Trails. Eventually, you’ll segue through San Francisco’s popular Inner Richmond neighborhood to reach the splendor of the Presidio.
FOOD SHOUTOUT
If you dig dim sum, turn left on Clement Street and sample the copious delicacies available at Good Luck Dim Sum (736 Clement St) or Xiao Long Bao (625 Clement St). For beers, sports score checks and the unbeatable atmosphere of a neighborhood dive bar, look no further than 540 Rogues (540 Clement St). Love to read? Then be sure to take a few minutes to inspect the shelves at used book paradise Green Apple Books (506 Clement St).
HIGHLIGHTS
- Rose Garden: with over 760 rose bushes, this is the best place in San Francisco to stop and smell the roses!
- Don’t be confused by the new name: Blue Heron Lake is the famous spot with pedal boats, bridges and romantic places to stroll but underwent a name change in 2024.
Section Five
Presidio, Sea Cliff, Lands End
Once a major military headquarters for the U.S. Army, the Presidio’s transformation into an oasis of redwood trees, beaches and museums makes it a perfect start for the Crosstown Trail’s coda. Discover the sand dunes and the boardwalk path of the Lobos Creek Valley Trail before concluding with the final stretch, in which you’ll wind across the rocky cliffs of the Land’s End Trail complete with jaw-dropping views of the Golden Gate Bridge at Baker Beach and a spectacular finale courtesy of the Sutro Baths ruins at the edge of the Pacific Ocean. Soak in stunning views of the water and beachscape before rewarding yourself with a well-earned feast to cap off a triumphant day.
FOOD SHOUTOUT
Feeling famished? Try the family-friendly fare of the ever-popular Beach Chalet (1000 Great Hwy).
HIGHLIGHTS
- Lands End trail is full of Golden Gate Bridge selfie opportunities and features some of the most beautiful parts of the trail.
- Best for last: the Sutro Baths ruins. Here you see signs of the once majestic heated pools that San Franciscans flocked to at the turn of the century.
DOUBLE CROSS
Want double the wonderment? The success of the Crosstown Trail has subsequently birthed a sibling in the form of the Double Cross Trail, which debuted in late 2020. Chartered by Arnie Thompson, John Trevithick and Chris Rupright, this 15-mile hike through San Francisco intersects with the Crosstown Trail just south of Twin Peaks but otherwise offers a fully separate, equally unique survey of the city’s nature, culture and history.
Here are some highlights to look forward to as you take on the Double Cross.
Section One
Fort Funston, Merced and Pine Lakes
Your day will start south of the San Francisco Zoo at Fort Funston, where the Pacific Ocean flanks a shoreline populated with hang gliders, pooches at play and a series of concrete bunkers that were once part of San Francisco’s coastal defense system. You’ll also get a chance to pay a visit to Lake Merced, then Pine Lake: two of the three natural freshwater lakes found in all of SF.
FOOD SHOUTOUT
Choose your own adventure from an abundance of delicious fare located throughout San Francisco’s charming West Portal neighborhood, such as Sam’s Grill (374 Bush St).
HIGHLIGHTS
- As you pass Lake Merced, contemplate the historical fact that on Sept. 13, 1859, this was the spot of what is referred to as the last duel to occur in the United States.
- The historical Trocadero Clubhouse, at the eastern end of Stern Grove, has recently undergone restoration after it was severely damaged by a 2023 storm.
Section Two
Edgehill Mountain, Twin Peaks, Mount Olympus
The charm of San Francisco’s West Portal neighborhood takes center stage for the initial chunk of the Double Cross’ second section, in which you’ll trek along “paths unknown to most outsiders” that include a chance to see a radiolarian chert rock quarry embedded with the remains of marine plankton who lived 100–200 million years ago. Next your gaze will turn from the ground to the sky as you visit several of San Francisco’s finest vista points atop Twin Peaks, Tank Hill and Buena Vista Park. Capping off the middle portion of the Double Cross is a stop at the Harvey Milk Center for the Arts for a bold, brilliant dash of local culture and history.
FOOD SHOUTOUT
From breakfast sandwiches to tuna melts and hummus plates, Duboce Park Cafe (2 Sanchez St) is a great spot to grab some calories as part of your Double Cross Trail adventure.
HIGHLIGHTS
- As you approach the entrance to Edgehill Mountain Park, you will come upon some beautiful homes, one of which is a corner home on the left decorated with whimsical pieces of art.
Section Three
Postcard Row, Civic Center, City Icons
You’re invited to play tourist during the final chapter of the Double Cross, which meanders past such popular photo ops as the Seven Sisters of Postcard Row (Alamo Square), City Hall, the California Street cable car line via Nob Hill, Chinatown’s Golden Gate Fortune Cookie Factory, the Transamerica Pyramid, storied bohemian North Beach cafes, Coit Tower and the steps and views from Telegraph Hill (and perhaps a wild parrot or two). As you wrap your day at the waterfront at Pier 23, you might just need a few minutes to digest how much one trail can pack in!
FOOD SHOUTOUT
If you’re hungry or thirsty in North Beach, simply let your eyes and stomach be your guide to a world of Italian treats, creative cocktails and unforgettable hole-in-the-walls. To properly celebrate crossing the finish line, you can also raise a toast in the waterfront auspices of Pier 23 Cafe Restaurant & Bar (23 Embarcadero).
HIGHLIGHTS
- Get your selfie in front of the famous Painted Ladies.
- Don’t miss a few extra steps as you stroll the labyrinth at Grace Cathedral. It’s up the stairs on the right.
