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Celebrate ‘Crosstober’: a great month to walk across San Francisco on the Crosstown Trail

Crosstown Trail view of downtown from Grandview Park in 2013. | Photo by Alexandra Kenin

Since its debut in 2019, the Crosstown Trail has connected people to the city and each other by opening their eyes to new trails, parks, stairways, gardens, and entire neighborhoods. 

The multi-use trail runs from Candlestick Point in the southeast corner of the city to Lands End in the northwest—or vice versa. One long, full-day route covers all 17 miles or many walkers divide the trek into sections for more digestible, half-day treks.

Courtesy of the Crosstown Trail

If you haven’t explored the trail yet, “Crosstober” is your excuse to get out there. Throughout the month of October, free walks will be hosted on and around the trail to celebrate both the epic views and unexplored parts of San Francisco. These include a hike across the entire Crosstown Trail, as well as trail-adjacent routes that visit urban farms, stairway gardens, restored natural habitats, and street art. The guided walks will also allow you to meet some of the volunteers who are building community by caring for these neighborhood treasures. 

Doing any one of these walks is guaranteed to not only get you a good workout, but also a better perspective on the city’s connected greenways, gardens, natural areas, and people.

While attendance for these walks is limited, you can hike or bike the Crosstown Trail any day of Crosstober (or any other month of the year) by downloading mobile route maps, printing out turn-by-turn directions and locating public transit stops, places of interest, food, restrooms and other useful info on the Crosstown Trail website

Courtesy of the Crosstown Trail

On all routes, walkers should be ready for changes in elevation, and mixed terrain, including pavement, stairs, and dirt paths. They should also bring water, snacks, and lunch. The full lineup of free Crosstober walks is below. Learn more and sign up on Eventbrite. Space is limited, so snag your spot quickly!

Walk 1: Walk the Crosstown Trail South-to-North 

Date: Sunday, October 2 at 9 a.m.

Meeting Point: Sunrise Point in Candlestick Point State Recreation Area

Crosstown Trail founder Bob Siegel will be leading a moderately-paced hike from Candlestick Point State Recreation Area along the full 17-mile route to Lands End. Walkers going the distance should prepare to hike through the late afternoon. And anyone who completes the full route will have the opportunity to walk just south to the Beach Chalet for a celebratory beverage. Sign up here to walk the entire Crosstown Trail. 

The Laguna Honda Trail System is one of many highlights of the Crosstown Trail. | Photo by Alexandra Kenin

Walk 2: Meet the OMI (Ocean View, Merced Heights, and Ingleside)

Date: Saturday, October 15 at 10 a.m.

Meeting Point: Unity Plaza, 1002 Ocean Avenue

Walking enthusiast and Walk San Francisco volunteer and board member Karen Rhodes will guide hikers on a 7-mile/4-hour loop through a stairway garden, an urban farm, a rocky outcrop with a panoramic view, and other pockets of greenspace that are being cared for by neighbors. Visits include Ridge Lane as well as several other sites getting TLC from the Friends of the OMI Mini Parks. Hikers will visit Urbano Drive, the site of a former racetrack, and the beloved Ingleside sundial! Along the way, participants will meet several community stewards and eat lunch at a park. Sign up here to walk the OMI.

Ridge Lane is a combination of a stairway and dirt path that winds through the Oceanview neighborhood. | Alexandra Kenin

Walk 3: Excelsior-McLaren Loop

Date: Sunday, October 23 at 10:00 a.m.

Meeting Point: Mansell St. and Visitacion Ave. in McLaren Park

Amy Kaeser, program manager for Habitat Conservation at the San Mateo Resource Conservation District — and an Excelsior resident — will guide walkers on a 6-mile/4-hour loop around the Excelsior and McLaren Park. In the Excelsior, walkers will visit the neighborhood’s colorful tiled stairway at Athens-Avalon Greenspace. And in San Francisco’s second-largest city park, sights will include a duck pond, a labyrinth, and the Jerry Garcia Amphitheater (home to a new concert series). Sign up here to walk the Excelsior-McLaren Park loop

The tiled stairway in Athens-Avalon Green Space is a neighborhood highlight. | Photo by Amy Kaeser

Walk 4: The Bayview 

Date: Saturday, October 29 at 10 a.m.

Meeting Point: Joseph Lee Recreation Center, 1598 Oakdale Avenue

Karen Rhodes’s second Crosstober walk will be a 7-mile/4-hour point-to-point walk through the Bayview, including Quesada Gardens, Nature in the City’s habitat restoration project at Palou-Phelps Mini Park, and the Calibird Pollinator Sanctuary. Walkers will continue on to Hilltop Park with its impressive sundial; Yosemite Slough, an extension of Candlestick Point State Recreation Area that’s currently under development; and Bayview Hill, with its stunning views of San Francisco and the new Bayview Letters. Walkers will make brief stops to meet several community stewards and eat lunch at a park.  Sign up here to walk the Bayview.

The Quesada Stairs are a part of the Quesada Gardens project. | Photo by Alexandra Kenin

Bonus Walk: Peak2Peak

Date: Saturday, October 8

Meeting Point: Sign up to find out about the secret route!

In addition to Crosstober, another walking event of note next month is Walk San Francisco’s annual Peak2Peak walk. On October 8, walkers will explore a 12-mile route featuring 10 different peaks. Proceeds from this walk support the walking advocacy organization. If you can’t make the in-person walk, you can also hike Peak2Peak on your own schedule with digital or printed turn-by-turn directions. Sign up here to walk Peak2Peak.

Trails with views are common in McLaren Park. | Photo by Amy Kaeser