Celebrate seven incredible years of the Crosstown Trail! This June, we are marking the milestone with a lineup of walks, adventures, and community celebrations spanning the Crosstown, Double Cross, and our brand new Roundabout route that launched last year.
Whether you are a seasoned urban walker or exploring the paths for the very first time, this is the perfect opportunity to experience fresh perspectives of San Francisco. Come connect with fellow trail enthusiasts, discover your favorite scenic stretches, and help us kick off another great year of urban trailblazing.
Browse the schedule below and secure your spot by clicking on any event title. Please note that end times are approximate based on the group pace. Tickets are $10, with all proceeds directly supporting the Crosstown Trail’s modest expenses and generous grants to local nonprofits and open space organizations along the trail routes.
ANNIVERSARY EVENTS
Golden Gate Park’s Oak Woodlands
Friday, June 5 | 4 – 6 p.m.
This walk will explore Golden Gate Park’s Oak Woodlands, San Francisco’s only designated Old Growth Forest. We’ll see and hear about the Oak Woodlands’ natural and park history and ongoing restoration efforts. The undulating route will follow the Bay Area Ridge Trail and Phil Arnold Trail for about a mile, and has some ups and downs and some steps. The Muni 33 and 5 routes serve the start and end points. Leader: Tom
The OG Crosstown: Candlestick to Forest Hill
Saturday, June 6 | 9:30 a.m. – 3:30 p.m.
Our original Crosstown Trail keeps evolving as we discover new delights across the city. We’ll head north along the southern half, about 10 miles in all. Our shoreline stroll through Candlestick Point continues through the Visitacion Valley Greenway, McLaren Park, the Bernal Cut, the Burnside mural and tiled stairway, Glen Canyon, and Laguna Honda. Finish at Forest Hill Muni Station, with multiple transit connections. Bring layers, water, snacks, and lunch. Join us on June 7 for the second half, going north to south. Leader: Karen
The OG Crosstown: Lands End to Forest Hill
Sunday, June 7 | 9:30 a.m. – 3:30 p.m.
Our original Crosstown Trail keeps evolving as we discover new delights across the city. We’ll head south along the northern half, about 9 miles in all. From Lands End, we’ll walk alongside the Pacific on the Coastal Trail, then to Baker Beach, Lobos Valley Creek, Mountain Lake, Golden Gate Park’s Rose Garden and Blue Heron Lake, and the stairway mosaics of Golden Gate Heights. Finish at Forest Hill Muni Station, with multiple transit connections. Bring layers, water, snacks, and lunch. Our start is convenient to Muni’s 38 Geary. Join us on June 6 for the first half, going south to north. Leader: Karen
Northern Waterfront Roundabout Walk
Friday, June 12 | 9:15 a.m. – 1 p.m.
Walk the most popular and scenic part of the Roundabout, from the Golden Gate Bridge to the Ferry Building, passing through Crissy Field and Presidio Tunnel Tops along the way, about 5.5 miles in all. Bring water, snacks, or lunch, and perhaps some quarters for Musee Mecanique. Arrive by the Muni 28 or multiple GG Transit lines; depart by BART or multiple Muni lines. Come early if you want Equator Coffee at the Roundhouse Cafe or time to browse the Welcome Center giftshop; both open at 9 a.m. Leaders: Double Crossers Arnie, Chris, John
The Double Cross: Fort Funston to Duboce Park
Saturday, June 13 | 9:30 a.m. – 3:30 p.m.
This urban adventure takes us from the Pacific Ocean to spectacular hilltop views and down into the heart of the city. We’ll walk two-thirds of the Double Cross from south to north, about 9.5 miles in all. Highlights include Lake Merced, Stern Grove, West Portal, Edgehill Mountain, Twin Peaks, Tank Hill, and Buena Vista Park. Finish at Duboce Park, with multiple transit connections. Bring layers, water, snacks, and lunch. Join us on June 14 for our finishing leg, from north to south. Leader: Karen
The Double Cross: Embarcadero to Duboce Park
Sunday, June 14 | 9:30 a.m. – 1:30 p.m.
Our adventure along the northern section of the Double Cross offers fresh views of San Francisco’s most iconic sights. With a transit-convenient start at the Ferry Building, we’ll walk up and over Telegraph Hill to North Beach, Chinatown, Nob Hill, City Hall, Hayes Valley, and Alamo Square, about 5 miles in all. Finish at Duboce Park, with multiple transit connections. Bring layers, water, snacks, and lunch. Join us on June 13 to walk the rest, from south to north. Leader: Karen
The Crosstown Triple Play
Monday, June 15 | 9 a.m. – 3:30 p.m.
Three trails. Three corners of the city. One urban adventure. This route weaves together segments of all three Crosstown trails. Expect a little bit of everything: hills, stairways, hidden paths, sweeping views, and neighborhood gems all bundled into a three-for-one walking experience.
The route clocks in at 13 miles with 1,263 feet of elevation gain. To get there, hop aboard the 38 Geary (make sure it’s a Rapid unless you’re in the mood for the scenic route) all the way to the end of the line at Lands End. We’ll meet at the Lands End Lookout Visitor Center at 9 am for a quick huddle before setting out. We’ll cruise south on the Roundabout through the edge of Golden Gate Park and Sunset Dunes to Fort Funston, hop onto the Double Cross through Lake Merced, Stern Grove, and West Portal, then bring it home to Glen Park on the original Crosstown.
Before hopping on BART at Glen Park Station and rolling home, we’ll celebrate our Triple Play win with cold drinks at Glen Park Station (the bar) gloriously tired, but victorious. Leader: Guy
The Crosstown Zigzag
Thursday, June 18 | 9 a.m. – 6:30 p.m.
Zig and zag with us through the northern half of the city on this mashup of all three Crosstown Trails. Think of it as a cross-sectional slice of the city: from gusty coastal bluffs to lush parks to bustling city centers, stitched together into one full-day walking tour of San Francisco.
This 20-mile urban adventure packs in 3,035 feet of elevation gain — that’s 30 floors of climbing! We’ll weave through the Presidio, Golden Gate Park, and the hidden forest in Laguna Honda before switching over to the Double Cross. We’ll summit Twin Peaks, then hop, skip, and jump through Nob Hill, Chinatown, and North Beach before strolling on a short stretch of the Roundabout on the Embarcadero to the grand finale at the Ferry Building.
We’ll grab drinks and dinner afterward at Gott’s Roadside at the Ferry Building before catching Muni or BART home from Embarcadero Station — satisfyingly tired and accomplished. Leaders: Guy and Harrison
Birds, Bay & History on the Roundabout, Section 2
Friday, June 19 | 10 a.m. – 4 p.m.
Join us on Section 2 of the Roundabout, offering fantastic opportunities to watch nature emerge from San Francisco’s heavily industrial southeast waterfront. We’ll take our time on this 8+ mile, slightly hilly, mostly sidewalk stroll through Bayview, Candlestick Point, and Little Hollywood, ending at the beautiful Visitacion Valley Greenway on Leland Avenue. We’ll honor Juneteenth by learning about these neighborhoods’ rich African American history and exciting future. Arrive early if you’d like to birdwatch along the Heron’s Head tidal marsh. Bring layers, a hat and sunscreen, good walking shoes, lunch, snacks and water, and a good spirit (there are limited food options along the route). Walk ends near several Muni stops: T Third; 8 Bayshore; 9 San Bruno. Co-sponsored by Nature in the City. Leaders: Helen and Lily
Sunset Dunes Pub Crawl
Saturday, June 20 | 4 – 8 p.m.
Take a walk on the wild westside, along the Sunset Dunes on the Roundabout Trail. Hit a couple of Outside Lands old favorites, the Riptide (built 1941), and Pitt’s Pub (various names, since 1959), with new sensation, Two Pitchers, in between. Hardy walkers/drinkers can extend to the Beach Chalet, just over 2 miles from the start. Good food options along the way. Easy transit – L Taraval, N Judah, 5, 18. Leaders: Double Crossers Arnie, Chris, John
2nd Annual Party A-Cross Town
Sunday, June 21 | 5:45 a.m. – 8:45 p.m.
The second annual Party A-Cross Town is here! Join us walking BOTH the Crosstown and Double Cross trails in a single sunrise-to-sunset push across San Francisco. It’s a strenuous, steady-paced day designed for faster walkers who are up for covering serious ground. The 32-mile route is split into four sections, so you can join for one, a few, or commit to the full double crossing. We’ll stop for lunch along the way before heading into the back half. Bring solid walking shoes, some endurance, and maybe your dad for Father’s Day. Leaders: Sevy and Liang
Hidden Nature on the Roundabout, Section 3
Sunday, June 21 | 11 a.m. – 4 p.m.
We’ll follow the sun west along Section 3 of the Roundabout on this Summer Solstice walk along the city’s southern border. We’ll find hidden parks, thriving community gardens, McLaren Park, Lake Merced, and more. This 6-7 mile mostly sidewalk walk has a few hills and some trails. Bring layers, a hat and sunscreen, good walking shoes, lunch, snacks and water, and a good spirit. Option to end at Daly City BART station (the official end of Section 3) or continue along Brotherhood Way to Lake Merced, ending at Fort Funston at the Pacific Ocean (part of Section 4). Co-sponsored by Nature in the City. Leaders: Helen and Amy
The Roundabout in a Day
Saturday, June 27 | 5:45 a.m. – 10 p.m.
Join us for the full 38-mile Roundabout in one glorious push: a steady, all-day lap around San Francisco from the Embarcadero to Hunters Point to Ocean Beach to the Golden Gate Bridge and along the northern waterfront. We’ll huddle up in front of the Ferry Building and head out at 6 a.m. sharp.
This is a big day out for walkers with solid stamina, good humor, and a high tolerance for sore feet. Expect a moderate pace (~2.5 mph) with short breaks, but enough stops to refuel and admire highlights along the way. If you’ve done an all-day hike or tackled one of the other Crosstown routes in a single go, you’ll be in good company. Come for the full 38, but if your dogs start barking too loudly, no shame in peeling off early.
This is a dawn-to-dark affair, so come prepared: dress in layers and bring a headlamp, your refillable water bottle, and plenty of food (breakfast, lunch, dinner, and snacks) to keep you moving all day. A spare pair of socks would be a wise choice. Leaders: Guy, Eric, Harrison
Crosstown Trail R.O.C.K.-a-Thon
Saturday, June 27 | 8:30 a.m. – 5 p.m.
In collaboration with the Real Options for City Kids (R.O.C.K.), Visitacion Valley Greenway, and Mission Blue, we’re excited to invite you to our third annual R.O.C.K.-a-Thon event! Check the scenic Crosstown Trail off your list while spreading awareness about R.O.C.K. and our community open spaces. Meet at the entrance of Candlestick Point State Recreation Area at 8:30 am; the walk will start promptly at 9 am. Walk the full 18 miles or any length you choose, at your own pace or at the moderate group pace. Highlights include the Visitacion Valley Greenway, where you’ll meet some R.O.C.K. students and Greenway volunteers, as well as trails through Glen Canyon and Laguna Honda, tiled staircases, the Presidio, and Baker Beach. Bring sunscreen, water, snacks, and lunch for our half-way stop. We expect to finish at the Lands End Lookout Visitor Center by late afternoon.
By RSVPing for R.O.C.K.-a-Thon, you are positively impacting 900+ youth in San Francisco’s Visitacion Valley. All event proceeds go directly back to R.O.C.K. programs, like camping trips, outdoor education, and literacy support. You’ll also receive a special R.O.C.K.-a-Thon gift and snacks! Leaders: Ken and Kellie
BART to BART Half Roundabout by Bike
Saturday, June 27 | 9 a.m. – 1 p.m.
With more ground to cover than on the two other crosstown trails, tackling the Roundabout by bike is a great fit. Bring bike, helmet, water, snacks, and money for a cafe stop or two. Station parking is free on Saturdays, or ride/BART to the start. Relatively flat, but expect a few hills, and be able to ride an 8-10 mph pace. Traffic should be light, and there are car-free stretches, but please be comfortable with urban riding. We’ll see under-the-radar gems like the Cayuga Playground, the Cow House, heartthrob Mae West’s Little Hollywood alleged hangout, the Hunters Point Shipwright’s Cottage in new India Basin Waterfront Park, and more. About 19 miles in all on this counterclockwise path, Daly City BART to Embarcadero BART. Leader: John