Crosstown Trails: Crosstober 2025: New Route, Big Adventure

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Joelle Kenealey

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Sep 22, 2025, 9:32:05 PMSep 22
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Check out our newest route and join us for a guided walk, run, or bike!
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A New Route and Guided Events

Here in the Bay Area, there’s no better time of year to get outdoors than October. For Crosstober 2025, we’re unveiling the Roundabout – a route that circles the outer edge of San Francisco over an audacious 38 miles. We took our inspiration from a rag-tag band of fanatics who walk the entire perimeter of San Francisco twice a year, in the spring and fall. You can run, walk, or bike the Roundabout all at once (!) or in sections. Find your own adventure in the listings below.

You’ll also see events that take you to the Crosstown, the Double Cross, and mash-ups of several routes, as well as some “Crosstown-adjacent” happenings. We’re delighted to be a part of the second annual SF Stairway Month, hosted by the Civic Joy Fund and organized by Glen Park Beautiful. This celebration of San Francisco’s 900+ public stairways includes events every weekend that showcase our city’s love and commitment to these spaces. Two of the guided walks will be offered by Crosstown Trails volunteers, on October 12 and on October 25. Jump to SF Stairway Month for the full calendar.

Check out all the Crosstober offerings below and sign up for any event you want to join by clicking on the title link. 

CROSSTOBER EVENTS
Click event titles to learn more and sign up.

The 38-Mile Walk Around Town in a Day Maybe
Saturday, September 27 | 8 a.m. to 10 p.m.

Follow the new 38-mile Roundabout route, taking periodic short breaks plus slightly longer breaks for lunch and dinner. This group includes folks who have done a similar 33-mile perimeter walk many times, so we reckon at least a couple of us will finish the walk. We'll set a brisk pace (>3mph), trying hard to be back at the Ferry Building before Gott's closes at 10 p.m. Walkers are welcome even if they don't think they'll complete the entire walk.

Nature on the Edge: Lands End to Tunnel Tops
Friday, October 3 | 10 a.m. to 3 p.m.

Keeping the Bay in our sights, we’ll do a leisurely, nature-focused walk on three Roundabout sections over three days: Lands End to Tunnel Tops (Oct. 3); Tunnel Tops to Ferry Building (Oct. 18); and Ferry Building to Heron’s Head (Oct. 26). Join us to explore what happens where land and water meet, what the San Francisco Bay shoreline used to look like, and what changes are happening now and in the future. Co-sponsored by Nature in the City

The Rim Run: Sections 1 and 2 of the Roundabout
Saturday, October 4 | 8:45 a.m. to 11 a.m. 

First stage of a three-part perimeter run around the city. We'll follow the official route of the Roundabout at an approximately 8-minute-per-mile pace. This stage is about 14 miles and will take us past highlights like Bayfront Park and Sunrise Point before ending at Arleta Station. This run is for those who are comfortable with the 8-minute-per-mile pace. The other two stages are Oct. 11 and Oct. 18. 

The Roundabout: Do It in a Day!
Sunday, October 5 | 6:30 a.m. to 7:30 p.m.

38 miles in a day! Yay? We think the distance will result in the appropriate self-selection, but just in case: this event is extended to those people who have confidence and experience in their bodies that they can handle an almost 40-mile day. We will be brisk and efficient, including eating while walking as much as possible.

The Ferry to Heron: Section 1 of the Roundabout
Sunday, October 5 | 9 a.m. to 12:30 p.m.

This 5.5-mile walk of Section 1 of the Roundabout will include some wonderful new parks along the eastern waterfront as well as a little-known industrial corridor. After we arrive at the end of Section 1, we’ll do an out-and-back in Heron’s Head Park before sitting down for our sack lunches. 

Section 3 of the Roundabout: Visitacion Valley Greenway to Daly City BART
Sunday, October 5 | 9 a.m. to 11:30 a.m.

We'll meet at Viz Valley’s Mission Blue, a wonderful neighborhood spot where you can fuel up on your choice of coffee, tea, and pastries. On our 6-mile walk, we’ll travel through popular sites including San Francisco's second largest park, McLaren Park; pass by hidden gems like Cayuga Playground; and explore a cluster of lesser known neighborhoods on the Westside known as “the OMI” by neighbors, aka Oceanview, Merced Heights, and Ingleside.

The Rim Run: Sections 3 and 4 of the Roundabout
Saturday, October 11 | 8:45 a.m. to 11 a.m. 

Second stage of the city's perimeter run. We'll follow the official route of the Roundabout at approximately 8 minutes per mile. After a sharp 9 a.m. blast-off, we’ll run due west exploring the southern stretch of SF. This stage is about 14 miles long and will take us to our endpoint at the N Judah terminus at Ocean Beach. This run is for those who are comfortable with an 8-minute-per-mile pace. The last stage will be October 18. 

The Upper Wedge Walk
Saturday, October 11 | 9 a.m. to 6 p.m.

Come walk the Upper Wedge – 25 miles of epic city views, hidden corners, and iconic San Francisco sights. We'll follow the Double Cross to Twin Peaks, then pick up the Crosstown Trail, detour out to the Pacific along JFK Promenade, and follow the Roundabout along the Golden Gate, ending at Pier 23. Join for the start or follow along the day of and meet us at a checkpoint. Expect sweeping views, quirky neighborhoods, urban climbs, and coastal breezes.

Fall Waterfront Stroll
Saturday, October 11 | 1 p.m. to 5 p.m.

Join us for a flat 5-mile stroll along the northeast waterfront. Highlights include: Fort Mason overlooking Aquatic Park, a tour of the historic Dolphin Club with vintage wooden boats, Seaman’s Chapel at Fisherman's Wharf, the gardens atop the Klamath ferry, Herb Caen Way, the Ferry Building, promenade outside the Giants ballpark, and Willie McCovey park. We end at the decidedly casual Mariposa Hunters Point Yacht Club, where we can refresh ourselves with a cold beverage. 

The Lands End to Ferry: Sections 5 and 6 of the Roundabout
Sunday, October 12 | 9 a.m. to 4:30 p.m.

We'll walk Sections 5 and 6 of the new Roundabout, finishing at the Ferry Building. Our 11-mile route keeps the magnificent Golden Gate strait and San Francisco Bay within sight, visiting Baker Beach, the Golden Gate Bridge, Presidio Tunnel Tops, Crissy Field, Fort Mason, and SF’s northern waterfront.

Stairway Gardens and More: The Excelsior and Portola Districts
Sunday, October 12 | 9:30 a.m. to 12:30 p.m.

A 3-mile walk through the Excelsior and Portola neighborhoods, featuring stops at stairway and greenways. We’ll visit the Athens Avalon Greenspace, Peru Ave Stairway, Philosopher’s Way, a new mural, and the Steps to Wisdom at Goettingen and Dwight. At each location, you’ll meet community stewards and public artists who have transformed overlooked urban spaces into magnets for civic and cultural pride. This walk is offered through SF Stairway Month.

The Big Hug Run
Saturday, October 18 | 8 a.m. to 6 p.m.

This is a route for those who love our city! We will run the lovingly and freshly curated 38-mile Roundabout, counter-clockwise, starting at the Ferry Building and heading north and west along the Embarcadero and coming back to the Ferry Building in the afternoon, from the south. While moving, we’ll aim for a pace of around 10-12 minutes per mile. With stops, it will average roughly 14-15 minutes. Enjoy the vistas, landmarks, hidden gems, treasured open spaces.

The Rim Run: Sections 5 and 6 of the Roundabout
Saturday, October 18 | 8:45 a.m. to 11 a.m. 

Third and final stage of the city's perimeter run. We'll follow the official route of the Roundabout at an approximately 8-minute-per-mile pace. This stage is about 11 miles and will bring us back to our starting point at the Ferry Building. This run is for those who are comfortable with the 8-minute-per-mile pace. See Oct. 4 and Oct. 11 for stages 1 and 2.

Plants, Birds, Rocks & Things: Trekking the History of Glen Canyon Park
Saturday, October 18 | 9 a.m. to 11:30 a.m.

This is a short and leisurely walk, led by Evelyn Rose, founder of the Glen Park Neighborhoods History Project. The walk will be along a flat portion of the Crosstown Trail’s Section 2. You’ll learn about Glen Canyon’s natural and cultural histories, from the Ramaytush Ohlone to the site of the first dynamite factory in America, and into the 20th century when women’s moxie saved the canyon several times over. To register, email GlenPar...@gmail.com.

Nature on the Edge: Tunnel Tops to Ferry Building
Saturday, October 18 | 10 a.m. to 3 p.m.

Keeping the Bay in our sights, we’ll do a leisurely, nature-focused walk on three Roundabout sections over three days: Lands End to Tunnel Tops (Oct. 3); Tunnel Tops to Ferry Building (Oct. 18); and Ferry Building to Heron’s Head (Oct. 26). Join us to explore what happens where land and water meet, what the San Francisco Bay shoreline used to look like, and what changes are happening now and in the future. Co-sponsored by Nature in the City.

Southside Ramble
Wednesday, October 22 | 8 a.m. to 3 p.m.

Get off the beaten path with the founders of the Double Cross Trail! This will be a longer walk at an intentional pace to explore lesser known southside neighborhoods, with options to shorten your day along the way. Start at the Daly City BART station to follow the new Roundabout to Visitacion Valley, then the Crosstown Trail through Glen Canyon, and finally the Double Cross back to Forest Hill Muni.

The Bird to Valley: Section 2 of the Roundabout
Wednesday, October 22 | 9 a.m. to 2 p.m.

This is an 8.3-mile walk of Section 2 where we’ll follow pathways through the India Basin and Hunters Point parks before ascending into several Bayview parks with stunning vistas of SF and the bay. The latter half of our walk will include Candlestick State Park, the streets of Little Hollywood, and several blocks of the Visitacion Valley Greenway. 

The Roundabout: Sections 1 and 2
Friday, October 24 | 9 a.m. to 5:30 p.m.

Choose your own adventure as we walk the new 38-mile Roundabout around the entire city in three days. Join for one day or multiple days. On Day 1, we'll start at the Ferry Building to walk Sections 1 and 2. Our 13.5-mile route includes long stretches of bayside parks, from China Basin, Bayfront, and Crane Cove to Heron’s Head, India Basin Waterfront Park, and Candlestick Point. We finish at the Visitacion Valley Greenway. See below for days 2 and 3.
 

The Roundabout: Sections 3 and 4
Saturday, October 25 | 9 a.m. to 5:30 p.m.

Day 2 of the three-day Roundabout. On Day 2, we meet at Mission Blue to walk Sections 3 and 4. Our 13.5-mile route follows the city’s southern edge out to the Pacific Ocean. We visit a variety of parks and greenways, from neighborhood treasures like Cayuga Playground and Sisterhood Gardens to the expanses of Fort Funston and Sunset Dunes. There’s even a roof cow. We finish at Lands End Lookout Visitors Center. 

BART to BART Half Roundabout by Bike
Saturday, October 25 | 9 a.m. to 1 p.m.

Bike the southeastern half of the new Roundabout, Daly City BART to the Ferry Building/Embarcadero BART, about 19 miles in all. The route is relatively flat, but expect a few hills, and be able to ride an 8-10 mph pace and be comfortable with urban riding. Along the way, learn about under-the-radar gems like the Cayuga Playground carvings, the Cow House, heartthrob Mae West's Little Hollywood alleged hangout, Albion Castle, and more.

Truly Terrific: Tiled to Tiled Stairway Walk and Party
Saturday, October 25 | 9:30 a.m. to 1 p.m.

The author of Urban Trails: San Francisco will take you on a walk where you’ll be dazzled by four of San Francisco’s beautiful tiled stairways. The walk starts at the Hidden Garden Steps, then goes on to the 16th/Moraga tiled steps, Grand View Hill, West Portal, Dragon’s Tale tiled stairway, Glen Canyon Park, and Burnside’s combo mural and tiled steps. Stay for a celebration of Stairway Month and the one-year anniversary of the Burnside Steps with special guests Aileen Barr and Colette Crutcher, tile artists for these four stairways, as well as Renee Berger, founder of SF Stairway Month. This walk is offered through SF Stairway Month.

The Roundabout: Sections 5 and 6
Sunday, October 26 | 9 a.m. to 4:30 p.m.

Day 3 of our three day Roundabout. On Day 3, we meet at Lands End Lookout Visitors Center to walk Sections 5 and 6. Our 11-mile route keeps the magnificent Golden Gate strait and San Francisco Bay within sight, visiting Baker Beach, the Golden Gate Bridge, Presidio Tunnel Tops, Crissy Field, Fort Mason, and SF’s northern waterfront. We finish at the Ferry Building. See Oct. 24 and Oct. 25 for Days 1 and 2.

Nature on the Edge: Ferry Building to Heron’s Head
Sunday, October 26 | 10 a.m. to 3 p.m.

Keeping the Bay in our sights, we’ll do a leisurely, nature-focused walk on three Roundabout sections over three days: Lands End to Tunnel Tops (Oct. 3); Tunnel Tops to Ferry Building (Oct. 18); and Ferry Building to Heron’s Head (Oct. 26). Join us to explore what happens where land and water meet, what the San Francisco Bay shoreline used to look like, and what changes are happening now and in the future. Co-sponsored by Nature in the City.

The Track to Trails Trek: Section 4 of the Roundabout
Wednesday, October 29 | 9 a.m to 1:30 p.m.

Our 7.3-mile walk of Section 4 will expose a bit of Daly City (including the site of California’s last duel) and a portion of Lake Merced’s perimeter path, before reaching the sandy trails of Fort Funston. From there we will advance approximately 6 miles along the Pacific, where we’ll walk down a car-free lane of the Great Highway through Sunset Dunes Park and Golden Gate Park. Finally, we'll stroll through Sutro Heights Park to arrive at Land’s End. 


Note event end times are estimates depending on the pace of the group.

Celebrate the Trail by Volunteering with our Affiliates

Glen Park Greenway 
Saturday, October 4 | 9 a.m. to 12 p.m.
Help out the greenway the first Saturday of every month, except when holidays conflict and push the work party to the second Saturday. 

Visitacion Valley Greenway 
Saturday, October 4 | 10 a.m. to 12 p.m.
Tend the garden every fourth Saturday. Meet at the Community Garden near 141 Arleta Avenue.

SF Urban Riders 
Saturday, October 11 | 9 a.m. to about 12 p.m.
Lend a hand to the Laguna Honda Community Trail System every second Saturday of the month. 

Nature in the City 
Saturday, October 18 | 10 a.m. to 12 p.m.
Volunteer at the Green Hairstreak Corridor every third Saturday of the month, in addition to other projects at places such as the Alemany Farm. 

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