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.
The 38-Mile Walk Around Town in a Day Maybe
Saturday, September 27 | 8 a.m. to 10 p.m.
We’ll meet in front of the Ferry Building, snap a photo, and leave at 8 a.m. sharp. We’ll follow the 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, and folks are also encouraged to join us along the way if they can track us down. Besides your 14-hour supply of food and snacks and other more standard gear, we recommend you bring a headlamp, layers, and a change of socks.
Nature on the Edge: Lands End to Tunnel Tops (1st of 3 walks)
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 (Friday, Oct. 3); Tunnel Tops to Ferry Building (Saturday, Oct. 18); and Ferry Building to Heron’s Head (Sunday, 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, a nonprofit that aims to connect everyone to nature. Sign up individually for one, two, or all three walks! This walk begins at Lands End Lookout Visitors Center.
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. We’ll meet at 8:45 a.m. in front of the Ferry Building, with a sharp 9 a.m. blast-off. This stage is about 14 miles and will take us past highlights like Bayfront Park and Sunrise Point before ending at Arleta Station (corner of Arleta and Bayshore). This run is for those who are comfortable with the 8-minute-per-mile pace. We’ll be stopping at water fountains and restrooms along the way. 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. Have you done one of the perimeter walks around San Francisco in the past? Have you done the Great Saunter in New York City? Have you run a marathon or completed an ultra trail race? This is the walk for you. We meet in front of the Ferry Building and leave at 6:30 a.m. sharp. 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. or so
We’ll meet in front of the Ferry Building to begin our 5.5-mile walk of Section 1 of the Roundabout. Our walk 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. The bus stops for Muni’s 44 O’Shaughnessy and 19 Polk are only a five-minute walk away from Heron’s Head Park.
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, 144 Leland Ave, a wonderful neighborhood spot where you can fuel up on your choice of coffee, tea, and pastries. You can pick up some Crosstown Trail merch if you like! 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 Ocean View, Merced Heights, and Ingleside. We’ll end this section at Daly City BART, where you can continue on the Roundabout or connect to public transit options to your next destination.
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. Meet at 8:45 a.m. at the Muni station at Arleta and Bayshore. 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. We’ll be stopping for water fountains and restrooms along the way. The last stage will be October 18.
The Upper Wedge Walk
Saturday, October 11 | 9 a.m. to 6 p.m.
Join the adventure! Come walk the Upper Wedge – 25 miles of epic city views, hidden corners, and iconic San Francisco sights. Meet at 9 a.m. at Levi’s Plaza to step off at 9:30 a.m. sharp. We follow the Double Cross to Twin Peaks, then pick up the Crosstown Trail, detour out to the Pacific along JFK Promenade, and then follow the Roundabout along the Golden Gate, ending at Pier 23. Bring snacks and 1+ bottle of water (hydration = happiness). Restrooms and refill stations are scattered along the route. We’ll pause 30 minutes for lunch near a bakery, grocery store, or taqueria, but BYO lunch if you prefer your own trail fuel. Want to only do a section of this long hike? Join for the start or follow along the day of and meet us at a checkpoint. Expect sweeping views, quirky neighborhoods, urban climbs, coastal breezes, and a whole lot of steps. Pro tip: comfy shoes, layered clothes, and good vibes required.
Fall Waterfront Stroll
Saturday, October 11 | 1 p.m. to 5 p.m.
Meet at the Fort Mason iron gate, Bay St and Van Ness Ave, convenient to Muni lines 49, 30, and 28, 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. Easy public transit back to the start via the Muni T and 30.
The Lands End to Ferry: Sections 5 and 6 of the Roundabout
Sunday, October 12 | 9 a.m. to 4:30 p.m.
We meet at Lands End Lookout Visitor Center, convenient to Muni’s 38 Geary, to 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. Bring layers, water, snacks, and lunch.
Stairway Gardens and More: The Excelsior and Portola Districts
Sunday, October 12 | 9:30 a.m. to 12:30 p.m.
Meet at Excelsior Playground for a 3-mile walk through the Excelsior and Portola neighborhoods, featuring brief stops at stairway gardens and greenways. We’ll visit the Athens Avalon Greenspace, one of SF’s earliest tiled stairways, followed by the Peru Avenue Stairway, with its native plant garden. We’ll climb up to McLaren Park to walk a stretch of the Philosopher’s Way. Dropping down into the Portola District, we’ll visit a colorful new mural and then SF’s latest stairway mosaic, the Steps to Wisdom at Goettingen and Dwight. We finish at the Green Between, a sliver of land along Hwy 101 that is now a hidden wonderland with gardens and art installations. At each location, you’ll meet community stewards and public artists who have transformed overlooked urban spaces into magnets for civic and cultural pride. Wear sturdy shoes and bring snacks, water, and layers. Both start and finish locations are convenient to public transit. 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. If you want to run faster, we may be able to identify a run leader for you. The run leader(s) will endeavor to stay on the official Roundabout. However, short-cutting or taking scenic detours is highly encouraged. So, enjoy the vistas, landmarks, hidden gems, treasured open spaces, etc. Please take advantage of SF’s great transit options to get to/from the run. Make sure you’ve got a plan for your hydration and nutrition. Invite friends and family to pace you or crew you. In addition to impromptu stops for filling water bottles, snacking, etc., we’ll identify some stops, with certain timing, that runners and their supporters can count on. Bring sunblock and layers. We’ll push on in light rain/wind/fog, but will be smart if the conditions turn significantly worse.
If you’d like to volunteer to support the runners, please text Mike Grade at 415-eight four six-7632.
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. Meet at 8:45 a.m. at the N Judah terminus at Ocean Beach, with a sharp 9 a.m. blast-off. 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. We’ll be stopping at water fountains and restrooms along the way. See Oct. 4 and Oct. 11 for stages 1 and 2.
Plants and Birds and Rocks and Things: Trekking the History of Glen Canyon Park
Saturday, October 18 | 9 a.m. to 11:30 a.m.
Meet under the Cow Sign at the entrance to Glen Park Recreation Center at Elk and Chenery, a 10-minute walk from Glen Park BART. 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 much 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. After the walk concludes at its beginning, you can walk back to BART and nearby restaurants via Paradise and the Glen Park Greenway, where you’ll get a chance to view the extraordinary Burnside mural and tiled staircase. To register for this walk, email GlenParkHistory@gmail.com.
Nature on the Edge: Tunnel Tops to Ferry Building (2nd of 3 walks)
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 (Friday, Oct. 3); Tunnel Tops to Ferry Building (Saturday, Oct. 18); and Ferry Building to Heron’s Head (Sunday, 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, a nonprofit that aims to connect everyone to nature. Sign up individually for one, two, or all three walks! This walk begins at the Presidio Transit Center.
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. Meet 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. Opportunity to end your day at the T streetcar in Visitacion Valley or the Glen Park BART station.
The Bird to Valley: Section 2 of the Roundabout
Wednesday, October 22 | 9 a.m. to 2 p.m. or so
We’ll meet at the entrance to Heron’s Head Park, a few minutes from the 19 Polk and 44 O’Shaughnessy stops at Jennings and Middle Point, and begin our 8.3-mile walk of Section 2. 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. Bring along water and plenty of snacks, but postpone your lunch until we finish. There, you will have the option of downing your sack lunch in the Vis Valley Greenway or grabbing your lunch at one of the local restaurants. After lunch, Muni’s 8 Bayshore can take you to Balboa Park BART, or the T streetcar can take you downtown.
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 us all three days, one or two days, or even a portion of each day. On Day 1, we meet in front of 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. Bring layers, water, snacks, and lunch. Convenient transit access throughout. See Oct. 25 and Oct. 26 for Days 2 and 3.
The Roundabout: Sections 3 and 4
Saturday, October 25 | 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 us all three days, one or two days, or even a portion of each day. 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. Bring layers, water, snacks, and lunch. Convenient transit access throughout. See Oct. 24 and Oct. 26 for Days 1 and 3.
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. Meet at the north end of the Daly City BART station, at St. Charles Ave. Bring a bike(!), helmet, water, snacks, and money for a cafe stop or two. Plenty of free Saturday parking at DC BART, or arrive by BART, SamTrans, SF Muni or bike. The route is 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. 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, the Hunters Point Shipwright’s Cottage in new India Basin Waterfront Park, 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 continues to the 16th/Moraga tiled steps. You’ll walk up perfectly named Grand View Hill, head through West Portal, and then venture on to the Dragon’s Tale tiled stairway at Miraloma Elementary School. From there, the walk transitions to rustic Glen Canyon Park before ending at Burnside’s combo mural and tiled steps. After the walk, stay for a party at the steps to celebrate the end of Stairway Month and the one-year anniversary of the Burnside Steps. Special guests at the party include 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.
Choose your own adventure as we walk the new 38-mile Roundabout around the entire city in three days. Join us all three days, one or two days, or even a portion of each day. 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. Bring layers, water, snacks, and lunch. Convenient transit access throughout. See Oct. 24 and Oct. 25 for Days 1 and 2.
Nature on the Edge: Ferry Building to Heron’s Head (3rd of 3 walks)
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 (Friday, Oct. 3); Tunnel Tops to Ferry Building (Saturday, Oct. 18); and Ferry Building to Heron’s Head (Sunday, 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, a nonprofit that aims to connect everyone to nature. Sign up individually for one, two, or all three walks! This walk begins at the Ferry Building.
The Track to Trails Trek: Section 4 of the Roundabout
Wednesday, October 29 | 9 a.m to 1:30 p.m. or so
We’ll gather at the western exit of Daly City BART, after which we’ll begin our 7.3-mile walk of Section 4. Our walk 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 and its friendly, meandering canines. 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. (At one of those coastal areas, we’ll pause for the sack lunches we packed.) To conclude our walk, we’ll stroll through Sutro Heights Park to arrive at Land’s End. Muni’s 38 will be available nearby for transport you to interior buslines, or to Montgomery BART.