Seven years after its opening, San Francisco’s popular Crosstown Trail is launching its first-ever Walktober, a month-long program of guided hikes and nature outings all over the city.
The festival brings together some of the Bay Area’s biggest players, including Walk San Francisco, the Bay Area Ridge Trail, and SF City Guides, for a great lineup of events from October 3 to 31, 2026.
From a casual after-work pub crawl to hilly, all-day treks, the calendar has a little bit of everything for every type of walker… here’s a closer look.
Walktober 2026
While many walks connect to the Crosstown Trail network, Walktober also introduces participants to routes that go well beyond the original trail. Events are hosted by guides from numerous partner organizations.
Some standouts include the Crosstown Trail Pub Crawl on October 6, which fits in as a nice after-wrok plan; the Muni History Walk on October 10, which traces three former Muni lines; and the “Beach to Brewery” Halloween finale on October 31, which ends with drinks at Standard Deviant Brewing.
Here’s the full lineup:
- Oct. 3: Landmark Trees along the Crosstown (10 miles)
- Oct. 3: Southern Stairway Saunter, Part 1: West Loop (15 miles)
- Oct. 4: Big Art Loop Walktober Challenge, Week 1 (1–2 miles)
- Oct. 4: Southern Stairway Saunter, Part 2: East Loop (16 miles)
- Oct. 6: Karen’s Birthday Walk: Top of the Town (8 miles)
- Oct. 6: Crosstown Trail Pub Crawl (3 miles)
- Oct. 8: Hunters Point (5.5 miles)
- Oct. 9: Presidio to Mission 250 Walk (4 miles)
- Oct. 10: Muni History Walk (6 miles)
- Oct. 10: Nature Delights on the Crosstown and Double Cross Trails
- Oct. 10: Walktober Camino Walk (6.5 miles)
- Oct. 11: Big Art Loop Walktober Challenge, Week 2 (1–2 miles)
- Oct. 11: The Eastern Wedge Walk (27+ miles)
- Oct. 11: Nature, Hills, and Stairs (5.2 miles)
- Oct. 11: Three Beaches
- Oct. 12: Bird Watching on Mount Sutro
- Oct. 15: Waterfront Walkabout: Free Art Stroll
- Oct. 17: Golden Gate Park Roundabout (8.5 miles)
- Oct. 17: Straight Up the City (11 miles)
- Oct. 18: Big Art Loop Walktober Challenge, Week 3 (1–2 miles)
- Oct. 18: Scaling the Heights: Telegraph Hill to Russian Hill (2.5 miles)
- Oct. 23: Southern Waterfront Walk with Walk SF (5 miles)
- Oct. 24: Walktober: SF Traverse (14 miles)
- Oct. 24: Truly Terrific: Tiled to Tiled Stairway Walk (5 or 8 miles)
- Oct. 24: Nurturing Nature on the Crosstown Trail
- Oct. 24: ArtSpan SF Open Studios Adventure (2–10 miles)
- Oct. 24: Visitacion Valley, McLaren Park & Excelsior (5.5 miles)
- Oct. 25: Big Art Loop Walktober Challenge, Week 4 (1–2 miles)
- Oct. 25: Full Double Cross Trail, South to North (15 miles)
- Oct. 25: ArtSpan SF Open Studios Adventure (2–10 miles)
- Oct. 25: From the Blue Water Tower to Yosemite Creek: A Watershed Ramble
- Oct. 27: All About San Francisco’s Stairways: No Walking Required!
- Oct. 30: Bernal Stairway Safari (3.3 miles)
- Oct. 31: Glen Park Gravel (3 miles)
- Oct. 31: Beach to Brewery: Far West to Far East (9.5 miles)
More about the SF Crosstown Trail
The San Francisco Crosstown Trail project connects the city through a network of parks, public paths, stairways, and neighborhood streets. It comprises a few different routes:
The original Crosstown Trail is a 17-mile route running diagonally from Candlestick Point to Lands End, crossing McLaren Park, Twin Peaks-area trails, Golden Gate Park, and more.
Its companion, the Double Cross Trail, is a 14-mile route running on the opposite diagonal from Fort Funston to the northeast waterfront at Pier 23, traveling through Lake Merced, Stern Grove, Civic Center, Chinatown, and North Beach.
The newer Roundabout route, which opened in September 2025, is a 38-mile perimeter loop which traces the outer edges of the city, starting and ending at the Ferry Building.
If you’ve never explored the SF Crosstown Trail routes, Walktober offers a great opportunity to learn about the network and connect with the city in a completely new way.
🌐 Learn more: SF Crosstown Trail / Walktober 2026