In cities across the world, outdoor enthusiasts are creating new hiking trails and organizing community hiking events built around the art of urban wayfinding. The Walking City Trail was directly inspired by one of these projects (the San Francisco Crosstown Trail) and has since inspired more like it. If you've just gotten your feet wet with urban hiking and you're hungry for more, you've come to the right place!
Here is our current roster of known urban trails and hiking events, with links to their respective websites. If you know of any others that we should add to this list, please get in touch and we'll hop right on it.
CROSSTOWN TRAIL (SAN FRANCISCO, CA)
The trail that inspired the WCT! The San Francisco Crosstown Trail runs 17 roly-poly miles across the SF cityscape, from the piers at Candlestick Point to the cliffs at Land's End. Divided into five sections, the trail features urban forests, canyons, beaches, mosaic-tiled staircases with city vistas, and neighborhoods like Visitacion Valley. (When you're passing through here, be sure to swing into Mission Blue for a damn good coffee and trail t-shirts, hats, and stickers.)
OLMSTED 50 TRAIL (SEATTLE, WA)
Frederick Law Olmsted, who essentially created the public park as we've known it in America, helped lay out a master plan for many of Seattle’s gorgeous parks and urban forests. The Olmsted 50 Trail allows you to visit many of them on a 30-mile journey from Golden Gardens Park to Rainier Beach; in five sections or in one long, ferny marathon of a hike. The route includes "off trail" landmarks like the memorial bench for Kurt Cobain in Viretta Park, on Lake Washington.
WALK AROUND PHILADELPHIA
Each fall and winter, Philly-based artist and community organizer JJ Tiziou leads walkers on a foot journey around the perimeter of the city, through landscapes that showcase the totality of Philadelphia; from ancient forests to less ancient industrial ruins. The exact route of the perimeter hike is chosen by the participants themselves. This means that no Walk Around Philadelphia is ever the same! It's an inclusive and democratic approach to epic urban wayfinding.
EAST-WEST TRAIL (WORCESTER, MA)
One of the earliest known examples of a park-to-park trail in a U.S. city, Worcester's East-West Trail snakes 14 miles across "Wootown" from the shores of Lake Quinsigamond to the more rustic woods and cascades on the west side of town. Not only does the trail navigate many curious spaces between bucolic and built environments, but it also includes signs and trail markers along most of the route; so you can spend minmal time checking the maps on your smartphone!
GIRAFFE PATH (NEW YORK, NY)
Central Park was the beginning of America's public parks, and thanks to the scouting work of Hike The Heights, you can now elevate your Manhattan parks experience and expertise by hiking through the lesser known parklands and urban wilds in The Heights. The Giraffe Path is a 6-mile city ramble from Central Park's north end to The Met Cloisters at Fort Tryon Park. And when viewed on a map, the shape of the trail resembles the neck and head of...well, a giraffe!
66 LAKES TRAIL (BERLIN, GERMANY)
The enormous perimeter of Berlin is rippling with lakes and it's entirely possible to vist more than 66 of these heavenly water bodies by walking the 66 Lakes Trail. Encircling the city in a 260 mile loop, the trail is a patchwork of forest paths and forgotten roads, and each of the trail's 17 segments can be reached by train or bus. This means that you can easily pair a day of Berlin hiking with a night of Berlin clubbing, if you want. (You'll just need to plan for an outfit change.)
STEPTREK (PITTSBURGH, PA)
Nestled in the hills of Pittsburgh are hundreds of staircases that were built to make it slightly less arduous for the city’s steel workers to commute down to the mills each day. Since then, the stairs have been reclaimed as recreational resources by Pittsburgh residents and largely preserved via grassroots organizing. Each fall, the StepTrek hike/fundraiser attracts ramblers for a curated hike up and down some of the city's most scenic and atmospheric steps.
WATERS OF LEITH (EDINBURGH, SCOTLAND)
While you don't need a shovel and a massive construction budget to create an urban trail, it's possible to take trail-building to a new level with these resources. Edinburgh's Waters of Leith walkway, a beautiful, sculpted 12-mile trail that follows the city's main river from the hills to the harbor, is an ethereal dream in trail form. You'll pass glens, cascades, historic villages, artwork, and plenty of nooks where you can grab some hearty cullen skink and a pint of Innis & Gunn.
DOUBLE CROSS TRAIL (SAN FRANCISCO, CA)
Not only can you build an urban trail in pretty much any city or suburb, but if people enjoy your trail, some of them might come up with a "sequel" to it! As is the case with the Double Cross Trail. Created by two Crosstown Trail superfans in 2023, this trail runs perpendicular to the Crosstown route, from the overlooks at Fort Funston to the Embarcadero marina. The steep steps on Telegraph Hill at the north end of the 14-mile trail are stunning at sunset.
DENVER ORBITAL (DENVER, CO)
The process of acclimating to the altitude of the Mile High City can be a gateway to getting out and experiencing its scenic wonders. On the Denver Orbital Trail , you can hike a circle around the city on 177 miles of connected paths. The gargantuan route is split into 28 segments that range from "easy" mostly level walks to full-on mountain climbing! In other words, this is the urban trail for someone who wants to discover and savor every bucolic dimension of Denver.
THE GREAT SAUNTER (NEW YORK, NY)
A classic sole-testing community hike, the Great Saunter is an epic 32-mile loop around the perimeter of Manhattan Island. Held on the first Saturday of May since 1982, the route is replete with oddities and vistas, and participants often start training for the Saunter months ahead of schedule, in hope of completing the entire traverse in 24 hours. But even if you can't make it to Manhattan for the big day, the route still makes for prime urban hiking in any season of the year.
PARK TO PLAYA TRAIL (LOS ANGELES, CA)
LA is a unique mix of mountains and ocean, and the 13-mile Park to Playa Trail is a slow-burn journey between these environments. It runs southwest from the sun-baked heights of the Baldwin Hills to the sands of Dockweiler State Beach, and along the way, you'll spend a lot of time following the Ballona Creek as it meanders through LA neighborhoods like Culver City and Del Rey. The public transit stops near the trail are numerous, as are the trail-adjacent restaurants.