Great Instant Urban Hikes: What They Are and How To Find Them

Updated July 2, 2025 08:57AM

The eucalyptus forest I am huffing through is a grand hall of emerald leaves, interlaced vines, and branches that feel removed from modernity. The trees are 100 feet tall, and from their uppermost limbs I hear the faint twittering of Western Sandpipers. The Jurassic vibe of the dense woodland reminds me of remote corners of the backcountry where hiking usually happens. But when I emerge from the trees, I see a subway station at the foot of the hill, and the possibility of carnitas tacos and an ice-cold Coke.

I am halfway through hiking the San Francisco Crosstown Trail. A 17-mile urban walking route across the cityscape from the docks of Candlestick Point to the seaside cliffs of Land’s End, the Crosstown Trail is a showcase of San Francisco’s overlooked natural spaces and the streets and environments that link them. It’s a curation of pre-existing walkable spaces, most of them far from the conventional tourist radar, with access to public-transit stops and restaurants along the way. The trail burrows through woodlands and canyons, ascends towering staircases, and occasionally pops by landmarks like Golden Gate Park and Baker Beach, where you can see the Golden Gate Bridge’s arches through the fog.

The Crosstown Trail was “built” in less than two years, with a budget of $600. Bob Siegel, a retired teacher and lifelong rambler who helped bring the trail to life in 2018, called the route an “Instant Urban Trail.”

“For years,” Siegel says, “I had been thinking about creating something that would get people in the city out of their neighborhoods and routines, and show them just how much more there is to explore here.” While Siegel originally discussed the idea for a connective park-to-park trail across the city with the parks department, he and fellow volunteer trail planners ultimately realized the project independently. They scouted the route, finding the connections between segments; created free maps and directions; and presented the trail on a dedicated website. Within months, the Crosstown Trail was featured in National Geographic and the New York Times.

I walked it two years ago. It was my first glimmer of the idea that you can create an urban trail without a seven-figure construction budget or the institutional buy-in of a city.

“There are hundreds of trails hidden [in] the pavement and dirt,” Siegel says. “We basically brought one to the surface.”

The day after my Crosstown traverse, waiting for my flight back to Boston, I was already imagining a trail in my hometown—studying a map of Boston, looking at adjacent parks, woods, and wetlands, and wondering if I could hike through them from the Neponset River on the city’s south edge to the Bunker Hill Monument that looms over the harbor. I spent the spring of 2022 chasing that question in the field; poking around over 30 green spaces in 17 neighborhoods, envisioning each as a chapter of a meandering urban trail with plenty of ups, downs, and rewarding lookouts. That summer, after cobbling together maps and turn-by-turn directions, I launched the website for the 27-mile Boston Walking City Trail.

Because these trails are on existing pathways that involve route connecting, pretty much anyone can invent an Instant Urban Trail.

As public interest in hiking soars, I expect more of these trails to materialize in American cities, crafted by hikers with rustic taste and civic pride. But don’t just take my word for it. Give cross-city hiking a try on any of these urban trails that range from industrious day hikes to thru-hiking adventures.

1. The Olmsted 50/70 Trails (Seattle)

Big, lush city parks as we’ve known them are originally the brainchild of Frederick Law Olmsted, the landscape architect who designed Central Park in the years after the Civil War. After Olmsted’s death in 1903, his sons kept the family business going and expanded the roster of Olmsted parks to West Coast cities. Now, in Seattle, you can hike 75 miles through some of the city’s most rustic Olmstedian work on the Olmsted 50 and 70 Trails. These co-joined Instant Urban Trails were assembled by hiking trip leaders with The Mountaineers, an outdoor recreation and conservation club, from 2022 to 2024.

Divided into 12 segments, the trails form a squiggly loop around the city, visiting beloved natural spaces like Golden Gardens Beach and lesser-known realms like the ferny trails of Ravenna Park and Interlaken Park. While the trail can be picked up and hiked from any point along the loop, the formal trailhead for Section 1 is the Ballard Locks.

King County Metro buses and light rail trains drop off and pick up from many points near the Olmsted 50 and 70 Trails.

2. The Giraffe Path (New York City)

New York City, where the birth of Central Park ignited a new era of parks and green spaces in American cities, is home to over 1,900 parks, which come in many sizes and range from playgrounds to sprawling conservation lands. The Giraffe Path, a six-mile trail through the leafier unsung gems of northern Manhattan, is an invitation to venture beyond Central Park.

On a map, the shape of the trail resembles the head and neck of a giraffe. The Giraffe Path runs north from the upper edge of Central Park to the blooming hilltop gardens of Fort Tryon Park, through hidden arboretums, cliffside paths, and staircases in Harlem and The Heights. Created by north Manhattan residents in collaboration with the city’s neighborhood health-focused CLIMB (City Life Is Moving Bodies) initiative, the Giraffe Path features serene spaces like Highbridge Park and St. Nicholas Park, with impressive city vistas, winding stone stairways, and cliffs of Manhattan bedrock bulging from the hillsides. The trail also passes lots of bodegas should you find you could use a bag of pork rinds or a new tube of sunblock.

Access: You can access the Giraffe Path by way of the MTA’s many subway and bus routes. To head north, aim for the Cathedral Parkway-110th Street subway station. Once you hit Fort Tryon Park, you can hop back on the train at 190th Street Station (which features a cool elevator ride from the hilltop park level into the depths of the subway system).

3. The Double Cross Trail (San Francisco)

If you’re still not convinced that anyone can create an Instant Urban Trail, consider this. In 2023, two fans of the San Francisco Crosstown Trail proposed a sequel: a companion trail that would run perpendicular to the original, visiting sumptuous green spaces like the grassy bluffs of Fort Funston Park and Telegraph Hill, where twisted staircases climb through passages of dense vegetation. The Crosstown Trailbuilders loved the idea and offered some advice and guidance on the “building” process. After less than a year of scouting and finessing, the Double Cross Trail debuted.

Heading northeast, the trail cuts 14 hilly miles from Fort Funston to the piers of The Embarcadero, summiting San Francisco’s 922-foot Twin Peaks in the process. It’s a slow-burn transition from the open spaces of the city’s southwest side to the skyscrapers and alleyways of downtown.

Access: As with the Crosstown Trail, Muni bus and subway stops and BART train stations offer access to multiple segments of the Double Cross Trail. To begin from Fort Funston, take the 58 bus to the John Muir Drive and Skyline Boulevard stop and make your way through Fort Funston to the observation deck: the west official trailhead. Once you reach Embarcadero Plaza, you can catch a number of trolleys and buses from The Embarcadero and Greenwich Street Station.

4. The Chicago Outerbelt (Chicago)

Chicago’s high-rises and lakefront parks are so visually iconic that they can eclipse the more ragged, quietly immersive beauty on the edges of town. Chicago is surrounded by preserved woodlands, sedge meadows, secluded beaches, and wildlife refuges like the Montrose Bird Sanctuary. And thanks to the hard work of the Outerbelt Alliance—a green-space advocacy organization founded by local outdoor enthusiasts—you can now thru-hike the fringes of the Windy City on the Chicago Outerbelt.

This 210-mile Instant Urban Trail loops around the city’s suburbs through eye-popping natural areas including the Lake County Forest Preserves and the Des Plaines River Trail, which starts near Oak Park and boasts greenery that can look downright tropical. And unlike most urban trails, tent camping is allowed at several campsites along the route. You might need to throw down for a hotel when completing the Downtown Chicago portion of the trail, but by that point, you will have earned some luxury.

Access: You can access the trail from the city by CTA buses and trains, as well as rideshares, depending on your entry point.

5. The Denver Orbital Trail (Denver)

When Michel Tormey, an American transportation planner, spent two years in the United Kingdom, he was introduced to the labyrinth of public walkways connecting town and country, and soon he started curating his own routes from existing pieces. In 2023, when Tormey moved to Denver, he decided to familiarize himself with the cityscape by creating the Denver Orbital Trail—a 177-mile loop around Denver’s boundary mountains, forests, and waterways. Scouted and mapped by Tormey alone in only 10 months, the “DOT” launched in 2024 to enthusiastic coverage from Denver media. The trail’s 28 segments run the gamut from paved greenways to steep mountain ascents with sharp dropoffs. (The total elevation gain for the DOT is an impressive 12,000-plus feet.)

“A lot of outdoorsy people often assume that being outdoorsy means driving hours away to the mountains, but I found so much to discover within the Denver metro area,” Tormey says, adding that while some parts of the cityscape aren’t going to be “pretty,” they’re still part of the broader urban environment. “There’s one piece of the Denver Orbital Trail that runs past what I believe is a cat food factory—it smells terrible, and it made my eyes water,” he says, laughing. “It’s weird and interesting and gritty, one strange moment of a big, long urban trail.”

Access: The Denver Orbital Trail’s 28 sections are reachable by RTD-Denver buses and/or rideshares.

More Urban Trails to Come, Here and Abroad

The atlas of Instant Urban Trails in America is growing year-by-year. In fact, while reporting this story, I learned about a brand-new Instant Urban Trail about to open in Providence—the PVD Crosstown Trail, with its official launch on September 28th.

The route mapping extends overseas, too. In Germany, you can hike a whopping 248 miles around Berlin on the 66 Lakes Trail, which winds through forests and meadows to visit a smorgasbord of water bodies. The Magnificent 11 in Glasgow traces a ragged loop through 11 miles of nature reserves on the city’s south side. Later this fall, I’ll be in both of these cities, on both of these trails—for work and pleasure—contemplating how each turn was chosen, and the heft of imagination it must have taken to weave the route together.

How to Make an Instant Urban Trail

Miles Howard, founder and lead organizer of the Boston’s Walking City Trail, is often seen leading groups through the forests, wetlands, beaches, and industrial zones within the greater Boston area (or recuperating at a local watering hole or ramen counter). When he’s not organizing urban hikes or trail-building projects, he writes about expanding public access to the outdoors. He publishes the hiking newsletter Mind the Moss, or you can follow him on Instagram at @milesperhoward.

Instant Urban Hikes Are Popping Up in U.S. Cities