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 . Within months, the Crosstown Trail was featured in and the .

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 .

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)

Miles: 75

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 . These co-joined Instant Urban Trails were assembled by hiking trip leaders with , 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)

Miles: 6

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 , which come in many sizes and range from playgrounds to sprawling conservation lands. , 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)

Miles: 14

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 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)

Miles: 210

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 .

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)

Miles: 175

When Michel Tormey, an American transportation planner, spent two years in the United Kingdom, he was introduced to the 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 —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 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 , 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 , which winds through forests and meadows to visit a smorgasbord of water bodies. The 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

Creating an instant urban trail usually involves three steps.

• Make a speculative map of where the trail could run. Go out into the field and test that speculative map, poking around every featured environment along the route and finding the most scenically interesting way to pass through it.
• Once the route has been identified and vetted, you create a GPX map using or whatever wayfinding app you prefer. Ideally you type up turn-by-turn directions, so that people can have a backup navigational resource.
• Create a simple website for the trail giving these navigational resources for people to download and print. You may add teaser images and descriptions, and ideally, information about public transit connections. The Crosstown Trail pioneered this website model, and other trail builders have replicated it.
• Once your trail website is live, share it with others, including local news media.

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 , or you can follow him on Instagram at .

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Some hikes seem to transport you to another world—and others to an entirely different time. A peaceful place where you pause today may be where another once stood in defense, defeat, or determination.

I love seeking out places that connect me to peopleĚýwho passed through long before. I’ve hiked the Reef Bay Trail in the U.S. Virgin Islands and the Towpath TrailĚýin Ohio—both described below—as well as the Battle Road Trail at Minute Man National Historic Park in Massachusetts. While many national historic trails in the United States retain physical evidence of long-ago travelers, including old foundations, artifacts such as copper kettles used for colonial sugar production, or visible wagon-wheel ruts, sometimes simply feeling the same earth under our feet helps connect us to another person’s journey years or centuries ago.

See if you feel the spirit or sadness of yore as you trace the footsteps of proud high chiefs or the victims of the Donner Party disaster, while walking these incredible historic trails. They’re also in beautiful places.

1. Ala Kahakai National Historic Trail, Hawaii Island

Traverse past lava fields, ancient petroglyphs, and the landscapes of Kailua-Kona, where ruling chiefs once presided over settlements that held rituals for rain and fertility on this 175-mile corridor. The “trail by the sea” passes through four ofĚýHawaii Island’s six regions, connecting prime west-coast beaches while preserving natural and cultural components like caves and anchialine pools (enclosed water bodies with subterranean links to the sea) within lava rocks, where red shrimp and fresh water supported early communities. According to legend, one such pool (in a cave now closed to visitors)Ěýsheltered the Hawaiian princess Popoalaea when she fled from her cruel husband.

The Ala Kahakai National Historic Trail follows the stunning white-sand coastline in the 16,451-acre parcel, which in July of 2022 became part of ĚýVolcanoes National Park ($30 per vehicle). Some parts of the trail cross through private lands, but you can always access it through any of (entrance fees vary).

Three rewarding, fairly flat hikes include the 2.8-mile round-trip Kiholo Bay walk, which takes you near sea turtles, over a black sand beach, and by an anchialine pool; the bumpy 1.8-mile portion from Spencer Beach Park past the white sands of Mau’umae Beach to Waiulaula Beach; and a pleasant through lava rock and soft sand at Kaloko-Honokohau National Historic Park.

2. Donner Party Trail, Truckee, California

Revisit a harrowing moment in American history on the moderate 6.2-mile (round trip) Historic Donner Pass Trail, which wends through flat, damp railroad tunnels before ascending an exposed loop path to mountaintop views. During the winter of 1846–47, emigrants en route from Springfield, Illinois, to California were stranded for months here in the Sierra by heavy snowfall. Forty-four of the 91-person Donner Party died, and it is generally accepted that others were forced into cannibalism to survive.

The disaster occurred in part because the group followed the harsher, less traveled Hastings Cutoff route, rather than the more traditional South Pass.

The train tunnels found on the trail today were built by Chinese immigrants in the 1860s, and within them are squeaky bats and gaps overlooking the valley below. Ambitious hikers can continue beyond the last tunnel onto a steep loop trail, which traverses loose, gravelly terrain to reach sweeping views over Donner Lake. This trail is best done in summer to avoid ice and snow, and a headlamp or flashlight will help you navigate the dark tunnels. Park across the road from the first tunnel entrance at Donner Ski Ranch on Donner Pass Road. You can also join the annual led by area guides. ( are other hikes in the area as well.)

3. Nez Perce Trail, Oregon, Idaho, Wyoming, and Montana

This 1,170-mile-long memorializes the bravery of the Nez Perce,Ěýforced from their ancestral territory. In 1877, in a reversal of treaties, Chief Joseph was ordered to relocate his people from their homelands in Wallowa Valley, Oregon, to the Lapwai reservation in Idaho. The contingent, which included the elderly as well as children, was forced to cross the Snake River on May 31 during high spring runoff, and many of their livestock were lost.

Hostilities broke out shortly after on the Salmon River, and Chief Joseph, initially seeking the protection of Crow allies to the east, fled with about 750 men, women, and children on a protracted route through Idaho, Wyoming, and Montana from late June to October, with the U.S. Army on their heels.

The Army caught up to the Nez Perce at Bear Paw, Montana, where the Natives surrendered just 40 miles shy of sanctuary in Canada. Here Chief Joseph is believedĚýto have said the famous words, “From where the sun now stands, I will fight no more forever.”

The trail passes through in four states. Notable hikes include the moderate 1.25-mile loop trail around Bear Paw Battlefield; a paved 0.5-mile loop path past Idaho’s Heart of the Monster, the Nez Perce people’s sacred creation site; and the moderate five-mile (one-way) in Oregon’s site of the Snake River crossing. The trailhead is two miles north of Cow Creek bridge on Forest Road 4260.

4. Reef Bay Trail, Virgin Islands National Park, U.S. Virgin Islands

I never knew how much one valley could encapsulate the history of a place until I hiked the moderate two-mile (one way) on the island of St. John, in Virgin Islands National Park. Beginning at the Centerline Road Trailhead, you’ll descend 900 feet on a well-maintained, initially rocky trail through shady Reef Bay Valley, passing kapok trees, pinguin plants, and petroglyphs left behind by the pre-Columbian Taino (1,000-1,300 years ago to the mid 1400s). There are sugar-plantation ruins dating from the Danish occupation (1718 to 1917) and traces of post-emancipation life, such asĚýthe Par Force plantation ruins, where from 1848 to the early 1900s, 25 newly freed African Americans continued to grow sugarcane, raise livestock, and tend coconut and lime trees despite a mass population exodus from the island.

If you’re hiking on your own, turn onto the quarter-mile petroglyph spur trail on the right, about a half-mile from Reef Bay Beach, to see an ancient site where the Taino communed with their ancestors.

Although I’d made the four-mile round-trip to Reef Bay before, I recently skipped the uphill on the return by joining ($75 per person) just after a 2022 post-pandemic reboot. The tour bused our group to the trailhead and guided us down the path, at the shoreĚýboating us back to our cars on The Sadie Sea, a 37-foot Lindsey Trawler with a smooth ride and a cheerful crew.

5. The Oregon Trail, Missouri, Kansas, Nebraska, Wyoming, Idaho, Oregon, and Washington

Nostalgic millennials who played The Oregon Trail computer game during the 1990s can experience the real deal by exploring a section of the over 2,000 well-trodden miles of this , which spans six states heading west from Missouri. Witness astounding landscapes like Wyoming’s Devil’s Gate and ±·±đ˛ú°ů˛ą˛ő°ě˛ąâ€™s Chimney Rock, once important landmarks for hopeful emigrants journeying west on covered wagons from the 1830s.

±·±đ˛ú°ů˛ą˛ő°ě˛ąâ€™s ($6 for residents; $12 for non-residents) offers views of miles of rugged prairie from atop the paved Windlass Hill Trail’s steep 0.5-mile (out-and-back) trek. Here too, you can see ruts created when pioneers’ locked wagon wheels scraped the earth while the occupants carefully navigated downhill to Ash Hollow’s freshwater spring, which hikers can reach by descending the easy 0.4-mile round-trip Ash Hollow Trail.

Additional simple hikes along the Oregon Trail include Wyoming’s Register Cliff (0.4 miles round trip) and Independence Rock (a 1.3-mile loop), where you can still see name carvings left by travelers heading west.

6. Towpath Trail, Cuyahoga Valley National Park, Valley View, Ohio

This 98-mile path transports you to the 19th century, when the Ohio & Erie Canal opened up trade between the East Coast and Midwest, bringing prosperity to northeast Ohio (my home for 29 years), as well as the nation, through accessibility to domestic goods. Having always wondered what became of this ĚýI recently wandered down the Towpath Trail, a canal-side path once traversed by mules hauling cargo and people.

Starting at the Lock 38 Trailhead (a lock is a chamber that raises and lowers water levels for boats to pass), my husband and I walked the flat dirt path north along the marshy canal for 1.8 miles to reach the overgrown stone-wall remains of Lock 39. The Native American Heritage Walking Tour interpretive signs along the way described the Indigenous groups who once lived here—from the Paleoindians (13,000 to 10,000 years ago) to the Whittlesy People (1,000 to 400 years ago)—hunting big game, fishing, and growing maize and beans in Cuyahoga Valley. You can peruse exhibits at the wheelchair-friendly Canal Exploration Center, which once served as a tavern, store, and residence, and on summer weekends, the center holds lock demonstrations.

7. Chilkoot National Historic Trail, Alaska and British Columbia

The 33-mile (one way) , designated as such in 2022, chronicles a former Tlingit trading route that transformed into a busy passage during the 1897–98 Klondike gold rush. The 16.5-mile U.S. portion travels from Dyea, Alaska, to and continues over the Canadian border to Lake Bennett, British Columbia.ĚýEn route you’ll see belongings—including canvas boats, a steam boiler, and a gas-engine winch—of the former gold seekers.

Flooding in 2022 closed all but the first mile and a half on the U.S. side, but the Canadian segment of the trail remains open. Bring a buddy, pack bear spray, and be prepared for no cell service. The full hike from Dyea to Bennett, which is , Alaska, is expected to recommence in May 2024, so you can start planning now. Permits (see and are required for summer hiking, and in shoulder season you must still register for all campsites.

8. Pueblo Alto Trail, Nageezi, New Mexico

This moderate 5.1-mile in ($25 per vehicle) transports hikers backĚýa thousand years to a time when the thriving Chacoan civilization dominated Chaco Canyon. Between 850 and 1250 CE, roads emanated from this ceremonial, administrative, and cultural center, leading outward to 150 great houses (multistory buildings that were likely public spaces) in the region.

This trail, leaving from the Pueblo de Arroyo Parking Area, begins with a steep, exposed scramble before delivering sweeping mesa-top views over the San Juan Basin, and it links archeological sites such as Pueblo Alto, the impressive ninth-century, 600-room Pueblo Bonito great house, and the Chacoan steps. This remains a spiritual place for Chacoan descendants, including several Navajo clans. Because Chaco Culture National Historical Park is remote, with few amenities, bring plenty of water, dress for varying weather, and expect a bumpy ride in.

9. Unicoi Turnpike on the Trail of Tears, Coker Creek, Tennessee

This 2.5-mile (one way) trail through traces part of an ancient pass that connected the Cherokee capital of Chota, located in what is now Vonore, Tennessee, to coastal Cherokee settlements before becoming a toll road called the Unicoi Turnpike in the early 19th century. In the 1820s, the discovery of gold near Coker Creek brought an influx of white prospectors to the Cherokee Nation, prompting the U.S. government to establish Fort Armistead in a half-hearted attempt to keep the interlopers from overrunning Cherokee lands. Ironically, this fort, which is currently , became a holding area for the Cherokee in 1838 after the Indian Removal Act of 1830 compelled them to leave their fertile lands on a forced journey west.

Thus the Unicoi Turnpike became part of the Trail of Tears, a network of trails covering 5,000 miles and parts of nine states as Natives from the Southeast were displaced to present-day Oklahoma. Numbers vary, but according to the 10,000 died en route or shortly after the relocation; according to a doctor who accompanied the Cherokees estimates that 4,000, or one-fifth of them, were lost.

The free parking area and trailhead for the hikeable portion of this sit 2.9 miles southeast on County Route 40 from the Coker Creek Welcome Center.

10. Wanderer Memory Trail, Jekyll Island, Georgia

At Jekyll Island’s St. Andrews Beach Park, take this 0.5-mile family-friendly down a flat, gravel path (which is wheelchair-accessible) to learn about the history of the Wanderer, one of the last ships to smuggle enslaved Africans into the United States. The Wanderer was carrying about 400 captured people when it ran aground here on November 28, 1858. The trail’s eight exhibits take you on the ship’s perilous journey through the eyes of Umwalla, a captive African boy. This trail has received a Unesco Slave Route Project “Site of Memory” designation as a .

Linger at the park to enjoy sunset views and dolphin sightings. provides free beachgoing wheelchair use on a first-come, first-served basis (call 912-635-2368 for reservations and delivery), and a ramp at St. Andrews offers access to hard-packed sand.

All vehicles entering the island must pay a $10 daily parking fee.

Theresa McKinney lets her keen interest in history guide her travels, whether it’s navigating a new city like Copenhagen, Denmark, or exploring a new trail in Virgin Islands National Park.Ěý

For more by this author:

National Parks After Dark: 12 Best Things to Do

For more info on Gaia mapping:

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