Five Iconic Trails Under 50 Miles

A trail need not be over 100 miles in length to become a travel destination. Plenty of people desire shorter trail experiences and are willing to design a trip around them just the same.

by Amy Camp, Founder and Owner, Cycle Forward

Some people believe that long-distance trails corner the market in terms of destination appeal – that it takes a certain number of miles to draw a crowd. A threshold I’ve heard mentioned over the years is 100 miles. The rationale around this idea is that a trail should be long enough to put “heads in beds,” (i.e., attract people for overnight stays). As I mentioned in my book, Deciding on Trails: 7 Practices of Healthy Trail Towns, this simply does not pass the sniff test. The idea that a trail needs to be a hundred miles or more to possess destination appeal seems to imply that only people seeking long-distance trail experiences are traveling to trails. This doesn’t take into account those who desire shorter trail experiences and are willing to design a trip around them just the same.

Admittedly, multi-day trail users (whether they be “thru-trekkers” or those just taking an overnight trip or long weekend) tend to be responsible for a disproportionate amount of trail user spending. This does not mean, however, that short- and medium-distance trails are not capable of destination appeal, contributing to local and regional economies, and becoming local sources of pride. The following iconic trails and greenways prove that (with the right investment and value proposition) trails of any length are capable of destination appeal.

The High Line - New York City

1.45 miles

The High Line in New York City has arguably become one of the most known greenways in the world. The elevated park and greenway in New York’s Chelsea neighborhood, first opened in 2009 after a decade-long effort to convert an abandoned rail-line. By far the shortest route on this list, the High Line is a great example of what’s possible when we intentionally activate public spaces. A whole of bunch of stimuli are packed into a short stretch, including gardens, art installations, public programs, and free performances.

Is the High Line iconic? Yes. Has it been perfect in its implementation? No.

The greenway has been so impactful that real estate values have skyrocketed and displaced longtime residents. When I think of the powerful potential of trails and greenways, the High Line comes to mind for this reason. As fantastic as trails can be, the potential for lasting harm is real. Learn more about how the Friends of the High Line have acknowledged these issues and how they are successfully attracting more people of color to the park. And learn more about what it took to get the High Line built via this Rails to Trails Conservancy 2011 profile.

High Trestle Trail – Central Iowa

photo credit: Amy Camp

25 miles

This central Iowa rail-trail might be like any other Midwest rail-trail if not for the High Trestle Trail Bridge. This spectacular bridge spanning the Des Moines River Valley is a work of art. In addition to the views it affords, the bridge pays homage to the region’s industrial past with 41 overhead steel “frames” that represent the support cribs of a historic coal mine. The bridge is further activated by the decision to light some of those frames by night. Residents and visitors can visit the bridge year-round to see a section of the steel cribbings lighted after dark. The section, lit in blue, marks the location of the main river channel, further reinforcing the connection between the artsy bridge and the river valley it spans. Here’s a short video to give you a sense of how special the bridge is.

This is how much the bridge (and trail) mean to the nearest community, Madrid, Iowa: do a Google image search for Madrid and you will see image after image of the bridge pop up. Both the community’s sense of place and its local economy are interwoven with the High Trestle Trail.

When I visited the trail in 2015, the tour group I was with stopped by the Snus Hill Winery. The owner told me that day that the trail is so important to their business that they consider the winery to be a secondary attraction to the High Trestle Trail. He drove home his point by telling me that his first six customers that day were cyclists.

The High Trestle Trail is embraced by local communities (Madrid’s wayfinding system incorporates the shape of the bridge’s steel frames), small businesses, and regional and statewide tourism agencies. Here’s Travel Iowa’s webpage on the bridge. It includes tips for how to access the bridge, day trip ideas that include stops at local bakeries, creameries, and breweries.

Monon Trail – Indianapolis

photo credit: Amy Camp

26 miles

The Monon Trail connects towns north of Indianapolis to the city’s downtown area via the Indianapolis Cultural Trail. Used for commuting, exercise, and recreation, the paved path is promoted as “one of the best urban biking experiences in the U.S.”

When I was in the Indianapolis area
(Carmel, specifically) in 2019, I could not
miss the fact that the Monon is treated as a
regional asset. Part of the Rail-Trail Hall of
Fame, the trail was prominently featured in
a local magazine available in area hotel
rooms. And in Carmel (about 16 miles north of Indianapolis), the community has invested heavily in the trail with interesting surface treatments, fun sculptures, and a trail counter that showcases daily counts.

Trails like the Monon, the Midtown Greenway in Minneapolis, and countless others remind us that a trail’s worth is not tied solely to tourism and recreation. Trails that tie into our urban cores and suburban communities are part of our active transportation infrastructure, playing in important role in getting people from here to there. It also doesn’t hurt that they are fun and appealing and, oftentimes, do contribute to the outdoor economy.

Fundy Footpath – New Brunswick

29.5 miles

The Fundy Footpath, named one of the “50 Best Hikes in the World” by Explore Magazine, offers a combination of breathtaking coastal views and challenging terrain that will leave you trying to catch your breath and maintain your footing. The 29.5-mile wilderness trail follows the Bay of Fundy coastline between Fundy National Park and Big Salmon River. The Fundy Footpath is not

for everybody and the trail managers want people to know this. It’s a trail that calls for extensive backpacking experience and takes 4-5 days to cover it from end to end.

I was able to put my boots on the footpath in 2018, something that reminded me that even the most challenging and aspirational of trails catch the attention of people who won’t hike, bike, or paddle the entire route. We are drawn to iconic trails even if we know we won’t cover every mile.

The thing about iconic trails is that they are often located in areas in which local communities embrace the trail and foster a trail culture. These areas, too, often have other points of interest that enable visiting trail users to extend their trips. Fundy Footpath users, for example, might spend additional time along the Upper Bay of Fundy, which boasts the highest tides in the world; visit the Fundy Biosphere Reserve, a UNESCO World Heritage site; and walk among the spectacular Hopewell Rocks, which have been shaped by the tides. They might also stop through the small town of Alma for sticky buns at the local bakery or eat, drink, and lodge in the city of Moncton, being sure to catch the tidal bore when, twice a day, the tides reverse the flow of the Petitcodiac River. The lure of the footpath may be what draws backpackers to the area, but they are able to get to know the area before and after their time on the trail.

Virginia Creeper Trail – southwest Virginia

photo credit: Amy Camp

34.3 miles

The Virginia Creeper Trail offers a great example of how local business offerings can manifest an outdoor economy. Located in rural southwest Virginia, the 34-mile Virginia Creeper Trail supports seven bike shops and outfitters in a town of fewer than 800 residents. Damascus, Virginia, home to the Virginia Creeper Trail, is known as Trail Town, USA. In addition to the Creeper Trail, the Appalachian Trail passes right through town, as do other trails and routes. The community that once subsisted by extracting resources from the Blue Ridge Mountains now attributes some of its vitality to trails. Perhaps this is why town manager, Gavin Blevins, uses one of the vital organs as a metaphor: “Damascus is the heart, and each of the trails is like an artery.” Of the Virginia Creeper and Appalachian trails, he says, “One brings economic prosperity, and the other brings the cultural aspect to our community.” Blevins is referring to the Creeper Trail when he speaks of economic benefit.

One popular way to enjoy the Creeper Trail is by taking a shuttle to White Top – the trail’s high point – and cruising 17 miles to Damascus, or 34 miles to nearby Abingdon. The thrill of the “cruise” lends itself to an outdoor economy that caters to cyclists with bike rentals and shuttle rides up the mountain.

The act (or investment) of offering shuttling services has both shifted and expanded the market, putting this 34-mile trail on the map. The scenery is quite amazing, but I believe that offering a fun and easy way for people to experience the trail is what has made it such destination and expanded the typical trail user demographic. The most common age demographic for rural rail- trails is 56-65. However, according to a 2011 Virginia Tech surveyi the largest age group on the Creeper Trail is 36-45. The outfitters, by offering a service that appeals to young families, have essentially shifted the trail’s demographics.

It's estimated that 175,000 – 200,000 people use the Creeper Trail each year, a good number of them taking advantage of the shuttling services. A large percentage of these users are thought to be from out of state, including those visiting from nearby North Carolina and Tennessee. The Virginia Tech study mentioned above used both trail user and small business owner surveys to measure the impact of the Creeper Trail. According to the study, one business owner aptly stated, “There is not a business in the community that is not impacted by the trail users.” Businesses with names like Bikes and Boots Cottages, Virginia Creeper Lodge, and Trails Artware demonstrate that there is plenty of benefit spread across Damascus and its neighboring communities.

Other Notable Trails

The above-shared list is subjective, of course. You surely are aware of other trails of similar lengths that you consider to be more iconic. The intent here is to demonstrate that a trail does not need to be long-distance to attract the hearts and minds (and boots and bikes) of trail users. Here are some other trails of note:

Elroy-Sparta State Trail (32.5 miles) and Illinois Prairie Path (61 miles): These are the first two rail- trails, both located in the Midwest. The Prairie Path was proposed first, by May Theilgaard Watts in 1963, but it was Wisconsin’s Elroy-Sparta State Trail that opened first in 1965. The Prairie Path opened soon thereafter.

Iron Ore Heritage Trail (47 miles): In Marquette, Michigan, a designated IMBA Ride CenterTM and a North Country Trail Town, a network of groomed singletrack trails contribute to a year- round outdoor economy. Marquette is also located along the 47-mile Iron Ore Heritage Trail, which serves as a spine joining nine communities and connecting other trails. A trail’s role as connector is not one to be underestimated.

Ohiopyle Confluence section of the Great Allegheny Passage (11 miles): The Great Allegheny Passage is a long-distance trail of 150 miles, but that route started with the first 11 miles opened in 1986 between Ohiopyle and Confluence, Pennsylvania. It’s one of the busiest and most iconic sections of the GAP. It’s no wonder one of the trail’s guidebooks calls this stretch of trail “The Original.”

Pike 2 Bike (8.5 miles): This central Pennsylvania unimproved trail may not be iconic, but its offer certainly is original. The route follows 8.5 miles of abandoned Pennsylvania turnpike. Its old tunnels and deteriorated roadbed make for a bumpy, fun, ride. Local trail advocates hope to make infrastructure improvements to further capitalize on the trail’s potential.

The Whole Enchilada (26.5 miles): Technically a combination of two trails, this route in mountain biking Mecca, Moab, Utah, allow for 7,000 feet of down hill riding. As with the shuttlers along the Creeper Trail, local companies (including one named for the trail – the Whole Enchilada Shuttle Company) are ready and willing to accommodate.


Many of these trails have been inducted into the Rails to Trails Conservancy’s Rail-Trail Hall of Fame. Learn more about trails of all lengths that have been inducted into the Hall.

About the Author

Amy Camp founded Cycle Forward in 2013 with the plan to help communities better connect to and benefit from their trails. She is a trails and tourism consultant, a placemaker, and a certified coach. She helped to launch the nationally recognized Trail Town Program® in 2007. She has since offered her consulting services throughout Appalachia, the Rust Belt, and other locations in the U.S. and Canada. Her book, Deciding on Trails: 7 Practices of Healthy Trail Towns, was published in December 2020. Amy served on the Board of American Trails from 2012-17, acting as Board Secretary and Chair of the Hulet Hornbeck Emerging Leaders Scholarship Program. She is an Associate Certified Coach through the International Coach Federation and firmly believes that her coaching certification makes her a better consultant. Amy lives in Pittsburgh, Pennsylvania, where she first grew to love communities and began her work to help improve them.

Contact: [email protected]

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