Ask anyone in Ankeny about "the trail" and they mean one thing: the High Trestle, the paved run north out of Uptown toward the lit blue bridge everyone has seen on a friend's Instagram story. That's not wrong. It's also not the whole picture, and treating it like the whole picture means missing the part of Ankeny's outdoor life that actually changed in the past few years.
Two miles south of Uptown, a plain pedestrian bridge crosses Oralabor Road, one of the busiest streets in the city. It doesn't get photographed the way the High Trestle Bridge near Madrid does. But that bridge is the reason a rider or a runner can leave home in Ankeny and connect, on pavement, without a car, to three separate regional trail systems, each with a different personality and a different destination. And since 2024, that same connection point has been folded into a paved loop that runs roughly 120 miles.
What the bridge actually did
The structure is called the Oralabor Gateway connector, and it was the final piece of a three-phase build-out that started with the Ankeny Market & Pavilion trailhead and continued with a tunnel under Ankeny Boulevard. Oralabor Road carries around 30,000 vehicles a day, which made an at-grade trail crossing impractical. The city's answer was a roughly $3 million overpass, a structure weighing more than 300,000 pounds, designed with abutment framing that pays homage to the original 1912 High Trestle Bridge over the Des Moines River, the one that was demolished and replaced in the 1970s to create Saylorville Reservoir. Its former west abutment still stands as an overlook near the current, much-photographed bridge.
Nick Lenox, Ankeny's Park and Recreation Director, put the significance plainly when the bridge was under construction:
"We like to say we're quickly becoming the trail hub here in Central Iowa, as you're able to hop on the trail Gay Lea Wilson, and the Neal Smith trail, all within about a mile of each other."
The project later picked up a 2023 ACEC Iowa Engineering Excellence Honor Award and a 2025 recognition for its concrete paving work, the kind of industry validation that rarely reaches residents but confirms the build was more than a routine overpass.
Three trails, three different rides
Before the bridge, these were three trails that happened to be near each other. After it, they're one system with three distinct characters, and knowing which one you're on changes what kind of ride you get.
| Trail | Direction from the bridge | What defines it |
|---|---|---|
| High Trestle Trail | North, straight through Uptown | Rail-trail character, breweries and coffee shops along the route, ends 25 miles out at the lit High Trestle Bridge near Madrid |
| Gay Lea Wilson Trail | Southeast | Follows Four Mile Creek toward Pleasant Hill and Altoona, quieter and more residential |
| Neal Smith Trail | West via the Oralabor Gateway Trail | Runs the Des Moines River corridor north to Saylorville Lake and Big Creek State Park |
The Oralabor Gateway Trail itself, the 4.25-mile connector piece that ties the west end together, isn't a destination trail. It's infrastructure, a Portland cement concrete pathway through rural land, city parks and residential streets that exists purely to make the other three usable as one network. That's an easy thing to overlook, and it's exactly why most people don't realize the confluence exists until they ride through it by accident.
Why the math changed again in 2024
Here's the part that shifts what this bridge actually means for daily use. In 2024, a further connection stitched the Gay Lea Wilson, Oralabor Gateway and Neal Smith trails together with the Chichaqua Valley Trail and on to the Raccoon River Valley Trail, which is the longest paved loop trail in the country. The result is a continuous paved loop of roughly 120 miles, with the Oralabor Road bridge sitting inside it rather than at the edge of it.
That reframes the bridge from a local convenience to a regional entry point. A rider who starts at Glenbrooke Park, the official east trailhead for the Oralabor Gateway Trail, isn't just choosing between three in-town options anymore. They're standing at one access point on a loop that, in theory, could carry them most of the way around central Iowa's trail network without ever touching a road shoulder.
The routes worth actually knowing
For someone using this system on a normal week rather than planning an epic ride, the useful information isn't the total mileage. It's which trailhead gets you to which kind of outing.
- Start at the Ankeny Market & Pavilion (AMP) for the High Trestle Trail north. This 3.1-acre park doubles as the Uptown farmers market site and sits on the location of Ankeny's original 1912 train depot. Riders headed north pass Firetrucker Brewery and Mistress Brewing Company before reaching quieter stretches toward Sheldahl and Slater.
- Start at Carney Marsh for the Gay Lea Wilson Trail south, the most residential of the three legs, following Four Mile Creek toward Pleasant Hill and Altoona.
- Start at Glenbrooke Park or Cottonwood Recreation Area for the Oralabor Gateway Trail west, which feeds into the Neal Smith Trail along the Des Moines River toward Saylorville Lake and Big Creek State Park.
- Cross the Oralabor Road bridge itself if you want to link any two of the above without driving between trailheads, which is the entire point of the structure.
None of these routes require a car to reach from most points in Ankeny. That's a different daily-life proposition than living near "a trail," which could mean a half-mile spur that dead-ends at a subdivision. This is a network with actual regional reach.
The part that doesn't show up on a map
The bridge gets attention because it's the visible piece of infrastructure, but the reason the system works day to day is the trailhead investment around it. Porch Light Coffeehouse owner Joel Cox, whose shop opened on Southwest Third Street in 2017, described the effect of the trail and market improvements on Uptown as a "perfect storm of activity." That kind of organic business growth along a trail corridor, rather than a single flagship development, is a sign the infrastructure is actually getting used rather than just built.
It also explains why the city keeps investing in the connective tissue rather than one marquee project. The bridge over Oralabor Road doesn't have the same visual drama as the lit crossing near Madrid, and it was never going to. Its job was structural, not scenic: solve the one gap that kept three separate trail systems from functioning as one.
What this means if you already live here
If you're within biking distance of any of the three trailheads mentioned above, that gap being solved is the difference between three separate outdoor options and one connected system that happens to reach Saylorville Lake in one direction and Pleasant Hill in another. The 2024 loop connection means that system now reaches further than most residents assume, out past Chichaqua Valley and onto the Raccoon River Valley Trail, without a car ever entering the equation.
That's worth knowing whether you're training for a long ride, taking the dog for a shorter loop, or just deciding which trailhead to park at this weekend. The bridge over Oralabor Road isn't the photogenic one. It's the one that made the rest of it work.
If you're curious how trail access, walkability, or any part of daily life in Ankeny lines up with a specific neighborhood or home search, that's exactly the kind of local detail Jill Budden works through with clients every day. Live somewhere you love. Let's get started.
