If you've lived in Ankeny for more than a summer, you've probably driven up to Madrid at least once for the postcard version of the High Trestle Trail: the bridge arcing over the Des Moines River, the kind of shot that ends up as someone's profile picture. That bridge gets the attention. It is not, however, the piece of trail infrastructure that has spent the last several years rearranging your own neighborhood.
The trail work actually reshaping Uptown sits closer to home, crosses two roads you drive every week, and has nothing to do with river views. It is also, according to the city's own Parks and Recreation director, the reason a handful of small businesses a few blocks from your house exist at all.
The three-phase build nobody outside Ankeny talks about
The project that matters locally has been built in three distinct phases, each solving a different problem than the famous bridge solves. The goal was straightforward: extend the High Trestle Trail south through town so it connects with the Gay Lea Wilson Trail and the Oralabor Gateway Trail, both of which sit on the south side of Oralabor Road. That connection also opens a direct route toward Saylorville Lake and the Neal Smith Trail, which meant the trail had to cross two of the busiest roads in Ankeny: Ankeny Boulevard and Oralabor Road.
Phase one built the trailhead in Uptown, the plaza-style space that now doubles as the home of the farmers market. Phase two took the trail under Ankeny Boulevard through a purpose-built tunnel, engineered so traffic could keep moving in both directions the entire time it was under construction. Phase three put a pedestrian bridge over Oralabor Road, a stretch of pavement that carries roughly 30,000 vehicles a day. That bridge structure alone weighs more than 300,000 pounds and cost the city about $3 million to build.
Ankeny's Park and Recreation Director, Nick Lenox, described the significance plainly when the bridge phase wrapped up:
"This project is very significant for Ankeny because it does connect three regional trails. We like to say we're quickly becoming the trail hub here in Central Iowa, as you're able to hop on the Gay Lea Wilson and the Neal Smith trail, all within about a mile of each other."
Notice what that quote is actually about. It is not about tourists riding in from Madrid to see the river bridge. It is about residents being able to get from one side of town to the other, and then out to Saylorville, without ever touching a car.
Two bridges, two very different jobs
It helps to see the contrast side by side, because the resemblance in the design is intentional even though the purpose is not the same.
| High Trestle Trail Bridge (Madrid/Woodward) | Oralabor Road Pedestrian Bridge (Ankeny) | |
|---|---|---|
| Completed | 2011 | Part of Ankeny's three-phase trail extension |
| Spans | The Des Moines River | Oralabor Road, roughly 30,000 vehicles/day |
| Design origin | New structure inspired by the 1912 High Trestle Bridge | Abutment frames modeled on the same 1912 bridge |
| Primary function | Scenic destination, regional draw | Local commuter and recreation connector |
| Who mostly uses it | Riders traveling the full trail corridor | Ankeny residents moving between neighborhoods and trail systems |
The design team that built the Oralabor bridge borrowed the abutment styling from the original 1912 High Trestle Bridge on purpose, the same structure the river crossing pays homage to. So the two bridges share a design language and a name, but one is a tourism landmark and the other is neighborhood plumbing. If you have only ever thought of "the High Trestle Trail" as the bridge in the postcards, the version doing the actual work in your daily life looks completely different and sits about twenty minutes closer to your driveway.
The businesses that bet on the local trail, not the famous one
Lenox made another point in that same conversation that's easy to miss: the trailhead the city built in Uptown, home to the Ankeny Market & Pavilion, has been drawing additional businesses along the trail. That is not a hypothetical. It already happened.
Uptown Dairy, the ice cream and coffee shop on SW 3rd Street, exists because its founder was riding the High Trestle Trail on a hot day, wanted ice cream, and didn't have anywhere nearby to get it. The shop opened directly on the trail in the original Uptown Ankeny district, built specifically to catch riders coming off the path.
A few doors down, Trailside Tap has spent years growing on the same logic. Owner Jake Happe has said the bar's business jumped once it became the default first or last stop for people riding the trail. That growth is now bumping against a ceiling. Since 2024, Happe has had plans on file with the city to raze an adjacent vacant house and expand Trailside from roughly 2,600 square feet to nearly 10,000, adding a rooftop bar and a second patio. As of the city's most recent economic development updates this year, the expansion still hasn't broken ground. Happe has been candid that the delay isn't a lack of demand, it's a matter of timing the cost correctly and not disrupting the restaurant's busiest patio season to do it. The expansion would also connect Trailside's kitchen to neighboring Firetrucker Brewery, letting the two businesses share foot traffic more directly than the current layout allows.
That's the pattern worth noticing. None of these businesses are chasing bridge tourists from Madrid. They're built around the version of the trail that runs through your own neighborhood, and they're expanding at the pace their actual, local customer base can support.
The farmers market clock is running out
The other piece of trail infrastructure doing double duty is the Ankeny Market & Pavilion itself, the 3.1-acre park at 715 W 1st Street that serves as both the trailhead and the home of the Uptown Ankeny Farmers Market. The park includes two pavilions, a restroom building, 108 parking spaces, and dedicated bicycle trailhead access, all built to handle both market crowds and trail traffic at the same time.
The market runs Saturdays from 8 a.m. to noon, May 23 through September 26, with roughly 55 vendors setting up each week. That means as of this week, there are only a handful of Saturdays left before the season wraps for the year. If a walk through the market has been on your list all summer, the window is closing fast, not reopening until next May.
What's landing before the season ends
The newest piece of this puzzle is smaller than a bridge but tells the same story. The city has been building a nearly 900-foot paved trail feature, often called a flowline, inside the Ankeny section of the High Trestle Trail park. According to Axios Des Moines reporting from earlier this year, the flowline is expected to open by the end of summer 2026, adding rolling terrain to a trail system that, until now, has mostly been flat, direct, and built for point-to-point travel rather than recreation for its own sake.
That's a small addition on paper. In context, it's another data point for the same thesis: the money and planning attention in Ankeny's trail system keeps going toward features that make the in-town network more useful and more fun for the people who already live here, not toward extending the reach of the scenic bridge up north. The bridge gets the photos. The flowline, the tunnel, and the Oralabor crossing get the daily use.
If you've been riding the trail without thinking much about how it connects, this is the season to notice. The market has a few Saturdays left, the flowline should be rideable before fall, and the businesses clustered around the trailhead didn't get there by accident.
The Mauro Team lives and works in this neighborhood too, and we like keeping an eye on the projects that quietly shape daily life here. If you ever want to talk through what's changing in Ankeny, or anywhere else in the metro, schedule your free consultation with us.
