On a Saturday morning at the Trailhead Depot on Main Street, the parking lot fills from two directions instead of one. Cyclists roll in from the east, dust and dew still on their tires from the run out past the bridge toward Madrid. Others arrive dressed for a longer haul, pointed west, toward Bouton and Perry, on pavement that didn't exist here two summers ago.
For thirteen years, that second group didn't exist. The High Trestle Trail opened in April 2011 as a 25-mile ribbon connecting five towns, Ankeny, Sheldahl, Slater, Madrid, and Woodward, with its famous half-mile, 13-story bridge over the Des Moines River drawing riders east from the depot toward the spiraling steel and blue LED lighting that made the bridge a postcard image for the whole state. West of the depot, though, the trail simply stopped. You rode out, you rode back, and Woodward was the edge of the map.
That stopped being true on August 17, 2024, when a nine-mile paved connector between Perry and Woodward, running through the tiny crossroads town of Bouton, was finished with a ribbon-cutting at the Bouton trailhead. The project had been years longer in the making than planned. Snyder & Associates, the engineering firm that designed it, built the first mile and a half starting from the Perry side in the summer of 2018 and a second phase just west of Woodward in 2019, with the remaining stretch originally expected to wrap by the spring of 2022. It took until August 2024 to actually connect.
Nine miles, built in four separate phases, over roughly six years, for a connection that now takes about forty minutes to ride start to finish.
What that connector actually did was link the High Trestle Trail to the Raccoon River Valley Trail in Perry, an 89-mile paved loop that's the longest of its kind in the country. Put the two systems together and you get a continuous loop of close to 120 miles of paved trail circling this part of central Iowa. Rails to Trails Conservancy, the national trail advocacy group, marked the connection as closing what it calls "gap #45" in the planned cross-country Great American Rail-Trail, creating an unbroken stretch of trail running roughly 57 miles between the small towns of Holland and Herndon.
For a Woodward resident, the practical shift is simpler than the mileage makes it sound. Before 2024, a ride from the depot only went one useful direction: east, toward the bridge, with a turnaround built into the plan from the start. Now the depot is a hinge. East still takes you to the bridge and on toward Madrid and Ankeny. West takes you through Bouton's short stretch of residential street, the only part of the new connector that isn't fully separated from car traffic, and out into open farmland toward Perry, where the trail meets the Raccoon River Valley Trail and its own loop toward Adel, Panora, and Jefferson.
What Riding Through Town Looks Like Now
The businesses that anchor a Woodward trail day haven't changed. What's changed is which direction the riders who stop at them are coming from.
Whistlin' Donkey Sports Bar and Grill sits at the western end of the trail in Woodward, and it's the kind of stop that used to catch riders on their way back from the bridge, tired and ready for a grill menu and a patio seat. On summer weekends the bar adds live music, timed for exactly that after-ride crowd. Now it also catches a second wave, riders coming in from Perry and Bouton who've been on the road for a couple of hours and are looking at Woodward not as a turnaround but as the first town with a kitchen.
A short drive or a longer pedal from the depot, Picket Fence Creamery offers a side trip that predates the connector but makes more sense with it: a working dairy where visitors can see the cows behind the ice cream and cheese curds sold at the trailhead. It's the kind of stop that works whether someone's heading out toward the bridge or just getting off the new stretch from Perry.
On the other end of the connector, riders who make the full run into Perry have their own reward waiting. Reviewers who've ridden the new stretch describe stopping for lunch at David's Milwaukee Diner once they reach town, a detail that only makes sense now that the ride from Woodward to Perry is a single, connected trip instead of two separate outings on two separate trail systems.
A Trail That Used to Dead-End Twice
It's worth sitting with how boxed-in the old geography actually was. Riders coming from Ankeny had one direction to go: west toward Woodward and the bridge, then back. Riders on the Raccoon River Valley Trail near Perry had their own separate loop, unconnected to anything east of town. Two of the most recognized trail systems in Iowa sat within nine miles of each other for over a decade without touching.
Conservation officials tracking the High Trestle Trail have put weekly usage in the thousands of riders and walkers, a number built almost entirely on out-and-back trips to the bridge. The connector doesn't just add nine miles of new pavement. It changes what a single ride out of Woodward can be: a there-and-back to the bridge is still available, but so is a one-way run to Perry, or a loop that borrows pieces of both trail systems without a car shuttle anywhere in the plan.
The Rest of a Woodward Weekend
The trail isn't the only thing that organizes a Saturday here, even if it's become the thing that brings the most new faces through town. The Woodward Public Library on South Main Street runs its own calendar of programming a few blocks from the depot. Woodward-Granger schools anchor the community's rhythm the way they do in most small Iowa towns, with a golf course and swimming pool nearby that fill up on the same warm weekends that bring cyclists through on the trail. A few miles north, Mitigwa Scout Reservation hosts Scouting groups from across the region, including the Mid-Iowa Council's Fall Fellowship gathering each August, a reminder that Woodward's outdoor draw extends well past the trailhead.
None of that changed when the connector opened. What changed is smaller and easier to miss if you're not paying attention to which direction the bike traffic is coming from on a given Saturday: Woodward spent thirteen years as the last stop on a line that ended here, and it's spent the last two years as the point where two of the state's biggest trail systems actually meet.
The bridge still gets the postcard. The depot gets the traffic from both directions now, and that's the part of the map that actually changed.
If you're curious how a shift like this, more trail traffic, a new through-route, a town that's become a connecting point instead of an endpoint, tends to show up in how people think about property here, Andrew Bruellman is always glad to talk through what's changing in Woodward and the towns around it.
