Trailside Tap or Town Square: Where Ankeny Actually Spends Its Summer Nights

It's Thursday. If you live in Ankeny, that single fact already splits your evening into two very different plans, and most people who've lived here for years have never noticed why.

Head toward SW 3rd Street and you land in Uptown, where the patios at Trailside Tap and Firetrucker Brewery fill up with cyclists coming off the High Trestle Trail and regulars who've been coming for a decade. Head the other direction, out to SW District Drive, and you land at The District at Prairie Trail, where Thursday Night Acoustics is putting live music on patios across a master-planned town square tonight, August 6, and again next Thursday, August 13. Same city, same night of the week, two completely different reasons people showed up.

Uptown grew up around a trail, not a developer

Uptown Ankeny wasn't built to be a destination. It became one. Trailside Tap sits at 710 SW 3rd St, right at the start of the High Trestle Trail, in a building that used to be a gas station and, before that, a heating and cooling shop. Owner Jake Happe grew up in Ankeny riding his bike to that same corner for slushies and candy. Now he and his wife Brenna run one of Uptown's busiest bars and restaurants, and the growth came directly from trail traffic, not from a marketing plan.

That growth created a real problem: not enough room. Happe has spent the past couple of years working through plans to nearly quadruple Trailside's footprint, from about 2,600 square feet to close to 10,000, with a rooftop bar and an expanded patio, according to reporting in the Business Record. It requires tearing down a vacant house on the lot next door, working through city approvals, and waiting for the numbers to make sense before breaking ground. As Happe put it, Uptown is full of

"local people doing what they love to do."

That's the pace Uptown runs on. A few doors down, Firetrucker Brewery shares a lot line with Trailside and will eventually share a menu with it once the expansion connects the two. RynoVelo Bike Shop, a dealer for Cannondale, Cervélo, and Felt, keeps trail traffic rolling with full-service repairs. Uptown Dairy, at 617 SW 3rd St, pours affogato and stocks 57 flavors of ice cream, and hosts a breakfast event the first Saturday of every month. None of these businesses opened because a developer drew them into a site plan. They opened because the trail brought people, and the people kept coming back.

The city's own economic development office has tracked what that's done to the neighborhood: property values in Uptown have more than doubled since 2010, according to Polk County assessor data cited in City of Ankeny economic development news. That's not a headline anyone in Uptown was chasing. It's what happens when a bike trail turns a sleepy commercial strip into a place people choose to spend their evenings.

The District runs on a different clock, and a different budget

Drive a few minutes southwest and the model flips. The District at Prairie Trail sits inside a 1,031-acre planned community, and it was built from the start to host programmed entertainment, not to grow into it. NASH Nights, the free Thursday concert series presented by NASH 97.3FM, has brought touring country acts like Josh Ross with Loess Hills and Lanie Gardner with Elizabeth Mary Band to Town Square Park this summer, with gates open at 5:30 p.m. and general admission free. Sips & Songs runs a parallel Friday series of acoustic duos. Fitness in the Park brings free outdoor workouts, including a YogaSix session scheduled for Saturday, August 8.

None of that is free to produce. NASH Nights lists sponsors including a local law firm and a private company alongside the radio station, the kind of underwriting that lets The District book a full concert calendar in a single season rather than growing one patio at a time. It's a different kind of Ankeny business entirely, one where the entertainment budget shows up before the customer base does, instead of the other way around.

Here's what a Thursday actually looks like on both sides of town this week:

Neither is better. They're just built on opposite assumptions about how a place earns its crowd.

The farmers market is Uptown's real institution

If the bars are where Uptown shows its personality at night, the Uptown Ankeny Farmers Market is where it shows up on Saturday mornings, and it's been doing that far longer than either entertainment district has existed. The 2026 season runs every Saturday from May 23 through September 26, 8 a.m. to noon, under the two permanent pavilions at the Ankeny Market & Pavilion at 715 W 1st St. It's weatherproof by design and only closes for lightning or dangerous wind.

An average of 55 local vendors set up most Saturdays, drawing more than 2,500 visitors from Ankeny and the surrounding area, and this is a market with real institutional weight behind it. Uptown Ankeny Association director Alexa Middleton has written that the 2024 season was the market's 33rd, which puts 2026 in its 35th year running. Kids ride the Uptown Express train around the market, and the Market Stories program hands out free books most Saturdays. The schedule bends for the city's biggest event of the summer: this year's market moved to a Thursday evening on July 2 for the holiday week, and skipped entirely on July 11 so everyone could head to Ankeny Chamber SummerFest's Grand Parade instead.

That kind of long-running, city-embedded routine doesn't exist yet at The District. It doesn't need to. The two places aren't competing for the same role in Ankeny's calendar.

What's left before the season turns

A few things worth putting on the calendar as summer winds down:

1. Thursday Night Acoustics continues at The District through the season, including tonight and August 13.
2. The Uptown Ankeny Farmers Market runs every Saturday through September 26 at AMP.
3. The District closes out its warm-weather run with Rocktoberfest, the area's Oktoberfest celebration, on September 25.
4. Uptown's patios stay in trail-traffic mode through the fall, with Trailside Tap's expansion still working through city approvals rather than a firm construction date.

None of this requires picking a side. Most people who live here end up doing both: a Saturday morning walking the farmers market with a coffee from one of the Uptown shops, then a Thursday evening catching a free show at The District two neighborhoods over. Ankeny built room for both kinds of nights, one that grew up slow along a bike trail and one that showed up with a season's worth of sponsors already lined up. Knowing which one you're standing in just makes the evening make a little more sense.

If you're curious how these two corners of Ankeny, or any other part of Central Iowa, fit into a bigger picture of where you might want to live, Laura Major is always happy to talk it through. Let's Connect.