Uptown Ankeny Keeps Promising a Rooftop Bar. Here's Why It's Still Not Built.

How long can a bar spend "about to expand" before the neighborhood stops asking when?

If you ride the High Trestle Trail into Uptown Ankeny with any regularity, you've probably heard some version of the Trailside Tap rooftop story. A bigger building. A rooftop bar. Three separate spaces instead of one cramped patio. The renderings have been out since early 2024. The building next door is still standing. And if you've wondered why nothing has actually moved, the answer isn't stalled paperwork or a dead deal. It's something more specific to how this corridor works right now, and it tells you more about Uptown's current rhythm than any list of new restaurant openings would.

The Building That Already Turned Over Once

The address is 710 SW Third Street, tucked at the start of the High Trestle Trail behind the Ankeny Market Pavilion. Before it was Trailside Tap, the same building briefly operated under a different name, a short-lived bar and restaurant that closed within its first year. Trailside Tap took over the space and opened in September 2020, and it's been the trail's anchor stop ever since, the place riders point to when they describe finishing a loop with a beer in hand.

Firetrucker Brewery sits right next door at 716 SW Third. The two businesses share a wall's distance and, if the expansion goes through, they'll eventually share more than that. Part of the plan calls for Trailside to offer Firetrucker's menu on-site, with easier access built between the two buildings. That's not a small detail. It's the kind of connection that only makes sense once you understand how tight this block already is and how much foot traffic it's absorbing.

What "Nearly Quadrupling" Actually Means

Trailside Tap currently runs about 2,600 square feet. The expansion plan, first reported by the Business Record, would take it to nearly 10,000 square feet, close to four times its current footprint. The plan includes an enclosed rooftop bar and an open patio, on top of the ground-floor space that's there now. Owner Jake Happe described it as giving the business three distinct spaces instead of one, with room to do things the current building simply can't fit.

To make room, a vacant house on the adjacent lot has to come down first. Happe grew up in Ankeny and has talked about riding his bike to that same building as a kid, back when it was a convenience store, so the expansion is personal as much as it is a business decision.

Here's the part that explains the timeline. When the plan was first reported in February 2024, Happe was clear that there was no fixed date:

"The timing is going to happen when it's right for us to pull the trigger."

And the reason construction keeps getting pushed isn't hesitation. It's the opposite. The patio at Trailside is busy enough, consistently enough, that tearing into construction during peak season would cost the business more in disrupted summers than it would gain by rushing the build. Happe said as much directly back in 2024: he didn't want construction interrupting the outdoor patio season, which pointed the earliest realistic window toward fall. The City of Ankeny has continued posting updates on the project into 2026, which tells you the plan is still active, just still waiting for the right off-season stretch to actually break ground.

That's a useful thing to know if you've been wondering whether the rooftop bar is real or vaporware. It's real. It's just sitting behind a business decision that only makes sense if you've seen how full that patio gets on a Saturday afternoon in July.

Meanwhile, Prairie Trail Isn't Waiting

While Uptown's biggest expansion sits in a holding pattern, The District at Prairie Trail, elsewhere in Ankeny, has already built a running calendar that doesn't wait on construction timelines. It's smaller-scale programming, but it's dated, repeating, and easy to plan a weekend around right now:

None of this replaces what Uptown offers along the trail. But it does mean the weekly pull toward Prairie Trail isn't dependent on any one business finishing a renovation. It's a calendar, not a countdown. If you're deciding where to spend a Thursday evening this month, that distinction matters more than it sounds like it should.

What This Means for Your Next Few Weekends

None of this requires you to pick a side between Uptown and Prairie Trail. It just means the two parts of Ankeny are operating on different clocks right now.

Uptown, and specifically the trail-to-tap stretch around Trailside and Firetrucker, is at its current best. The patio season Happe is protecting is the same one you get to enjoy without a single piece of construction fencing anywhere near the trailhead. If you've been meaning to ride the High Trestle Trail down into that block and grab a beer, this is the version of that experience that exists before any building work starts, whenever that ends up being.

Prairie Trail, meanwhile, is worth checking on a weekly basis rather than a seasonal one. The acoustics nights and the free yoga sessions aren't waiting on anyone's timeline. They're just there, most weeks, if you know to look.

Understanding why a business hasn't expanded yet, and reading that as a deliberate choice rather than a stall, is the kind of thing you only pick up by paying attention to a place over time. That's true of restaurant openings and expansion plans, and it's just as true when the questions get bigger, whether that's timing a home sale around a neighborhood's momentum or figuring out what a listing near a busy commercial corridor is actually worth once construction eventually starts.

If you're keeping an eye on Ankeny for reasons that go beyond where to eat this weekend, Crispin Parker has been tracking this market long enough to know which local shifts matter and which are just noise. Schedule a consultation whenever you're ready to talk through what's actually happening in your corner of Central Iowa.