Uptown Ankeny in Late Summer and Fall: A Resident's Guide to What's Actually on the Calendar

The strip of SW 3rd Street between the Ankeny Market & Pavilion and Cherry Street is three blocks long. From now until New Year's Eve, it will host a farmers market, a glow-in-the-dark concrete trail, a month of Halloween light displays, a four-block trunk-or-treat, a champagne stroll, more than fifty animated holiday displays, and a snowfall around a twenty-five-foot show tree. If you live within a mile of it, you already know some of this. The point of this post is the rest.

The thesis, in one paragraph

Uptown Ankeny does not really have a "peak season." The High Trestle Trail cuts straight through it, and the Uptown Ankeny Association has spent the past decade layering programming on top of that trail so the same three blocks reset every six to eight weeks. Once you learn the cadence, you stop asking "is there anything going on this weekend" and start noticing that the answer is almost always yes. What follows is the cadence, with the specific places attached to it.

The next five months at a glance

What "right now" actually looks like

The Saturday market is the load-bearing event of the summer. The 2026 Uptown Ankeny Farmers Market runs on Saturdays from 8:00 a.m. to noon starting May 23 through September 26, with vendors bringing fresh seasonal produce, home-made baked goods, specialty food items, perennial plants, and hand-made crafts. An average of about 55 local vendors sell each week, and highlights include the Uptown Express train ride for kids, live music, and the Market Stories program that hands out books to visiting children most Saturdays.

The 3.1-acre Ankeny Market and Pavilion is a trailhead for the High Trestle Trail and home of the Uptown Farmer's Market, which is why parking gets tight after 8:30 and why locals tend to walk or ride in. If you have not been down there after dark yet this summer, the other reason to go is a small piece of concrete. The concrete trail that glows in the dark is part of the first phase of Ankeny's new High Trestle Trail Experience Park. It's tough to notice a difference as you walk up to the trail, but once you stare down at it, sure enough, the concrete gives off a warm little glow. It runs 425 feet long, separate from the main trail, near SW 4th and Railroad. The City of Ankeny said the trail contains materials that take in sunlight during the day to create a glow after dark. Along the same three-quarter-mile stretch from S. Ankeny Blvd. north to W. 1st St., crews have added mounds that will one day have sculptures perched on top of them.

Thursday nights are quieter than they were a month ago. The Beats & Eats series wrapped its last event of the summer on July 25 with Blacktop Rock Band and food trucks including Brick and Ember Pizza Co, Main Street Café, and Nina's Tacos. The trail traffic is still there, just without the beer truck.

The one block of food and drink that holds it all together

Everything above only works because the businesses have followed the trail. If you had walked SW 3rd a decade ago, you would not have recognized it. Alexa Middleton, director of the Uptown Ankeny Association, grew up in Ankeny and has witnessed the neighborhood's rebirth, which started about a decade ago when the High Trestle Trail extended south into Uptown. A number of bike-friendly businesses have opened in the last ten years, many of which cater to hungry and thirsty cyclists.

The cluster now includes:

• Uptown Dairy, 617 SW 3rd St. #105. 57 flavors of ice cream, and affogato on the menu, an Italian dessert where espresso is poured over a scoop of ice cream. While affogato is mostly served with vanilla ice cream, Uptown Dairy has 32 flavor options. A breakfast event happens the first Saturday of every month with affogatos, Belgian waffles with ice cream on top, and cannoli.
• RynoVelo Bike Shop, 604 SW 3rd St. A dealer for Cannondale, Cervélo and Felt bikes, focused on higher-end, niche bikes used for triathlons or gravel rides, with a full service repair shop.
• Firetrucker Brewery, Mullets, and Porch Light Coffeehouse, all among several other eating and drinking establishments that have opened since the trail's expansion.
• Uptown Garage Brewing, whose backyard shares space with Porch Light for the outdoor cinema series.
• Pig 'n Pedal at 710 SW 3rd, positioned specifically at the trailhead. The restaurant added a 2,400-square-foot outdoor patio with fireside lounges and an outdoor bar seating up to 80, plus an area where bicyclists can park their bikes.

"We were built around a train track and that was converted into the High Trestle Trail. We were incredibly lucky to be in the right place at the right time," Middleton told DSM Bike Notes.

The reason this block matters for the fall calendar: every event listed in the table above is designed to end at, start at, or route past one of these doors. The programming assumes you will eat and drink there. That is why residents can treat Uptown as a habit rather than a destination.

October flips the switch

The transition happens fast. The last farmers market is September 26. Five days later, the lights come on. Every October, Uptown Ankeny transforms into a hauntingly fun destination, and wandering through the historic district reveals spooky light displays glowing to life every evening all month long. From ghostly ghouls to eerie pumpkins, Fright Lights sets the atmosphere for family strolls, date nights, or a spooky adventure with friends. The 2026 run is October 1 through October 31.

The big night is October 8. Uptown Ankeny's beloved Trunk-Or-Treat event is growing once more, with four blocks of trunk-or-treating, spooky tunes from DJ Big Lare, a costume contest, rides on the Uptown Express, and more surprises. Halloween In Uptown is presented by Veridian Credit Union. The costume contest has three categories, Best Single Costume, Best Group Costume, and Best Handmade Costume; check-in runs from 4–6 p.m., judging is at 6:30, and prizes are awarded at 7, with the signup booth on the Uptown Ankeny Association's front lawn at 601 SW 3rd Street. Rides on the Uptown Express are $2, cash or Venmo, with tickets sold on SW 3rd west of RynoVelo.

The Friday-night pattern in October is worth planning around too. In prior years, each Friday in October the Uptown Ankeny Outdoor Cinema has hosted a different Halloween movie from the Spooky Series in the Uptown Garage Brewing and Porch Light Coffeehouse Backyard, with movies beginning at 7:30 and lawn chairs and blankets welcome.

From November 1 to New Year's Eve

The turnaround is a matter of days. Once October 31st has passed, it's a mad dash to transform Uptown into a holiday wonderland, with Fright Lights displays coming down and Winter Wonderlights displays going up.

The main attraction: Uptown Wonderlights, more than 50 animated light displays including a light tunnel and a 25-foot show tree, in and around six blocks of SW 3rd Street and throughout the Ankeny Market and Pavilion park and along the High Trestle Trail, lit each evening from November 13 through December 31, free and open to the public on foot, by bicycle, or from your vehicle. Mullets Uptown Ankeny is the 2026 presenting sponsor.

The show tree performs a light show set to music every 30 minutes, and the light tunnel spans the High Trestle Trail. The tunnel is the thing to bring out-of-town relatives to. It garnered more than 800K Facebook impressions from one viral post in 2023.

The season closes with two more events. Every year the Winter Wonderlights displays are lit for the first time on the same night the holiday shopping season kicks off with the Champagne & Mistletoe event, with Uptown businesses open late and horse-drawn carriage rides picking up in the Ankeny Area Historical Society Museum parking lot from 5–7 p.m. The final event on the calendar is Miracle On 3rd Street, a family-focused holiday event with visits with Santa, visits with Santa's reindeer, Uptown shops open late, giveaways, hot cocoa warm-up stops, and a magical snowfall around the Uptown Ankeny Show Tree at 7 p.m.

One Saturday, front to back

If you have friends visiting for a weekend between now and September 26, here is a plan built entirely from what is already on the schedule:

1. Park at the Albaugh Family Senior Center across 1st Street, or at Ankeny First United Methodist Church across Cherry Street. Both are the market's overflow lots.
2. 8:30 a.m., walk into the market, coffee from Porch Light, breakfast from one of the prepared-food vendors.
3. Put the kids on the Uptown Express train loop while you finish the coffee.
4. 10:30, walk two blocks to Uptown Dairy for an affogato. Yes, before lunch.
5. Bike or walk 20 minutes north on the High Trestle Trail. Turn around at Irvinedale Trailhead.
6. Late lunch on the Pig 'n Pedal patio.
7. Come back after dark to stand on the 425 feet of glow trail near SW 4th and Railroad. Bring the visiting friends. They will not have seen it before.

The point

Everyone who moves here eventually realizes the same thing: the High Trestle Trail is not an amenity you drive to. It is a corridor that pulled a business district up around itself and now runs a rolling calendar of free programming past your front door for roughly nine months of the year. If you already live in Ankeny, the value of Uptown is not any single event on the list above. It is that there is always another one four to six weeks out, and you can walk to it.

When you are ready to talk about homes near this corridor, the team at Boutique Real Estate knows the blocks north and west of Uptown well and can help you match your Saturday habits to the right street.