At 3 p.m. on Saturday, Oct. 31, The Dalles Main Street opens downtown trick-or-treating, and its listing encourages younger kids to parade from business to business in costume. Eleven hours later, at 2 a.m., the 21-and-over Halloween show at Sunshine Mill Winery wraps up. Halloween lands on a Saturday this year, and in between those two times the town hands the holiday from one age group to the next. The handoffs happen at times you can plan around.
The rest of the week works the same way, starting Friday, Oct. 23. I went through the Halloween listings for The Dalles in the Columbia Gorge News 2026 roundup and on the hosts' own pages. Each event says plainly who it's for, and the earlier it starts, the younger the crowd it was built for. If you know who in your house is going, the schedule nearly sorts itself.
The audience is spelled out in each listing
These are the lines from the listings themselves:
- Wonderworks Halloween Party: best for children under 10, and scary costumes are "not encouraged to keep all children comfortable."
- Kids Story Hour at The Dalles Art Center: "not too scary" Halloween stories for preschool and elementary-age kids, with costumes encouraged but optional.
- Art Center trick-or-treat: kids fill their treat bags while adults get complimentary drinks and browse the gallery.
- Sunshine Mill Winery on Oct. 31: costumes encouraged, 21 and over, 8:30 p.m. to 2 a.m.
Read in that order, the costume rules get looser as the start times get later. The places that ask for gentle costumes are the ones that close by early evening. The one event with an age minimum doesn't start until after dark. That pattern holds across every day of the week below.
Weeknights belong to the after-school crowd
Every weeknight event on the calendar starts between 4 and 5 p.m.
Friday, Oct. 23: Grossology STEM Night, 5 to 8 p.m. at the Columbia Gorge Discovery Center & Museum, 5000 Discovery Drive. It's free. The museum promises spooky, slimy science experiments, cauldron nachos and chili, and room to show off a costume. It's the longest window of the week, and the food means you can make dinner part of the trip.
Wednesday, Oct. 28: Kids Story Hour: Halloween Fun, 4 to 5 p.m. at The Dalles Art Center, 220 E. Fourth St. The Art Center runs it with The Dalles-Wasco County Public Library: not-too-scary stories, then a themed art activity, free. The Columbia Gorge News roundup also lists a 4 p.m. Halloween story hour at the library the same afternoon, so check the location before you head out.
Thursday, Oct. 29: Trunk or Treat, 5 to 7 p.m. at Columbia Gorge Toyota & Honda, 1900 W. Sixth St. It's free, with a costume contest, a bounce house, face painting and candy. It's the only trick-or-treating of the week on the west side of town, and it comes two days before the big Saturday.
All of them end by 8 p.m., and the story hours are aimed at grade-school kids and younger. If one costume has to last the whole week, a weeknight test run before Saturday comes cheap.
Saturday, Oct. 24, opens with horses and closes with under-10s
The first Saturday makes the age-by-hour pattern easy to see in a single day.
The morning event is the Fall Fun O-Rama, listed for 10 a.m. at the Fort Dalles Riders Club, 1023 Irvine St. W. The Columbia Gorge News roundup describes a costume contest, a potluck-style fall lunch, fun classes and prizes, and asks you to bring your horse, your costume and a dish. It's the only event on the week's calendar where the horse gets a costume too. The club's own site still shows last year's listing, so the newspaper roundup is the source for the 2026 date.
The evening goes to the youngest trick-or-treaters. The Wonderworks Halloween Party runs 5 to 7 p.m. at 206 Madison St., with games, prizes, sensory play, crafts, themed activities, treats and a scavenger hunt. Admission is $5 per person, and infants and adults get in free. A parent with a toddler pays nothing for themselves, while a family of three kids pays $15, so the cost really depends on how many children you bring.
One more Saturday option sits just outside town. The Columbia Gorge Winegrowers Association's HalloWine Walk runs 1 to 5 p.m. that afternoon in downtown Hood River, if the adults want an outing while the kids rest up for Wonderworks.
Saturday, Oct. 31, hour by hour
Halloween itself compresses the whole week into one afternoon and night. Here's the schedule for The Dalles:
| Time | Event | Where | Who it's set up for |
|---|---|---|---|
| 3 to 5 p.m. | Downtown trick-or-treat, hosted by The Dalles Main Street | Downtown businesses | Younger children, encouraged to parade in costume; free |
| 4 to 6 p.m. | Trick-or-treat at The Dalles Art Center | 220 E. Fourth St. | Kids collecting treats, adults with complimentary drinks; free |
| 6:30 p.m. | Halloween party with a disco-themed costume contest | Bargeway Pub | Costume-contest crowd |
| 8:30 p.m. to 2 a.m. | The Gathering Presents: Halloween 2026 at The Mill | Sunshine Mill Winery | 21 and over; ticketed |
The two afternoon events overlap from 4 to 5 p.m., and the Art Center sits on East Fourth Street downtown. A family that starts with the Main Street businesses at 3 can move on to the Art Center's gallery for the second hour. The Art Center keeps going until 6, an hour after the business trick-or-treat ends, and by its own description it's open to all, with free admission.
The Art Center's drinks for adults are the first hint that the day is turning over. From there the schedule moves away from kids.
After the candy runs out
Bargeway Pub's party starts at 6:30 p.m., half an hour after the Art Center closes its doors. Its disco-themed costume contest is the only themed contest on the Oct. 31 schedule, which matters if your costume is still waiting on a decision.
The night ends at Sunshine Mill Winery. Viktop, Archila and Channel Freed play from 8:30 p.m. to 2 a.m., the show is 21 and over, and tickets are sold online through The Gathering Presents. It's the second Halloween event at the Mill this month. The Witches Walk weekend on Oct. 16 and 17 was scheduled to open there with a 21-and-over Masquerade Ball before the next day's parade and walk downtown.
If your evening is split, with one adult on candy duty and one heading out, the times line up neatly. Downtown and the Art Center cover 3 to 6 p.m., Bargeway takes over at 6:30, and the Mill picks up at 8:30.
The Art Center stays busy into November. Its second annual Student Art Show runs Nov. 19 to 21, with free submissions and sale proceeds going to the student artists. The Holiday Artisan Market follows, Nov. 27 through Dec. 24, featuring work by local artists and makers.
I put this schedule together because Halloween is one of the easiest weeks of the year to meet your neighbors at the curb. If you see me downtown on the 31st, come say hi. And whenever you have questions about The Dalles beyond the candy route, Tiffany Hillman is a call or text away. Contact Tiffany to start your Eastern Oregon search.
