For one Saturday morning each October, a stretch of Sheridan's Main Street fills with superheroes, princesses, ghosts and at least one or two dinosaurs. The third annual Main Street Monster Mash, organized by the Downtown Sheridan Association, runs from 10 to 11 a.m. on Saturday, Oct. 24, 2026, with a costume contest in front of City Hall and trick-or-treating at downtown businesses afterward.
The format is simple and free. The costume contest begins at 10 a.m., with four children's age categories and, new this year, a family costume category. Local celebrity judges do the scoring. At 10:30 a.m., trick-or-treating starts along Main Street and Grinnell Plaza, where participating businesses mark themselves with small ghosts displayed on their doors or windows so families know which storefronts are handing out candy. Main Street and Grinnell Plaza close to vehicle traffic from 8 a.m. to noon.
DSA Executive Director Zoila Perry, who announced the new family category on Sheridan Media's Pulse program, said the point is less about spectacle than safety. Some activities will be available, but Perry described the goal as providing safe trick-or-treating for Sheridan's kids.
The event is younger than it looks. The DSA's Marketing and Promotions Committee announced the first Main Street Monster Mash for Saturday, Oct. 26, 2024, billing it as a way to bring together local businesses and community members for "a day of fun, festivities, and safe trick-or-treating in downtown Sheridan." That first edition followed the same template: a kids costume contest at 10 a.m. in front of City Hall, then trick-or-treating at participating businesses, with monsters in the windows marking the way.
By the second year, the event had outgrown its original footprint. Ahead of the Oct. 25, 2025 edition, organizers described an event that had drawn more than a thousand participants in its first year and was successful enough that organizers decided to make safety a bigger focus. That meant moving the costume contest to Grinnell Plaza and adding temporary road closures so families could move between storefronts without competing with traffic. Organizers said the closures would ensure a safe and festive experience for everyone.
That trajectory explains the shape of this year's event. What began as a contest in front of City Hall with trick-or-treating spilling onto the sidewalks has become a morning-long street closure, with the contest back in front of City Hall and the plaza and Main Street given over to pedestrians. The ghost markers on shop doors are a small but telling detail: they turn a scattered set of individual businesses into a single, legible route for a parent herding costumed children.
The Monster Mash fits naturally into the work of the Downtown Sheridan Association, a not-for-profit volunteer organization founded in 1985 and incorporated in 1987. The DSA follows the Main Street Program approach of the National Trust for Historic Preservation, working through four areas -- organization, promotion, design and economic restructuring -- to keep the historic district healthy. Its stated mission is to preserve, enhance and promote historic downtown Sheridan to ensure future prosperity. In 2025 the association was designated an Accredited Main Street America program, its 20th year at that level.
The setting is part of the appeal. Sheridan's Main Street Historic District was added to the National Register of Historic Places in 1982 and holds more than 60 contributing structures from the town's early decades. Trick-or-treating there means walking a route that runs past buildings older than the holiday traditions most families now associate with it. The DSA's promotion committee describes its job as promoting downtown as the center of commerce, culture and community life for residents and visitors alike -- and a Saturday morning in October, with Main Street closed and full of children, is about as literal a version of that as a town gets.
For families, the practical details are straightforward. The event is free and open to anyone who shows up in costume; no registration is mentioned. The contest starts at 10 a.m. in front of City Hall, trick-or-treating at 10:30 a.m., and the streets reopen at noon. Residents who want to help can donate unopened bags of candy at the DSA office at 121 S. Main St.
What the Monster Mash really sells, though, is a version of Halloween that happens in daylight, on foot, in the middle of town, with neighbors doing the judging. In a downtown that has spent four decades being deliberately preserved and promoted, it is a morning when the preservation work and the community it was meant to serve are visible in the same frame -- ghosts in the shop windows, a thousand small costumes on Main Street, and the street itself closed so the kids can cross it.