Things to do in Cheboygan for Halloween: Children’s Trail trick-or-treat and a fire-benefit comedy Oct. 24, downtown candy Oct. 30 and trunk-or-treats Oct. 31

CHEBOYGAN, Mich. — Cheboygan families have two weekends of Halloween ahead, starting Saturday, Oct. 24, with a free trick-or-treat party on the Cheboygan Children’s Trail and an Opera House comedy whose proceeds help northern Michigan businesses and families hit by recent fires, and ending with trunk-or-treats around town on Halloween.

The Children’s Trail party runs from 1 to 3 p.m. Oct. 24, with trick-or-treating, stories, music and door prizes, and it costs nothing, according to the Cheboygan Main Street Downtown Development Authority. The DDA lists it at Major City Park, 400 Cleveland Ave.; a separate regional listing gives a Cheboygan Point Road address, so check before heading out.

That evening at 7:30, the Fine Arts Society of Detroit brings Jerry Nehr’s new comedy “The Therapist,” about a psychotherapist who is not very good at his job, to the Cheboygan Opera House, 403 N. Huron St. Tickets run $10 to $20, according to the Northern Express calendar. The society has named four recent northern Michigan fire victims as beneficiaries of the show, among them Onaway’s 211 Bar & Grill, which burned in early October, according to Bonz Beach Farms, which is helping sell and donate tickets. The Opera House box office, 231-627-5841, is open noon to 4 p.m. Tuesday through Friday and three hours before showtime.

Earlier on Oct. 24, the Cheboygan Farmers Market sets up from 8 a.m. to 1 p.m. at Festival Square, 115 Backus St., in one of its last weeks of the season; the DDA lists one more Wednesday market on Oct. 28. Adults can try Haunted Hall Bingo Night at 6 p.m. at the Knights of Columbus hall, 9840 N. Straits Highway, according to Northern Michigan Guides. Downtown, the DDA’s Scarecrow Stroll keeps displays by local businesses, families and groups on the sidewalks through Oct. 31.

The second weekend opens Friday, Oct. 30, when downtown Cheboygan businesses hand out candy from 3 to 5 p.m., according to Northern Michigan Guides’ trick-or-treat list. From 4 to 6 p.m. that day, Faith Baptist Church, 1036 W. Western Ave., holds a trunk-or-treat with games and crafts, and Medilodge of Cheboygan, 824 S. Huron St., welcomes trick-or-treaters.

On Halloween, Saturday, Oct. 31, Kat Fisher Bait & Tackle, 9872 N. Straits Highway, hosts a trunk-or-treat from 2 to 7 p.m., and neighborhood trick-or-treating in the city runs from 5 to 8 p.m., the same guide says. Families who want a second stop can head to Mackinaw City, where the chamber of commerce holds a trunk-or-treat at Old School Park from 5 to 7 p.m.

Hours for church, business and nursing-home events are set by their hosts and can change with the weather, so it is worth checking each host’s page or calling ahead.

Sources:
Cheboygan Main Street DDA, events calendar, accessed Oct. 18, 2026, https://www.cheboyganmainstreet.org/events/
Northern Michigan Guides, “There are an Abundance of Halloween Events in Northern Michigan,” accessed Oct. 18, 2026, https://northernmichiganguides.com/halloween-trick-or-treat
Northern Express, “‘The Therapist,’” event calendar, accessed Oct. 18, 2026, https://www.northernexpress.com/calendar/2026/10/24/the-therapist/
The Cheboygan Opera House, upcoming events and box office, accessed Oct. 18, 2026, https://theoperahouse.org/
Bonz Beach Farms, “Northern Michigan Fire Benefits,” accessed Oct. 18, 2026, https://bonzbeachfarms.com/blogs/journal/northern-michigan-fire-benefits-2026
Fine Arts Society of Detroit, events, accessed Oct. 18, 2026, https://www.fineartsdetroit.org/upcoming/
Photo: rossograph, “Cheboygan Opera House.jpg,” Wikimedia Commons, CC BY-SA 4.0 (https://creativecommons.org/licenses/by-sa/4.0/), cropped and color-adjusted; derivative under the same ShareAlike license, https://commons.wikimedia.org/wiki/File:Cheboygan_Opera_House.jpg

The Straits

Tags: The Straits · Cheboygan · Halloween · Trick-or-Treat · Trunk-or-Treat · Cheboygan Opera House · Things to Do