Halloween in Chicagoland: What's Actually Happening This October
5 min readActive Chicagoland
Our directory is built around recurring programs — the weekly chair-yoga class, the standing Thursday chess club. Halloween doesn't work that way. It's one month, a handful of dates, and then it's over for a year. So instead of a permanent category, here's a dated roundup: what's actually happening across Chicagoland this October, verified against each event's own source.
Most of this isn't "senior programming" in the usual sense — it's just genuinely open to everyone, including grandparents who want to hand out candy, watch a parade, or wander a glowing pumpkin garden. We've flagged accessibility where it matters and called out the few events built specifically for 55+.
Built for 55+
All three are Chicago Park District events, part of its citywide fall programming.
🏓 Halloween Pickleball Boo Bash
Sheil Community Center Park · Lakeview, Chicago
Tuesday, October 27, 9:30am–2pm · $10
A costume-optional pickleball tournament just for adults 55+, run by the Chicago Park District. Bring your own paddle or borrow one on-site.
Source & details →🎃 Halloween Party
Grand Crossing Park · Greater Grand Crossing, Chicago
Thursday, October 29, 11am–2pm · Free
A senior-focused Halloween party in the park, with costumed characters and the usual park-district warmth. No registration mentioned — just show up.
Source & details →🍿 Halloween Bash
Kennedy Park · West Lawn, Chicago
Thursday, October 29, 4–7pm · Free
Games, contests, candy, prizes, and a Halloween movie with popcorn — a relaxed evening option if the daytime parties don't fit your schedule.
Source & details →Open to Everyone, Worth Going To
None of these are senior events specifically — they're just good, and good to know about.
🎃 Night of 1,000 Jack-o'-Lanterns
Chicago Botanic Garden · Glencoe
Select evenings through October 25, 6:30–10:30pm · $20 member / $24 nonmember (timed tickets)
More than 1,000 hand-carved pumpkins light up the Garden after dark, including show-stoppers up to 150 pounds, plus live carving and costumed performers.
Flat, paved paths throughout — one of the more genuinely accessible evening events on this list, though it does get crowded on weekends.
Source & details →🏺 Glass Pumpkin Patch & Fall Color Festival
The Morton Arboretum · Lisle
Glass Pumpkin Patch: October 9–11. Fall Color Festival events run through October 31. · Included with general admission
More than 8,000 hand-blown glass pumpkins on the West Lawn, with live glassblowing demonstrations, alongside the Arboretum's broader fall-color programming.
Wheelchair rentals and multiple paved accessible trails on-site, plus the Acorn Express tram tour for anyone who'd rather ride than walk the grounds.
Source & details →🌽 St. Charles Scarecrow Weekend
Downtown St. Charles
October 9–11, Fri 12–6pm, Sat 10am–6pm, Sun 10am–5pm · Free
The 41st annual edition: more than 85 handmade scarecrows line the downtown streets for viewing and voting, alongside vendors and live music.
A flat, walkable downtown river district — easy to cover at any pace, with plenty of benches and places to sit along the way.
Source & details →🚙 La Grange Trunk-or-Treat
Sedgwick Park · La Grange
Saturday, October 10, 10am–12pm · Free
A community trunk-or-treat with games and activities — the kind of small, walkable neighborhood event that's as much about seeing your neighbors as it is about candy.
Source & details →🎭 Arts in the Dark Halloween Parade
Columbus Drive, Grant Park · Chicago
Saturday, October 24, 6–8pm · Free, no tickets required
Chicago's official Halloween parade in its 12th year — giant spectacle puppets, elaborate floats, and performances from local arts groups, drawing a crowd of around 100,000.
A spectator event, not a walking one, so mobility isn't a barrier — but it is genuinely crowded. Arrive early for curb space if standing for a while is a concern.
Source & details →⚰️ Forest Park Casket Races
Beloit Ave. between Madison & Adams · Forest Park
Saturday, October 24, 9:30am–12:30pm (racing starts 11am) · Free to watch; $40 per team to race
The 14th annual edition of exactly what it sounds like: teams race homemade caskets down the street, competing for "most frightfully funny," "creepiest," and "dead last." A kids-and-pets costume parade runs before the final heats, with food vendors from 9:30am. Easily the most purely fun entry on this list.
A sidewalk spectator event on a flat street — no walking required to watch, and benches/vendor seating are typically available along the route.
Source & details →A Note on Timing
This list is current as of October 7, 2026. Some of these events run on a single weekend — check the source link before heading out, since hours and dates occasionally shift. If you're reading this well after October 2026, most of these are annual events and will likely return next fall, just not necessarily on the same dates.
Know a Halloween or fall event in your town we missed — especially a senior-specific one? Tell us.