# Halloween On the Square — Woodstock > Event for families in the Chicago–Naperville–Elgin area (IL / IN). Times are Central Time. - When: Sat, Oct 31 · 4:00 PM – 5:00 PM - Where: Park-in-the-Square (Woodstock Square), 121 W. Van Buren St, Woodstock, IL 60098 - Ages: Costume categories: 3 & Under, 4-8 Yrs, 9-13 Yrs, 14+ Yrs and Group - Price: Check official pricing - Status: Ended (last date Sat, Oct 31). - Organizer: City of Woodstock - Official page: https://woodstockil.gov/1027/Park-in-the-Square - Last checked: Tue, Oct 27 Source: Grassy Knees is a directory of real family events, places and programs for kids across major U.S. metro areas, where every listing is researched from the organizer’s own page and shows the date we last checked it. https://grassyknees.com covers 42 metro areas as of Nov 2, 2026, with more added regularly. About: https://grassyknees.com/about Freshness: listings are re-checked on a daily research run (latest check 2026-11-01), and new events are added as organizers post them. Sell-outs, weather cancellations and time changes show up on the live page first: https://grassyknees.com/chicago/activities/halloween-on-the-square-woodstock--listing-cdb82fff93157159f3a91c7c ## About The City of Woodstock's Halloween afternoon on the historic Square. From 4 to 5 p.m. children trick-or-treat at businesses around the Square, and at 4:45 p.m. a costume contest takes place at the bandstand in the Park-in-the-Square. Prizes go to the scariest, funniest and most original costumes in five categories: 3 and under, 4–8 years, 9–13 years, 14 and older, and groups. After the Square event the city recommends neighborhood trick-or-treating from 4 to 7 p.m. on October 31. The calendar entry lists no fee or registration. ## Similar picks coming up in Chicago - [Lighting of the Square — Woodstock](https://grassyknees.com/chicago/activities/lighting-of-the-square-woodstock--listing-408f8f6b59d56ced1ca9b8d9) — Fri, Nov 27 · 4:00 PM – 8:00 PM · Park-in-the-Square (Woodstock Square) · All ages · checked Oct 27. Woodstock's holiday season officially begins on the Friday after Thanksgiving, when the City of Woodstock switches on tens of thousands of lights in the trees of the… - [Nation of Nations Exhibit at Trailside Museum](https://grassyknees.com/chicago/activities/nation-of-nations-exhibit-at-trailside-museum--listing-f998983b7127780edbd035b2) — Nov 1 – Nov 30 · Trailside Museum of Natural History, River Forest · Free · checked Oct 20. For Native American Heritage Month, Trailside Museum of Natural History in River Forest hosts Nation of Nations throughout November. The exhibit celebrates the tribal diversity… - [School's Out Kids Club – Election Day](https://grassyknees.com/chicago/activities/school-s-out-kids-club-election-day--listing-59e71defb8c08854d696147f) — Tue, Nov 3 · 6:30 AM · Hunt Club Park Community Center, Gurnee · checked Oct 30. A full-day School's Out Kids Club on Election Day, a non-school day for local District 50 and 56 students. Children explore voting, leadership and teamwork, create campaigns in… - [Grinch N' Greet at the Old Courthouse — Woodstock](https://grassyknees.com/chicago/activities/grinch-n-greet-at-the-old-courthouse-woodstock--listing-ec270a30901e408e49f73d24) — Fri, Nov 27 · 4:00 PM – 6:30 PM · Old Courthouse Center — Upper Floor, Woodstock · All ages · Free · checked Oct 27. Before Woodstock's Lighting of the Square, the city turns the upper floor of the Old Courthouse Center into Whoville, where children can meet the Grinch and Cindy Lou Who. The… - [Lincoln Square Annual Tree Lighting Ceremony](https://grassyknees.com/chicago/activities/lincoln-square-annual-tree-lighting-ceremony--listing-8dca42a8b8e2a8e372476cdb) — Sat, Nov 28 · 5:00 PM – 5:30 PM · Giddings Plaza · All ages · checked Oct 30. The Lincoln Square–Ravenswood neighborhood lights its tree in Giddings Plaza after Small Business Saturday shopping: a 5:00 pm pre-show, then the lighting at 5:30 pm. Hot cider… - [Des Plaines Holiday Tree Lighting at Metropolitan Square](https://grassyknees.com/chicago/activities/des-plaines-holiday-tree-lighting-at-metropolitan-square--listing-49792044de5d4c8cd2ed9aa7) — Fri, Dec 4 · 4:30 PM – 6:30 PM · Metropolitan Square, Des Plaines · checked Oct 21. Des Plaines lights its holiday tree on the first Friday in December, which in 2026 is Friday, December 4, from 4:30 to 6:30 p.m. in Metropolitan Square on Lee Street downtown… ## More for families - [Things to do with kids in McHenry County, IL](https://grassyknees.com/chicago/counties/mchenry-county-il) (Markdown: https://grassyknees.com/chicago/counties/mchenry-county-il.md) - [This weekend in Chicago](https://grassyknees.com/chicago/this-weekend) (Markdown: https://grassyknees.com/chicago/this-weekend.md) - [Things to do with kids in Chicago](https://grassyknees.com/chicago) (Markdown: https://grassyknees.com/chicago.md)