For years, Halloween in Clarendon Hills meant one Saturday afternoon downtown. The Clarendon Hills Chamber of Commerce Halloween Walk was already listed as an annual Chamber event on the Village calendar in 2020. It returns on Saturday, Oct. 24.
This year there's a second event. The Clarendon Hills Park District is holding a new event called Boo on the Block at Prospect Park on Thursday, Oct. 29. The two events are five days apart, and each is run by a different organization in a different part of the village. The Saturday Walk leans on downtown businesses and sponsors, while the Thursday event takes place in a park and is free for residents. Halloween itself lands on Saturday, Oct. 31, so the village's Halloween season now covers most of a week.
For a family in Clarendon Hills, there are two separate events to plan for. They have different hosts, different hours, and different rules about who gets in free.
The Two Events Side by Side
| Chamber Halloween Walk | Boo on the Block | |
|---|---|---|
| Date | Saturday, Oct. 24 | Thursday, Oct. 29 |
| Organizer | Clarendon Hills Chamber of Commerce | Clarendon Hills Park District |
| Hours | Trick-or-treating 3 to 5 p.m., DJ and downtown evening 5 to 6 p.m. | 4 to 7 p.m. |
| Home base | Downtown storefronts, plus Trunk-or-Treat at the North Metra parking on Burlington Avenue | Prospect Park |
| What's there | Sponsor trick-or-treat tents, a haunted bus, trunk-or-treating | Trick-or-treating, local vendors, food trucks, inflatables, entertainment |
| Cost | No admission listed | Free for Clarendon Hills residents |
Saturday is a short afternoon downtown with an hour of music at the end. Thursday is a three-hour after-school evening in a park. They fit different weeks, and some families will go to both.
Saturday Belongs to the Storefronts
The Chamber's 2026 page splits the Walk into two parts. Trick-or-treating with local businesses runs from 3 to 5 p.m. From 5 to 6 p.m., downtown Clarendon Hills has live DJ music, and shops and restaurants stay part of the evening.
The sponsors' names are already posted:
- Birches is the 2026 presenting sponsor, and the Chamber says to look for its haunted bus.
- Clarity, Park Planners, Primrose Schools and BODY20 are hosting sponsor trick-or-treat tents.
- BIG Gymnastics and the Clarendon Hills Police Department are listed for Trunk-or-Treat at the North Metra parking on Burlington Avenue.
The downtown storefronts are organized separately. The Chamber's Downtown Business Trick-or-Treat participation page says participating businesses will appear on an event map, and it set an Oct. 10 deadline to sign up. The full list of participating businesses wasn't public at the time of writing, so the map is the guide to check once it's out. The Chamber's page doesn't mention a costume parade or contest this year. Come in costume, but don't plan around a judged event.
Since the Trunk-or-Treat is in the North Metra lot on Burlington Avenue, the afternoon has two hubs: the storefront blocks and the commuter lot by the tracks. Families who want to cover both can start at whichever end is closer and walk to the other.
Thursday Moves the Party to Prospect Park
Boo on the Block is new this year. The Park District calls it "a brand-new Halloween celebration at Prospect Park" and lists trick-or-treating, local vendors, food trucks, inflatables and "festive entertainment" for all ages, from 4 to 7 p.m. on Thursday, Oct. 29.
The Park District says the event is free for Clarendon Hills residents. The family events listing Kidlist describes it as residents-only and drop-in, with no registration needed. The Park District's own posts don't say whether nonresidents can attend or what they would pay. If cousins from Westmont or friends from Hinsdale are coming along, call the Park District before Thursday.
No food trucks or vendors have been named yet. The schedule is still easy to plan around. A 4 p.m. start on a school night leaves time to get there after school, and a 7 p.m. finish lands before bedtime for younger kids. The weekday evening also makes it a different kind of outing from Saturday's afternoon downtown.
The Thursday Slot Changes Hands
Boo on the Block also lands on the night of the week the village has used for gatherings all season. The Chamber lists the 2026 Farmers Market on Thursdays from 7 a.m. to 1 p.m., May 14 through Oct. 15, at Village Hall Plaza, 1 N. Prospect Ave. The Village calendar confirms that the final market is this Thursday, Oct. 15, during the same hours.
That leaves one more Thursday morning at the plaza before the season ends. The Chamber's list of regular vendors includes:
- Azteca Catering Co.
- Lavanaway Farms
- Hahns Bakery
- Spartan Gourmet Foods
- Maly's Foods
- Les Delices de Nic
- Lincoln Land Kettle Corn
- Flock & Field Naturals
- Boa Acai Bowls
- Dragonfly Bath and Body
- Pet Wants Hinsdale
Sew Becoming, which came on a rotating schedule all summer, is listed for Oct. 15. Cousins Maine Lobster's last listed date was Sept. 10, and Dough Bunny Bakery's last was July 30, so neither is scheduled for the final week.
Two Thursdays after the last market, the Park District's evening event takes the same night of the week at Prospect Park. After the market, Thursday becomes a Halloween night.
The Playgrounds Getting New Equipment This Fall
Prospect Park's evening event comes while two other parks are in the middle of upgrades. The Park District's renovation page says all the old playground equipment at Blackhawk Park and Steeves Park will be removed and replaced. Both projects are estimated to begin in October and finish by mid-November. The page links design plans for each playground.
Those are estimates, and the page doesn't say whether either project has started. If your after-school routine runs through Blackhawk or Steeves, the playground there could be fenced off for part of Halloween week or all of it. Check before you promise anyone a stop on the way home.
Prospect Park has its own project. The Park District hired Hitchcock Design Group to design improvements to the athletic fields there, including a renovation of Baseball Field No. 2. The page says construction would begin "approximately in August." It doesn't confirm whether work has started or how much of the park it affects. Families heading to Boo on the Block may find part of the park set aside for field work.
The renovation page also lists a longer-term master plan for Hosek Park. The preliminary plans include an accessible pathway to the sports fields, a gazebo, a basketball court renovation and a natural area overlook. The Park District says it may apply for an OSLAD grant next year to help pay for them. None of that work is on this fall's calendar.
From Now to Mid-November, in Order
- Thursday, Oct. 15: Final Farmers Market of the season, 7 a.m. to 1 p.m., Village Hall Plaza, 1 N. Prospect Ave.
- Monday, Oct. 19: An LRS e-waste event is on the Village calendar for the whole day, and the Village Board meets at 6:30 p.m.
- Saturday, Oct. 24: Chamber Halloween Walk. Trick-or-treating runs 3 to 5 p.m., followed by the DJ and downtown evening from 5 to 6 p.m. Trunk-or-Treat is at the North Metra parking on Burlington Avenue.
- Thursday, Oct. 29: Boo on the Block at Prospect Park, 4 to 7 p.m., free for Clarendon Hills residents.
- Saturday, Oct. 31: Halloween.
- By mid-November: New playground equipment at Blackhawk and Steeves parks is expected to be finished, per the Park District's estimate.
Some details aren't public yet: the downtown business map, the names of the Boo on the Block vendors and food trucks, and the Park District's policy for nonresident guests. The Chamber and the Park District are the places to watch as those dates get closer.
At The Anne Monckton Group, we track Clarendon Hills events like these because we live and work in the western suburbs too. If you'd like to talk about how the walk from your front door to Prospect Park and the Burlington Avenue storefronts adds up for your own household, book an appointment and we'll go over it with you.
