Halloween lands on a Saturday this year, but most of Naperville's one-time Halloween events happen the weekend before. From Friday, October 23, through Sunday, October 25, Naper Settlement, the Naperville Park District, the Downtown Naperville Alliance and the Turning Pointe Autism Foundation run six separate Halloween events, two of them on more than one day. Halloween itself adds just two events of its own, a farmers market parade in the morning and a carillon concert at night. Trick-or-treating fills the hours between, and the city sets no official times for it.
If you're reading this on Thursday, the big weekend starts tomorrow. Families who wait for the 31st will miss most of the one-day events.
Friday and Saturday: The Settlement Hosts Two Different Crowds
Naper Settlement at 523 S. Webster St. carries more of the early weekend than any other venue, and on Saturday it hosts two audiences on the same grounds within hours of each other.
Howlin' at the Moon, its 21-and-over Halloween party, runs from 5 to 10 p.m. on both Friday, October 23, and Saturday, October 24. Positively Naperville's 2026 guide lists Birkenrocks and Six Foot Blonde on Friday and Mr. Blotto and Neighbor on Saturday. Around the music there are fire dancers, a costume contest, a Moonlight Market of Halloween vendors, a 15-foot werewolf sculpture, and the Food Truck Graveyard and BOOze Bar. Tickets are $25, or included with a Settlement membership, and IDs are checked at the gate. Tips at the beverage tents go to The Exchange Club of Will-DuPage Counties on Friday and Easterseals DuPage & Fox Valley on Saturday.
New this year, the Settlement has added a daytime program for younger children. Positively Naperville reported that the first-ever Family Spooktacular runs 10 a.m. to 2 p.m. Saturday and noon to 4 p.m. Sunday across the 13-acre campus, aimed at kids ages 3 to 12. Kids trick-or-treat along a route past the museum's historic homes. There's also a fright-free haunted house inflatable, slime-making at "Ghoul School," canvas painting with Pinot's Palette, laser tag and food trucks. The headliner is The Little Mermen & The Princess Pals, a Disney tribute band playing two 60-minute sets each day: 10:30 a.m. and 12:30 p.m. Saturday, then 12:30 and 2:30 p.m. Sunday. Admission is $15 for adults, $10 for ages 4 to 12 and free under 4, with a Spooky Spirits Bar for adults.
On Saturday, that means the family event ends at 2 p.m. and the adult party opens at 5 p.m. on the same lawn. If you're juggling both, it's one location with a three-hour gap.
Two more Friday and Saturday events round out the first half of the weekend. The Park District's Kids Night Out, with a Spooktacular theme, starts at 6 p.m. Friday at Fort Hill Activity Center. It includes Halloween games, dinner and juice, and you have to register ahead. At noon Saturday, the Turning Pointe Autism Foundation holds its 10th annual Naperville Pumpkin Race on Rotary Hill along the Riverwalk. It's free, with a pumpkin decorating contest, a costume contest and food vendors. The City of Naperville's events listing shows it running until 3 p.m. Positively Naperville traces the race back to its first year, which coincided with the 2016 World Series.
The Full Early Weekend at a Glance
| Day | Event | Time | Where | Cost |
|---|---|---|---|---|
| Fri., Oct. 23 | Kids Night Out: Spooktacular | 6 p.m. | Fort Hill Activity Center | Registration required |
| Fri., Oct. 23 | Howlin' at the Moon, 21+ | 5–10 p.m. | Naper Settlement | $25 |
| Sat., Oct. 24 | Family Spooktacular | 10 a.m.–2 p.m. | Naper Settlement | $15 adults, $10 ages 4–12 |
| Sat., Oct. 24 | Naperville Pumpkin Race | Noon–3 p.m. | Rotary Hill | Free |
| Sat., Oct. 24 | Howlin' at the Moon, 21+ | 5–10 p.m. | Naper Settlement | $25 |
| Sun., Oct. 25 | Halloween Hop | 10 a.m.–noon | Downtown Naperville | Free |
| Sun., Oct. 25 | Family Spooktacular | Noon–4 p.m. | Naper Settlement | $15 adults, $10 ages 4–12 |
| Sun., Oct. 25 | Halloween Happening | 1–4 p.m. | Riverwalk Grand Pavilion | Free |
Sunday Works as One Walk
On Sunday, the three family events sit close together and are spaced through the day, so you can do them back to back on foot.
- Start downtown at 10 a.m. The Downtown Naperville Alliance's Halloween Hop runs until noon. Pick up a map in the Top Fashion parking lot. There's door-to-door candy, face painting and free Trick or Treat Trolley rides on two loops, Main and Water, or Webster and Van Buren. On Chicago Avenue alone, participating businesses include Cookie Dough Creations, Empire Burgers, Features Bar & Grill, Penzey's Spices, Rosebud and The Lantern. The Alliance also lists Evereve, Kendra Scott, Kilwins, Two Bostons, Barnes & Noble, Pinot's Palette and Tapville Social, plus a Minions meet-and-greet at Innovative Dental Partners. Positively Naperville notes free parking in the downtown decks, including Van Buren and Water Street.
- Head to Naper Settlement after noon. The Spooktacular opens Sunday at noon, and the band plays at 12:30 and again at 2:30.
- Finish on the Riverwalk between 1 and 4 p.m. The Park District's free Halloween Happening at the Riverwalk Grand Pavilion, 912 Sindt Court, is for children 10 and under. It's presented by Woody Buick GMC, and the Park District asks that costumes be family-friendly, that masks leave the eyes fully visible and that props not look like real weapons.
Pinot's Palette appears twice that morning: on the Hop's participant list and at the Settlement's painting tables. That's one sign of how much this weekend leans on the same downtown businesses.
October 31 Itself Is a Short Calendar
Apart from the month-long programs below that keep going through the 31st, Halloween day adds only two events of its own, one at each end of the day.
- Morning: The 5th Avenue Naperville Farmers Market at the 5th Avenue Train Station, 200 E. 5th Ave., runs 7 a.m. to noon and closes its 2026 season with a Halloween parade. Kids can come in costume.
- Evening: The Park District's SCARE-illon has the Millennium Carillon playing classic Halloween music from Rotary Hill at 7 p.m.
The rest of the day happens on residential streets, and the city leaves that open-ended. Patch reported in September that Naperville doesn't set trick-or-treating hours, and that families are encouraged to head out before nightfall and be home by 8 p.m. Positively Naperville describes roughly 4 to 8 p.m. as the usual window. It adds that Naperville Police recommend younger children wrap up when it gets dark and older kids finish by 8 p.m. It also asks drivers to slow down and stay off their phones between 4 and 8 p.m.
That makes the SCARE-illon a natural finish if you trick-or-treat near downtown. The 7 p.m. start falls inside the suggested window, and Positively Naperville's guide suggests bringing a blanket and listening from the hill.
What Runs Through the Week in Between
A few longer-running events fill the gap between the two Saturdays, and some continue past Halloween.
Naperville Trolley & Tours runs its Halloween Lights tours every evening through Halloween night. The rides last about an hour, and most leave between 7 and 10 p.m. Pickup spots include Freedom Brothers Pizzeria, Gemato's Wood Pit BBQ and Bar Louie at Naperville Crossings, with select 21-and-over tours leaving from Quigley's Irish Pub.
During the day, the Park District's Creepy Critters Month continues through October 31 at Knoch Knolls Nature Center, 320 Knoch Knolls Road. It offers free self-guided activities and an indoor scavenger hunt. Weekday hours are 9 a.m. to 1 p.m. and 1:30 to 4:30 p.m., and Saturday hours are 9 a.m. to 3 p.m.
On Tuesday, October 27, the Naperville Public Library holds Halloween Storytime at the Riverwalk Amphitheater from 6 to 6:45 p.m. It moves indoors to the Community Room if the weather turns. That afternoon, the 95th Street Library hosts Teen DIY: Spooky Snacks from 4 to 5 p.m. It's for grades 6 through 12. No registration is needed, but it's limited to the first 16 participants.
After Halloween, two events follow. ALMAS holds its fourth annual Día de Muertos celebration from 1 to 6 p.m. Sunday, November 1, at the Riverwalk Grand Pavilion. That's an hour earlier at both ends than the 2 to 7 p.m. schedule NCTV17 reported for last year's edition. Then on Saturday, November 7, the Park District's free Pumpkin Smash runs from 9 a.m. to noon at Ron Ory Community Garden Plots, 811 S. West St. Pumpkins are weighed, smashed and composted, which gives porch jack-o'-lanterns somewhere to go.
At Jill Clark, we keep up with Naperville's calendar from downtown out to the Riverwalk. If you'd like to talk about the parts of town that sit closest to the Riverwalk and downtown, we're glad to set up a Private Consultation.
