Naperville Halloween Events Oct 23–25: Prices Compared
Next weekend is the real Halloween decision in Naperville: six Naperville Halloween events land Oct. 23–25, ranging from a $25 adults-only bash to two completely free trick-or-treat events on the same Sunday. Here they are side by side — times, ages, and what each one actually costs.
By Naperville Guide · Published October 17, 2026
Next weekend is bigger than this one (see our Oct. 16–18 weekend guide). Naper Settlement runs an adults-only party and a brand-new family event on the same grounds, the free Halloween Happening shares Sunday with the free downtown Halloween Hop, and pumpkins race down Rotary Hill on Saturday. Two of these need tickets bought this week — decide now, not on Friday.
For adults: Howlin' at the Moon, Oct. 23–24 ($25, 21+)
Howlin' at the Moon — Naper Settlement, 523 S. Webster St.
The one Naperville Halloween event where kids are explicitly not allowed. Expect live music (Saturday's lineup is Neighbor and Mr. Blotto), a costume contest, fire dancers, the Moonlight Market of Halloween vendors, the Food Truck Graveyard, and the BOOze Bar. This is the ticket to buy this week — it is the Settlement's flagship fall night, and Saturday is the bigger draw.
For families who want one big paid event: Family Spooktacular, Oct. 24–25
Family Spooktacular — Naper Settlement, 523 S. Webster St.
The Settlement's newest event, built for children ages 3–12: trick-or-treating at the historic homes across the 13-acre campus, The Little Mermen & Princess Pals performing Disney favorites, inflatables including a fright-free haunted house, laser tag, a costume contest, and slime-making at Ghoul School — all included in admission. A family of four pays $50: the priciest option here, and the most packed into one ticket.
Free on Sunday: the Halloween Hop and Halloween Happening stack
Downtown Naperville Halloween Hop — downtown Naperville
Door-to-door candy at participating downtown businesses, face painting, and free Trick-or-Treat Trolley rides around downtown. Two hours only, so this is the morning move — check downtownnaperville.com for the participating-store list before you go.
Halloween Happening — Riverwalk Grand Pavilion, 912 Honorary Sindt Memorial Court
The Park District's long-running free celebration: Halloween activities and games where kids collect treats and win prizes. Costume rules are specific — costumes must be family-friendly, masks must allow clear peripheral vision with the eyes fully visible, and no props that resemble real weapons. It starts an hour after the Hop ends, and the Grand Pavilion is a short walk from downtown, so the two events are designed to be done back-to-back.
Saturday's wild card: pumpkins on wheels and Pumpkin Palooza
10th Annual Naperville Pumpkin Race — Rotary Hill, by the Millennium Carillon
Participants race decorated Pumpkin Racers in single-elimination heats down Rotary Hill — trophies, prizes for best design and costume, community and business heats, and food trucks. It overlaps Spooktacular's Saturday hours, so pick one as your main event. Check the Turning Pointe site this week for racer kit details if you want to enter, not just watch.
Pumpkin Palooza — DuPage Children's Museum, 301 N. Washington St.
The indoor hedge if Saturday's weather turns: the Children's Museum's seasonal celebration, costumes encouraged. It is the earliest start of the weekend, which makes it the best fit for toddlers who nap by noon. Confirm how admission works for the day on the museum's site before heading out.
The weekend, priced out
- $0 plan: Halloween Hop (Sun. 10 a.m.) → Halloween Happening (Sun. 1 p.m.). Add Pumpkin Race spectating on Saturday at no ticket cost.
- One-ticket family plan: Family Spooktacular — $50 for two adults and two kids ages 4–12; free if your children are all under 4.
- Adults' night out: Howlin' at the Moon — $25 a person, either Friday or Saturday, 5–10 p.m.
- Do-everything weekend: Palooza Saturday morning, Howlin' Saturday night (with a sitter), Hop and Happening on Sunday — about $75 in tickets for a family of four before food.
Still picking a costume? Our earlier Naperville Halloween guide covers the season's other staples, and our Naperville events page refreshes daily with anything new added this week. And if December is already on your mind, Santa's Workshop registration opens Tuesday, Oct. 20 — before any of these Halloween events even happen.
Frequently asked questions
What are the biggest Naperville Halloween events on Oct. 23–25?
Howlin' at the Moon (adults, Oct. 23–24) and the new Family Spooktacular (Oct. 24–25), both at Naper Settlement; the free Halloween Hop and Halloween Happening on Sunday, Oct. 25; the Naperville Pumpkin Race on Saturday, Oct. 24; and Pumpkin Palooza at DuPage Children's Museum on Saturday morning.
How much does Family Spooktacular cost in Naperville?
$15 per adult and $10 per child ages 4–12, with children under 4 free. It runs Saturday, Oct. 24 from 10 a.m. to 2 p.m. and Sunday, Oct. 25 from noon to 4 p.m. at Naper Settlement, and all activities and performances are included.
Is Halloween Happening in Naperville free?
Yes. The Naperville Park District's Halloween Happening is free, runs Sunday, Oct. 25 from 1 to 4 p.m. at the Riverwalk Grand Pavilion, and is designed for children ages 10 and under. The downtown Halloween Hop the same morning (10 a.m.–noon) is also free.
Can kids go to Howlin' at the Moon?
No. Howlin' at the Moon at Naper Settlement is strictly for ages 21 and over — no one under 21 is permitted, and IDs are checked at the entrance. Tickets are $25; it runs 5–10 p.m. on Friday, Oct. 23 and Saturday, Oct. 24.
When is the Naperville Pumpkin Race in 2026?
Saturday, Oct. 24 from noon to 3 p.m. at Rotary Hill, next to the Millennium Carillon. It is the 10th annual race, hosted by the Turning Pointe Autism Foundation, with single-elimination heats, a costume contest, and prizes for best design.
Sources & verification. Details verified October 17, 2026 against organizer listings; hours and prices change — confirm before heading out.