Naperville and Warrenville are a wonderful area for spending the holidays with young children, and the season starts earlier here than many families expect! Naper Settlement lights its tree in the middle of November, the new ice rink at Block 59 opens the same week, and the closest Christkindlmarket to both towns opens the Friday before Thanksgiving. This guide includes some of our favorite ways to kick off the holiday season in Naperville and Warrenville with toddlers and preschoolers, with 2026 dates, times, and costs so parents can plan around naps and early bedtimes.
Holiday season kickoff events near Naperville and Warrenville, November 2026
- Naper Settlement’s Holiday Tree Lighting is Wednesday, November 18, from 5 to 7 p.m., free with registration, with the lighting at 5:15 p.m. and visits with Santa.
- Christkindlmarket Aurora opens Friday, November 20, at RiverEdge Park, 360 N. Broadway in Aurora, and runs Thursdays through Sundays through December 24 with free admission.
- The Rink at Block 59 in Naperville holds its grand opening on Friday, November 13, and the Grinch visits the rink on Sunday, November 22, at noon.
- Downtown Naperville’s Holiday Open House Weekend is November 14 and 15, and Downtown Holiday Glow kicks off the season on Friday, November 27, at 3 p.m.
- NaperLights returns to Water Street beginning November 27, and Santa’s Naperville Workshop runs November 30 through December 20 at 441 Aurora Avenue, reservations required.
- Warrenville’s Holly Days tree lighting with Santa’s arrival and free carriage rides is traditionally the first Friday in December at Tracy Place and Warren Avenue.
Naper Settlement Holiday Tree Lighting
The season officially begins at Naper Settlement, 523 S. Webster Street, on Wednesday, November 18, from 5 to 7 p.m. The ceremony starts at 5:15 p.m., when the historic buildings and grounds light up for the first time, and the evening includes hot drinks, cookies, and a visit with Santa. Admission is free with registration, and the early hour makes this one of the few holiday events a family with a toddler can attend start to finish and still make bedtime. Families who enjoy the grounds can return for Holly Jolly Days on December 11 through 13, with crafts, stories, and a Victorian Christmas photo stop, for $6 per person and free for children under 4.
Christkindlmarket Aurora at RiverEdge Park
A favorite holiday destination is Christkindlmarket Aurora at RiverEdge Park, 360 N. Broadway, which is about 15 minutes from both Naperville and Warrenville. It opens Friday, November 20. The market runs Thursdays through Sundays through December 24, with hours of 11 a.m. to 7 p.m. on Thursdays, 11 a.m. to 9 p.m. on Fridays and Saturdays, and 11 a.m. to 6 p.m. on Sundays, plus Wednesday, November 25, and Thanksgiving Day from 11 a.m. to 4 p.m. Admission is free, and more than 60 vendors sell ornaments, wooden toys, pretzels, and the chimney cakes that are as fun to eat as they are to watch as they are made. Consider a weekday or an early Sunday visit for a smaller crowd and room for a stroller.
The Rink at Block 59
The Rink at Block 59, the dining and entertainment district at Route 59 and Aurora Avenue, holds its grand opening on Friday, November 13, at 5 p.m. and sits between Yard House and The Cheesecake Factory, so dinner is a short walk from the ice. The Grinch visits the rink on Sunday, November 22, at noon, which is a fun first outing for a preschooler who is not yet ready to skate. Families who would rather skate outdoors for free can watch for natural ice at Centennial, Nike Sports Complex, Wolf’s Crossing, and Gartner parks once the Naperville Park District opens them in mid-December, weather permitting.
Thanksgiving weekend in downtown Naperville
Holiday Open House Weekend begins on November 14 and 15 in downtown Naperville. It’s a fun environment, where shops host holiday open houses and more. The season kicks into full swing on Friday, November 27, with Downtown Holiday Glow at 3 p.m. The same evening, NaperLights returns to Water Street along the Riverwalk, with the display lit from 4 to 10 p.m. through the season, and the Naperville Trolley runs its first hour-long Holiday Lights Tour at 8 p.m. Saturday, November 28, is Small Business Saturday downtown. Santa’s Naperville Workshop, hosted by the Naperville Park District at 441 Aurora Avenue, runs November 30 through December 20 with reservations required, and the reserved time slot gives a young child a scheduled visit with Santa rather than a long line.
“The holidays are a joyful time in our classrooms, and families often tell us how much their children enjoy talking about the lights and the outings they saw over the weekend,” said Michelle Cardone, School Director of The Gardner School of Warrenville. “Those conversations are wonderful for language and for building the sense of community we want every child to feel.”
Holly Days in Warrenville
Warrenville saves its tree lighting for early December. Holly Days, hosted by the Warrenville Park District at Tracy Place and Warren Avenue, is traditionally held on the first Friday of December from 6 to 8 p.m. and opens with a short parade and Santa’s arrival, followed by the lighting of the city tree. Families enjoy free horse-drawn carriage rides, fire pits with hot cocoa and cookies, performances by local school groups, and a Merry Market of crafters and bakers at City Hall. The event is free, and the Warrenville Park District posts this year’s date each fall.
Holiday season at The Gardner School of Naperville and The Gardner School of Warrenville
The Gardner School of Naperville welcomes children from six weeks through private kindergarten at 28W611 Ferry Road, just off I-88, and The Gardner School of Warrenville serves children from six weeks through kindergarten at 27W457 Warrenville Road. Both schools are NAEYC accredited and open from 7 a.m. to 6 p.m., and the Warrenville school hosts yearly family and community events. Parents comparing preschools in Naperville and Warrenville are welcome to schedule a tour at The Gardner School of Naperville or The Gardner School of Warrenville and ask about hours, meals, and enrollment for the new year.
