Naperville's holiday season has no single start date. The city's 2026 calendar lists a new "Lights at Naper Settlement" starting November 1, though no hours or details have been published yet. The Downtown Naperville Alliance lights up downtown on November 2. Block 59 opens its rink November 13. Naper Settlement holds its tree lighting November 18. Naperville Sunrise Rotary turns on Naper Lights the night after Thanksgiving. No single group runs the season. Four organizations each set their own clock, and in 2026 the first nights are spread across nearly a month, with the free Water Street show starting last.
Four Organizations, Six Dates
All the dates below come from the organizers' own 2026 listings, including the City of Naperville's 2026 special events calendar.
| Date | What starts | Who runs it | Cost |
|---|---|---|---|
| Sun., Nov. 1 | Lights at Naper Settlement, listed as new | Listed on the city calendar | Not yet announced |
| Mon., Nov. 2, 5 p.m. | Downtown Lights Up for the Holidays | Downtown Naperville Alliance | Stroll through downtown |
| Fri., Nov. 13 | The Rink at Block 59 opens | Block 59 | $14 admission, $5 skate rental |
| Sat.–Sun., Nov. 14–15 | Holiday Open House Weekend | Downtown Naperville Alliance | Shopping event at downtown businesses |
| Wed., Nov. 18, 5–7 p.m. | Holiday Tree Lighting | Naper Settlement | Free with registration |
| Fri., Nov. 27 | Rotary Holiday Parade of Lights | Rotary | Not listed |
| Fri., Nov. 27 | Naper Lights | Naperville Sunrise Rotary | Free |
| Fri.–Sun., Dec. 11–13 | Holly Jolly Days | Naper Settlement | $6, under 4 free |
Downtown is the first event with a published start time. The best-known free display in the city starts 25 days later.
Downtown Goes First, and the New Storefronts Are Part of the Display
The Downtown Naperville Alliance's Downtown Lights Up for the Holidays is set for Monday, November 2, at 5 p.m. The Alliance describes it as a stroll past decorated storefronts, lights, and holiday displays, so whatever opened downtown this fall is part of the walk.
A lot has opened. The Daily Herald reported in late September that Lola's Handcrafted Churros was holding its grand opening at 8 W. Jefferson Ave. It's the business's third location, and it's known for churro sundaes. That makes it an easy stop for a warm treat on a cold walk. On East Chicago Avenue, Bonci Pizza held its grand opening August 28, according to Patch. Its Roman-style pizza menu changes often with the seasons, so the menu you find in November may not match the one from opening week.
Several more openings are timed close to the holidays, though none has a firm date. The same Daily Herald report covered these:
- SEE Eyewear, 214 S. Main St., was aiming for mid-October. It will be the boutique's fifth location, joining one in Skokie and three in Chicago.
- State & Liberty Clothing Co., 144 W. Jefferson Ave., is aiming for a mid- to late-November opening. That puts it close to the Holiday Open House Weekend.
- I Heart Gyro, 22 E. Chicago Ave., was finishing its last steps with the city. Its owner hoped to open within two weeks of the September 28 report.
- Taco Grill Cantina, 15 W. Jefferson Ave., pushed back its planned September 15 opening and is now targeting "this fall." It plans to serve breakfast, lunch, and dinner seven days a week.
Downtown Naperville Alliance Executive Director Dawn Portner also told the Daily Herald that Deep Purpl Acai Bowls, Lizzano Foccacia & Spritzeria, and Slyce NY are coming downtown, with no dates given.
The Alliance's second date matters more for shoppers. Holiday Open House Weekend runs Saturday and Sunday, November 14 and 15, at downtown businesses. If the November targets hold, that weekend is the first chance to see this fall's storefronts dressed for the season at the same time.
Route 59 Opens the Night Before
The Open House Weekend starts one day after the second clock. The Rink at Block 59 opens Friday, November 13, with real ice. The grand opening runs 5 to 10 p.m., and Block 59 lists Skate with Santa, A Visit from the Grinch, and Stan's Cocoa with Mrs. Claus as seasonal events.
This is the rink's second season. The Daily Herald covered its first opening in November 2025. At that time it was a 60-by-120-foot outdoor rink between Cheesecake Factory and Yard House, run in partnership with Magic Ice USA. Block 59 hasn't restated those details for 2026, so last year's layout may or may not carry over.
These are the 2026 practical details from Block 59's own page:
- Tickets. Presale opens October 15 at noon. Sessions last 1 hour and 45 minutes, and timeslots are limited. Block 59 recommends buying ahead and says walk-up tickets may be available depending on demand.
- Price. Admission is $14, and skate rental is $5 more per pair.
- Hours. Monday through Thursday, 2 to 9 p.m. Friday and Saturday, 10 a.m. to 11 p.m. Sunday, 10 a.m. to 9 p.m.
Block 59's page doesn't give a clear closing date for the season, and the holiday-hours section has some date errors. Check the page before planning a skate after New Year's.
The Route 59 side of town also has a new holiday shopping stop. L.L.Bean opened its 16,000-square-foot store at 336 Illinois Rte. 59 in Westridge Court on September 25, Patch reported. With weekend skate sessions starting as early as 10 a.m., you can pair a morning skate with a shopping errand on the same stretch of road.
Naper Settlement Adds a Season of Its Own
The third clock belongs to Naper Settlement. Its Holiday Tree Lighting is Wednesday, November 18, from 5 to 7 p.m. The ceremony itself starts at 5:15. The listing promises lights on the historic buildings and grounds, hot drinks, cookies, and visits with Santa. It's free, but registration is required.
The city's 2026 calendar also lists something new here. "Lights at Naper Settlement" is marked "*New" and runs all of November and December. As of mid-October, no hours, ticket details, or description have been published beyond the name and dates. Naper Settlement's own calendar is the place to watch for them. If it runs the full two months as listed, it would be the longest-running light display on any of the four calendars.
Settlement programming continues into December with Holly Jolly Days, Friday through Sunday, December 11 to 13. The weekend includes holiday crafts, stories, and a blacksmith demonstration. Admission is $6 per person, and children under 4 get in free.
Thanksgiving Weekend Is When All Four Clocks Line Up
The free display on Water Street is the last to start. The city calendar puts the Turkey Trot on Thanksgiving, November 26. The next day, Friday, November 27, brings both the Rotary Holiday Parade of Lights and the first night of Naper Lights.
Naperville Sunrise Rotary describes Naper Lights as a free light-and-sound show along Water Street, Foyo Plaza, Jaycees Park, and the Riverwalk. Free 3D viewing glasses are handed out at the event. Rotary lists general hours of 4 to 10 p.m. from Thanksgiving through New Year. The 2026 calendar has it running November 27 through December 31. Rotary hasn't posted a separate 2026 nightly schedule, so the general hours are the best guide for now.
By Friday, November 27, all four organizations have something running. Downtown storefronts have been lit since November 2, the rink has been open for two weeks, the Settlement lights have been on the calendar since November 1, and Water Street turns on last.
Which Nights Line Up
Since the clocks start at different times, a few dates stand out for doing more than one thing:
- Friday, November 13, into the Open House Weekend. The Rink opens Friday night on Route 59. Downtown stores hold their open house that Saturday and Sunday.
- Wednesday, November 18. The Settlement tree lighting runs 5 to 7 p.m. on a weeknight, and the rink stays open until 9.
- Friday, November 27. The parade and the first night of Naper Lights happen together downtown.
- December 11–13. Holly Jolly Days runs during the day at Naper Settlement, while Naper Lights and The Rink are both running in the evening.
For a larger market, the nearest Christkindlmarket on these calendars is in Aurora, not Naperville. The Christkindlmarket Aurora runs November 20 through December 24 at RiverEdge Park, 360 N. Broadway.
Several details are still missing as of today: firm opening dates for the November storefronts, a schedule and ticket details for Lights at Naper Settlement, and the rink's closing date. Each organizer's page is the place to check, and the four can update at different times.
If you'd like to talk about which parts of town make an easy walk to Water Street on a December evening, or what a holiday-season listing looks like when the neighborhood is lit up, Sarah Diana knows these calendars and the blocks around them. Schedule a Free Consultation with Sarah.
