Fun Things To Do In Naperville For The Holidays

holiday fun in naperville

There is plenty to do this holiday season in downtown Naperville!  Below are a number of fun events for you and your family, so mark your calendars!

Friday, November 8 to Sunday, November 10

The season will kick off on Friday November 8 from 6 to 8 p.m., with the city flipping the switch to turn on over 300,000 lights – transforming the downtown area into a winter wonderland. Gingerbread Holiday Painted Sculptures will also be revealed for the first time. Guests can check in at the corner of Main and Jefferson for a gingerbread goodie bag and start their hunt to find all 25 sculptures! There will even be gift card drawings, prizes and photos with the gingerbread man!

Shops will have early-bird savings on Saturday and Sunday, with live entertainment, special sales and surprises at many downtown shops.

Come support the runners at the first annual Naperville Marathon and Half Marathon beginning Sunday, November 10 at 7a.m. The race will start and end at the North Central College Athletic Complex at Loomis and Porter.

Saturday, November 23

On Saturday, November 23, from 10 a.m. to 12 noon, guests can enjoy an informal magical winter fashion show and brunch.  Held at Sullivan’s Steakhouse (244 Main Street), tickets are $15 per person (tax & gratuity extra). There is limited seating.  Please call (630) 305-0230 for reservations.

Thanksgiving Weekend (November 28-December 1)

The 16th Annual Naperville’s Turkey Trot, will be held on Thanksgiving day, Thursday, November 28 at 8a.m. This popular 5K starts and ends at Naperville Central High School.  Register for the Turkey Trot.

Enjoy big sales and lots of fun during the entire Thanksgiving weekend at downtown stores and restaurants.

Washing Street Holiday Market at 47 E. Chicago at Washington, will take place Friday to Sunday of Thanksgiving weekend.  Run by Room 363 and Little Luxuries, this free festive market will feature over 40 vendors with holiday and vintage merchandise and unique gifts. Hours are Friday from 4 to 9p.m., Saturday from 9a.m. to 9p.m. and Sunday 10a.m. to 4p.m.

The free holly trolley can drive you around town while you shop and explore.  Sponsored by the Main Street Promenade, the trolley offers six convenient pick-up and drop-off locations including the Main Street Promenade, Dandelion Fountain (near the Santa House), Main & Chicago (near Sugar Monkey Cupcakes), Chicago & Washington (near Barnes & Nobles and the Holiday Market) and the Van Buren Parking Deck. The trolley will be running on Friday from 12 to 6p.m. , Saturday from 12 to 4p.m., and Sunday from 12 to 3p.m.

Sunday, December 1

The school of Creative and Performing Arts – Show Choirs and SPA-kettes will perform from the main state of the parade (Main & Van Buren) from 3:45-4:15p.m.  with holiday tunes as families wait for the parade to start. Followed by area high school singers belting out solos and duets from 4:15-4:50.

The Little Friends Parade of Lights will be Sunday, December 1 at 5p.m. Brightly lit floats and musical entertainment will line the streets of downtown, starting at Water Street, head north on Main Street, west on Van Buren and end at Eagle Street, near Naper School. Complimentary hot chocolate will be provided from 4-6p.m.  at the Main Street Promenade.

After the parade, the high school singers will hit the stage again as the crowd waits for Santa and Mrs. Claus to arrive. After they join in on the singing, Santa and Mrs. Claus will visit with children until 8p.m.

Tuesday, December 3

The Santa House at Jackson Avenue and Webster Street official opens. Admission is free and photos with Santa may be purchased for a small fee.

Saturday, December 7

Pet pictures with Santa!  For just $5 (or only $3 with a non-perishable food item), you can get your pet’s picture taken with Santa and emailed to you.

Location:  VCA Clinic of Bolingbrook, 570 Concord Lane – Bolingbrook, IL

Hours:  9am to 12pm

Proceeds benefit the Naperville Jaycees

Tuesday, December 31 – New Year’s Eve

A Family-Friendly New Year’s Eve Celebration will take place downtown from Noon until 5p.m. Browse downtown with shopping, dining, scavenger hunts and more until the 6p.m. countdown to ring in the New Year at the base of the Carillon at Rotary Hill. There will be another countdown at Midnight!

More Holiday Fun…

Second Annual Gingerbread House Display will be held by the Naperville Public Library. Families can make and decorate their own Gingerbread House.  Creations must be dropped off at Nichol’s Library before 4:00 p.m. on Saturday, December 7. Houses will be displayed in the Children’s Department through December 14, for the public to admire and choose their favorites. Ribbons will be awarded to all entries.

The Downtown Naperville Cookbook – Dishes & Delights makes the perfect gift! This limited edition cookbook can be bought at various downtown Naperville shops for $20. With proceeds going directly to the Parade of Lights and Little Friends, Inc!

Winter Window Walk – Look for this year’s holiday mascot – George – hidden in many downtown Naperville festive store window displays. Step inside those stores and register to win George too!

Downtown Naperville Gift Cards – For use at more than 150 downtown shops and restaurants, downtown Naperville Gift Cards make the perfect gift!  Gift cards may be purchased at the Naperville Area Chamber of Commerce, Twisted Olive, Heaven on Seven or Elan Boutique.  You may also order them online and postal mailed directly to you or a recipient.


This article was contributed by Your Naperville community member, Suzanne Flynn.

About John Reh

I moved to Naperville in 1981 and I love this city. As a Naperville-focused real estate agent, I publish this website to promote our community and help current and soon-to-be residents discover the best of Naperville homes and lifestyle. Contact me at any time.

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