2026 Holiday Events
the best holiday events
We’ve rounded up celebrations, seasonal outings, and family fun across Oak Park and Beyond so you can spend less time searching and more time making "merry". Consider it your holiday list, ready for checking twice.
Just a quick train ride from Chicago, discover cheerful business districts, independent shops with gifts worth giving, and local restaurants perfect for a holiday get-together. Bring the family, gather your friends, and make a day of it. The magic doesn’t stop at city limits.
.png "STICKERS_DoWest-3x2 (1)")
your go-to holiday events guide
holiday magic
November 21 - January 3
Holiday Magic is back, marking more than 40 years of sparkling lights, festive fun, and holiday memories.
Step into a sparkling winter wonderland as you explore themed areas filled with larger-than-life holiday displays, interactive experiences, glowing tunnels, a maze, and animal-themed light displays.
Experience the magic, make new memories, and discover why Holiday Magic is a beloved holiday tradition.
northriverside park mall tree lighting
November 13
From 4 p.m. - 6 p.m.
Enjoy festivities, DJ dance party and games to set the vibe at 4 p.m. near the lower level Christmas tree. Then join us at 5:30 p.m. at the food court entrance to help JS Morton High School 201 Drumline lead Santa and Mrs. Claus from the North Riverside fire truck through the food court. Enjoy some North Pole trivia and help Santa light the tree.
reindeer run
November 14
Gather your family, friends, holiday cheer and join us on Saturday, November 14 for the Reindeer Run. With a two-mile course entirely within Brookfield Zoo Chicago, walk, jog, or run under the lights while being one of the first to see Holiday Magic!
All registered Reindeer Run participants will receive a commemorative Reindeer Run hat and complimentary carousel rides
winter greens market
November 20
The Oak Park Conservatory’s Winter Greens Market offers an array of fresh greens including balsam, fir, boxwood, winter berries, magnolia tips, spruce tops, and more along with many other natural items for your winter decoration needs.
Shop online or in-person Tuesday-Sunday, 10:00A-4:00P through December 18.
holiday Movie trivia
November 20
Think you know every line from Elf, Home Alone, or Love Actually?
Can you name all the reindeer and all the versions of The Grinch?
Join Chicago Trivia Guys for a night of merry movie madness and test your holiday film knowledge in a fast-paced, laugh-filled trivia showdown.
saturday with santa
November 21
Join the Oak Park Art's District for Saturday with Santa, a fun-filled day featuring Pictures with Santa and Toy Drive, Letters to Santa and Craft, Candy Cane Walk, Face Painting, Local Art Vendors, Food and Drink Specials and more!
Plus the Toddlin’ Around Town Scavenger Hunt along Harrison!
Small business saturday in dtop
November 27 - 28
The team at Downtown Oak Park invites you to their Shopapalooza Weekend. On Black Friday, November 27th, and Small Business Saturday, November 28th, take advantage of special sales, gift with purchase deals and custom experiences.
la grange flash sale
November 28th
For customers looking for great deals, La Grange businesses will be holding a Flash Sale with special offers and deep discounts for a limited time, making it the perfect way to kick off your holiday gift-buying.
charlie brown brunch at pleasant home
November 28
Presented by Fitzgerald's Nightclub and the Park District of Oak Park, experience the nostalgia of Vince Guaraldi’s A Charlie Brown Christmas played live with The Chris White Trio in the equally classic setting of the landmark property, Pleasant Home. Beautiful brunch buffet by BABYGOLD Barbecue. Two time slots available. All are welcome! Each person needs to be registered. Infants one year and younger do not need to be registered. All Ages
hop district winter market
December 2
It’s Hop District’s 4th Annual Winter Market, coming up Wednesday, December 2nd from 4 - 9pm.
forest park holiday walk
December 4
Live window displays, merchant open houses, horse-drawn carriage rides, balloon twisting, face painting, Santa & Mrs. Claus and an Ice Sculpture photo op are just part of the magic of this annual Holiday Walk on Madison Street.
riverside holiday stroll
December 4
From, 6:30 - 8:30 p.m. Bundle up, bring a friend, and come spend the evening in Riverside! Local shops, restaurants and other businesses are at the heart of the Stroll. Pop into a place you’ve been meaning to try and enjoy music and treats along the way.
Stop by the library to visit Santa, hop aboard the trackless train, or find a handmade gift at the Artisan Market inside the historic train station.
Also stop by Riverside Art Center for the opening reception of a new exhibition that celebrates the creativity of the community, bringing together artwork by RAC members, children enrolled in RAC classes throughout 2026, ceramics studio members, and RAC staff and board members. The exhibition offers a wonderful opportunity to highlight the artistic talent and community spirit of Riverside.
dtop cookie walk/winterfest
December 5
11am–3pm – Cookie Walk
The Cookie Walk begins as participating Downtown Oak Park businesses hand out cookies, chocolates, and sweet surprises to those with a 2026 Cookie Walk tin.
Free Hot Cocoa & Letters to Santa!
Warm up with complimentary hot cocoa generously provided by Wise Cup and served by the Collaboration for Early Childhood! Kids can also write their letters to Santa while enjoying the holiday festivities.
Winterfest Entertainment Schedule
Kris Kringle Market Brookfield
December 5
4th Annual Kris Kringle Market on Saturday, December 5, 2026, from 10 AM–6 PM. Join in for a full day of holiday shopping, festive entertainment, family activities, delicious food, and all the little moments that make this season so special.
la grange holiday walk
December 5
La Grange's premier event of the holiday season takes place Saturday, December 5 throughout downtown. Activities are spread across Village Hall, Calendar Avenue, and both La Grange Metra Stations. The Lyons Township High School Madrigals perform on the steps of Village Hall at 5 p.m. Then Santa and Mrs. Claus arrive by fire truck, followed by the lighting of the Village Hall tree at 5:30 p.m., The All-Village Sing follows at 5:40 p.m. Santa and Mrs. Claus then greet children inside Village Hall for photos from 6 to 7:45 p.m., as the Salt Creek Chamber Orchestra performs for those waiting in line.
home for the holidays
December 12
Get into the holiday spirit with free horse-drawn carriage rides, a visit with Santa, and hot cocoa at coffee shops throughout the district!
11 a.m. – 2 p.m. – Enjoy free horse drawn carriage rides departing from Marion Street.
11 a.m. – 3 p.m. – Cocoa Walk – Stop by a participating business for a free 5oz cup of hot cocoa:
wonderworks noon years eve
December 31
Count down to 2027 at Wonder Works!
Dress in your festive best and join in for the last PLAY date of 2026. Wonderwork's New Year’s celebration will include a balloon drop, full access to the museum, a New Year’s art project, encounters with costumed characters, and a fun photo booth to capture the special day as a family, all long before bed time!
To provide family flexibility, we have TWO celebration sessions at 10:00AM and 12:00PM on Thursday, December 31. The countdown to the new year and the balloon drop will happen at 11:00AM and 1:00PM.
robert's westside new year's eve
December 31
Robert's New Year's Eve Party with THE ELECTRIC CARS performing 80's New Wave Rock & Pop. General Admission: $25 + Service Fees. Tickets Include Champagne Toast.
Sleigh the Holidays This Year.
Join us for a Festive Scene That’s Anything But Ordinary.
Sure, it’s the suburbs, but not the kind where the holiday magic stops at the front door. Oak Park, Forest Park, and the neighboring towns just west of the city are ready to help you sleigh the holidays with festive events, seasonal celebrations, and plenty of reasons to make merry.
No sleigh? Even better.
Hop on the train and make a day of discovering the holiday spirit just west of Chicago. Gather your favorite people, bundle up, and let our communities put a little extra sparkle in your season. This isn’t just another holiday outing—it’s the start of a new tradition.
