Time for A Winter Stroll! 2021 Holiday Walks in Chicagoland

Outdoor Activities

It’s so exciting to look forward to all the 2021 holiday walks that are happening soon! What better way on a frosty evening to get in the holiday spirit than with a festive stroll amidst some beautifully crafted store-front windows and tree-lined streets, all magically lit with sparkling lights? Bundle up the family, grab some hot cocoa, and check out one (or more) of these outdoor holiday walks near you. It’ll feel great to get outside with kiddos, celebrate the beauty of the season, and get some holiday shopping in, too!

2021 Holiday Walks in Chicago’s Western Suburbs

Deck the Green: Holiday Festivities (Burr Ridge)
November 19, 2021 | 5:00 pm – 7:00 pm
Shop and stroll through the Village Center, listen to a holiday concert, meet and greet with Santa, and more kid-friendly fun.

City Centre Penguin Contest (Elmhurst)
November 19, 2021 – January 7, 2022
Look for over 100 plush penguins hidden in the windows of stores. Be sure to download the contest game card here.

Winter Lights at Central Park (Oak Brook)
November 25, 2021 – January 9, 2021 | 4:30 pm – 9:30 pm
Stroll through the beautifully lit scenic pathways and see dancing trees, inspirational signs, vibrant rainbow arches, and more.

Holiday Walk & Tree Lighting (Glen Ellyn)
November 26, 2021 | 6:00 pm – 8:00pm
An evening in downtown Glen Ellyn of shopping and holiday festivities. Seeing the decorated storefront windows, Santa, and the sparkling tree lighting event.

Holiday Parade of Lights (Naperville)
November 26, 2021 | 7:00 pm
Watch the parade in downtown Naperville under the lovely twinkling lights. After the parade, Santa and Mrs. Claus will make a visit inside the Naperville Public Library.

Holiday Homecoming Weekend (St. Charles)
November 26-27, 2021
Kick off the season with the lighting of the lights, a holiday tree trail, holiday movie (Frozen II), Santa’s house, and an electric Christmas parade.

Gingerbread House Contest (Downers Grove)
November 26 – December 12, 2021
Families will appreciate the colorfully crafted gingerbread houses displayed all throughout downtown Downers Grove as part of this annual tradition.

Reindeer on Parade & Christmas Window Walk (Wheaton)
November 26, 2021 – January 9, 2022
Check out all the festive painted windows and adorably decorated evergreen reindeer on display as you kick off the holiday season in downtown Wheaton.

Parade of Gingerbread Houses (Bloomingdale)
November 27, 2021 – December 31, 2021
Visit local businesses in the area, and then vote for your favorite gingerbread house.

Celebration of Lights Festival (Batavia)
November 28, 2021 | 5:00 pm – 7:00 pm
A walk down Christmas Tree Lane, hayrides, holiday crafts, ornament-making, music, tree lighting, and a visit with Santa rounds out this fun holiday tradition.

Tree Lighting in Wilder Park (Elmhurst)
December 2, 2021 | 5:30 pm – 7:30 pm
Annual holiday tree lighting event that includes a visit with Santa/Grinch, holiday music/games, and more.

Holiday Tree Lighting & Christmas Walk (Hinsdale)
December 3, 2021 | 5:00 pm – 7:00 pm
Celebrate the holiday season, visit all the local merchants, listen to live music, and see all the holiday characters.

Christmas Walk & Holiday Market (Clarendon Hills)
December 3, 2021 | 5:00 pm – 9:00 pm
Shop the local merchants on a festive evening that includes a tree lighting, strolling carolers, horse drawn carriage rides, roasted chestnuts, refreshments, a visit with Santa, and more.

Village Tree Lighting and Winter Wonderland (LaGrange Park)
December 3, 2021 | 6:00 pm – 7:00 pm
Gather with neighbors at Memorial Park as the tree is lit and walk through the festive winter wonderland lined with an array of decorated trees sponsored by local businesses.

Holiday Walk & Festival of Windows (Forest Park)
December 3, 2021 | 6:00 pm – 9:00 pm
Be a part of the magical holiday walk on Madison Street and catch the live window displays, horse-drawn carriage rides, balloon twisting, Santa & Mrs. Claus, and ice sculptures.

Hometown Holiday and Holiday Walk (La Grange)
December 4, 2021
An annual tree lighting with festive activities and the arrival of Santa, too, all amongst the magnificently lit downtown shops.

Winter Wonderland (Western Springs)
December 4, 2021
See all the beautifully decorated holiday trees, watch Santa arrive, listen to holiday music, take a hayride, and visit the petting zoo. Don’t miss the annual tree lighting.

Tree Lighting at City Hall (Wood Dale)
December 4, 2021
Enjoy seasonal treats, holiday crafts, a visit with Santa, and fireworks, too.

Holiday Celebration (Brookfield)
December 4, 2021 | 2:00 pm – 6:00 pm
Downtown Brookfield celebration with food, drinks, holiday market, petting zoo, ice skating, pictures with Santa, and entertainment!

Winterfest & Cookie Walk (Oak Park)
December 4, 2021 | 4:00 pm – 6:00pm
Enjoy a festive evening in downtown Oak Park featuring family-friendly music, entertainment, and the annual cookie walk. You might catch a glimpse of St. Nicholas, too!

Joyful Traditions (Villa Park)
December 4, 2021 | 4:00 pm – 8:00 pm
Build-your-own s’mores, greet Santa, and enjoy food, shopping, a holiday sing-along, petting zoo, and more!

Tree Lighting & Snowman Lane – Heritage Park (Homer Glen)
December 4, 2021 | 4:30 pm – 7:30 pm
After Santa lights the holiday display, stay for music, hot cocoa, and holiday costumed characters while you walk through the dazzling glow.

Holly Days (Westmont)
December 4, 2021 | 5:00 pm – 7:00 pm
All the downtown businesses will be open on this festive night featuring the Frosty & Friends parade, entertainment, visits with Santa and Mrs. Claus, and more!

Holiday Lights in Lilacia Park (Lombard)
December 4, 2021 – January 2, 2022 | 4:30 pm – 10:00 pm
A gorgeous annual holiday lights display illuminating Lilacia Park with magical light shows, tree decorations, gingerbread houses, and more.

Red Sled Neighborhood Stroll (La Grange)
December 11, 2021 | 1:30 pm – 4:30 pm
See how many Red Sleds (and other surprises) you can spot as you stroll around the neighborhood!

Merry & Bright, A Victorian Christmas (Downers Grove)
December 11, 2021 | 3:00 pm – 6:30 pm
Learn about Victorian-era Christmas traditions, get toasty around the campfire, listen to Victorian-era carolers, and see all the decorated trees while you stroll around the park on a lovely luminary walk. Registration for various time slots required.

If your holiday stroll got you in the mood for more walking, check out our Winter Hikes list for some beautiful spots to go hiking or cross country skiing! We love to see your winter adventures; tag us on social media!

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