Celebrate the Holidays through Chicago’s North Shore! | Chicago North Shore Moms

We’re starting in Evanston and jingle-belling all the way North along Lake Michigan all the way to Lake Bluff with Chicago North Shore community’s best holiday bets for you and your family!


Holiday Light Celebration | December 4, 5-7:30pm
Celebrate with the community at the annual holiday tree lighting at Fountain Square!  Enjoy performances by Evanston Children’s Choir, Purple Haze Acapella and special characters from The Actor’s Gymnasium. At 5:30pm, Mayor Biss, Santa and Mrs. Claus will make an appearance to light the tree at Fountain Square. There will be hot chocolate and other treats available for purchase at the event.

Small Business Saturday – Holiday Shopping Passport, Nov 27th – Dec 18th
Shop unique, shop local this holiday season! Starting on the nation wide Small Business Saturday, pick up or download a Shopping Passport with special offers from local businesses. When you spend a minimum of $100 (or more) at local shops, you’ll receive a holiday gift from Downtown Evanston! More details coming soon to our Small Business Saturday.


Santa’s Mailbox! Nov 19-Dec 3rd
Mail your LETTER TO SANTA at the magical North Pole Mailbox located in Mallinckrodt Park! Include a self addressed, stamped envelope so that Santa can write you back. LAST DAY TO DROP OFF YOUR LETTER IS DECEMBER 3! Don’t miss out on this special holiday tradition!

The Wilmette Center for the Arts:The Nutcracker, Dec 3-5th
Enjoy this magical holiday tradition as young actors and dancers perform our rendition of the classic Nutcracker story. Toy soldiers, mouse kings and sugar plum fairies will take to the stage for 4 shows this season.

Our Wilmette Park District Tradition is back in person! Start with a box house and cover with our handmade frosting. Embellish with candy, cookies and goodies. Be sure to bring your imagination and a box or tray to carry your confection home. Adults are welcome to make their own or work alongside their child, or register for the popular Adult Gingerbread House Workshop! TAKE HOME KITS AVAILABLE TOO! 


Holiday Festivities & LightingDec 4th, 4:00-8:00 pm
Annual Tree Lighting, Menorah Lighting, Holiday Market and Santa on a Firetruck! At 4 PM, Santa is coming to town! He’ll be riding on a fire truck through the village, starting at Assembly Hall. Watch from home or wave from Assembly Hall!  After, little ones can create a craft while parents mingle, enjoy a cash bar, and shop the holiday market.

Gingerbread House Decorating PartyDec 12th, 24:00pm

Northbrook & Deerfield 

Festival of Trees, Northbrook, Nov 20th
On November 20th, Stepping Stones Network’s 3rd annual Festival of Trees benefit will auction off 24 one-of-a-kind, holiday themed trees of all sizes crafted by talented local designers. The proceeds from these uniquely decorated trees will support the beloved women and children that Stepping Stones Network serves.

Turkey Shoot Free throw Contest, Northbrook, Nov 21st, 1-4pm
Join us for the inaugural contest. Register for the individual or team competition. Teams can consist of one child and one parent or guardian, two children of any age combination or two Adults. Each participant shoots 15 free throws, in the team competition the scores are added up to determine the winners. First place in each division receives a turkey. Second place in each age division receives a pie.
Individual Age Divisions: 6-7, 8-9, 10-11, 12-13, 14-15, 16-18, 18+

JEWETT JINGLE JAM, Deerfield, Dec 4th 12-2:00 PM
Come celebrate the magic of December at Jewett! This program will be hosted “Open House” style with something for everyone! Activities include: Winter, Christmas, and Hanukkah crafts, visit with Santa, additional photo opportunities, Bingo and storytime. Adults are free with a paid child.

BRUNCH WITH BUDDY THE ELF, Dec 11th, 10:30-12:30pm
Don’t be a Cotton-Headed Ninny-Muggins, instead join us and Buddy the Elf for a festive brunch! Celebrate the holiday season with delicious food, fun-filled activities and everyone’s favorite elf, Buddy!


Santa’s Mailbox, Winnetka Park District, Nov 24th
Elves will sneak into Winnetka to drop off this magical mailbox at the Winnetka Park District so children can mail their letters to Santa. The elves will pack up the mailbox Sunday, December 19 to take back the letters to the North Pole for Santa. Don’t forget to include names and a return address to ensure the elves know where to send Santa’s response!

Turkey Day Skate! Nov 25th, 10:30-2pm
Burn off a few calories before Thanksgiving dinner and enjoy a special skate day at the Winnetka Ice Arena. Skates may be rented for $4.

Celebrate with Family Friends and Neighbors!  6-FT. MENORAH LIGHTING, DOUGHNUTS, GIVEAWAYS, DANCING, MUSIC & MORE!  Station Park (Elm Street Metra Station)

Tree Lighting, Dec 3rd 4-6pm
Join us for this Annual Holiday Tradition at Dwyer Park on (Dwyer Park is located behind the post office at the corner of Elm and Birch) From 4:00 pm to 6:00 pm there will be music and local choirs singing carols for your entertainment. Free hot chocolate, hot apple cider and cookies will be given out while you are enjoying this festive night! The tree will be lit at 6:00 pm sharp with a visit from Santa, Mrs Claus and an Elf coming right after! Candy canes will then be passed out and there will be an opportunity to visit with Santa!  **Remember to please bring a mask so Santa doesn’t catch a cold!

Candy Cane Lane, Dec 3rd, 8am-9pm
Do visions of sugar plums dance in your head? Use that creativity and register your organization, club, neighborhood, or family to decorate your very own tree.

Fireside Photos with Santa, Dec 4th, 10-2pm
Santa’s sleigh will make one final stop in Winnetka before the big day! He is scheduled to land at Crow Island Woods to give families the opportunity to take a socially distant picture! Families will be able to spend five minutes with Santa for a holiday greeting and take a picture to cherish this memory for years to come. Staff will be available to take photos with your camera or phone. Pictures will be taken around the fireplace located in the shelter at Crow Island Woods.

Red Invitation Event, Dec 5th, ALL DAY!
Shop local this holiday season and come away with unique gifts for everyone! Even when it’s snowing, Winnetka, Northfield and Glencoe can’t stop/won’t stop opening doors in support of small businesses. Find the perfect gift while supporting your community in the process! Check out these holiday shops this season. Participating shops in Winnetka, Northfield and Glencoe are offering unique sales and special holiday promotions throughout the day!

Winnetka Winter Express, Dec 10th, 5:00-7:00pm
All aboard! Next stop, Winnetka Golf Club! Yes, you heard that right. Come out and watch Polar Express from your car. The movie starts at 5pm. Please arrive an hour early. During the movie, each child will receive hot chocolate, a cookie, popcorn, and a letter they can write to Santa. Ages: All Fee: $50 per car Registration Residents: Registration begins Monday, November 22 at 8:30am Non-Residents: Registration begins Monday, November 29 at 8:30am   Register Online  

Ugly Sweater Skate, Dec 11th, 1:40-12:55pm
Wear your ugliest holiday sweater and take a few laps skating to festive holiday music. Be sure to stick around for the Holiday Skating Exhibition following the skate.

Holiday Sing, Dec 24th, 6-6:30pm
Join families, friends, and neighbors for the 25th annual Holiday Sing. Bring your singing voices, candles (or flashlights), and gather around Village Green to sing everyone’s favorite holiday songs. This event lasts approximately 25 minutes. Ages: All Fee: Free!



Highwood for the Holidays, Saturday, November 27th, from 2-5PM
Held at City Hall Park (17 Highwood Ave), with a Santa appearance at 4PM!  Enjoy the Holiday Season at Highwood for the Holidays by participating in holiday choo-choo train rides, make-your-own-ornament station for kids, festive music, and of course, arrival of both Santa and Mrs. Claus on a firetruck followed by visits with Santa!  This Highwood for the Holidays also falls on Small Business Saturday, where guests can participate in a “Shop Local, Win Local” receipts raffle. Anyone shopping in the area can turn in their receipts from any Highwood business to be entered to win a $50 gift card!

Elf Invasion Run/Walk, Dec 4th 9am
RUNNERS SIGNUP: https://runsignup.com/Race/IL/Highwood/ElfInvasion5KRunWalkStroll
For those who love to channel their inner elf, but are too young or not able to participate in the Annual Elf Invasion Pub Crawl, Celebrate Highwood is welcoming all-ages of elves to grab their best elf wear and running shoes and come out for its Inaugural Elf Invasion 5K Fun Run, Walk & Stroll. Starting at 9AM from Enjoy Highwood Park at the southeast corner of Walker and Waukegan Avenues (just north of The Bent Fork Bakery), this festive cold weather Fun Run courses through Downtown Highwood and through Historic Fort Sheridan.

Elf Invasion Pub Crawl, Dec 4th, 7pm
Get “Elfed Up” at the 3rd Annual Elf Invasion Pub Crawl as attendees visit five of the City of Highwood’s most popular establishments to enjoy live music, food & drink specials, and raffle prizes at each participating venue.

Highland Park

Dreidels and Donuts, Dec 1st, 4-4:45pm
This festive family event features a holiday-themed craft, and in the spirit of the traditional Hanukkah sufganiyot, jelly donuts will be served. Open to all. Registration is per person. Children must be accompanied by a paid adult.

Light the Night, Nov 6th, 3 – 5 PM
Join Mayor Rotering and the City Council for the lighting of over 200 trees for the 2021 holiday season. Family-friendly activities include Santa, music and more, including a community dance mob! Information about performances is coming soon.  Ready to put on your dancing shoes and join the community dance mob? You have plenty of time to learn both dances with the videos below. Be sure to arrive at 3 PM and be prepared to dance – you never know when the music will start!

Family Skate Night, Dec 22nd, 5-7pm
Skating coaches are available to assist new skaters. Children must be accompanied by an adult. Pre-registration is required. Skate rentals are available for $3 at the front desk on the night of the event.

Campfire Trivia, Dec 3rd, 6:30pm
Test your all-around knowledge with a friendly game of trivia. Form your own team or create one that night. Stay warm with the heat from a campfire, hot cocoa, and that fuzzy feeling of knowing the correct answers! S’mores and hot cocoa are be provided. The winning team also receives a prize. All participants, including children and adults, must register for the program. Bring warm clothes and be prepared to be outside.

Sugar Plum Shopping Spree, Nov 27th, 10-5pm
Downtown Highland Park Alliance is proud to host their annual Sugar Plum Shopping Spree conjunction with Small Business Saturday. Shoppers are invited to get their holiday shopping done while enjoying seasonal special deals, holiday treats, and incentives, including the opportunity to win a $250 gift card at their Downtown Highland Park business of choice.  With every purchase made at participating Downtown Highland Park businesses on the Sugar Plum Shopping Spree map, shoppers will be entered to win a gift card of their choice business by filling out a raffle ticket. The more purchases, the more opportunities to win! The winner will be announced on December 1st. Look for the sign at right to spot participating businesses.

Heart of the Holidays, Highland Park, Nov 27th-December
Celebrate the heart of the holiday season in the heart of the North Shore! Every Saturday from Thanksgiving until Christmas, 2:00 – 4:00 PM in Port Clinton Square, enjoy festive entertainment, delicious treats and more as you browse the unique shops and restaurants of Highland Park’s Central Business District. Joining us each week will be Ravinia Brewing Company, with cider and festive beers available for purchase.
-November 27: The Heart of the Holidays begins with seasonal music, a visit from Santa, roaming carolers, and more on Small Business Saturday, with holiday cookies.
-December 4: Celebrate Hanukkah with the music of the Maxwell Street Klezmer Quartet and sufganiyot (jelly doughnuts) from That Little French Guy.
-December 11: Sing along to your favorite holiday songs – and some others! – with Frankie Valli and the Four Seasons-inspired quartet, The Four C-Notes, with roasted chestnuts.
-December 18: Join us for an ice carving demonstration from World Class Ice Sculpture, roaming carolers, and holiday treats.

Lake Forest

LAKE FOREST LIGHTS UP THE PARKS November 27, 2021 – January 10, 2022
In addition to the central business district and Market Square holiday decorations, this year eight Lake Forest community and neighborhood parks will be decorated with holiday trees and lights, which will remain on for the entire season.

You’re a Good Man Charlie Brown, Citadel Theater Nov 19th through Dec 23rd

Kids Only Holiday Shop, December 8th, 2-6pm
A community favorite, our Kids Only Holiday Shop allows children ages 4-10 to conduct holiday shopping without mom or dad!  Santa’s Helpers will escort your child through the boutique, visiting local vendors and talented artisans who feature items all $10 or under (and that includes tax). Give your kids the gift of independence and let them experience the joy of giving. Wonder Wrappers will be on hand to make sure each purchase is wrapped and ready for under-the-tree.

Lake Forest’s COCOA CRAWLNov 27th 12:00-3:00 pm
Bring friends and family and join for a very special celebration – grab a cup of hot cocoa and treats and jump on board the Holly Trolley for a swing through the wonderful businesses in downtown Lake Forest – what better way to celebrate ‘Small Business Saturday’!!  Be sure to stop first at the “Cocoa Crawl Station” in Market Square to grab a cup of cocoa and delicious fresh, warm mini donuts courtesy of Market Square, then hop on the festive ‘Holly Trolley’ sponsored this year by Realtor Andra O’Neill of @properties – there will be trolley stops throughout downtown Lake Forest and you can hop on and off to visit participating businesses and enjoy shopping discounts, nibbles and sips, and some good old-fashioned fun.

Annual Tree Lighting Ceremony, Market Square, Nov 26th, 3:00 pm – 5:30 pm
The Annual Tree Lighting Ceremony is back for 2021! Don’t miss this holiday tradition for the entire family! Enjoy an afternoon and evening of live entertainment, warm drinks, carolers, LFDA dancers, and Santa! This free community event is held at Historic Market Square in downtown Lake Forest.

Lake Bluff

It’s a Wonderful Life… In Lake Bluff, December 4th
Gather in Lake Bluff for holiday cheer! 2-5 pm Holiday Market & Entertainment
5 pm Caroling & Lighting Ceremony

Santa Ride, December 12th 10am-1pm 
Santa will make an early appearance in Lake Bluff on December 12th! He will be riding up top on one of the Lake Bluff Fire Department Engines beginning at 10:00 a.m., so when you hear the Village warning siren, be sure to look for Santa coming your way!




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