Woodstock Christmas Events & Things to Do 2025

Experience the enchanting 'Winter in Woodstock' season, a town recognized for its festive spirit. From the dazzling Lighting of the Square to the beloved Christmas Parade and unique shopping events, there's a magical holiday atmosphere for everyone. Enjoy live entertainment, charming carriage rides, and festive activities that capture the heart...

Experience the magic of the McHenry Downtown Holiday Walk, a festive celebration featuring a vibrant Holiday Market with local vendors and entertainment. Stroll through charming 'Living Windows' displays, enjoy horse-drawn sleigh rides, and meet Santa. The event culminates with a dazzling tree lighting ceremony, illuminating the park and downtown streets.

Experience the joy of selecting the perfect real Christmas tree at Conifera Tree Farm. They offer a delightful choose-and-cut experience with a variety of spruce, fir, and pine trees, alongside premium pre-cut options from Wisconsin. Visitors can also find beautifully crafted wreaths and garlands made fresh on-site, adding a festive...

Discover the magic of the Ice Sculpture Cocoa Crawl in Downtown Huntley Square. This festive event showcases incredible ice sculptures, inviting attendees to warm up with delicious cocoa from local vendors. It's a perfect way to embrace the winter spirit and enjoy a unique community celebration.

Experience the magic of 'A Very Merry Huntley,' a festive celebration packed with holiday cheer. This event features a lively Kris Kringle Market, a special parade with Santa and Mrs. Claus, and a dazzling fireworks display. Enjoy family-friendly activities like train rides, hot cocoa, and meeting live reindeer, making it...

Experience the charm of Downtown Libertyville during First Friday events, running from October through December 2025. Shops stay open late, offering exclusive discounts, festive refreshments, and personalized shopping assistance. Enjoy live music, special offers from local businesses like The Bootery Boutique and Rocky Mountain Chocolate Factory, and a delightful community...

Embark on a festive Hot Cocoa Stroll through Hawthorn Row, where local businesses offer delightful samples of warm, comforting hot cocoa. It's a perfect way to experience the holiday spirit, discover unique shops, and enjoy a sweet treat during the festive season.

Get a head start on your holiday shopping at the annual Holiday Craft Fair. Browse a diverse selection of handmade crafts and unique gifts from local artisans. Admission is free, and attendees receive a complimentary raffle ticket.

Experience the magic of the holiday season at Woodfield Mall's Santa Photo Experience. Santa arrives on November 6th and will be available for photos through December 24th. Special events include Santa's grand arrival parade, dedicated pet photo sessions, and sensory-friendly visits for children with special needs. Reservations are encouraged to...

Experience the magic of the holiday season at the 31st Annual Elburn Chamber Christmas Stroll! Join the community on Saturday, December 6th, 2025, from 4-7 pm in Downtown Elburn for a delightful evening filled with festive activities. Meet Santa and Mrs. Claus, enjoy live music, explore local shops, and discover...

Roselle Winterfest invites you to celebrate the start of the holiday season with a vibrant community gathering. Enjoy live entertainment, delicious food from local trucks, and engaging activities for all ages. Don't miss the chance to meet Santa, participate in a gingerbread house decorating contest, and witness the magical Holiday...

Experience the magic of 'The Golden Age of Christmas' at the Woodstock Opera House's annual Christmas Tree Walk. This beloved holiday tradition transforms the venue into a festive wonderland with beautifully decorated trees, each telling a story of holidays gone by. It's a heartwarming celebration of the season's spirit, showcasing...

Embark on a magical holiday journey at Santa's Village with their one-of-a-kind drive-thru Christmas experience. Glide through millions of lights synchronized to festive music, creating a dazzling spectacle from the comfort of your car. At the end of the route, park to meet Santa, capture memorable family photos, and savor...

Step into a winter wonderland at Kringle's Christmas Village, a charming holiday attraction in Antioch. This indoor event showcases dozens of oversized, illuminated shadowboxes filled with delightful miniature scenes. Explore the magic of the season with festive displays, a new miniature Dickens Village, and a dazzling array of community-decorated Christmas...

Discover Christmas Town at Summerfield Zoo for a magical family tradition! Meet live reindeer, visit Santa at his cottage for photos, and enjoy festive train rides. Explore the zoo to see a variety of animals, including cold-climate species, and find unique gifts at The Flying Reindeer Gift Shop. Mrs. Claus'...

Experience the magic of Mundelein's Winter Tree Lighting Festival, a cherished tradition combining the Village's Holiday Tree Lighting Ceremony with Winterfest. This festive event features live music, ice sculpting, and visits with Santa. Explore the Kris Kringle Market for unique gifts and enjoy a variety of family-friendly activities, culminating in...

Experience the magic of the holiday season at the Village Tree Lighting & Downtown Holiday Walk in Libertyville. Festivities commence with carols and entertainment, culminating in Santa's grand arrival to light the Village Holiday Tree. Capture memorable photos with Santa and explore the charming shops and restaurants that make downtown...

St. Charles transforms into a winter wonderland for the Holiday Homecoming Weekend. This spectacular event kicks off the festive season with the enchanting Lighting of the Lights Ceremony. Families can enjoy a free screening of 'Elf,' a dazzling Electric Christmas Parade, and a chance to visit Santa in his new...

Join the Village of Arlington Heights for a magical start to the holiday season! Experience the enchanting Tree Lighting at North School Park, adorned with thousands of lights, and enjoy festive family fun at Harmony Park. Delight in live ice carving, meet real reindeer, and enjoy carols from local school...

Immediately following the Annual Woodstock Christmas Parade, families can head to the Historic Woodstock Square for a delightful 'Cookies and Churros with Santa' event. This festive gathering offers children a perfect opportunity to share their Christmas wishes with Santa, indulge in sweet treats, and embrace the holiday spirit.

Get ready for a naughty and nice holiday celebration at Backyard Bar's "Bad Santa" Party. This adult-themed event promises a unique twist on festive fun, offering a memorable night out with a playful and irreverent atmosphere. It's the perfect place to embrace the holiday spirit with a touch of mischief.

Join the magic of the holiday season with a delightful Brunch with Santa at Grand Geneva Resort & Spa. This event is specially crafted for children, offering a memorable breakfast experience served right at your table. Guests are encouraged to bring their Christmas wish lists and capture cherished photos with...

Escape the ordinary and embrace the festive spirit with the Igloo Experience at Grand Geneva Resort & Spa. These charming igloos offer a private and picturesque setting for up to six guests, perfect for intimate gatherings with friends and family. Reserve your spot in advance for a memorable holiday outing.

Celebrate the holiday season with a magical breakfast at Chevy Chase Country Club. This festive event offers a delicious holiday meal and the chance for children to meet and take photos with Santa Claus. It's a perfect way to create lasting holiday memories for the whole family.

Charles Dickens’ enchanting tale of redemption, generosity, and hope comes to life in Arlington Heights’ favorite holiday tradition. On a snowy Christmas Eve brimming with memorable characters, ghostly apparitions, and festive holiday music, miserly Ebenezer Scrooge visits the past, present, and future and discovers the true meaning of Christmas. Metropolis’...

Get ready for the return of Woodstock's cherished 'Legend of the Pickle' Holiday Scavenger Hunt! This beloved tradition invites participants of all ages to follow a trail of clues, uncover hidden pickles, and immerse themselves in festive fun. It's a perfect way to spread holiday cheer and create memorable experiences.

Get ready for a delightful holiday experience with Jolly Jingles, a Santa Sing-Along Celebration. This event promises a heartwarming gathering where families can come together to share in the joy of the season through music and festive cheer. It's a perfect opportunity to create lasting holiday memories.

Experience the magic of the holiday season at the annual Woodstock Christmas Parade. This cherished tradition features dazzling floats and decorated vehicles, bringing festive spirit to life. Following the parade, join in for a special meet-and-greet with Santa, complete with cookies and churros, to officially welcome the holidays.

Woodstock transforms into a winter wonderland, offering a magical holiday experience for all. From the festive Lighting of the Square to charming horse-drawn carriage rides and a lively New Year's Eve Bash, the town buzzes with seasonal spirit. Enjoy unique shopping, delightful performances like 'The Nutcracker Ballet' and holiday concerts,...

Join the festive kickoff to the holiday season at Woodstock's Annual Christmas Parade. This beloved event features a vibrant procession of local organizations and businesses showcasing their creativity on decorated floats. The highlight of the parade is the arrival of Santa and Mrs. Claus, bringing holiday cheer to all.

Get ready for a magical evening at the Festival of Lights! The celebration kicks off with a vibrant parade, followed by the enchanting Annual Tree Lighting Ceremony. Enjoy festive songs and meet Santa Claus himself to usher in the holiday spirit.

Step into a festive winter wonderland at the Holly Jolly Holiday Family Event! This delightful celebration features a variety of indoor activities, including craft stations for kids, a gingerbread house contest, and a fun cake walk. As dusk settles, gather for outdoor holiday carols before the grand Tree Lighting Ceremony,...

Winterville at the Park promises a delightful community celebration, bringing festive cheer and winter activities to Carpentersville. This event is a wonderful opportunity for residents to gather and enjoy the holiday spirit together in a welcoming park setting.

Join Hawthorn Mall for a magical Santa's Arrival event on Friday, November 21, 2025. Santa will make a grand entrance with a festive parade, kicking off the holiday season. The celebration includes activities like face painting, balloon twisting, crafts, and entertainment, plus a special 'A Christmas Story' themed set. Registered...

Unleash your creativity this holiday season at the Plant & Sip: Holiday Wreath Make & Take event. Participants will craft their own unique holiday wreath, perfect for adding a festive touch to their homes. Enjoy a relaxed atmosphere while sipping on beverages as you learn to assemble a beautiful, custom...

Get ready for the Christmas Classic Chicago South, a two-day national championship event filled with holiday spirit! This exciting competition features holiday music, opportunities for photos with Santa, and the thrilling World's Largest Indoor Snowball Fights. Teams will compete for prestigious awards, including Grand Champion Rings and National Champion Bracelets,...

Join the Schaumburg community for their annual Tree Lighting Ceremony, a cherished tradition that officially ushers in the holiday spirit. This festive event brings residents together to celebrate the season and witness the magical illumination of the village's holiday tree.

Join the St. Charles community for the magical Holiday Homecoming Lighting of the Lights Ceremony, marking the official start of the holiday season. This spectacular event features a stunning display of holiday lights, festive music, and a special visit from Santa. The celebration continues with the Electric Christmas Parade, free...

Gather your family for a delightful gingerbread house decorating session. Each group receives a gingerbread house, frosting, and an assortment of candies to create a festive masterpiece. Little ones will also enjoy a special gingerbread craft activity, making it a sweet and memorable holiday experience for all ages.

All aboard for a magical 1-hour train ride to the North Pole! Families can relive the classic story of 'The Polar Express,' sing cheerful Christmas carols, and enjoy milk and cookies. The highlight of this enchanting journey is a special visit from Santa Claus himself, making it a memorable holiday...