Welcome to Woodstock:
Your Home for Holiday Cheer
| | Welcome to December—Woodstock’s most enchanting month. With festive events, twinkle-lit traditions, and something joyful around every corner, there’s no better place to soak up the spirit of the season. | | | |
Lighting of the Square
Friday, November 28 from 4-8:00 PM
Visit the historic Woodstock Square on the Friday after Thanksgiving and help the City of Woodstock usher in the official start to the holiday season with this beloved annual tradition. Enjoy shopping, delicious food and drinks, and plenty of merry moments before the ceremony at 7:00 PM.
Get the Detailed Itinerary >
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Small Business Saturday
Saturday, November 29
Discover the magic of Small Business Saturday in Woodstock! Stroll local businesses to find unique gifts, local treasures, and festive treats. Every purchase celebrates the creativity and heart of our community while supporting the shops that make Woodstock shine.
Visit our List of Shops >
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Annual Christmas Parade
Sunday, November 30
Sleigh what? Santa is coming to town…on a parade float! Bundle up and join us as Woodstock’s Square fills with decorated floats, holiday music, and all the merry magic that makes this annual celebration the perfect start to the season.
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Cookies & Churros with Santa
Sunday, November 30
Santa’s got a sweet tooth! And he's ready to share with you! Create tasty memories with the entire family at Cookies & Churros with Santa. After the parade, head to Trademark Events (240 N. Throop St.) and enjoy delicious treats, meet the big guy in person, and share your holiday wish list.
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Santa Hut Visits
December 1 - 23
Step into the holiday spirit at Woodstock’s festive Santa Hut! Nestled on the southeast corner of the Square, this charming spot is perfect for photos and soaking in seasonal magic. A heartfelt thanks to the Rotary Club of Woodstock for keeping this cherished tradition alive! Be sure to sign up in advance to secure your visit with Santa. While you’re here, explore the Square, enjoy warm drinks, and let the twinkling lights and festive atmosphere carry you into the season.
Learn More and Sign Up to Visit >
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Ladies Night Out
Thursday, December 4
Sip, shop, and sparkle! Woodstock’s Ladies Night Out is the perfect evening to explore the Square’s boutiques, enjoy seasonal drinks, and treat yourself (or a friend!) to some holiday cheer. Grab your gals and make it a night to remember thanks to the Woodstock Area Chamber of Commerce!
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Carriage Rides on the Square
December 7, 14, 21
2-4:30 PM
Step into a storybook while you are out doing your holiday shopping! Cozy up and enjoy a magical horse-drawn carriage ride around Woodstock’s historic Square, weather permitting. Twinkling lights, crisp winter air, and festive holiday decor make it a picture perfect holiday outing in downtown.
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Christmas Tree Walk
November 28-December 27
Rock around this year’s Woodstock Opera House (121 W. Van Buren St.) Christmas Tree Walk. With the theme The Golden Age of Christmas, beautifully decorated trees capture the nostalgic charm and timeless traditions of the season. Wander the festive display and see local organizations showcase their creativity.
Learn More >
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Gingerbread Walk
November 28-December 21
Sweeten your season with the Friends of the Old Courthouse Center’s annual Gingerbread Walk at 101 N. Johnson St.! Explore a whimsical display of gingerbread creations, each crafted with festive flair. It’s a deliciously charming holiday tradition that delights visitors of all ages.
Learn More >
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Make the Kids on Your List Smile
Fill Their Wishlist with Revelry Toys
Santa called—he wants to see those wish lists! Woodstock’s very own Revelry Toys (205 N. Throop St.) is the ultimate spot for little dreamers to fill their lists with toys, games, and treasures they’ll love. Bonus: they can keep a copy of the wish lists so friends and family can help Santa keep track. Big smiles guaranteed!
Plan Your Visit to Revelry Toys >
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The Holidays Take the Stage
The Woodstock Opera House (121 W. Van Buren St.) is taking the spotlight this season with a lineup that’s sure to sleigh you with holiday cheer!
- It’s a Wonderful Christmas Carol
- The Nutcracker Ballet
- Axiom Brass Holiday Concert
- The Four C Notes
- White Christmas Sing-Along
- Ed Hall’s Christmas Guitar Night with Ryanhood
Grab Your Tickets >
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Step Into the Knight Before Christmas
A Whimsical Holiday Pop-Up
Step inside The Knight Before Christmas, Woodstock’s whimsical pop-up holiday restaurant at The Squire on the Square (101 N. Johnson St.)! The space is decked out in stunning holiday décor, offering themed cocktails and festive bites. Whether you’re toasting with friends, planning a family dinner, or starting a new holiday tradition, this is one Knight you won’t want to miss.
Feast Your Way to Squire on the Square >
| | | | Don't Miss These Other December Highlights | | |
Wine, Chocolate and Cheese Pairing
December 5
Learn More >
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The Bittersweet Christmas Band
December 5
Learn More >
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The Woodstock Indoor Farmers Market
December 6, 13, 20
Learn More >
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Breakfast With Santa
December 14
Learn More >
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Jolly Jingles: A Santa Sing-A-Long Celebration
December 14
Learn More >
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Mystic Menagerie: Winter Solstice Market
December 20
Learn More >
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