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Holidays in Woodstock

Don't miss these wonderful holiday happenings all season long in Woodstock! Get into the holiday spirit with a festive lineup of events and activities for the whole family! Kick off the season with the whimsical Legend of the Pickle tradition, then enjoy the charm of the Christmas Parade and indulge in sweet treats like Cookies and Churros with Santa. Make magical memories with a visit to Santa’s Hut, where little ones can share their holiday wishes. Ladies can enjoy a special Ladies Night Out, while a Carriage Ride through the historic square sets the perfect holiday scene. Explore unique shopping opportunities with Shop, Dine, Save, and Win promotions, where you can find great gifts, enjoy delicious meals, and even win prizes. Woodstock, Illinois offers the perfect blend of small-town charm and holiday cheer – come make unforgettable memories this season!

Events

Pickle Card for FB Event Cover

2024 Legend of the Pickle

November 10th-December 11th

Locations Vary

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Lighting of the Square

November 29 | 7:00pm

Woodstock Historic Square

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ChristmasParade-Logo

Woodstock Christmas Parade

December 1 | 2:00pm-3:00pm

Woodstock Historic Square

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Cookies & Churros Event Graphic - Main

2024 Cookies and Churros with Santa

December 1 | 2:30pm-4:30pm

Woodstock Historic Square

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Parade - Santa & Mrs Claus Waving

2024 Santa Visits

December 2-December 23

Monday-Friday, 5:00pm-7:30pm

Saturday, 10:00am-Noon and 1:00pm-5:00pm

Sunday, 1:00pm-5:00pm

Woodstock Historic Square

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Ladies Night Out

December 5 | 4:00pm-9:00pm

Woodstock Historic Square

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2022 Carriage Riders (Iversen Family)

Carriage Rides

Every Sunday starting December 8th through the end of December | 2:00pm-4:30pm

Woodstock Historic Square

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Shopping

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2024 Shop, Dine, Save & Win

November 29th-December 31st

View link to see participating locations!

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