Category: Events and Festivals

Best Outdoor Things to Do This Summer in Woodstock, IL

By Real Woodstock on May 27, 2026

At last, the sun peeks out from behind the clouds, car windows roll down so you can breathe in the fresh air, and the shorts and flip flops are dusted off and finally make their way back out after a long winter. This is the time of year when Woodstock starts to buzz again. Patios fill up, music…

Read More

MCYSA International Youth Baseball Tournament Returns to Woodstock, Illinois This Summer

By Cecelia Bertelsman on May 18, 2026

This summer, Woodstock becomes an international destination for youth baseball as the MCYSA International Youth Baseball Tournament returns July 10–19, 2026. Hosted throughout McHenry County, the annual tournament welcomes more than 80 teams from around the world for ten days of competition…

Read More

Memorial Day Weekend in Woodstock, IL: Your Guide to A Holiday Weekend Getaway

By Real Woodstock on Apr. 29, 2026

Make it a REAL holiday weekend! Memorial Day in Woodstock brings together long-standing events, great food and fun experiences worth the trip, all set in our charming, historic community. We've put together a full weekend itinerary to help you make the most of it, from meaningful traditions to…

Read More

A Book Lover's Guide to Woodstock, IL

By Cecelia Bertelsman on Apr. 17, 2026

Independent Bookstore Day – April 25 Imagine a dew-kissed Spring morning in Woodstock, Illinois on the Historic Square...the kind where the birds are chirping, a sweet latte in hand and the only thing on your agenda is a quiet stroll through towering bookshelves of local shops. This carefree start…

Read More

Tips for Your First Groundhog Day in Woodstock, IL

By Heather Arnold on Jan. 12, 2026

Welcome to Woodstock, where February 2 isn’t just a date, it’s a full-blown experience worth repeating. If it feels like déjà vu, you’re doing it right. The 1993 cult classic Groundhog Day was filmed right here, and every year Woodstock turns that movie magic into a weekend-long celebration filled…

Read More

Reliving Movie Magic at the Cherry Tree Inn Bed & Breakfast in Woodstock, IL

By Maddy Neubauer on Jan. 07, 2025

When it comes to charming getaways, the Cherry Tree Inn Bed & Breakfast in Woodstock, Illinois, is a destination that effortlessly blends history, hospitality, and Hollywood magic. Nestled in the heart of this picturesque Midwestern town, the inn has gained international fame as a key filming…

Read More

Experience the Magic of Winter in Woodstock, Illinois: Holiday Lights, Festivities, and Local Charm

By Maddy Neubauer on Nov. 07, 2024

With tens-of-thousands of lights and classic charm, Woodstock makes a great winter destination! Here's how you can spend your visit: Holiday Lights & Festivals: Start your holiday experience with the Lighting of the Square on the Friday after Thanksgiving. The historic Woodstock Square is…

Read More

Celebrate Groundhog Day in Woodstock, IL as experienced by Olio

By Real Woodstock on Mar. 08, 2023

Woodstock hosted travel writer and Goundhog fan Megan from Olio this past Groundhog Days Festival and we wanted to share her insights to our favorite holiday! Gobbler’s Knob in Punxsutawney, Pennsylvania garners a lot of the Groundhog Day fanfare. But lovers of the 1993 cult classic Groundhog Day…

Read More

Town in 'Groundhog Day' celebrates movie's 30th anniversary

By Real Woodstock on Feb. 02, 2023

Town in 'Groundhog Day' celebrates movie's 30th anniversary The city of Woodstock, Illinois, is celebrating the 30th anniversary of the classic Bill Murray comedy “Groundhog Day” which was filmed in the small town that is proud of its place in Hollywood history. NBC’s Maggie Vespa reports for TODAY…

Read More

‘Today’ show to stop in Woodstock on Friday for Christmas segment

By Real Woodstock on Dec. 07, 2022

‘Today’ show to stop in Woodstock on Friday for Christmas segment Public is invited, with coffee, hot chocolate, doughnuts to be served By James T. Norman | of Shaw Media - Northwest Herald December 07, 2022 at 3:00 pm CST Some of the ten thousand lights shine during the Lighting of the…

Read More