Follow the Keys: The Woodstock Typewriter Trail

June 23 - November 23, 2026

Step into Woodstock's story and discover the city that helped change the way the world wrote. The Woodstock Typewriter Trail is a free, self-guided walking experience through downtown that celebrates the legacy of the Oliver Typewriter Company and the innovation that put Woodstock on the map.

At its peak in the 1920s, Woodstock produced nearly half of the world's typewriters. Today, that remarkable history comes to life through 14 authentic Oliver Typewriters displayed in local storefronts, many originally manufactured right here in Woodstock. Each stop shares the story behind the machine, the people who built it, and the company's lasting impact on the community.

Whether you're a history enthusiast, writer, collector, or simply looking for a unique way to explore downtown, the Typewriter Trail offers a fascinating glimpse into Woodstock's past while introducing you to its locally owned shops, restaurants, and attractions.

Don't miss the special exhibit at the Woodstock Public Library, featuring additional historic typewriters and artifacts. You can also browse The Oliver Typewriter: The Standard Visible Writer by Morton, available for purchase at Read Between the Lynes.

Want to learn more about the history? Check out the Woodstock Public Library's archives on the Oliver Typewriter Company.

How It Works

Exploring the Woodstock Typewriter Trail is easy. Download the Naturally McHenry County app, then follow the trail to discover all 14 typewriter locations throughout downtown Woodstock.

At each stop, you'll:

• View an authentic Oliver Typewriter displayed in a protective case.
• Read the story behind the machine and Woodstock's rich manufacturing history.
• Enter the unique check-in code in the Naturally McHenry County app to track your progress.

Complete the required number of stops and submit your digital passport through the app for a chance to win a grand prize.

Download the Naturally McHenry County App:
Android: https://play.google.com/store/apps/details?id=com.visitwidget.mchenrycountyil&hl=en_US
IOS: https://apps.apple.com/us/app/naturally-mchenry-county/id1481631818