Follow the Keys: The Woodstock Typewriter Trail


June 23-November 23, 2026

 

Step into Woodstock’s story and experience history in a whole new way. The Woodstock Typewriter Trail is a self-guided journey through downtown, celebrating the legacy of the Oliver Typewriter Company and the innovation that helped shape our community.

At its peak in the 1920's, Woodstock produced nearly half of the world’s typewriters. Now, you can see that legacy up close.

Find authentic Oliver Typewriters in local storefronts, many originally made right here in Woodstock, each paired with a unique story that brings the past to life.
 

Explore the Trail

Take a walk through downtown Woodstock and uncover history around every corner. Each stop along the trail offers a closer look at the craftsmanship, innovation, and stories behind these remarkable machines.

 

How It Works

Getting started is easy and fun! 

1. Find the Typewriter
Look for trail stops in participating storefronts throughout Woodstock beginning June 23, 2026.

2. Discover the Story
Each typewriter is displayed in a protective case and paired with a story or prompt highlighting its history.

3. Check In
Use the Naturally McHenry County App to enter the unique code at each stop. 

4. Win a Prize
Complete the required number of stops and submit your digital guide for a chance to win a grand prize. 

Vintage postcard of the Oliver typewriter Company in Woodstock, IL
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Oliver Typewriter Original No 2
2
Oliver Typewriter Company in Woodstock IL Noontime break
3
Light colored Oliver Typewriter in plaid case
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Oliver Typewriter and Case
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Oliver Typewriter Accessories
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(1) Oliver Typewriter Factory Post Card, (2) Oliver Typewriter No 2, (3) Oliver Typewriter Company in Woodstock Noon Break, (4) Oliver Typewriter with Case, (5) Oliver Typewriter with Box, (6) Oliver Typewriter Accessories

A Legacy You Can See Up Close

In the early 1900s, Woodstock was a global leader in manufacturing, producing nearly half of the world’s typewriters at its peak. The arrival of the Oliver Typewriter Company in 1896 transformed the city into an industrial powerhouse and introduced groundbreaking innovations like visible writing.

Today, that legacy lives on through the Typewriter Trail, connecting Woodstock’s past to its vibrant present in a way that is interactive, walkable, and uniquely local.

 

Plan Your Visit

Trail Dates
June 23 to November 23, 2026

Kickoff Event
Celebrate National Typewriter Day on June 23 with author and collector Jett Morton. More details coming soon.

 

Start the Trail on June 23, 2026

Explore the stops, uncover hidden stories, and experience Woodstock from a new perspective.

Coming Soon - You'll be able to download the Naturally McHenry County App to get started and begin your journey through history.