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Find authentic Oliver Typewriters in local storefronts, many originally made right here in Woodstock, each paired with a unique story that brings the past to life.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 of the 14 stops 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

To get started, download the Naturally McHenry County App so you can follow the 14 trail stops in participating storefronts throughout Woodstock beginning June 23, 2026. 

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

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. 

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 the written word and Woodstock’s rich industrial history this National Typewriter Day! 

Join the City of Woodstock and the Woodstock Public Library on June 23, 2026, at 6:30 PM for a special evening launching the new Woodstock Typewriter Trail in honor of the 130th anniversary of Woodstock’s legacy as the “Typewriter Manufacturing Center of the World.”

Moderated by Woodstock Mayor Mike Turner, the event features author and collector Jett Morton, who will share the fascinating history of the Oliver Typewriter Company and its lasting impact on the growth and identity of Woodstock.

Whether you’re a history buff, writer, collector, or simply curious about Woodstock’s unique past, this is your chance to celebrate a legacy that helped shape the community we know today.

Guests can explore historic typewriters on display at the library and throughout the city as part of the new Typewriter Trail, discovering the stories behind these iconic machines while entering for a chance to win a grand prize. Read Between the Lynes will also be onsite selling Morton’s book, The Oliver Typewriter: The Standard Visible Writer.

Register for the event HERE!

Start the Trail on June 23, 2026

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

Download the Naturally McHenry County App to get started and begin your journey through history.

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