Cleveland, Connecticut? How an 18th-Century Charter Shaped Ohio’s Most Famous City
The Curious Case of “Cleveland, Connecticut”
Welcome to Episode 131 of Travel in Time with Dan! Standing in a historic graveyard in Canterbury, Connecticut on a late October evening under a glowing “Halloween moon,” we are brought face-to-face with an astonishing piece of forgotten American history: the major midwestern city we know today as Cleveland, Ohio was nearly a permanent part of Connecticut!
The “Long Connecticut” and the Birth of the Western Reserve
To understand how Ohio inherited a New England footprint, you have to look back to Connecticut’s original royal charter granted by the King of England. Under this charter, the colony operated under the vast geographic concept known as the “Long Connecticut.” Legally speaking, Connecticut’s western boundary didn’t stop at the New York border. It extended all the way to the Pacific Ocean!
Following the Revolutionary War, the individual state colonies found themselves burdened with massive war debts. To secure federal financial relief, many states surrendered their sprawling western land claims to the national government. Connecticut agreed to give up most of its western territory, but struck a bargain: “Hold on a second… we’re going to save what’s called the Western Reserve.”
Connecticut retained a strategic tract in modern-day Ohio known as the Connecticut Western Reserve (or “New Connecticut”). Within this reserve, they designated a specific area called the “Firelands,” set aside specifically for Connecticut residents whose homes had been burned down by the British during the war. However, moving out there was no simple task…. it required a grueling 500-mile walk from Connecticut, which meant very few local residents actually uprooted their lives to make the journey.
Original Scope vs. Retained Reserve
| Cities Included Under Original Charter | Retained “Western Reserve” / “New Connecticut” Area |
| Chicago | The “Connecticut Western Reserve” (or “New Connecticut”) in present-day Ohio. |
| Omaha | The “Firelands” set aside for Connecticut citizens whose homes were burned by the British. |
| Cheyenne | Land surveyed and retained by Connecticut prior to surrendering outer western claims. |
| Salt Lake City | Capital territory surveyed along Lake Erie and key inland river trade routes. |
| Sacramento | Regional tracts later organized into Northwest Territory counties like Trumbull County. |
Moses Cleaveland: The Man, The Survey, and The New England Footprint
To survey and lay out this newly secured wilderness, Connecticut dispatched one of its prominent citizens: Moses Cleaveland.
Moses Cleaveland’s Background:
- Residence: Canterbury, Connecticut (buried right here in this historic Canterbury cemetery!)
- Education: Yale graduate
- Military Service: Captain in the Revolutionary War
- Profession: Lawyer and politician
- Role: Lead Surveyor for the Western Reserve
Moses Cleaveland made the arduous 500-mile trek out to Ohio to inspect the territory. He fell in love with the area, surveyed the land, and established the site that would serve as the central capital of the Western Reserve. While surveying, he held a forward-looking vision of connecting Lake Erie directly to the Ohio River… a concept later realized through the building of the Erie Canal.
Because Cleaveland and his survey team hailed from New England, they designed the new settlements to look just like home, featuring central public squares and public town greens. They also named many of the new Ohio towns after familiar Connecticut locations:
Connecticut’s Ohio Namesakes
- Norwich
- New London
- Litchfield
- Danbury
- Portland
- New Haven
- Southington, and many more…
After completing his survey work, Moses Cleaveland walked right back to Connecticut to resume his law practice and family life. In a striking twist of historical irony, Cleaveland never ever returned to Ohio or set eyes on the bustling city that bore his name again… yet a statue of Moses Cleaveland stands proudly in the heart of Cleveland today.
From Treaty to School Fund: How Land Sales Financed CT Education
The acquisition, division, and monetization of New Connecticut followed a clear historical chain of events that directly transformed public education back in Connecticut:
- Native American Negotiations: Moses Cleaveland arrived in the territory equipped with the Treaty of Greenville. Local Native American tribes were unfamiliar with this paper claim, but Cleaveland persuasively negotiated with tribal leaders through gifts, promises, and talks to secure signatures surrendering the land.
- Transfer to Developers: With land claims secured, the territory was transferred to the Connecticut Land Company.
- Private Land Sales: The Connecticut Land Company surveyed the acreage and sold tracts to private buyers and settlers for profit.
- Territorial Reorganization: The region was eventually incorporated into the Northwest Territory, establishing counties like Trumbull County (named directly after Connecticut Governor Trumbull) before officially becoming the state of Ohio.
- The “ Old Deluder Satan Law” & Education Mandate: All revenues from these land sales were funneled directly into the Connecticut School Fund. This tied directly into an early colonial “Old Deluder Satan Law,” which mandated that whenever a town reached 50 families, it was legally required to establish a school to educate children and keep them from following Satan or falling into temptation.
- Taxpayer Relief: Money generated from selling New Connecticut lands fully funded these local schools, meaning Connecticut residents no longer had to reach deep into their own pockets to pay for their children’s education.
Losing the “A”: The Spelling Transformation
Historical Curiosity: How “Cleaveland” Became “Cleveland”
> The city was originally spelled “Cleaveland,” matching the exact surname of its founder, Moses Cleaveland. The letter “a” was dropped later on to shorten the name. The primary historical explanation is that a local newspaper editor ran out of space on the newspaper’s masthead and removed the “a” so the city’s name would fit on a single line. While other rumors and stories exist regarding the change, the newspaper masthead constraint remains the most widely recognized explanation for how “Cleaveland” became “Cleveland.”
Leadership Key Takeaway: Evaluating the Impact on Others
A great leader must stay focused and work hard to accomplish a goal, but they must always remember to consider the consequences their actions have on others. Moses Cleaveland was driven and persuasive enough to secure signatures and fulfill his mission, but he failed to evaluate the devastating long-term consequences imposed on the Native American tribes whose ancestral lands were surrendered.
Conclusion & Travel Reflection
From a 17th-century royal charter claiming land all the way to the Pacific Ocean, to public school funds and New England village greens in northern Ohio, the story of Cleveland is deeply interwoven with Connecticut history.
Standing here in this historic Canterbury graveyard under the late October twilight moon… just steps away from Moses Cleaveland’s final resting place… reminds us why travel is so powerful. Visiting these physical sites brings history to life and gives us space to reflect on how travel, historical decisions, and modern leadership principles intersect across centuries.
Uncovering History. Inspiring Leadership. The Travel in Time Show is where travel, history, and leadership intermingle with history teacher, author, and speaker Dan Blanchard
*Check out Dan’s book, “Travel in Time in Connecticut: https://www.amazon.com/Travel-Time-Co…
*Watch Dan’s YouTube video on this: https://www.youtube.com/watch?v=3iEcPvF9WUo&t=328s
*Listen to Dan’s podcast on this episode: https://open.spotify.com/episode/2VkkruarF1h2l1N90J2N0N?si=86P6Sy2NQmWqjCX40G6zTA
*See Dan’s interview with General Moses Cleaveland: (Coming soon)
*Learn more about Dan: https://granddaddyssecrets.com/
Travel in Time with Dan – Mixing Travel, History, and Leadership with me, Dan Blanchard!