LEAVITTSBURG, Ohio – In May 1811, 19-year-old Henry Leavitt Ellsworth set off on horseback on a journey west from his home state of Connecticut. His destination? large tracts of land – 41,000 acres in all – that his father, Oliver Ellsworth, had owned in the Western Reserve section of northeastern Ohio. 

A portrait of Oliver Ellsworth.

It wasn’t a pleasure trip, but nonetheless adventurous. Ellsworth, freshly graduated from Yale University, had inherited the sizable real estate empire in the burgeoning west after the death of his father in 1807. Now, he wanted to examine the family’s holdings and spend time in what was then mostly Ohio wilderness. 

The younger Ellsworth passed through the toughest terrain, opting to take the Forbes Road route to the west near Pittsburgh through the Allegheny Mountains, rather than the more populated and organized northern route that hugged the Great Lakes. Once in Ohio, he was able to visit all of his family’s vast landholdings, including what is today most of Cleveland.

There were also more lands to the southeast, including property in the vicinity where Ellsworth’s relatives had already established themselves. These landholdings surround and once were part of what is today Leavittsburg, an unincorporated village in Trumbull County just west of the city of Warren. Henry Ellsworth spent a month in the territory, attempting to iron out irregularities with the family’s land agent.

Diplomat, Speculator

His father, Oliver Ellsworth, would rise to become one of the most influential men in the country. Oliver’s mother, Jemima Leavitt, heralded from a prominent Connecticut family. 

Ellsworth, born in 1745, graduated Princeton University, entered the legal profession, married the daughter of the colonial governor of Connecticut, and served as a captain in a New York regiment during the American War for Independence. In 1777, he was selected by Connecticut to serve in the Continental Congress until the war’s end in 1783.

During the early years of the republic, Ellsworth also served as a Connecticut delegate to the Constitutional Convention in Philadelphia in 1787. Here, he is often credited for helping push forward the Connecticut Compromise – a solution to break the impasse during the convention over representation in the national legislature. It was the Connecticut delegation’s proposal that forged the House of Representatives, whose membership was apportioned by population, and a Senate, in which state legislatures would appoint two senators representing each state. Ellsworth would then serve as one of the first two U.S. senators from Connecticut, siding with the Federalist Party.

Ellsworth was a confidante of George Washington, who would in 1797 appoint him as the third chief justice of the United States. Ellsworth administered the oath of office to incoming president John Adams on March 4, 1797, the first chief justice to do so.

“As preparation for your departure will not conveniently admit of your receiving any more visits, you will suffer me in this manner, to bid you a most respectful and cordial farewell,” Ellsworth wrote to the outgoing president on March 6. 

Two days later, Washington replied from Philadelphia: “Dear Sir, before I leave this city, which will be less than twenty-four hours; permit me, in acknowledging the receipt of your kind and affectionate note of the 6th, to offer you the thanks of a grateful heart for the sentiments you have expressed in my favor, and for those attentions with which you have always honored me.”

During his tenure as chief justice, Adams selected Ellsworth as an envoy to help negotiate an end to tensions with France, which had erupted in 1797 over trade issues. However, it was in Europe that Ellsworth became ill, forcing him to resign from the court in 1800.

Throughout his successful tenure in law and politics, Ellsworth was an active land speculator, especially in the frontier that opened in the Ohio country after the Revolution. In 1795, Ellsworth was among 58 investors that created the Connecticut Land Co., which was organized to purchase Connecticut’s claim to the Western Reserve, which encompassed more than 3.3 million acres across northeastern Ohio from west of the Cuyahoga River to Pennsylvania. In 1800, the company purchased the territory for $1.2 million. Once the land was secure, the plan was to resell plots at a profit to those headed west. The names of other investors are still evident in northeastern Ohio today: for example, Moses Cleveland and Henry Champion.

Among the other investors in the company was John Leavitt, Ellsworth’s cousin, who paid $51,000 to acquire land in the Western Reserve. Unlike Ellsworth, Leavitt settled in the region in 1800, followed by other family members in what became Warren Township. Thus Leavittsburg, situated today in the township along a bend in the Mahoning River, was named for the Leavitt family. The family members helped establish Warren as the administrative center of Trumbull County, which then included present-day Mahoning County.

Oliver Ellsworth died in 1807, never once setting foot on the land he owned in the Western Reserve.

‘New Connecticut’

His son, nevertheless, did, and Henry Leavitt Ellsworth’s trek to the Western Reserve in 1811 opened his eyes to the complexities of land speculation in this part of Ohio. 

In his journal, later to be published as “A Tour to New Connecticut” in the 1980s, Ellsworth noted the sparse population, observing towns that were “quite settled, though there are many townships without a single inhabitant.” 

He also writes of deplorable living conditions among the settlers there, exclaiming he’d never experienced “so much dirt and filth in any human habitation.” 

If there was any relief at all during the trip, it was a brief visit with his friend, Margaret Van Horn Dwight, who a year earlier had departed from Connecticut for the Western Reserve and was now residing in Warren. Dwight, the niece of Yale president Timothy Dwight, married a successful merchant in Warren and relocated to Pittsburgh. 

Leavittsburg’s Promise

Today, the small community is centered at the crossroads of West Market Street and South Leavitt Road. A local tavern grocery, and a feed mill are among the more visible businesses in the hamlet. Along West Market stands the Leavittsburg Heritage Museum and Train Depot, a repository dedicated to the community’s history.

“We were a big railroad town,” says Linda Cowin, a member of the Leavittsburg Heritage Association, noting several tracks converged at a depot located in town. “It was a major stop.” 

Before the railroad, Leavittsburg sat along the Pennsylvania & Ohio Canal – an east to west cut that connected the Beaver Canal in Pennsylvania with the Ohio & Erie Canal in Akron. That canal threaded through the cities of Youngstown, Warren, Leavittsburg, Newton Falls and Ravenna, before terminating in Akron. 

By the mid-19th century, railroad interests eclipsed the canal business, and in 1854, the Cleveland and Mahoning Railroad – which eventually became part of the Erie Railroad – purchased the canal bed. By 1872, Levittsburg was known as a railroad center, replete with a hotel to serve guests.

Trolley service to the small town also encouraged development, Cowin adds. “The trolley came from Warren to Leavittsburg,” she says. 

In 1912, the Mahoning Park and Land Co. paid $25,000 for a 212-acre plot along the Mahoning River, across from what is today the Canoe City launch. There, the company constructed an amusement park and subdivided the rest of the land to build summer cottages for visitors. The amusement grounds’ dance hall also attracted some of the best bands in the
region.

“They also had big regattas every year” across the river at Canoe City, Cowin says. A water taxi would ferry patrons across the river back and forth from the amusement park and the launch. 

Once the trolley service ended, Mahoning Park fell into disrepair, while other parks, such as Idora Park in Youngstown, continued to thrive, Cowin says.

Meanwhile, Warren’s prominence as an industrial center and county seat led to additional investment and growth there, which would in future decades lead to the annexation of portions of Leavittsburg. 

While there are plenty or references to the Leavitt family name in this part of Trumbull County, there are virtually no physical reminders of Ellsworth. To find that, you would need to travel approximately 18 miles south. 

There, in 1810, residents of this part of what was then still Trumbull County decreed a new township be named for the recently deceased chief justice – a township consisting of land he never owned.