About 1650, a handful of English colonists began settling Middletown - then called by its Native American name, Mattabesseck or Mattabesett. The first colonists did not come directly from England, but from early New England settlements like Boston Cambridge, and Hartford. The settlers laid out their home lots along what is now the north end of Main Street, and here built their houses and barns.
Their neighbors were Wangunks, Native Americans who had lived in this area for many generations. Their leader, Sowheag, had granted a large parcel of land here to the Colony of Connecticut.
In 1651, Connecticut's General Court designated "Mattabesseck" a town; three years later the name was changed to Middletown, probably because of its location between Saybrook and Hartford.
The first English families here were primarily farmers, but many men also worked as millers, stonecutters, weavers, joiners (carpenters), or shipbuilders.
Families were large, and from their marriage day, most women faced over two decades when they were either pregnant, nursing an infant, or both. Many couples had as many as ten children, although not all survived to adulthood.
The settlement boulder, placed here for Middletown's 250th anniversary in 1900, honored the men who first settled here in the
1650s, as well as the "Indian Grantors" - Wangunks who in the 1670s formally granted their people's land to the English. Another plaque added for the city's 350th anniversary honors Middletown's first female settlers.
English settlers did not build their first meetinghouse until 1652, near what is now Main and Spring Streets. Before that time, tradition holds, the colonists held their worship services under the branches of a large elm tree on this site. When the elm was taken down in 1842, its rings showed it to be several hundred years old. Mary Hulbert, a Middletown girl, painted this view of the elm tree and the cemetery about 1840.
- Courtesy the Middlesex County Historical Society
"1695-6 Sarah the wife of John Bacon lyes here who died being aged but 31 years, who has lying by her six children deare, and two she has left her husband to cher."
Childbirth always carried the threat of death in the 1600s and 1700s. Sarah Bacon died just a few days after giving birth to her eighth child. Death had already claimed six of her children, including the new baby. In the days before antibiotics and surgery, childhood mortality was tragically high.
Riverside Cemetery (also called Macdonough Cemetery) was Middletown's first burying ground. Although English families buried their dead here from the town's beginning, the earliest gravestone dates from 1689 - nearly four decades after settlement. Gravestones were expensive, not every family could afford them, leaving hundreds of graves unmarked.
Riverside's gravestones tell many sad stories. A triple headstone from 1755 recalls Jabez, John and Ebenezer Starr, triplet brothers who all died before reaching their first birthday. In the back right corner stand two simple stones to African-American slaves known only as Fillis and Sambo (pictured above). Nearby is a monument to 16-year-old Comfort Starr "who sailed from this town in Dec. 1764 and never has been heard of since." The stone of Isaac and Nathaniel Cornwel tells of young brothers who were "both slain by lightning in an instant" in 1739.
Most local gravestones from the 1600s and 1700s were carved of brown stone, which was plentiful Just across the Connecticut River in Portland (then a part of Middletown). Stonecarvers often used skulls or death's heads to ornament the earliest stones, while angel's faces came into style about 1740. By about 1800, white marble had become the stone of choice.
Commodore Thomas Macdonough
Thomas Macdonough was a dashing naval lieutenant from Delaware when he Lucy Shaler of Middletown in 1812. The Macdonoughs made their home here, but for several years Thomas was away much of the time, fighting in the War or 1812 against Great Britain.
For two years, the war went badly for the United States. British forces were better trained and outnumbered the Americans. But on September 11, 1814, the United States got the decisive victory it needed when Commodore Thomas Macdonough soundly defeated the British navy on Lake Champlain, using brilliant strategy to overcome the stronger British fleet. His victory helped lead to the signing of the peace treaty with Great Britain three months later.
Middletown welcomed Macdonough as a hero. After his death in 1825 and interment here with his wife and several children, the city officially named this Macdonough Cemetery.
Commodore Thomas Macdonough, Painted by Margaret Vandeursen of Middletown Courtesy of the Middlesex County Historical Society