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Take An Urban Stroll Along Middletown's Main Street

Special to The Courant
Middletown's Main Street offers the perfect urban stroll

Mindful that we need exercise even in the oh-so-busy month of December, consider a winter walk among the holiday decorations and the historic sites and buildings in downtown Middletown.

Middletown is one of the oldest cities in the state, with a rich history well worth a morning or afternoon of sidewalk sauntering. Its booming maritime economy in the late 18th Century made it Connecticut's most populous community at the time.

The Middlesex County Historical Society makes it easy to get a sense of the city's past with a Middletown Heritage Trail brochure highlighting 20 notable sites, some of them right on the city's mile-long Main Street, others within a few blocks of Main.

Starting perhaps at the historical society, housed in the historic General Mansfield House at 151 Main St. where there is on-street parking, a hike of 1, 2 or even 3 miles can easily be put together. Just decide which sites you'd most like to see, and how much exercise you'd like. The brochure includes a simple map of the area identifying locations of key sites. Brochures also are available at the Middlesex County Chamber of Commerce at 393 Main St.

You'll pass by dozens of stores decorated for the holidays, along with restaurants galore on Main Street and many of the other streets in the downtown district. There is a restaurant or two on virtually every block.

Just up the street from the historical society, next to the police station, is a four-panel graphic display that provides a very accessible, brief history of the city from the 1600s to the present. It has some nice detail; for example, you learn that in 1800, when the city was especially prosperous, there were 22 grocery stores, 11 dry goods stores, 2 bookstores, 2 goldsmith shops and 3 furniture makers.

In those years, the city was inseparable from the Connecticut River, which parallels Main Street and flows only a few blocks away. In fact, the river is why Middletown exists. While not formally part of the heritage trail, a walk to the river takes only minutes, a well-lit tunnel taking you safely under the heavily traveled Route 9 and right to the waterfront.

On lower Court Street by City Hall is a heritage stop with a graphic display that explains the city's maritime history. By the 1660s, shipyards were producing wooden vessels that sailed the Atlantic coast, to the West Indies, sometimes to Europe. Steamboats appeared on the river in the early 19th Century.

At the north end of Main Street, don't miss the Riverside Cemetery, cared for by the Middletown Old Burying Ground Association. It is the city's oldest graveyard, small, and the resting place for many early residents of the community.

You'll need to borrow the key to the cemetery gate, available nearby at the fire station at 533 Main St. The cemetery itself is behind the well-known O'Rourke's Diner.

Among the gravestones are those of two slaves who died in the late 18th Century, identified only as Fillis and Sambo. That their graves are marked with stones indicates they were highly regarded by their masters because gravestones were considered expensive.

Many of the markers convey poignant messages from centuries gone by. "Here lies one dead which in her life was my loveing (cq) pious wife. Abigail Harris died May the 22, 1723."

Note also the memorial to Commodore Thomas MacDonough, who is buried in the cemetery and who led his men to a key victory over the British on Lake Champlain during the War of 1812. That victory helped bring an end to the war just a few months later.

Endnote: The Middlesex County Historical Society is located at 151 Main St. Website is Hours are Monday through Thursday and Saturday from 10 a.m. until 2 p.m. A special exhibit on Middletown and the Civil War will continue through 2015.

Contact Steve Grant at

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