“Middletown, I think, is the most beautiful Town of all…” John Adams, 1771

With 20 stations sited at various landmarks throughout the city’s downtown, this historic walking tour provides the first permanent exploration of Middletown’s illustrious and diverse past. Colorful, highly illustrated plaques reveal the city of yesteryear: the shipbuilding glory days, clashes between Tories and Patriots, efforts by local Abolitionists to end slavery, and how newly arrived immigrants build the majestic churches that stand today. Along the way you will meet the wide range of people who have called Middletown home, from American presidents to newly-freed enslaved people, Academy Award-winning composers to immigrant stone masons, army privates and Civil War generals, even a scientist who theorized that dinosaur footprints were the marks of a prehistoric four-toed man.

The Heritage Trail can be explored on foot or bicycle either in its entirety or one or two panels at a time. The trail’s introduction is located next to the Middletown Police Station at 222 Main Street, where four large panels give an overview of the city’s past.

Free descriptive brochures, which include a map of the trail, are available at the General Mansfield House at 151 Main Street, Russell Library at 123 Broad Street and the Middlesex County Chamber of Commerce at 393 Main Street, Middletown, Connecticut.

All stops, except #5 Riverside Cemetery and #11 Washington Green, are wheelchair accessible.

The Middletown Heritage Trail is the project of the Middlesex County Historical Society, with grants from the Connecticut Humanities Council, Liberty Bank, and the Middlesex County Community Foundation.

Guided tours of the Heritage Trail for school groups and organizations can be arranged by contacting the Middlesex County Historical Society. A small fee is charged.