Middletown Heritage Trail (Completed!)

In the Middle of it All
Middletown Heritage Trail
20 sites within a few square miles in Middletown

“Middletown I think is the most beautiful town of all…” – John Adams

trail_map-1.gifYes, THE John Adams. You’ll find this quote all over the historical spots in Middletown… but I do wonder what the rest of his quote was. Could it have been, “Middletown I think is the most beautiful town of all the towns named Middletown in New England.” Perhaps, but Middletown is very proud of that quote, so let’s not try to ruin it for them.

I was able to complete this trail during my hypothetical lunch break from work. Since my work location would be changing soon, I’ve been trying to bang out as much within 20 minutes as possible.

With 20 stations sited at various landmarks throughout the city’s downtown, this historic walking tour provides the city’s 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 slaves, 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.

(2010 Update: I must note that during my original efforts, the first two panels were missing. I was contacted by the trail’s designer who explained that the dopey merchants there missed the point of this whole thing and asked the city to remove the signs because they were “blocking merchant’s views” of their storefronts. I’m happy to report that two years after my initial efforts, the signs have been restored and now I’ve truly completed the whole trail.)

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


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.

(2011 Update: I’ve recently been out in Ridgefield and Danbury. Both towns have things called “Museum in the Streets” which are EXACTLY the same as the Middletown Heritage Trail. Just probably more expensive since they were put together by a private firm.)

I’ll guide you through the trail in the order that the town numbers the 20 sites. It’s actually a pretty neat little bit of history and I had fun finding the spots along the way. There is also a Freedom Trail stop in town as well as an Underground Railroad Trail site as well. Enjoy.


1. Introduction to Middletown signs
2. Bigelow Tavern
3. Connecticut River
4. deKoven House
5. Riverside Cemetery
6. St. John Church
7. Jehosaphat Starr House
8. Saint Sebastian Church
9. Russell Library
10. Russell House
11. Washington Green
12. Indian Hill Cemetery
13. Freedom Church
14. Wesleyan’s College Row
15. Abolition Site
16. Adath Israel Synagogue
17. Danforth Pewter Shop
18. Henry Clay Work bust
19. Civil War Monument
20. General Mansfield House

One response to “Middletown Heritage Trail (Completed!)”

  1. ebbie says:

    hey man, what the hell? why didn’t you put the quote on the sign?

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