Being part of the oldest towns in Connecticut is a pretty big deal, because that makes you one of list of oldest towns in the country! But just because these towns have been around a while doesn’t mean they don’t pack a big punch. Like a good bottle of wine, Connecticut only gets better with age.

1. The oldest town in Connecticut is Windsor! Settled in 1633, the town was originally named Dorchester. But it became the Windsor we know and love in 1637.
Doug Kerr/Flickr
Oliver Ellsworth was born in Windsor, and went on to be the third Chief Justice of the United States. Must be something in the water!
2. Founded in 1634, Wethersfield comes in at a close second. Formerly knows as Watertown, its name was also changed in 1637. Must have been a good year for names!
Susy Morris/Flickr
Wethersfield is also home to three designated historic landmarks, which makes this town a cultural center.
3. If you weren't convinced that 1637 was a lucky year for names, you will be now. That's also when the 1635 Newtown became Hartford!
Doug Kerr/Flickr
Hartford went on to be the state's capital, growing increasingly diverse every year.
4. Deep River, settled in 1635, is one of Connecticut's best kept secrets, and home to a very charming Main Street.
Doug Kerr/Flickr
Sitting along the Connecticut River, go here for a boat ride and stop in during the Deep River Ancient Muster.
5. The spring of 1638 brought us New Haven, famous for being home to Yale University.
Aidan Wakely-Mulroney/Flickr
This town has graced the silver screen a number of times, including an Indiana Jones chase scene!
6. Named Wepawaug by the Native Americans, Milford was settled in 1639, although it went without an English name for over a year.
Doug Kerr/Flickr
Milford has over 14 miles of shoreline, the most of any Connecticut town!
7. Guilford, settled in 1639, was named from Guilford Parish in Surrey, England.
Doug Kerr/Flickr
With 9 parks and over a dozen historic places, this town is just begging to be explored.
8. Settled in 1639, Stratford played its part in history with famous resident William Samuel Johnson being one of the framers of the U.S. Constitution.
Adam Moss/Flickr
Visit the rose garden at the Sterling House for a well spent Saturday afternoon.
9. Fairfield was settled in 1639, but it's not clear whether it was so named for being such a nice patch of land, or in honer of Fairfield in Kent, England.
Conner Downey/Flickr
This town stays young by being home to Fairfield University, but honestly, you can find everything on Post Road!
10. Greenwich joined the dream team on July 18, 1640 and has been a pretty cool spot ever since.
Doug Kerr/Flickr
If you thought New Haven was famous, scenes of Greenwich have appeared in over 40 films. They should nickname this place Hollywood!

Did you know these towns were so old? Tell me which one is your favorite!

OnlyInYourState may earn compensation through affiliate links in this article.

Related Articles

Explore Connecticut