10 Oldest Cities In Connecticut

You might think your town is old, but it probably isn’t the oldest in the country.

That is unless you live in St. Augustine, FL. Which looks pretty good for being 454 years old.

That’s older than America for those playing at home.

So that got us thinking, what is the oldest city in Connecticut? And how old is that when you put it into perspective of St. Augustine or American Independence in 1776?

Because even if your Connecticut city or town is old, it isn’t really all that old in the grand scheme of things. For example, the Pyramids in Egypt were built around 2600 BC, a cool 4100 years before St. Augustine.

And now that we have you thinking about how the time line of your existence is really kind of unimpressive on the timeline of history, let’s drop right into the analysis.

These are the 10 oldest cities and towns in the Constitution State according to their ‘date of foundation’:

1. Trumbull
2. Norwalk (Photos)
3. Westport (Photos)
4. Winsted
5. Bridgeport (Photos)
6. New London (Photos)
7. Wethersfield
8. North Haven
9. Darien (Photos)
10. Wallingford Center

For being 379 years old, Trumbull doesn’t look a day over 40. And the newest city in Connecticut? That would be Portland — a brand spanking 113 years old.

Read on for a look at the oldest places in Connecticut or feel free to check out the best places to live in Connecticut or the safest.

How We Determined When A City Was Founded In Connecticut… Or Is It Settled?

Surprisingly, there’s not a definitive data set that contains the dates of incorporation or settlement for cities in America. Put differently, there’s no official data set from the Census that contains when every place in America was founded.

So what did we do instead?

Use the internet’s version of official government data — Wikipedia of course!

For the majority of cities in Connecticut, Wikipedia offers data on some kind of ‘date of foundation’ in the infobox. Unfortunately, because it’s Wikipedia and not a sprawling government bureaucracy, that can take the form of any of the following nomenclature (plus others):

• Founded
• Settled
• Incorporated
• Approved
• Chartered

And then even more stuff — for example Atlanta has a ‘Terminus’ date, whatever that is.

If no ‘date of foundation’ was found in the infobox, we looked to the general text in the History section of the city for ‘Founded in XXXX’.

All in all, we were able to collect data on 46 out of 61 in Connecticut with over 5,000 people. That’s good for a 75.4% completion rate.

We then ranked them from oldest to newest with Trumbull turning out to be the matriarch of Connecticut at the ripe old age of 379.

Here’s a look at the top ten and a snippet of their history from Wikipedia.

1. Trumbull

Population: 36,455
Founded: 1639
Age: 379
This area was long occupied by the Paugusset Indian nation in historic times, before European encounter. During the late 1630s, English colonists started settlement at what became the Town of Trumbull, as part of the Great Migration from England. This was related to the coastal settlement of Stratford, Connecticut.

2. Norwalk

Population: 88,537
Founded: 1640
Age: 378
Norwalk was settled in 1649, incorporated September 1651, and named after the Algonquin word noyank, meaning ‘point of land’, or more probably from the native American name ‘Naramauke.’

The city boundaries originally included parts of the current municipalities of New Canaan, Wilton, and Westport. Ancient records describe the boundaries as ‘from Norwalk river to Sauhatuck river, from sea, Indian one day walk into the country’. Thus a disputing source, and common tradition, describes Norwalk’s name deriving from the northern boundary extending from the sea covering one day’s ‘north walk’ into the countryside. An additional source found this analysis to be improbable, given that the name ‘Norwalk’ was used by natives, who were called the ‘Norwake Indians’. Additionally a nearby river was known as the Norwake River when the area was first colonized. Roger Ludlow’s 1640 land purchase was from ‘the Indians of Norwalke’ and the land is described as lying between ‘the twoe rivers, the one called the Norwalke, the other Soakatuck.’ The earliest town records list the city name as Norwalke (the ‘w’ likely silent, as in Warwick). Bradley’s [Connecticut] Register describes that the early Colony Records call it ‘Norrwake’. Around 1847 the elderly used the ancient pronunciation ‘Norruck’.

3. Westport

Population: 27,777
Founded: 1835
Age: 183
The earliest known inhabitants of the Westport area as identified through archaeological finds date back 7,500 years. Records from the first white settlers report the Pequot Indians living in the area which they called Machamux translated by the colonialists as beautiful land. Settlement by colonialists dates back to the five Bankside Farmers; whose families grew and prospered into a community that continued expanding. The community had its own ecclesiastical society, supported by independent civil and religious elements, enabling it to be independent from the Town of Fairfield. The settlers arrived in 1693, having followed cattle to the isolated area known to the Pequot as the ‘beautiful land’. As the settlement expanded its name changed: it was briefly known as ‘Bankside’ in 1693, officially named Green’s Farm in 1732 in honor of Bankside Farmer John Green and in 1835 incorporated as the Town of Westport.

4. Winsted

Population: 7,482
Founded: 1858
Age: 160
Settled in 1750, the city of Winsted was formed at the junction of the Mad River and Still River, and was one of the first mill towns in Connecticut. Manufactured products started with scythes at the Winsted Manufacturing Company in 1792. The city is within the town of Winchester, and its name derives from the fact that it is the business center for the towns of Winchester and Barkhamsted.

5. Bridgeport

Population: 147,586
Founded: 1904
Age: 114
The first documented English settlement within the present city limits of Bridgeport took place in 1644, centered at Black Rock Harbor and along North Avenue between Park and Briarwood avenues. The place was called Pequonnock (Quiripi for ‘Cleared Land’), after a band of the Paugussett, an Algonquian-speaking Native American people who occupied this area. One of their sacred sites was Golden Hill, which overlooked the harbor and was the location of natural springs and their planting fields. (It has since been blasted through for construction of an expressway.) The Golden Hill Indians were granted a reservation here by the Colony of Connecticut in 1639; it lasted until 1802. (One of the tribe acquired land for a small reservation in the late 19th century that was recognized by the state. It is retained in the Town of Trumbull.)

Bridgeport’s early years were marked by residents’ reliance on fishing and farming. This was similar to the economy of the Paugusset, who had cultivated corn, beans, and squash; and fished and gathered shellfish from both the river and sound. A village called Newfield began to develop around the corner of State and Water streets in the 1760s. The area officially became known as Stratfield in 1695 or 1701, due to its location between the already existing towns of Stratford and Fairfield. During the American Revolution, Newfield Harbor was a center of privateering.

6. New London

Population: 27,147
Founded: 1904
Age: 114
The area was called Nameaug by the Pequot Indians. John Winthrop, Jr. founded the first English settlement here in 1646, making it about the 13th town settled in Connecticut. Inhabitants informally referred to it as Nameaug or as Pequot after the tribe. In the 1650s, the colonists wanted to give the town the official name of London after London, England, but the Connecticut General Assembly wanted to name it Faire Harbour. The citizens protested, declaring that they would prefer it to be called Nameaug if it couldn’t be officially named London. The legislature relented, and the town was officially named New London on March 10, 1658.

7. Wethersfield

Population: 26,395
Founded: 1904
Age: 114
Founded in 1634 by a Puritan settlement party of ’10 Men’ including John Oldham, Robert Seeley, Thomas Topping and Nathaniel Foote, Wethersfield is arguably the oldest town in Connecticut, depending on one’s interpretation of when a remote settlement qualifies as a ‘town’. Along with Windsor and Hartford, Wethersfield is represented by one of the three grapevines on the Flag of Connecticut, signifying the state’s three oldest European settlements. The town took its name from Wethersfield, a village in the English county of Essex.

8. North Haven

Population: 23,877
Founded: 1904
Age: 114
In his will of 1714, the Reverend James Pierpont (1659–1714) of New Haven gave 8 acres (32,000 m2) to his neighbors in the Northeast Parish, as North Haven was called, ‘provided those neighbors will set their meeting house there and make their training and burying there.’

9. Darien

Population: 21,742
Founded: 1904
Age: 114
According to early records, the first clearings of land were made by men from the New Haven and Wethersfield colonies and from Norwalk in about 1641. It was not until 1740, however, that the Middlesex Society of the Town of Stamford built the first community church, now the First Congregational Church of Darien (which stands on the original site at the corner of Brookside Road and the Boston Post Road).

10. Wallingford Center

Population: 17,756
Founded: 1904
Age: 114
The Connecticut General Assembly created the town on October 10, 1667. This original plot of land near the Quinnipiac River is now considered Main Street. Starting on May 12, 1670 there were 126 people who lived in temporary housing, and five years later in 1675 there were 40 permanent homes.

Oh How Time Flies For The Oldest Towns And Cities In Connecticut

So there you have it, a look at some of the oldest places to live in Connecticut. If we missed your city’s ‘date of foundation’, let us know in the comments. Or feel free to take a look at the table of the oldest places in Connecticut.

And now, let’s raise our glasses, to the next 100 years of existence for these cities and towns in the Constitution State.

And for those wondering, here are the newest additions to Connecticut:

1. Portland (Founded in 1905)
2. Thompsonville (Founded in 1905)
3. Ansonia (Founded in 1905)

Detailed List Of The Oldest Cities In Connecticut