When exchanging pleasantries with friends, the question often arises as to which is the oldest? Oldest what? If children are being introduced then it’s them but when speaking of towns and cities, well this can be interesting indeed. It might not be as pleasant a conversation when they each vie for the honor of being the oldest to be established, especially when that honor holds such an important status. Status? If one thinks about the manner in which the earliest settlers came to Connecticut, the hardships they endured, being the first carries a good deal of “status”.
Connecticut has 169 towns, albeit some are cities but many of them look just like Orange. The typical New England Green can be found in many of them and even they have a “status”. Milford has the 2nd longest Green. Now, who would think that would be special? Well, to the citizens of Milford it IS. If it’s any consolation to Milford, many of their ancestors, who ventured west to establish New Milford can most likely be credited with creating a long Green, now, the longest in the state.
History is its own worst enemy as those who make it and those who report it are often at odds but giving a shot at the oldest Connecticut town depends on several factors, the least of which is pride in your town. Using dates alone, the towns of Windsor, Weathersfield, yes I know it’s Wethersfield now and Hartford are considered to be the first 3 towns in our state, in that order. In fact, some think that the 3 grape vines on the State of Connecticut flag stand for the three earliest colonies. The dates for the three are 1632, to 1634 with Old Saybrook in 1635, not far behind.
Next in the running is New Haven with 1638 and our very own history, as begun in Milford in 1639. If that date looks familiar it’s probably because the only chronicle history we have of Orange is the “History of Orange” by Mary R. Woodruff 1639-1949 with the subtitle North Milford. In making the determination of which town is the oldest, it is necessary to ascertain which nation had the predominant citizenry. If you factor in the Dutch and the English, then the list changes. If you factor in the difference between a trading post and a settlement, then the list changes again. If you continue to factor in the difference between a charter and a constitution, yes, it changes once more.
By 1639, Peter Prudden and his company founded Milford, the colonies of Fairfield and Guildford, yes Guilford, followed and the race was on. Having left England in 1637, the Rev. Peter Prudden led a group from Hertfordshire to Boston following the leadership of John Davenport and Theophilus Eaton. The names Buckingham, Fowler, Platt, Bryan and East were among those who are remembered as early Milford colonists. Their names are inscribed in stones along the bridge toward New Haven Avenue, as you leave the center of Milford. The new arrivals remained in the Boston area for almost a year and were asked to stay but both Davenport and Prudden had other plans, wanting to establish their own colonies.
In April of 1638, both groups ventured down to the Quinnipiac region establishing themselves and forming the New Haven Colony. The only difference was that the Prudden group had a separate allotment known as the Hertfordshire section within the nine squares that the colony created. After preaching in Wethersfield during the summer of 1638, Rev. Prudden gathered a great number of followers who asked that he lead them to a new colony and the names Tapping, Tibbals, Treat and Miles were added to the Hertfordshire group that founded Milford on February 12, 1639. The name Treat is an important one to us, here in Orange as the young Treat, sixteen years old became a surveyor like his father and Treat families and homes are part of this town with Joseph Treat’s house on Turkey Hill Road having been in the news, now a shell after being dismantled*.
From the early records, we find that there was no distinction between church and state, as we know it today. In fact, it was just the opposite. At a meeting of the new colony of Wepawaug, later Milford, it was determined that the power of electing officers and persons to divide land and manage the interest of the plantation should be in the church. It was further decreed that all the business of the plantation, in their meetings and by their officials should be done according to the written word of God, the Bible being the code of laws. There was much discussion as to whether or not voting and office holding should be confined to church members and it was decided that it should be. The leaders in the church were the leaders in civil affairs.
While I have your attention. The history for the 169 Connecticut towns can take you a good bit of time tracking down the “which is and the which isn’t” but I have a solution for that. A recently published book boasts a brief history of all 169**. “The Connecticut 169 Club,” written by a member of each town and compiled by Marty Podskoch will give you a visitor’s guide to explore Connecticut. The idea is to visit all towns, have someone in the town sign the town’s page and then you’ll have all the local history you will need.
To go on. As the Wepawaug Colony was settled, the English were not the only inhabitants as there were at least 100 Native Americans, the Paugussetts. Living chiefly on shellfish and wild game, these people were peaceful and welcoming. Land was purchased on several occasions, each time increasing the land owned by the settlers until what we know as Orange, Milford, West Haven and part of Woodbridge became the colony of Milford. The sales were not altruistic but a hope on the part of Ansantawae, sachem of the Paugussetts, to help against their constant foe, the Mohawks, who continually made raids upon their settlement. There was, of course, payment for these treasured lands in coats, blankets, knives, hatchets, kettles and what is most interesting, mirrors.
It wasn’t until 1665 that the Natives complained that they did not have enough land, that they had sold too much and had no appropriate place to live and hunt. Upon request for land, it was agreed to give them 100 acres on the ridge overlooking the Housatonic River, a steep hill known as Turkey Hill, its name derived from the numerous turkeys that flew across the river at Two Mile Island. The names Alexander and Richard Bryan appear in Milford’s history many times as original planters who appear to have been the first to own a considerable amount of land in the northern part of the colony, having been purchased from the Paugussetts. With land at Old Tavern Road to the Green, the area was called Bryan’s Farms and is noted on land deeds far into the 18th century, as a legal town. Although the number of homes at that time is uncertain, it would appear to have been substantial enough to appropriate money for a school in 1750, the location of which is unknown.
In 1804, the citizens of Bryan’s Farms petitioned the general Assembly for permission to establish a church as travel to Milford had become difficult. After some discussion and opposition, a new church society was organized on March 13, 1805 and North Milford was established.
*The Orange Historical Society has been fortunate to be able to buy two walls and two doors from the Treat house that are now part of the garret at the Bryan-Andrew house.
**“The Connecticut 169 Club” book can be purchased at the Academy on Saturdays from 10-3, cost $24.95. As a citizen of Connecticut it is interesting and for those who have moved away, memories.