Colonial Days: The Oldest of the Old

The earliest days of European settlement are still visible here and there in Connecticut, especially in the houses that have survived the passage of time to become living testaments to an earlier era. The houses do not always have regular viewing hours, so be sure to check carefully beforehand.

1-2 days

  • Spring
  • Summer
  • Fall

  • General David Humphreys House
  • Captain David Judson House
  • Henry Whitfield State Museum
General David Humphreys House (c.1698), Ansonia

General David Humphreys House

Begin at the General David Humphreys House in Ansonia, which was built from 1695 to 1698. It was the birthplace of David Humphreys, a Revolutionary War colonel and a friend of General George Washington. When Washington became President, he made Humphreys his first appointee to a foreign ambassadorship (Portugal). Today, the house is fitted out with 18th-century furnishings and serves as the home to the Derby Historical Society.

Stratford Historical Society, Stratford

Captain David Judson House

Next, it’s on to Stratford, where the local historic society is headquartered in the Captain David Judson House, whose stone foundation and central chimney date from 1639. The house that today meets the eye was built in 1723 or so by Capt. Judson, the great-grandson of the man who built the original structure. Be sure to check out the very fine “broken scroll pediment” that surrounds the front door and the 18th-century piano inside. Next, drive north along the coast.

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Henry Whitfield State Museum, Guilford

Henry Whitfield State Museum

In many respects, Guilford's Henry Whitfield State Museum has to be considered the grand-daddy of them all. This house, completed in 1639, is Connecticut’s oldest house and the oldest stone house in New England. Its massive stone walls and chimneys, steeply pitched roof and casement windows reflect the style of post-medieval England – rare in 17th-century America. Check out the special events and monthly programs.