Quick History Stops: Windsor, CT

I had a history-packed, three-day trip to the Windsor, CT area back in August 2025, when I visited the Connecticut Trolley Museum, East Windsor Historical Society, Northwest Park, Vintage Radio & Communications Museum, and Windsor Historical Society. Between stops at amazing venues that exceeded expectation, I took a few quick history stops around Windsor, CT to see the usual small town New England sites, including historic buildings, memorials, a cemetery, and a classic New England church. This area, called Palisado Avenue Historic District, has been on the National Register of Historic Places since 1987.

A two-story red painted wooden Federal style building with two red brick chimneys A one-story red brick building with a cupola at the end of a driveway A two-story light yellow wooden two-story Federal style house with Greek Revival additions

A wide range of architectural style show the changes in design preferences from the early 18th century through the early 20th. Thomas Hayden House built in 1789 is a wooden Federal style building near the historical society. The house was named for its architect, American Revolutionary War veteran Lt. Thomas Hayden, while its first owner was Dr. Hezekiah Chaffee II who had grown up in the brick house next door. The house was originally dated to 1767. Nearby is Windsor Montessori School & Discovery Center, housed in the red brick Milo Peck Building. Milo William Peck was a World War II veteran who became the mayor of Windsor for six two-year terms, a record in Connecticut. He died fairly young at age fifty-six while serving his sixth term.

A stone monument with a metal 17th century ship and names of founders carved in the stone A green metal statue of a colonial era soldier on a stone pedestal A two-story whitewashed Georgian style house.

Next door is James Hooker House built in 1772 for Capt. James Hooker, a Revolutionary War veteran and the great-great grandson of Hartford, CT’s founder, Rev. Thomas Hooker. The two-story Federal style house with more recent Greek Revival embellishments demonstrates the wealth and prestige of the family. James Hooker was good friends with the neighboring Chaffee family, as his business partner was John Chaffee (son of Dr. Hezekiah Chaffee II), and his third wife was Mary Chaffee (daughter of Dr. Hezekiah Chaffee II).

A white painted wooden sign with black text reading Entering Windsor Historic District A whitewashed Greek Revival style church with a bright red door A white painted wooden sign with black text reading First Church in Windsor

A nearby patch of grass is called Palisado Green and hosts a pair of memorials. The Founders of Windsor Monument was erected on the site of the first congregational church in Windsor by the Connecticut branch of the National Society Sons and Daughters of the Pilgrims in 1930. The area includes a pair of time capsules to be opened in 2033 and 2076. Also on the green is the controversial statue of Captain John Mason, a colonial military leader who co-led the Pequot Massacre that resulted in the deaths of over four hundred Native Americans in the Mystic, CT area. The statue was erected in Groton, CT in 1889 but moved to Palisado Green in 1996 after protests. Modern Pequod leaders actually support keeping the statue available for public viewing as a reminder what happened.

In the foreground, several gravestones and monuments. In the background, a classic whitewashed New England church A pair of white painted wooden signs with black text. The top reads Palisado Cemetery and the bottom reads First Church Entrance An elegant neoclassical statue of a mourning woman atop a stone pillar.

Across the main road is First Church in Windsor and the former parsonage, Rev. William Russell, Jr. House. The church is the oldest extant Congregational church in the state of Connecticut with its congregation dating to 1630. This is the third meetinghouse built in 1755 after a fire had burned down the second meetinghouse a few months earlier. Rev. Russell, the eighth minister at the church, got a matching parsonage out of the deal. Greek Revival decorative elements were added in 1844. The congregation joined the United Church of Christ in 1961.

A pair of brown gravestones with eerie angel faces carved at the top. A pair of brown headstones covered in lichen with eerie angel faces carved at the top. A brown gravestone with the face of a bearded angel

Behind the church is a mid-sized Palisado Cemetery, also known as Old Burying Ground, with gravestones dating back to the early colonial era. My favorites designs included eerie angels, bearded angels, somber urns, and an elegant neoclassical statue of a mourning woman. Matching eerie angel headstones of Alexander Allin and Hannah Ellsworth Allin date from the 1790s, while a similar designs appear on early 19th century headstones, including one shared by Deacon Nathaniel and Naomi Hayden, and another for Sarah Hosford. The bearded angels for Captain David Barbur (an apparent misspelling of Barber) and Lieut. Samuel Stiles II date from the same period. For those who love a good cemetery, this is an ideal stop.

A pair of mismatched brown headstones. The left has the face of a bearded angel, while the right has a mournful urn. A double wide brown headstone with a pair of eerie angel faces. A greyish-brown headstone with an eerie angel at the top
Location: Windsor, CT, USA