Hezekiah Chaffee House

The First Church in Windsor, Connecticut is the oldest Congregational church in Connecticut. Its origin can be traced back to 1630, when 140 men and women sailed out of Plymouth, England on the Mary & John. This was the first of 17 ships in the so-called Winthrop Fleet, bound for the Massachusetts Bay Colony. When they heard from the Indians about the fertile land along the Connecticut River in what is now called the Connecticut River Valley, a small contingent of settlers travelled southwest and established the first settlement in Connecticut at Windsor in 1633. Word soon spread that Windsor was a good place in which to settle: in 1635, the congregation of the First Church departed from their homes in Dorchester, Massachusetts to relocate to Connecticut.

A statue of John Mason is installed in Windsor, Connecticut, United States. The memorial is slated for removal, as of July 2020. As of January 2021, it has yet to be removed. Sculptor was James G. C. Hamilton.

The Farmington River Railroad Bridge spans the Farmington River in Windsor, Connecticut, just west of Palisado Avenue and north of Pleasant Street. It carries two tracks of the main railroad line between Hartford, Connecticut and Springfield, Massachusetts. Built in 1867, it is one of the state's finest examples of a stone arch railroad bridge. It was listed on the National Register of Historic Places in 1972.

The Palisado Avenue Historic District encompasses a predominantly residential streetscape in northeastern Windsor, Connecticut. Extending along Palisado Avenue (Connecticut Route 159) between the Farmington River and Bissell Ferry Road, it is a basically 18th-century street view, populated mainly with houses from the 18th to the 20th centuries. The district was listed on the National Register of Historic Places in 1987.

The First Church Parsonage is a historic parsonage house at 160 Palisado Avenue in Windsor, Connecticut. Built in 1852 for the new minister of the First Congregational Church, it is a well-preserved example of transitional Greek Revival-Italianate architecture in brick. The house was listed on the National Register of Historic Places in 1988.

Windsor station is a historic railroad station on Amtrak's New Haven–Springfield Line, located in downtown Windsor, Connecticut. It is served by Amtrak Northeast Regional and Valley Flyer intercity service and CT Rail's Hartford Line commuter rail service. The nearby Hartford & New Haven Railroad-Freight Depot serves as the home of the Windsor Arts Center.

Windsor is a town in Hartford County, Connecticut, United States, and was the first English settlement in the state. It lies on the northern border of Connecticut's capital, Hartford. The town is part of the Capitol Planning Region. The population of Windsor was 29,492 at the 2020 census.Poquonock () is a northern area of Windsor that has its own zip code (06064) for post-office box purposes. Other unincorporated areas in Windsor include Rainbow and Hayden Station in the north, and Wilson and Deerfield in the south. The Day Hill Road area is known as Windsor's Corporate Area, although other centers of business include New England Tradeport, Kennedy Industry Park and Kennedy Business Park, all near Bradley International Airport and the Addison Road Industrial Park.

The Hartford & New Haven Railroad Freight Depot is a historic building at 40 Mechanic Street in downtown Windsor, Connecticut, across the street from the equally historic Hartford & New Haven Railroad Depot. Built about 1870, it is a well-preserved example of a Gothic Revival freight depot. It was listed on the National Register of Historic Places in 1988. It is now the home of the Windsor Arts Center, a non-profit place that exhibits the work of visual and performing artists.

The Broad Street Green Historic District encompasses the historic late-19th century town center of Windsor, Connecticut. It is centered around the Broad Street Green, a public park extending on the east side of Broad Street (Connecticut Route 159) between Union and Batchelder Streets, and includes a diversity of architecture spanning much of the town's long history. It was listed on the National Register of Historic Places in 1999.

The Colonel James Loomis House is a historic house at 208-210 Broad Street in Windsor, Connecticut. Built in 1822 for a prominent local family, it is a good local example of Federal architecture executed in brick. It was listed on the National Register of Historic Places in 1988.

The former Grace Church Rectory is a historic church rectory and house at 301 Broad Street in Windsor, Connecticut. Built about 1865, it is a good local example of Gothic Revival architecture executed in brick. It was listed the National Register of Historic Places in 1988.

The building at 14 Maple Avenue in Windsor, Connecticut, United States, is a Former Fire Station of the town. It was built about 1882, and was the town's first purpose-built firehouse. Now converted to commercial use, it was listed on the National Register of Historic Places in 1988.