In 1635, Reverend John Warham brought 60 of his congregation overland from Dorchester, Massachusetts and stopped here where the Farmington River flows into the Connecticut River. They had arrived in America five years earlier on the ship Mary and John from Plymouth, England. Reverend Warham promptly renamed the settlement Dorchester. During the next few years, more settlers arrived from Dorchester, outnumbering and soon displacing the original Plymouth contingent, who mostly returned to Plymouth. In 1637, the colony’s General Court changed the names of Connecticut’s three original river towns - Dorchester to Windsor, Watertown to Wethersfield and Newtown to Hartford.

It did not take long for the settlers to find a way to make a living. In 1640 the first tobacco was planted in Connecticut in Windsor and the first curing shed brought from Virginia. By 1700, tobacco was being exported via the Connecticut River to European ports and the use of Connecticut tobacco as a cigar wrapper leaf began was widespread by the early 1800s. Eventually there would be over 15,000 Connecticut River Valley in cultivation to grow tobacco. More than 2,000 acres remain so today. Before the 18th century arrived the brick-making trade was also flourishing in Windsor; there was time when the town boasted more than 40 brickyards.

The original town of Windsor comprised what is now the towns of Windsor, Windsor Locks, East Windsor, South Windsor, Granby, East Granby, Simsbury, Ellington, and parts of several other Connecticut towns. Even so, today’s Windsor is spread out geographically, covering some 30 square miles. And our walking tour will be spread out as well, connecting the Broad Street Green with the Palisado Green on either side of the Farmington River, a distance of about a quarter-mile... 

1.
Windsor Station
41 Central Street

Windsor Station was originally built in 1871 as the Hartford & New Haven Railroad Depot and rebuilt to its original Victorian architecture by the Greater Hartford Transit District in 1988, the same year it was listed on the National Register of Historic Places. A former freight house is located nearby, which now serves as the home of the Windsor Arts Center.

WITH YOUR BACK TO RAILROAD TRACKS WALK LEFT AROUND THE STATION AND ONTO MAPLE AVENUE. TURN LEFT ON BROAD STREET GREEN.

2.
Visitor Center/Chamber of Commerce
261 Broad Street

Built in 1921 by John E. Luddy, this was the home of the manager of the Connecticut Leaf Tobacco Association and founder of the Windsor Company, a major textile provider. In 1964, the house and carriage house were sold to the Town of Windsor.  

3.
Town Hall
275 Broad Street 

The Georgian Revival Town Hall displays many of the hallmarks of the style - symmetry, corner quoins, balustrades and a center hall plan. It opened in 1966.

4.
Loomis Fountain
Broad Street Green in front of Town Hall 

The Loomis Fountain was commissioned by Euphemia Anderson Loomis in memory of her husband, a founder of the Loomis Institute. In 1983 the 80-year old fountain was restored as part of a town-wide 350th anniversary celebration. 

5.
Huntington House
289 Broad Street

Henry Huntington, a lawyer and judge, had this eclectic Edwardian mansion built in 1901 in the style of a Newport, Rhode Island “cottage.” The house remained thefamily home until 1998, when the last family died at the age of 93. In the early 2000s it operated as a house museum but has since been converted into office space. 

6.
Grace Episcopal Church
311 Broad Street

In 1842 the Reverend Arthur C. Coxe, Rector of St. John’s Church, Hartford, began the organization of an Episcopal mission in Windsor. By November of that year St. Gabriel’s Church was founded and a cornerstone laid for a new church. The current church, the first on this site, dates to 1865, the year before it was rededicated as Grace Church. The 1930s brought a flurry of enlargements and repairs to bring the church to its present appearance on the Green.

WALK ACROSS THE GREEN TOWARDS BROAD STREET. 

7.
Windsor Eagle
south end of Broad Street Green 

The Windsor Eagle monument was erected in 1929 as a war memorial to all the soldiers and sailors from Windsor who had fought in defense of the town and the nation. The monument was designed by Evelyn Longman Batchelder, who married Loomis Institute headmaster Nathaniel Horton Batchelder and moved to Windsor in 1920. She had previously created several noteworthy works, including the bronze doors for the United States Naval Academy chapel in Annapolis, Maryland. She donated here services to produce this town landmark. 

TURN RIGHT ON BROAD STREET.

8.
Plaza Theater
282 Broad Street

In the 1930s Pauline W. Shulman designed two Art Deco movie houses in the Connecticut River Valley, the Webster in Hartford and the Plaza. Windsor Federal Savings bank opened its doors above the theater in 1936. The screen went dark in 1997.

CONTINUE WALKING NORTH ON BROAD STREET, PAST THE GREEN, AND BEAR RIGHT ON PALISADO RIVER. WALK UNDER THE RAILROAD OVERPASS AND DOWN TO THE FARMINGTON RIVER.

9.
Railroad Bridge
Farmington River  

When the railroad came to Windsor in 1844 it arrived on a wooden bridge. The brownstone bridge you see today to your left replaced the wooden trestle in 1867. Wide arches allowed barge traffic upriver to Poquonock. A unique feature is the horizontal curve in the bridge. Designed by E.M. Reed, this bridge is listed on the National Register of Historic Places as a significant example of 19th century engineering.

CROSS THE RIVER AND WALK ON THE WEST (LEFT) SIDE OF THE ROAD. 

10.
First Church of Windsor
107 Palisado Avenue

This is the first church not only of Windsor but the state of Connecticut, throwing back to 1635. The early days of the town and church, which was first built in the center of Palisado Green and enclosed by a protective stockade, are intertwined. The meetinghouse, the fourth for the oldest congregation in the New World, was sited in its present location in 1794. Major changes in the meetinghouse were undertaken in 1844, 50 years after its construction, prominent among them the installation of a Greek-Revival portico that replaced a tower with its tall steeple. The adjoining cemetery, which is not managed by the church, includes tombstones from graves dug in the 1600s. Reverend Ephraim Huit, an assistant pastor to the church, died in 1644. His is the oldest original grave marker in Connecticut.

11.
William Russell House
111 Palisado Avenue 

This house was built by Reverend William Russell in 1755. It has long been admired for the quality of its front doorway, emblematic of the formal entranceways favored in the Connecticut Valley in the 1700s. The doorway is flanked by fluted pilasters that support a capping entablature. After long being a private residence First Church now owns the house that was built by its one-time minister over 250 years ago. 

12.
Martin Ellsworth House
115 Palisado Avenue 

Oliver Ellsworth, ardent Revolutionary patriot, jurist and statesman who helped frame the United states Constitution, built this house for his son Martin in 1807. The broad gable faces the street and you can compare the addition detail involved with the Federal period of architecture by comparing this doorway with the earlier one at the Russell House. It is also now owned by First Church. 

WHEN THE SIDEWALK ENDS TURN RIGHT AND CROSS THE ROAD ONTO THE PALISADO GREEN AND WALK AROUND IT, HEADING BACK TOWARDS THE FARMINGTON RIVER. 

13.
Palisado Green
Palisado Avenue

This town green comprises part of the site of the Stockade built during the Pequot War of 1637. The green contains the Founders Monument which lists names of the Windsor settlers who came from England in 1630 on the ship Mary and John. The statue is a depiction of John Mason who was a founder of Windsor, Saybrook and Norwich. The first great military leader of the Connecticut colony, Mason organized the state militia in ousting the Pequot Indians from their fort in Mystic. The statue was actually dedicated in New London in 1889 and resided there for over 100 years until it was relocated here in 1995.

14. 
The Dr. Hezekiah Chaffee House
108 Palisado Avenue

This substantial Georgian-style house was constructed in the 1760s for Dr. Hezekiah Chaffee. The 15-room mansion house under a Dutch-Style gambrel roof is one of the oldest brick houses standing in Connecticut. The house was later used by the Loomis Institute, founded by descendants of Hezekiah - his daughter Abigail married Colonel JameS Loomis in 1805. Today the house is owned by the Windsor Historical Society and is open to the public, furnished with invaluable antiques, many made by local and regional artisans.

15.
Windsor Historical Society/Fyler House
96 Palisado Avenue

Records show that Lieutenant Walter Fyler built a one-room dwelling here in 1640 so somewhere inside the rambling complex of the Windsor Historical Society may be the oldest frame house in Connecticut. Fyler was deeded several pieces of land, including this lot, for services in the Pequot War. The Fyler House is also home to the town’s first post office and an 18th century general store which specialized in imported fabrics. 

WALK BACK TO PALISADO AVENUE AND TURN LEFT, RECROSSING THE FARMINGTON RIVER. MAKE YOUR FIRST LEFT ON UNION STREET, BEFORE THE INTERSECTION.

16.
Union Street Tavern
20 Union Street

The Windsor Fire Company organized in September 1830 when twenty prominent Windsor men each paid a subscription of five dollars. Nearly a century later, on September 17, 1927 the company, amidst great fanfare, moved into this new two-bay home. Constructed at a cost of $23,009, it replaced the much smaller 1880 station at the rear of 20 Maple Street. The second cornerstone on the building front bearing the date 1915 commemorates the establishment of the Windsor Fire District and its legislative charter as a taxing district. Both the fire and police stations moved to the present headquarters on Bloomfield Avenue in 1965.

WALK AROUND THE OLD FIREHOUSE TO THE RIGHT TO RETURN TO THE TOUR STARTING POINT AT THE RAILROAD STATION.