The first settlers from Hartford and Wethersfield found this spot on a big bend in the Connecticut River in 1650. They laid out a street above the flood plain that ran parallel to the water, today’s Main Street, and named the village Middletown because it was more or less midway between Saybrook and Hartford on the river. The fertile alluvial plain and the favorable geography allowed the town to flourish immediately. By 1756 Middletown, with its population of 5,664, was the largest and wealthiest town in the state of Connecticut. It was Connecticut’s most important port because it was the leading shipping center for the West Indies trade. Later it was a key player in the China trade.

Other Middletown citizens were busy on the land with carpenters and shipwrights and stonecutters and artisans. A local mine produced lead. Middletown rivaled Boston and Philadelphia as a pewter center. Unfortunately inland sea ports faced a disadvantage with the arrival of larger sea-going ships and Middletown’s trade slipped away in the 19th century. Wesleyan College was established in 1831 which helped attract other cultural institutions. As the town’s industry diversified, Main Street grew ever more commercialized and residents moved up the hill to High Street. 

Through Middletown’s connections with three railroad lines, the Air Line, the Berlin Branch and the Connecticut Valley, the city was linked to local and national networks of rail transportation by the early 1870s. This encouraged the growth of both established industries which continued to serve regional needs and specialized industries supplying national markets. Rubber was an early product line here. And pumbs. And silverware. And typewriters. The U.S. Census of Manufacturers listed 131 firms in Middletown in 1870. 

Our walking tour will start on Main Street where most of the commercial buildings are of 20th century vintage and work our way to High Street that is lined with high-style 19th century mansions, most of which have been absorbed into Wesleyan College... 

Church of the Holy Trinity

381 Main Street

The Episcopal Church in Middletown had its beginnings as early as 1724; this is the third meeting house of the parish, which was formally established as Christ Church in 1750. Henry Dudley designed the Gothic building that was built of local brownstone between 1870 and 1874. The church displays a large rose tracery window in a symmetrically arranged facade with a buttressed bell tower at the southeast corner. The tower lacks a spire but features narrow arched windows which emphasize its verticality, and echo the fenestration of the facades.  


Pythian Building

360 Main Street

The Order of Knights of Pythias was the first fraternal order to be chartered by an Act of Congress when it was established in 1864. This lodge must have been one of their most impressive after this 1874 Italianate commercial building received a Neoclassical makeover in 1938 with two stories of resplendent green marble. The third story picked up a Palladian window and a pair of decorative urns adorn the roofline.

Guy & Rice Building

335 Main Street 

This three-story Renaissance Revival building was constructed for the insurance and real estate firm of Guy & Rice in 1930. The decorative stucco and concrete facade is punctuated by large arched windows. 

Liberty Bank

315 Main Street

Liberty Bank began as Middletown Savings Bank and has been a presence on Main Street since 1825. It is the oldest mutual savings bank in Connecticut. The bank opened in Samuel Southmayd’s pharmacy on the corner of Main and William streets and deposits were placed an oaken cupboard that served as the bank’s vault; it is now in Yale University’s museum collection. In 1837, we moved into a building on the corner of Main and College Streets. The bank moved into this Neoclassical headquarters with a rusticated stone base in 1929.

In 1844, Frederick Sheffield, a young merchant from Old Saybrook rode his horse to Middletown to deposit $8 with the bank; six months later, he made an additional deposit of $18. He then moved away from the area, leaving his money on deposit. In 1994, Sheffield’s descendents finally closed his account, which had grown through interest alone to more than $32,000 and was the oldest individually owned savings account in America. A descendent of Sheffield holds an account at Liberty Bank to this day. 

Middletown Post Office

291 Main Street at southwest corner of Court Street

This prominent corner at Court Street has been federally owned since 1841. In 1911 it was decided to place a new post office here. Government architect gave the town a new look with this two-story Renaissance Revival limestone building rising in a city center dominated by brick and Portland brownstone. The classical facade displays an arrangement of arched windows and pilasters supporting an elaborate entablature. It operated as a post office until 1977 when it was sold into the private sector for use as office space.

Middlesex Mutual Assurance Building

179 Main Street

This 1867 building once housed the Middlesex Mutual Assurance Company, formed in 1836.  Today it provides a clear look at how a decorative facade was attached to an ordinary brick building. This one has elements of the Italianate style (tall windows), Colonial affects such as corner quoins and keystones over the window, and triangular pediments studded with dentils.  

General Mansfield House

151 Main Street

This part of Main Street was a fashionable residential neighborhood when Samuel Mather, a local merchant, built this brick Federal-style house in 1810. The character of the street was to change substantially in the coming decades, however, and businesses steadily replaced family homes. This was the one of the few to soldier on, dodging the wrecking ball in the 1950s to serve as the headquarters for the Middlesex County Historical Society and picking up a $175,000 restoration in the 1990s.

Mather’s daughter Louisa and her husband, General Joseph King Fenno Mansfield, a West Point graduate and career Army man in the Corps of Engineers lived in the house next. Mansfield distinguished himself in the Mexican War and was a general by the time of the Civil War. He died at the head of his lines on September 17, 1862 during the Battle of Antietam, the bloodiest day of the Civil War. He was 58 years old. 

Baptist Church

93 Main Street

This modest brick church is one of the town’s earliest, dating to 1842.


Soldiers’ Monument

South Green 

This monument was installed in 1874 to honor the town’s 110 soldiers and sailors who died in the Civil War. The bronze infantryman at rest was cast in Chicopee, Massachusetts; the base is surrounded by captured Confederate cannons. 

South Congregational Church

9 Pleasant Street on south side of the Green 

In 1747, Ebenezer Frothingham, a staunch Separatist of the Great Awakening, gathered a congregation in Wethersfield. His preaching landed him in and out of jail and in 1753 he came to Middletown in pursuit of religious tolerance, holding services in his house that still stands on Mill Street. In 1830, the church moved to the corner of Main and Pleasant Streets. The present building, much renovated today, is the second on the site, constructed in 1867. The bell was hoisted into the tower by oxen in 1884. 


First United Methodist Church

24 Old Church Street on the north side of Green

Methodism began stirring in New England in the 1740s But it was Jesse Lee’s preaching in 1791 that finally inaugurated a Methodist Circuit on the Connecticut River. By 1804, Middletown had become the center of the Circuit. This present Gothic chapel of cream and tan-colored limestone is the fourth church for the congregation on the South Green. At the time of its construction in 1931 it was considered “one of the finest Methodist Church buildings in the country.”

Henry Clay Work Bust

center of South Green 

Henry Clay Work, an American composer and songwriter, was born near here in 1832 into an abolitionist family. His family’s home became a stop on the Underground Railroad, assisting runaway slaves to freedom in Canada, for which his father was once imprisoned. Work was self taught in music and was said to compose without any instruments, creating songs in his job as a printer as he set musical type.    

Masonic Lodge

33 Pleasant Street on south side of Green 

St. John’s Lodge as chartered back in 1754, first meeting in Burnhams Tavern. The current brick lodge building was constructed in 1870, known over the years as the White-Stoddard House. It is one of the town’s foremost examples of the French-inspired Second Empire style with prominent mansard roof and heavy bracketing and window molds.  

Danforth Pewter Shop

across west side of Green, inside junction of South Main Street and Church Street

Thomas Danforth II was a pioneer in the Colonial craft of pewtersmithing, crafting household items from a tin alloy beginning in 1756. He had six sons, all of whom went into the pewtering trade. Each specialized in several forms of holloware, such as plates, mugs, bowls, candlesticks, communion flagons, or teapots. Pewter was the American tableware of choice until the rise of imported chinaware in the mid-nineteenth century. This combination workshop and store was part of a busy artisan’s colony a few blocks north on College Street but was moved here in the 1980s ahead of a new parking lot there. 

Congregation Adath Israel

Broad and Church Streets, opposite the northwest corner of the Green

In the 1870s Jews began to arrive in Middletown in significant numbers, largely from German and Austria-Hungary. Urban and middle-class, most did not stay, and within a decade were supplanted by the poorer and more rural Eastern European Jews, escaping oppression in their homelands. After worshiping in private homes and rented halls for many years by 1908 there was enough money in the community to purchase a brick building on Union Street and incorporated Congregation Adath Israel. The more spacious synagogue on the Green came along in 1929.


College Row

west side of High Street 

Wesleyan was founded by Methodist leaders and prominent residents of Middletown, and was the the first academic institution to be named after John Wesley, the Protestant theologian who was the founder of Methodism. Early buildings were fashioned from Portland brownstone, as typified by this attractive hilltop row. In the chapel are commemorative windows in honor of Wesleyan men killed in the Civil War and past college presidents.

17.     Psi Upsilon
242 High Street 

Psi Upsilon was established on the Wesleyan campus in 1843, ten years after the fraternity’s founding at Union College - the fifth in the United States. Their new house came along on the 50th anniversary, designed by Colin C. Wilson in a modified Dutch Renaissance style. The house is constructed of thin Yellow Roamn bricks.

First President’s House

255 High Street 

The Greek Revival President’s House was erected in 1837-38 for Wilbur Fisk, who was the school’s first president. Every subesquent president lived here until 1904. It stepped down to house school deans for a while after that. 

Wesleyan University President’s House

269 High Street

This Italianate Villa style house was built in 1856 for Gabriel Coite who retired from New York business a few years earlier. It is an exuberant cube with a projecting pavilion, prominent porte cochere, and elaborate scrolled brackets beneath the eaves of the roof and cupola. Coite entered state politics and moved to Hartford and Jane Miles Hubbard, widow of Samuel D. Hubbard, co-founder of the Russell Manufacturing Company, moved in. The house was purchased in 1904 by Wesleyan University for its presidents, which it remains to this day.

Richard Alsop IV House

301 High Street

Richard Alsop IV owned a business trading with Chile and the West Indies from Philadelphia. He built this house in 1838-1839 for his twice-widowed mother. This house is significant architecturally for its transitional Greek-Tuscan Italianate appearance. The central block displays a decorative frieze and a veranda supported by delicate ironwork and surmounted by an intricate balustrade. 

Edward Augsutus Russell House

318 High Street 

Another house that erupted on the Russell estate on High Street, this was built for Edward Augustus Russell in the high style Greek Revival in 1841-42. Edward was the younger brother of Samuel Russell, who owned the estate and worked in the woolen trade. This was the last example of Greek Revival architecture to be built in the prestigious area of High Street. 

Duane Barnes House

327 High Street 

This striking brownstone Gothic Revival cottage was built in the late 1840s. Of particular note are the decorative bargeboards of the eaves and the window over the central bay, which is shielded by an intricate glass and wooden hood. Duane Barnes was a schoolteacher, bookseller, and poet. 

Thomas MacDonough Russell House

343 High Street

This well-proportioned Colonial Revival house was constructed in 1902-03 for a member of the Russell family who dominated this block. 

Samuel Wadsworth Russell House

350 High Street

This monumental Greek Revival building was the home of Samuel Russell who made his fortune in China, trading in fine teas and silks and, most profitably, illegal opium. Connecticut architect Ithiel Town designed the house with six mammoth Corinthian columns built of brownstone. Stucco scribed to resemble large block ashlar covers the masonry brick walls.The house was built in 1828 when Russell was still overseas; he returned in 1831 after 20 years in China to see the house for the first time. He lived here until his death at the age of 73 in 1862. Five generations of Russells resided here until it was deeded to Wesleyan University in 1937.  


St. Sebastian’s Roman Catholic Church

147 Washington Street

During the worst years of the Depression, the Italian population of Middletown raised $51,000 to make possible the construction of this Renaissance Revival church. The building is very similar to the fourteenth century Church of St. Sebastian in Melilli, Sicily. 

Wetmore-Starr House

110 Washington Street

This house was built around 1752 by Jeremiah Wetmore, on property that had once been part of the 1670 land grant to Reverend Samuel Stow, the town’s first minister. The house was purchased by Jehosaphat Starr in 1756, who enlarged the original central chimney home with an addition to the east elevation.


Captain Benjamin Williams - deKoven House

27 Washington Street

This impressive brick house is the legacy to the wealth of sea captains in pre-1800 Middletown. Captain Benjamin Williams built it in Middletown in 1791. Only the richest could build in bricks and for good measure he embraced the Georgian house in decorative stone quoins. The house was later owned by Henry L. deKoven, who was also involved in merchant shipping and was the first president of the Middlesex County Bank in 1830.