A river city on the west bank of the Connecticut that in 1816 owned more shipping than any town in the state, where Greek Revival mansions still line High Street above a Main Street that has been the center of town since 1650.

Middlesex County · Record checked October 11, 2026

47,717Population2020 census1
1651Became a townas Mattabesett, renamed Middletown in 16531
1816The portmore shipping owned here than in any other Connecticut town2
5,140 lbsLead for the Revolutionon hand from the Strait Hills mine in November 17763
36National Registerplaces, all still standing4

Then and now

The same town 149 years apart. Click either map to look closer.

Bird's-eye view map of Middletown, Connecticut from 1877 by O.H. Bailey & Co., restored by KNOWOL

1877

The 1877 bird's-eye view

By O.H. Bailey & Co.

Middletown drawn as if from the sky when about 7,000 people lived here and manufacturing was the mainstay of the city, with Wesleyan University, the Connecticut Hospital for the Insane, Berkeley Divinity School, Union Railroad Station and the Portland Ferry.5

More about this map
Bird's-eye view map of Middletown, Connecticut from 1915 by T.M. Fowler, restored by KNOWOL

1915

The 1915 bird's-eye view

By T.M. Fowler

Thaddeus Mortimer Fowler's hand-drawn view of the city at the beginning of the 20th century, with Wesleyan University, the Russell Manufacturing Company, the Hubbard Motor Company, the Goodyear Rubber Company, Dalton's Cafe, the Germania Cafe and Hazen's Book Store.6

See the 1915 printMore about this map
Map of Middletown, Connecticut in 2026, with Main Street, Wesleyan, the Arrigoni Bridge, Higby Mountain and 34 numbered landmarks

2026

Middletown today

By KNOWOL

Shaded hills from Higby Mountain in the west to the Connecticut River, every street and the city line, with Westfield, South Farms, the Coginchaug River and Wadsworth Falls State Park, and a guide of 34 numbered landmarks with the National Register sites marked.7

See the 2026 printMore about this map

The story of Middletown

The lead mine at the Strait Hills

On the north side of the Strait Hills, near where Butler's Creek runs into the Connecticut, there was a vein of lead ore that foreigners had already spent large sums on before the Revolution. In May 1775 the colony put Jabez Hamlin, Matthew Talcott and Titus Hosmer in charge of finding lead for the war. Hosmer wrote that seven tons of ore had been raised, and that if they could only refine it, the mine would supply all the colonies with lead. Smelting works were finished that September, and by November 1776 the committee held 5,140 pounds. But the vein was locked in granite and dove into the earth as it neared the river. In 1778 the Assembly called the work unprofitable and shut it down.3

Under the great elm

When the first settlers came in 1650, they held their Sunday services for about two years in the shade of a great elm near the river. In 1652 they built a rough little log church close beside it. The First Church was gathered in 1668 with Nathaniel Collins as pastor, and when he died in 1684, Cotton Mather called the Middletown church the golden candlestick from which Collins lit more than the whole colony. The old burying ground by the river was laid out in 1650, and in 1832 the elm was still standing in it, 26 feet around near the ground. For the town's 250th anniversary in 1900, a big granite boulder with bronze tablets naming the first settlers was placed on the site of the old stockaded meetinghouse.891011

Liberty, property and no stamps

Middletown lived by the river. Ships were built here as early as the winter of 1669 and 1670, and in 1726 Izrahiah Wetmore won the right to run a ferry across to the east side, at sixpence for a man, a horse and a load. By 1816 more shipping was owned here than in any other town in Connecticut. The port had spirit, too. On November 1, 1765, the day the Stamp Act took effect, the town bell tolled all day with its tongue muffled, and every vessel in the harbor flew its pennant at half mast. That night effigies were shown at every door in town and then burned, and a newspaper reported that small children who could hardly talk went singing through the streets: Liberty, Property and no Stamps.1213214

Through the years

25 moments from 1650 to today.

  1. 1650The first settlers arrive and hold their services in the shade of a great elm.8
  2. 1651On September 11 the General Court establishes the town of Mattabesett.1
  3. 1652The settlers build a rough log church close to the great elm.8
  4. 1653The town is renamed Middletown, about halfway between Windsor and Saybrook.1
  5. 1668The First Church is gathered, with Nathaniel Collins as its first pastor.9
  6. 1670In the winter of 1669 and 1670 a shipwright is allowed to build vessels here.12
  7. 1712Edward Higby settles Westfield at the foot of the bluff now called Higby Mountain.15
  8. 1726Izrahiah Wetmore is granted a ferry across the river, sixpence for a man, horse and load.13
  9. 1765On Stamp Act day the town bell tolls all day with its tongue muffled.14
  10. 1775The colony takes over the lead mine at the Strait Hills to make lead for the war.3
  11. 1784The center is incorporated as a city, with Jabez Hamlin as its first mayor.16
  12. 1789George Washington visits, and Boston Road is renamed Washington Street.17
  13. 1795The first Baptist church in Middletown is formed in the city with eleven members.18
  14. 1814Commodore Thomas Macdonough of Middletown wins the battle on Lake Champlain.1
  15. 1816More shipping is owned at Middletown than at any other town in Connecticut.2
  16. 1828Ithiel Town's temple-fronted Samuel Wadsworth Russell House is built on High Street.19
  17. 1831Wesleyan University is founded in the buildings of Partridge's military academy.1
  18. 1841Middletown opens the first public high school in Connecticut.1
  19. 1850The Russell Manufacturing Company's three mills employ about 200 people making suspenders and webbing.12
  20. 1868The Connecticut Hospital for the Insane opens, the state's first public mental hospital.1
  21. 1877O.H. Bailey & Co. publishes its bird's-eye view of the city.5
  22. 1884A state review says Middletown's maples and elms have earned it the name the Forest City of New England.20
  23. 1900For the 250th anniversary a granite boulder marks the site of the first meetinghouse.11
  24. 1923The city and the town are consolidated into one.1
  25. 1938The Arrigoni Bridge opens across the Connecticut River to Portland.1

Places to see

The numbers match the landmark guide printed on the 2026 map.

  • 2Arrigoni BridgeNorth end, across the river. Twin steel arches to Portland, 1938.
  • 5Wesleyan UniversityWest of Main Street. Founded by Methodists in 1831.Visit their website
  • 11Connecticut Valley HospitalSouth Farms. The state's first public mental hospital.
  • 12Main Street Historic DistrictDowntown. The center of town since settlement.
  • 14Samuel Wadsworth Russell HouseHigh Street. Ithiel Town's Greek temple of 1828.
  • 17Middletown South Green Historic DistrictUnion Park. Italianate and Second Empire houses.
  • 18Russell LibraryBroad Street. Frances Russell's gift in an old church.Visit their website
  • 22Wadsworth MansionWadsworth Street. Colonel Wadsworth's Long Hill estate.Visit their website
  • 26Wadsworth Falls State ParkCoginchaug River. Big Falls over a basalt shelf.Visit their website
  • 27Highland Historic DistrictAtkins Street and Country Club Road. Farmhouses of the early 1700s.

On the National Register

21 of the 36 places in Middletown on the National Register of Historic Places that still stand today, oldest first, and why each one matters. See the full list of National Register places in Middletown.4

  • Highland Historic District

    Listed 1982 · Atkins Street and Country Club Road

    Settled in the early 1700s by the Warner, Wilcox and Bacon families, it keeps the rural look of old Middletown, with four Georgian farmhouses from that century. The Wilcox family's tinware trade here later grew into Meriden's silver industry.21

  • Seth Wetmore House

    Built 1746 · Listed 1970 · CT 66 and Camp Road

    Judge Seth Wetmore served 48 terms in the General Assembly. His house is Middletown's finest Georgian colonial, with a shell cupboard and overmantel painting in the northeast parlor, and it stayed in the Wetmore family for more than two hundred years.22

  • Washington Street Historic District

    Listed 1985 · Roughly bounded by Washington and Main Streets, Washington Terrace, and Vine Street

    Merchants and ship captains built fine houses on what was then Boston Road, renamed for George Washington after his 1789 visit. It's centered on Washington Terrace Park and includes St. Sebastian Church, built by Italian masons to look like a church in Melilli, Sicily.17

  • Captain Benjamin Williams House

    Built in the 1790s · Listed 1978 · 27 Washington Street

    A fine late Georgian brick house with brownstone corners, built for a well-to-do sea captain when Middletown traded with the West Indies. Later the deKoven House, it's now a community center run by the Rockfall Foundation.23

  • Main Street Historic District

    Listed 1983 · Roughly Main Street between College Street and Hartford Avenue

    Main Street has been the center of community life since the earliest days of settlement. Its blocks hold banks, theaters and stores from the Old Banking House Block of 1796 to the 1930s.24

  • Starr Mill

    Built 1812 · Listed 1993 · Middlefield Street and Beverly Heights

    Nathan Starr and his son made swords, pistols and rifles here on government contracts, some 70,000 arms in all, along with presentation swords for heroes like Andrew Jackson. The Russell Manufacturing Company added the second mill in 1865.25

  • Middletown Alms House

    Built 1814 · Listed 1982 · 53 Warwick Street

    The town built it in 1813 and 1814 to house its poor, and it's the oldest surviving building in Connecticut built for that purpose. After 1853 it became a factory for tools, hardware and stoves.26

  • Wilcox, Crittenden Mill

    Listed 1986 · 234-315 South Main Street, Pameacha and Highlands Avenues

    John Watkinson's woolen mill of 1814 stands on Pameacha Creek, where a mill had stood since the 1650s. Wilcox, Crittenden made marine hardware here, and after a fire in 1907 rebuilt within two years without losing a customer or laying off a worker.27

  • Samuel Wadsworth Russell House

    National Historic Landmark

    Built 1828 · Listed 1970 · 350 High Street

    Designed by Ithiel Town in the form of a Greek temple with six Corinthian columns, it's counted among the finest Greek Revival mansions in the Northeast. Samuel Russell founded Russell & Company, the leading American firm in the China trade. A National Historic Landmark since 2001.19

  • Broad Street Historic District

    Listed 1988 · Roughly bounded by High, Washington, Broad and Church Streets

    As the port declined, the gardens between Wesleyan and Main Street filled with houses, and the housing here tripled between 1830 and 1850. It holds the city's largest group of Greek Revival houses.28

  • Russell Company Upper Mill

    Built 1836 · Listed 1986 · 475 East Main Street

    The oldest textile mill building left in the city. In 1841 elastic webbing was first woven on power looms here, and by 1896 the Russell company was the nation's largest maker of suspenders.29

  • Alsop House

    National Historic Landmark

    Built 1839 · Listed 1970 · 301 High Street

    Richard Alsop IV built it for his mother, and it's a National Historic Landmark for the paintings on its walls: figures in niches in the stair hall and scenes with local birds and insects in the morning room. Wesleyan has owned it since 1948.30

  • Metro South Historic District

    Listed 1980 · Main and College Streets

    The southern stretch of downtown, with colonial and Federal houses, the Greek Revival Baptist and Universalist churches, the 1892 Middlesex Opera House and the General Mansfield House of 1810.31

  • Beman Historic District

    Listed 2026 · Cross Street, Knowles Avenue and Vine Street

    A 3.44-acre triangle that was a free, property-owning African American neighborhood in the 1800s, from George Jeffrey's land purchase in 1828 until 1937. Wesleyan owns nearly all of it today, and archaeologists have studied its house lots.32

  • Connecticut General Hospital for the Insane

    Listed 1985 · Silver Street east of Eastern Drive

    Opened in 1868 on a hilltop in South Farms, with broad lawns and views over the city. By 1896 it was one of the largest institutions of its kind in the country. Shew Hall, the first building, is still its center.33

  • Church of the Holy Trinity and Rectory

    Built 1874 · Listed 1979 · 381 Main Street and 144 Broad Street

    Henry Dudley's brownstone Gothic church with a great rose window, built from 1870 to 1874 for a parish whose worship goes back to 1724. One rector, Edward Campion Acheson, was the father of Secretary of State Dean Acheson.34

  • Middletown South Green Historic District

    Listed 1975 · Union Park area, on South Main, Crescent, Pleasant and Church Streets

    Ninety acres around Union Park with Italianate and Second Empire houses from the city's growth in the 1860s to 1880s, Queen Anne houses on Crescent Street and two of the city's oldest homes.35

  • Xi Chapter, Psi Upsilon Fraternity

    Built 1893 · Listed 2009 · 242 High Street

    Built from 1891 to 1893 to a design by English architect Colin C. Wilson, it was the first purpose-built residential fraternity house in the United States and a model for those that followed.36

  • Old Middletown High School

    Built 1896 · Listed 1985 · 251 Court Street

    The city's second high school, built from 1894 to 1896 in brick, brownstone and terra cotta with a corner turret. It's the city's only Romanesque Revival civic building, and it has been housing for older residents since 1978.37

  • Wadsworth Estate Historic District

    Listed 1996 · Laurel Grove Road, Wadsworth Falls State Park and 421 Wadsworth Street

    Colonel Clarence S. Wadsworth's Long Hill estate, with Francis Hoppin's mansion of 1908 to about 1911 and grounds shaped with John Charles Olmsted. Its reinforced concrete saved the house from a fire in 1990, and the city bought it in 1994.38

  • U.S. Post Office

    Built 1916 · Listed 1982 · 291 Main Street

    A Renaissance Revival post office of smooth limestone, a source of civic pride when it opened on a site the government had owned since 1841. Federal use of the corner ended in 1977.39

In their words

“The traveler can see but little of the city from any of its approaches by land or water, so completely is it embosomed in the foliage of the maple and the elm, which has given to it the well-merited name of "The Forest City" of New England.”

The historical, statistical and industrial review of the state of Connecticut, 188420

“The church of Middletown, upon the Connecticut River, was the golden candlestick from whence this excellent person illuminated more than the whole colony.”

Cotton Mather on Rev. Nathaniel Collins, quoted in the History of Middlesex County, 18849

“Our young children, that can hardly speak, have already learnt this lesson well, Liberty, Property and no Stamps, which they sing along the streets.”

A Middletown newspaper report of November 2, 1765, in Barber's Connecticut Historical Collections, 183614

Nearby towns

Sources

  1. Middletown, Connecticut, Wikipedia
  2. Connecticut historical collections, John Warner Barber (1836), on Middletown's shipping and manufactures, Internet Archive
  3. History of Middlesex County, Connecticut (1884), on the lead mine, Internet Archive
  4. National Register of Historic Places listings in Middletown, Connecticut, Wikipedia
  5. Bird's eye view of Middletown, Connecticut in 1877, restored by KNOWOL
  6. Vintage map shows Middletown, Connecticut in 1915, restored by KNOWOL
  7. Map of Middletown, Connecticut in 2026, KNOWOL (USGS elevation, Census Bureau roads)
  8. Historic towns of the Connecticut River valley (1906), on Middletown's churches, Internet Archive
  9. History of Middlesex County, Connecticut (1884), on the First Church and Nathaniel Collins, Internet Archive
  10. Connecticut historical collections, John Warner Barber (1836), on the ancient burying ground and its elm, Internet Archive
  11. Genealogical and family history of the state of Connecticut (1911), on the 250th anniversary memorial, Internet Archive
  12. History of Middlesex County, Connecticut (1884), on shipbuilding and the industries of 1850, Internet Archive
  13. History of Middlesex County, Connecticut (1884), on the Middletown ferry, Internet Archive
  14. Connecticut historical collections, John Warner Barber (1836), on the Stamp Act day of 1765, Internet Archive
  15. Connecticut historical collections, John Warner Barber (1836), on the settling of Westfield, Internet Archive
  16. The Connecticut quarterly (1895), on the Hamlin family and the first mayor, Internet Archive
  17. Washington Street Historic District (Middletown, Connecticut), Wikipedia
  18. A statistical account of the county of Middlesex, in Connecticut (1819), on the Baptist churches, Internet Archive
  19. Samuel Wadsworth Russell House, Wikipedia
  20. The historical, statistical and industrial review of the state of Connecticut (1884), on Middletown, the Forest City, Internet Archive
  21. Highland Historic District (Middletown, Connecticut), Wikipedia
  22. Seth Wetmore House, Wikipedia
  23. Captain Benjamin Williams House, Wikipedia
  24. Main Street Historic District (Middletown, Connecticut), Wikipedia
  25. Starr Mill, Wikipedia
  26. Middletown Alms House, Wikipedia
  27. Wilcox, Crittenden Mill, Wikipedia
  28. Broad Street Historic District (Middletown, Connecticut), Wikipedia
  29. Russell Company Upper Mill, Wikipedia
  30. Richard Alsop IV House, Wikipedia
  31. Metro South Historic District, Wikipedia
  32. Connecticut State Historic Preservation Review Board, minutes of September 12, 2025, on the Beman Historic District
  33. Connecticut Valley Hospital, Wikipedia
  34. Church of the Holy Trinity and Rectory (Middletown, Connecticut), Wikipedia
  35. Middletown South Green Historic District, Wikipedia
  36. Xi Chapter, Psi Upsilon Fraternity, Wikipedia
  37. Old Middletown High School, Wikipedia
  38. Wadsworth Mansion at Long Hill, Wikipedia
  39. Old Middletown Post Office, Wikipedia