A hill town made in 1807 from the edges of Waterbury, Woodbury and Southbury, with its green on a high plateau, Breakneck Hill where Rochambeau's army camped, and Lake Quassapaug, a summer resort since 1874.

New Haven County · Record checked October 11, 2026

7,574Population2020 census1
1807Became a townfrom parts of Waterbury, Woodbury and Southbury1
296Lake Quassapaugacres, with Quassy on its shore2
67 to 0Joined New Haven Countythe town's vote in April 18083
1874Resort on the lakeHiram J. Wallace's pleasure grounds4

Middlebury on the map

Click the map to look closer.

Map of Middlebury, Connecticut in 2026, with the town green, Lake Quassapaug, Quassy, Tranquility Farm and 34 numbered landmarks

2026

Middlebury today

By KNOWOL

Shaded hills from Bradleyville in the east to Lake Quassapaug in the west, every street, Middlebury Center and its green, Long Meadow Pond and Fodder's Folly, and a guide of 34 numbered landmarks with the National Register sites marked.5

See the 2026 printMore about this map

The story of Middlebury

Steamboats on Quassapaug

Long before the trolley, Lake Quassapaug was already a place to spend a summer day. An 1892 county history called its waters clear, cool and in parts very deep, full of bass and pickerel and loved by sportsmen. In 1874 Hiram J. Wallace bought the old Uri Manville farm at the south end of the lake and started a pleasure resort. By 1888 it had a hotel, a score of rowboats and a steam yacht called the White Deer that carried 36 people. Across the water, Eben E. Richardson opened Richardson's Grove in 1878, and it became known for its shore dinners. In 1908 the lake became a stop on the trolley line from Waterbury to Woodbury, and that stop grew into Quassy.46

Casks, cloth and pocket knives

Middlebury was mostly farms, but its brooks kept a surprising number of small trades going. Coopers made casks for the West Indies trade, the Benhams and the Tuttles made hats, and fruit distilleries brought good money into town. At Bradleyville on Hop Brook, Enos Bradley built a sawmill and cloth works some time after 1795. He was a fine cloth dresser, and people brought rough cloth to him from all over the county. Later the mill made wagon wheels and then pocket knives, and Samuel Root ran the cutlery works with skilled English workmen until 1887. Up north, Daniel Abbott made a new kind of pump, and Leonard Fenn made axes on Hop Brook.7

Breaking away from Waterbury

Middlebury began as West Farms, the far western edge of Waterbury. In 1786 its families won the right to have preaching at home for eight Sundays of the winter, and in 1790 West Farms joined nearby corners of Woodbury and Southbury as the society of Middlebury. A meetinghouse went up at the center in 1793, and twelve people formed the church in 1796. Then came the hard part. Waterbury fought the new town's petitions for five years, until the General Assembly agreed in October 1807. Hard feelings lingered, but Middlebury got straight to work. In April 1808 it voted 67 to none to join New Haven County, and that fall it sent President Jefferson a paper on the hardships of the embargo.89103

Through the years

24 moments from 1687 to today.

  1. 1687Settlers of Woodbury buy the Quassapaug tract from its native owners. Part of southern Middlebury lies inside it.11
  2. 1738About this year Josiah Bronson builds the house on Breakneck Hill Road that's now the town's oldest.12
  3. 1771Middlebury's first burying ground is laid out. It has long since vanished.13
  4. 1778Lafayette probably stops at Captain Isaac Bronson's tavern at Breakneck.14
  5. 1781Rochambeau's French army camps at Middlebury on its march to Yorktown.15
  6. 1784Dr. Abel Bronson opens a pest-house for smallpox in Middlebury.14
  7. 1786West Farms wins eight Sundays of winter preaching at home.8
  8. 1790West Farms and nearby parts of Woodbury and Southbury become the society of Middlebury.8
  9. 1793A meetinghouse 38 by 54 feet goes up at the center.10
  10. 1796Twelve people sign the covenant and form the Middlebury church.10
  11. 1807After five years of opposition from Waterbury, Middlebury becomes a town.9
  12. 1808The town votes 67 to none to join New Haven County.3
  13. 1808Five townsmen send President Jefferson a paper on the hardships of the embargo.3
  14. 1810One of the town's first bridges is built at the outlet of Lake Quassapaug.16
  15. 1814A two-story academy is built at the center. It teaches for about 30 years.17
  16. 1818Middlebury votes 76 to 23 against Connecticut's new constitution.3
  17. 1822Bennet Tyler, born near Lake Quassapaug, becomes president of Dartmouth College.18
  18. 1874Hiram J. Wallace opens a pleasure resort at the south end of Lake Quassapaug.4
  19. 1881The railroad arrives, with a flag station at Bradley's.16
  20. 1887The pocket cutlery works at Bradleyville shut down.7
  21. 1890sJohn H. Whittemore lays out Tranquility Farm, his summer estate on the lake.19
  22. 1908Quassy becomes a stop on the trolley line between Waterbury and Woodbury.6
  23. 1909Westover School, designed by Theodate Pope Riddle, welcomes its first class.20
  24. 1935A fire takes the Congregational church and the town hall. Both are rebuilt that year.5

Places to see

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

  • 4Westover SchoolMiddlebury Center. Girls' school opened in 1909.Visit their website
  • 5Middlebury GreenMiddlebury Center. Elms planted here in 1872.
  • 6Tranquility FarmLake Quassapaug. Whittemore's summer estate of the 1890s.
  • 8Middlebury Town HallMiddlebury Center. Brick town hall built in 1935.
  • 16Middlebury Center Historic DistrictMiddlebury Center. Churches, schools and North Street houses.
  • 21Meadowview ParkArtillery Road. Home of the 2026 Rochambeau monument.
  • 26Josiah Bronson HouseBreakneck Hill Road. Oldest surviving house, about 1738.
  • 27Quassy Amusement ParkLake Quassapaug. A trolley park since 1908.
  • 28Ledgewood Memorial ParkNortheast Middlebury. Honors the town's veterans.
  • 29Middlebury Historical SocietyLibrary Road. In the Center School of 1897.Visit their website

On the National Register

All 3 places in Middlebury on the National Register of Historic Places that still stand today, oldest first, and why each one matters.22

  • Josiah Bronson House

    Built about 1738 · Listed 1982 · Breakneck Hill Road

    Middlebury's oldest surviving house, probably built by Josiah Bronson, whose family was among the first to settle the Breakneck Hill area. It keeps much of its original woodwork, with Federal touches added about 1800, and two old barns stand behind it.12

  • Middlebury Center Historic District

    Listed 1985 · Roughly bounded by Library Road, North and South Streets, and Whittemore Road

    The town's civic and religious center, where several roads meet at the green. It takes in the Greek Revival Methodist church of 1832, the Congregational church and town hall rebuilt in 1935 after a fire, Saint John of the Cross Church of 1908 and every house along North Street.21

  • Tranquility Farm

    Built in the 1890s · Listed 1982 · Tranquility Road

    John H. Whittemore's summer estate of nearly 300 acres on the east side of Lake Quassapaug, with buildings by McKim, Mead & White and grounds shaped mainly by Warren H. Manning. The Shingle Style main house was taken down after listing, but the meadows, stone walls and farm buildings of the estate are still there.19

In their words

“Its waters are clear, cool and in parts very deep. The lake abounds with fish, mostly bass and pickerel, and the locality has always been a favorite resort of sportsmen.”

History of New Haven County, 1892, on Lake Quassapaug4

“It is located on a plateau overlooking much of the surrounding country, and has a pleasant and healthy situation.”

History of New Haven County, 1892, on Middlebury Center17

“He was a fine cloth dresser, and rough cloths were brought to this mill from all parts of the county.”

History of New Haven County, 1892, on Enos Bradley of Bradleyville7

Nearby towns

Sources

  1. Middlebury, Connecticut, Wikipedia
  2. Lake Quassapaug, Wikipedia
  3. History of New Haven County, Connecticut (1892), on Middlebury's early town votes, Internet Archive
  4. History of New Haven County, Connecticut (1892), on Quassapaug Lake and its resorts, Internet Archive
  5. Map of Middlebury, Connecticut in 2026, KNOWOL (USGS elevation, Census Bureau roads)
  6. Quassy Amusement Park, Wikipedia
  7. History of New Haven County, Connecticut (1892), on Middlebury's mills and Bradleyville, Internet Archive
  8. The town and city of Waterbury, Connecticut (1896), on West Farms becoming Middlebury, Internet Archive
  9. The town and city of Waterbury, Connecticut (1896), on Waterbury's opposition to Middlebury, Internet Archive
  10. History of New Haven County, Connecticut (1892), on the Middlebury church, Internet Archive
  11. History of New Haven County, Connecticut (1892), on the Quassapaug purchase, Internet Archive
  12. Josiah Bronson House, Wikipedia
  13. The town and city of Waterbury, Connecticut (1896), on Middlebury burying places, Internet Archive
  14. The military history of Waterbury from the founding of the settlement in 1678 to 1891 (1891), Internet Archive
  15. The history of Ridgefield, Connecticut (1927), on Rochambeau's camps, Internet Archive
  16. History of New Haven County, Connecticut (1892), on Middlebury's roads, bridges and railroad, Internet Archive
  17. History of New Haven County, Connecticut (1892), on Middlebury Center, Internet Archive
  18. History of New Haven County, Connecticut (1892), on Bennet Tyler, Internet Archive
  19. Tranquility Farm, Wikipedia
  20. Westover School, Wikipedia
  21. Middlebury Center Historic District, Wikipedia
  22. National Register of Historic Places listings in New Haven County, Connecticut, Wikipedia