The center of Woodbury is distinctive for its mile-long stretch of older buildings lining both sides of the road. The public buildings in the National Register Historic District include the First Congregational Church (1818), the Old Town Hall (1846), the United Methodist Church, the St. Paul's Episcopal Church (1785), and the North Congregational Church (1816).
The most eye-catching of the public buildings is the Masonic Temple (1839). It is a modest, clapboard, Greek Revival temple, notable less for its architecture than for its dramatic location, situated atop a high cliff accessed by a long flight of steps (there is a modern road at the rear). It is visible from a distance and is especially dramatic at night, when it is illuminated by spotlights. The Woodbury Temple echoes the many temples of the Greek world that were perched at the edge of high places from which they could be seen from miles around and from far out at sea.
Originally, the many historic houses on the street were residential. In the late twentieth century, they were occupied by a series of antique shops. Woodbury is often referred to as Connecticut's antiques capital.<ref>Template:Cite web</ref>
Two groups of settlers came from Stratford. The first, religious dissidents unhappy with the church in Stratford, was led by Woodbury's first minister, the Reverend Zachariah Walker. The second, led by Deacon Samuel Sherman, had been given approval by the general court to purchase land from local Native Americans in order to establish a new settlement. Together, fifteen families (about fifty people), arrived in ancient Woodbury, known as "Pomperaug Plantation", early in 1673.
In 1673, these original settlers drew up an agreement called the "Fundamental Articles", which proclaimed that as many settlers as could be accommodated would be welcomed to the new settlement. The Fundamental Articles stated that expenses of establishing the settlement would be shared by its inhabitants, and that no one was to be given more than twenty-five or less than ten acres of land. Other sections of the articles provided for common land and for land saved to be divided up for future inhabitants of the settlement.<ref>Template:Cite web</ref>
The settlement was named Woodbury, which means "dwelling place in the woods", and was first recognized as a town in 1674. Deacon and captain John Minor was the first leader of the community during Woodbury's early years. Minor was the first town clerk and, along with Lieutenant Joseph Judson, served as the first deputy to the Connecticut General Court from the town of Woodbury. On October 9, 1751, the town of Woodbury was transferred from Fairfield County at the formation of Litchfield County.
The German composer Hanns Eisler, who had taken asylum in the United States after fleeing from the Nazi rule in Germany, spent three and a half months (from June 15 to September 30, 1941) in Woodbury as the guest of another German refugee, Joachim Schumacher, and his wife Sylvia. Joachim taught classes in art history, musicology, philosophy, and other subjects at the Westover School in Middlebury. Sylvia taught piano at Westover School and privately in her home.<ref>Westover School - Giving Girls a Place of Their Own, Laurie Lisle, Wesleyan University Press, Middletown, CT (2009), page 106</ref> Joachim enticed Eisler to compose 20 songs on 16 US children's verses or nursery rhymes and four texts in the German language by Goethe, Eduard Mörike and Ignazio Silone. The songs were composed for female voices and suitable for a school chorus.<ref name="Songbook-booklet" /> This was published as The Woodbury Songbook, or, in German, Das Woodbury Liederbüchlein with the lyrics in English and German, unfortunately with a wrong spelling of Woodbury (with two "r"s). The German translations are by Wieland Herzfelde.<ref name="Songbook-Noten" />
Woodbury lies in the Pomperaug River valley, a tributary of the Housatonic River. The Pomperaug River is formed in Woodbury by the confluence of the Nonnewaug River and the Weekeepeemee River.
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At the 2010 census there were 9,984 people, 4,219 households, and 2,772 families in the town. The population density was Template:Convert. There were 3,869 housing units at an average density of Template:Convert. The racial makeup of the town was 97.25% White, 0.53% African American, 0.22% Native American, 1.15% Asian, 0.07% Pacific Islander, 0.22% from other races, and 0.57% from two or more races. Hispanic or Latino of any race were 1.65%.<ref name="GR2">Template:Cite web</ref>
Of the 3,715 households 31.4% had children under the age of 18 living with them, 58.9% were married couples living together, 8.0% had a female householder with no husband present, and 30.7% were non-families. 25.4% of households were one person and 8.7% were one person aged 65 or older. The average household size was 2.48 and the average family size was 2.99.
The age distribution was 24.0% under the age of 18, 4.4% from 18 to 24, 29.3% from 25 to 44, 29.3% from 45 to 64, and 13.0% 65 or older. The median age was 41 years. For every 100 females, there were 95.3 males. For every 100 females age 18 and over, there were 91.8 males.
The median household income was $68,322 and the median family income was $82,641. Males had a median income of $53,246 versus $35,298 for females. The per capita income for the town was $37,903. About 2.3% of families and 4.5% of the population were below the poverty line, including 4.9% of those under age 18 and 6.3% of those age 65 or over.
At the 2000 census, there were x people, 618 households, and 336 families in the CDP. The population density was Template:Convert. There were 644 housing units at an average density of Template:Convert. The racial makeup of the CDP was 98.07% White, 0.85% African American, 0.15% Native American, 0.39% Asian, 0.31% from other races, and 0.23% from two or more races. Hispanic or Latino of any race were 1.16% of the population.
Of the 618 households 25.1% had children under the age of 18 living with them, 41.9% were married couples living together, 9.5% had a female householder with no husband present, and 45.5% were non-families. 39.3% of households were one person and 15.7% were one person aged 65 or older. The average household size was 2.10 and the average family size was 2.82.
The age distribution was 20.6% under the age of 18, 5.2% from 18 to 24, 30.2% from 25 to 44, 28.1% from 45 to 64, and 15.9% 65 or older. The median age was 40 years. For every 100 females, there were 85.4 males. For every 100 females age 18 and over, there were 79.1 males.
The median household income was $51,136 and the median family income was $65,227. Males had a median income of $50,625 versus $40,729 for females. The per capita income for the CDP was $30,277. None of the families and 4.6% of the population were living below the poverty line, including no under eighteens and 8.9% of those over 64.
Woodbury is one of the most reliably Republican towns in the United States. Since its founding in 1854, every Republican presidential candidate has carried Woodbury, even in nationwide Democratic landslides such as 1912, 1936, and 1964 in which Democratic candidates won Connecticut. Only four times, in 1884, the aforementioned 1912, 1992, and 1996 has the GOP candidate for president not received an absolute majority of the vote. In the eleven elections from 1920–1960, the Republican candidates all broke 70% of the vote in Woodbury, with the party's best showing coming in 1928 when Herbert Hoover received 84.17% of the vote. The best showing for any Democrat in Woodbury since the founding of the GOP occurred in 1964 when Lyndon Johnson received 48.82% of the vote in an election where he won Connecticut with 67.81% of the vote.
Similarly, Woodbury has also supported the last 36 GOP campaigns for governor of Connecticut.
Prior to the GOP’s founding, Woodbury supported Whig presidential nominees Winfield Scott, Zachary Taylor, Henry Clay, and John Quincy Adams in 1852, 1848, 1832, and 1828 respectively. Adams of whom has the largest percentage of the vote since 1828 for a presidential candidate in Woodbury at 88.36%. In 1836, 1840, and 1844, Martin Van Buren, and James K. Polk carried Woodbury, they remain the only two Democratic presidential candidates to carry the town, as of the 2020 presidential election.
The results for Woodbury in all presidential elections since 1828, and all gubernatorial elections since 1916 can be found below:
Woodbury town vote by party in presidential elections<ref name="General-Elections-Statement-of-Vote-1922">Template:Cite web</ref>
Woodbury is part of the Region 14 School District consisting of Nonnewaug High School, Woodbury Middle School, Bethlehem Elementary School, Mitchell Elementary School, and STAR Preschool Program.<ref>Template:Cite web</ref>
Voices, a local newspaper serving Southbury, Middlebury, Oxford, Seymour, Naugatuck, Woodbury, Bethlehem, New Preston, Washington, Washington Depot, Roxbury, Bridgewater, Monroe, Sandy Hook and Newtown
Leroy Anderson (1908–1975), composer ("Sleigh Ride" and many other works); lived in Woodbury from 1948 until his death in 1975.<ref>Template:Cite web</ref> His widow Eleanor Anderson (1918–2014) lived in Woodbury from 1948 until her death<ref>Template:Cite web</ref>
Robert Templeton (1929–1991), presidential portraitist and civil rights artist; lived in Woodbury and maintained his studio there from 1965 until his death
Rob Zombie, musician and movie director; moved to the town in January 2009 with his spouse Sheri Moon and has since sold his house and moved from town.
