Wooden Warrior

Quassy Amusement Park is an amusement and waterpark in Middlebury, Connecticut, and is one of only 11 trolley parks still operating in the United States. It has 20 rides on its 20 acres (81,000 m2). Quassy consists of a full-fledged amusement park plus a waterpark called Splash Away Bay. Swimming in Lake Quassapaug is available. In 1901, a writer pronounced Lake Quassapaug as "the handsomest bit of natural water on Earth". Today, beach clubs and houses surround the entire lake. The park is home to the award-winning Wooden Warrior roller coaster, which opened in 2011. Quassy offers swimming, picnicking, a catering service, an arcade, a waterpark, and live entertainment including school bands, dance groups and magic shows. The park uses an all-day ride and waterpark wristbands or pay-by-ride system. A wristband is required to enter the waterpark and beach area, or guests may pay a separate admission. Admission to the park is free but a parking fee is charged.

Lake Quassapaug is a 296-acre (120 ha) reservoir located in Middlebury, Connecticut. It is home to Quassy Amusement Park.The lake also hosts six private outing clubs, including the Lake Quassapaug Outing Club and the Quassapaug Sailing Center. The Lake Quassapaug Association (LQA) manages the reservation of the lake and is composed of interested individuals, groups, and property owners on the lakefront. The LQA was formed in 2012 to preserve the lake’s high water quality and promote responsible enjoyment of the lake.

Tranquility Farm is a historic summer estate located on Tranquility Road in Middlebury, Connecticut. The estate was developed in the 1890s by industrialist John H. Whittemore, with architectural design by the noted firm of McKim, Mead & White, and landscape design by Charles Eliot and Warren H. Manning. The main house was a rare inland example of Shingle Style architecture in the state. The property was listed on the National Register of Historic Places in 1982. The main house was demolished sometime after listing.

The Middlebury Center Historic District encompasses the historic civic and religious center of Middlebury, Connecticut. Centered at the junction of North and South Streets with Whittemore Road, the district includes churches, schools and municipal buildings, many from the late 19th or early 20th centuries, as well as a diversity of residential architecture. The district includes all the residences along the entire length of North Street, which leads up to the town green. The district was listed on the National Register of Historic Places in 1985.

Pomperaug High School (PHS) is a public high school in Southbury, Connecticut. It is part of Regional School District 15 which serves Southbury in addition to Middlebury.

Middlebury is a town in New Haven County, Connecticut, United States. The population was 7,574 at the 2020 census. The town is part of the Naugatuck Valley Planning Region.

The Westover School, often referred to simply as "Westover," is an independent college-preparatory day and boarding school for girls. Located in Middlebury, Connecticut, United States, the school offers grades 9–12.

The Josiah Bronson House is a historic house on Breakneck Hill Road in Middlebury, Connecticut, built about 1738. It is one of the town's few surviving 18th-century houses, and a good example of residential architecture from that period. It was listed on the National Register of Historic Places in 1982.

The David Sherman House is a historic house on Middle Quarter Road in Woodbury, Connecticut. Built about 1760, it is a well-preserved example of Colonial architecture. In 1781, David Sherman is reported to have hosted a ball for officers of the French Army of the Comte de Rochambeau during their march across Connecticut. The house was listed on the National Register of Historic Places in 2002.

Nonnewaug High School is a public school in Woodbury, Connecticut, United States, which serves the towns of Woodbury and Bethlehem, Connecticut. It is part of Regional School District #14. Before 1970, students in the district attended Woodbury High School, which has now become the middle school. The school houses the Ellis Clark Regional Agri-Science and Technology Center, which draws students from additional surrounding areas. Nonnewaug serves approx 750 students, around a third of which are from the agriscience program. The name "Nonnewaug" comes from a local Native American Chief. The word, originally Nunnaw-auke, means “dry land".

Gunntown Cemetery is an old cemetery in Naugatuck, Connecticut which was established in 1790. Many of Naugatuck's citizens who supported independence from British rule during the Revolutionary War are buried in the cemetery. The cemetery is also considered by many to be haunted.