Middlebury Center Historic District

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.

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.

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 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.

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.

Wooden Warrior is a wooden roller coaster located at Quassy Amusement Park in Middlebury, Connecticut, United States. The coaster was designed and built by American wooden coaster designer The Gravity Group. Wooden Warrior features a 45-foot (14 m) drop, with a maximum speed of 35 miles per hour (56 km/h) and a total track length of 1,239 feet (378 m). Despite the coaster's small size, it has been well received by enthusiasts for its air time and thrilling experience. The coaster features Gravitykraft's Timberliner trains, and was the first wooden coaster in the United States to use such trains.

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.

The Nathaniel Richardson House was a historic house on Kelly Street in Middlebury, Connecticut. With an estimated construction date of 1800, it was one of the community's oldest houses. It was listed on the National Register of Historic Places in 1977. It appears to have either been demolished or moved; it is no longer standing at its listed location.

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.

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.

Post University is a private for-profit university in Waterbury, Connecticut. It was founded in 1890 as Post College. From 1990 to 2004 it was affiliated with Teikyo University in Tokyo, Japan and during that time it was named Teikyo Post University. The university offers over 25 undergraduate and graduate programs in day, evening, and online courses with most of its students participating exclusively online and its main campus is struggling with steady enrollment.