Middlebury

About Middlebury

Tucked into the rolling hills of New Haven County, Middlebury is a quiet, residential gem that balances suburban comfort with genuine New England charm. Sitting just north of Waterbury, it offers residents a peaceful retreat without sacrificing convenience — think tree-lined roads, lakeside living, and a strong sense of neighborly pride. It's the kind of town where people tend to stay once they arrive.

What to Know

• Lake Quassapaug is a beloved local landmark, home to Quassy Amusement & Waterpark — a classic, family-friendly park that's been delighting Connecticut kids since 1908.
• Middlebury is served by Naugatuck Valley regional planning, and students attend the well-regarded Pomperaug Regional School District 15, shared with neighboring Southbury.
• The town sits at a notably elevated 712 feet above sea level, giving it cooler temperatures and stunning seasonal foliage compared to the valley towns below.
• Middlebury's name is charmingly literal — it was named for its central position between Waterbury, Woodbury, and Southbury when it was carved out as its own town.

History

Incorporated in 1807, Middlebury has a name that tells its own story — early settlers simply acknowledged the town's geography by placing it squarely in the middle of its neighbors. What began as a small agricultural community slowly transformed through the 20th century into a sought-after residential suburb, with its population more than doubling between 1940 and 1960 alone as families flocked to the area.

Community & Living

Middlebury consistently ranks among Connecticut's more desirable small towns, drawing families who value good schools, safe neighborhoods, and easy access to both Waterbury and Interstate 84. The community has a tight-knit, low-key character — residents enjoy the natural beauty of the town's lakes and open spaces while appreciating that the pace here is refreshingly unhurried.