Best of Middlebury, CT
The best restaurants, cafés, bars, shops and things to do in Middlebury, CT — mapped and organized by category.
About Middlebury
Middlebury is a town in New Haven County, Connecticut, serving as a suburb of Waterbury to its south. It lies within the Naugatuck Valley Planning Region and sits on the northern fringe of the New York metropolitan area. The population was recorded at 7,574 during the 2020 census.
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Quassy Amusement Park
Quassy Amusement Park sits within the Middlebury Center Historic District, offering 20 rides across its 20 acres.
It is one of only 11 trolley parks still operating in the United States.
View details →Best Hotels in Middlebury
1 places · Where to stay, from budget-friendly to boutique.
Best Things to Do in Middlebury
2 places · Museums, landmarks and the experiences worth your time.
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Middlebury Historical Society
Middlebury Historical Society is an attraction located in the Middlebury Center Historic District.
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Quassy Amusement Park
Quassy Amusement Park sits within the Middlebury Center Historic District, offering 20 rides across its 20 acres.
Best Parks & Outdoors in Middlebury
1 places · Green space, gardens and room to breathe.
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Meadowview Park
Meadowview Park offers a peaceful green space within the Middlebury Center Historic District, ideal for strolls or casual gatherings.
Nearby cities to explore
More guides within driving distance of Middlebury.
- Waterbury, CT 55 places
- Naugatuck, CT 33 places
- Southbury, CT 66 places
- Prospect, CT 6 places
- Wolcott, CT 4 places
- Plymouth, CT 28 places
- Cheshire, CT 24 places
- Cheshire Village, CT 1 places