Middlebury has seven distinct business areas
This well-traveled area centered on the intersection of Middlebury Road, Glenwood Avenue and Regan Road currently includes six restaurants, three gas stations, a grocery store, hair salons, and many other retail and small commercial businesses built up over the years. The town intends to gradually adopt Village District regulations to improve the appearance and pedestrian-friendliness of the area.
Straits Turnpike North
This area consists primarily of automobile dealerships adjacent to the Watertown town line and office buildings, with some small retail uses closer to Route 64. Middlebury Edge is the most prominent anchor within this area with many health care offices. Other nearby multiple tenant buildings contain health care offices, light manufacturing, restaurants and retail stores.
Straits Turnpike South
This area from Route 64 to the Naugatuck line contains small retail uses and a large concentration of multi-story office structures. It is adjacent to Post University and helps serve student and faculty retail needs.
Judd's Corner. Route 64 – Route 188
This is an area along Route 64, centered upon the intersection of Route 188. It includes a portion of West Street, adjacent to the Middlebury Green area. The area has four restaurants and includes a small plaza along Route 64 and small commercial uses along West Street, and most prominently, the widely known Middlebury Consignment.
This is the historic center of town, listed as a Historic District on the National Register in 1985, an iconic New England townscape with churches, historic residences and the Westover School are all clustered around an unspoiled Green. The historic Town Hall is at the edge of the Green with the Shepardson Community Center and Public Library a short distance away. There currently are no commercial businesses on the Green.
Gateway District. Route 188
Much of this area is undeveloped and ready for commercial use under specific zoning regulations enacted in 2010. Current uses include the former Trucking Museum, which has become a furniture outlet, plus two office buildings, fitness, swimming and racquet clubs, medical offices and day care. Interstate 84 and the Crown Plaza Hotel are just to the southwest. An upscale grocery store is under construction.
This area encompasses the southwest corner of the town and is generally bound by the Southbury and Oxford town lines, Interstate 84 and Benson Road. Some campus office and light industrial development has occurred, but large "shovel ready" acreage remains vacant. The area provides easy access to Oxford Airport and Interstate 84.