New Canaan

A charming town called New Canaan can be found in Fairfield County, just 20 minutes from Stamford and an hour from New York City. New Canaan, another haven for commuters, has a downtown area that is much larger than the Main Streets in the other small towns on this list because it is so charming. The majority of the upscale stores, cafés, and eateries are located on Elm Street. The prices should reflect the clientele since this is a very wealthy town. Children can find ice cream shops in abundance.

The renowned Glass House is New Canaan's top tourist destination. This eclectic residence, which was created and lived in by architect Philip Johnson, is among the most interesting homes you'll ever see and one of the best places to visit in Connecticut. You will be talking about it for years to come because it is so fascinating and special. Plan accordingly as it is only open from mid-April to mid-November. It is worthwhile to stop by the Silvermine Arts Center, especially to explore the area that bears the same name. It's like strolling through a postcard, this picture-perfect part of town. This region truly has it all: babbling brooks, old houses, white picket fences, and waterfalls. One of the most well-liked lodging options in the area is The Inn at GrayBarns. It is stunning, cozy, and home to a tavern where hungry patrons can enjoy delectable fare.