Connecticut has more adorable main streets per capita than most states. With such an abundance of charming towns, it’s no surprise that the most adorable Main Street in America just might be in Connecticut.

The Main Street running through Ridgefield, CT has been called "a Norman Rockwell painting come to life."
Facebook/Town of Ridgefield, CT
You don't need to look very hard to find dashes of Americana. This enormous flag on the town hall is one of the more obvious signs, but you'll also find more subtle signs like creaky hardwood floors and delicious handmade treats in the local shops.
Wikimedia Commons/Pepper
This little town nestled in the Berkshire foothills was founded in 1708, which means you'll find more than a few buildings dating back to the colonial era.
Wikimedia Commons/Pepper
While there's plenty of historic charm, local businesses in Ridgefield are very much in the present. Walking along Main Street, you'll find cute shops and restaurants catering to 21st Century tastes.
Flickr/Maggie Deegan

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Not far beyond Main Street, stately homes give the town dignified flair.
Wikimedia Commons/MagicPiano
Ridgefield residents love decorating the already-adorable town for holidays.
Flickr/Maggie Deegan
Ridgefield does the holiday season especially well. Walks through the perfectly-decorated Main Street are legendary in Connecticut.
Flickr/Chris Burke
But, it's too early in the year to get excited about the holidays associated with lights and presents. For now, we'll look forward to the candy-fueled day coming up a little bit sooner.
Flickr/Maggie Deegan

We know, there will be some disagreement over whether Ridgefield is absolutely the most charming Connecticut Main Street. Whether or not you agree with us, it’s hard not to admit Ridgefield is adorable.

Which other Main Streets in Connecticut do you love? Here are a few of our favorites.

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