8) Westport, Connecticut
Just 12 miles north of Stamford, Westport is another coastal Connecticut city in a prime location. Its proximity to NYC appeals to residents, however there’s no need to leave Westport – it’s got everything you need. Westport is known for its wealth; however, it values its reputation as an authentic New England town. The downtown waterfront still bustles with commercial businesses and charm with its rugged quaintness. Shopping the specialty stores around the harbor and lunching at a unique bistro is a day you’ll enjoy in Westport. Additionally, Westport residents have access to three beaches as well as boating and sailing, two popular warm weather activities. The craft brewery scene is strong in Connecticut. Westport is located a few miles from Lock City Brewing and Two Roads Brewing Company. Finally, a full events calendar creates a close-knit community perfect for families and welcoming to new residents.