Portland, CT

Sitting directly across the Connecticut River from Middletown, Portland offers a peaceful, small-town feel with a population of under 10,000. It is best known for the historic brownstone quarries that once supplied building stone to cities across the country, including New York and Boston. Today, those flooded quarries have found new life as popular recreation spots, featuring scenic hiking trails and an adventure park with ziplines and water sports.

ATTRArtsistra / CC BY-SA 4.0

Waterfront living is a big part of the local appeal, supported by several active marinas, boat clubs, and riverside parks. Families are served by a dedicated, close-knit public school system, while golfers can choose between multiple local courses. Whenever you want more dining or entertainment options, a quick trip across the Arrigoni Bridge brings you straight into downtown Middletown, giving you convenient access to city amenities while keeping a relaxed home base.