Another lovely harbor-side village on the North Shore that is well worth a visit is Port Jefferson. Spend some time strolling along Main Street and East Main Street, the two main shopping hubs in town. The town harbor is a hive of activity all year round and Harborfront Park is a major draw, featuring a 350-foot pier, a winding, waterfront promenade, and pretty, coastal-inspired landscaping. Summer means movies and concerts on the lawn, while in the winter, an outdoor skating rink offers cold-weather fun.

Right across from the harbor, don’t miss Rocketship Park, a fantastic kids’ play area with swings, ball courts, and the namesake rocketship slide. Nearby, the Little Red Barn offers children’s shows during the warmer months. On Main Street, TheaterThree is another option for live, kid-friendly productions with its One Hour Musicals series. If you have little ones, visit the Maritime Exploratorium, a small, interactive children’s museum perfect for younger travelers.