Newburyport is a great place to walk around shop and eat - even in the winter! Lots of shops and good restaurants. A couple of our favorites are Mission Oak Grille, the Black Cow, Sea Level.
We both love Gloucester and can't wait to move back there! We went on our first date at Minglewood tavern (tavern isn't there anymore but the restaurant is). On our second date we walked the boulevard and went for a drink at Drift Cafe. Third date we went for a hike at Lily Pond. Our favorite restaurants here are Passports, Tonno, and the old classic Stones Pub! Halibut Point State Park is also a great place for a hike, in Rockport not too far away.
Walking the paths and boardwalk here in the Winter is beautiful!