Last spring I made a conscious effort to create a list of day trips that I wanted to take in the summer. Focusing on beaches and seafood, my fiancé and I hit our fair share of towns along Boston’s North Shore, including Crane Beach in Ipswich and Singing Beach in Manchester-by-the-Sea. The quaint seaside towns of Rockport and Gloucester were on my list of places to go, but due to time constraints, we never went. So, on a freezing winter Sunday, I did the reasonable thing and suggested that we take an off-season day trip.
Winter Day Trip to Rockport, Massachusetts
Knowing that there would be significantly less traffic than in the summer, we hopped in the car and made the drive up to Rockport in record time. In just less than an hour we found ourselves at the tip of the Cape Ann peninsula in the heart of Rockport.
Since it’s right on the Atlantic Ocean, Rockport is more of a warm weather town. Summers are bustling with locals and tourists alike, seeking a quintessential New England experience. Rockport is 100% New England—from the fishing boats in the harbor and the rocky shoreline, to the stretch of stores in converted lobster shacks on Bearskin Neck.
That being said, the winter in Rockport is a much different story. Much of the seaside town was closed for the off-season, but we were happy to walk around and enjoy the gorgeous views.
The day was gorgeous—one of those blindingly sunny days with a cerulean blue sky. As any New Englander knows, it’s also the type of weather that makes cold days feel even colder. The 30 degree day felt more like 13 thanks to the wind, so we knew our trip to Rockport would not be an all day affair.
We walked around town and Bearskin Neck taking in the seaside sights. We managed to find a few open stores to browse through, including Tuck’s Candy, where I picked up some penny candy and saltwater taffy. Unfortunately due to the season, pickings for food were slim. Craving seafood and chowder, we drove to nearby Gloucester, less than 5 miles south of Rockport.
Lunch and a Brewery in Gloucester, Massachusetts
I had heard good things about Latitude 43 in Gloucester so we made a quick OpenTable reservation (I’m a sucker for any app with loyalty points) and within minutes we were snuggled in a warm table overlooking the harbor. Oyster addicts, we started with a dozen from Duxbury, Massachusetts. While some oysters leave you hungry, Duxbury oysters do not. They’re are large, meaty, and deliciously briny and paired well with a glass of Rosé.
We followed the oysters with a cup of New England Clam Chowder, fitting for a cold winter day, and split the local fish and chips. The haddock in the fish and chips is locally caught fried to perfection. Fresh and oh so delicate, I threw table manners to the blustering wind and ate the dish with my hands! Call me uncouth, but I believe there’s no better compliment to a chef than having someone devour a meal like an animal—thankfully I don’t think anyone saw me do it!
Following an amazing meal at Latitude 43, we popped over to Cape Ann Brewing Company next door. The Gloucester-based brewery, known for its signature Fisherman’s Brew amber lager, has a restaurant and tap room at the brewery. The beers were delicious—we split a flight of six and relaxed in front of the floor-to-ceiling windows overlooking the harbor.
Warmed up with food and drink, we eventually hit the road back to Boston, promising ourselves to go back to visit Rockport and Gloucester in the summer. Have you been to either of these towns? What are your favorite things to do there?
