A Day Trip to Rockport

One of the many great things about Watertown is how easy it is to get places. Whether you’re biking to Harvard Square for some shopping or jetting to Cape Cod for a beach day, Watertown’s access and convenience is unparalleled.  Since summer’s only weeks away, we thought we’d set our sights on a day trip to what some call the other Cape – Cape Ann, that is – and plan a day in the beautiful town of Rockport!

If you’ve never been, Rockport is a charming seaside town just an hour’s drive from Watertown Square. Surrounded on three sides by ocean, Rockport offers a great mix of beachcombing, shopping, art gallery browsing, and delicious dining options – enough for a longer vacation, but perfect for a day trip too! Here are some highlights worth checking out.

Bearskin Neck

Jutting out from downtown Rockport, Bearskin Neck is one of the easternmost points in Cape Ann, a peninsula of cozy narrow streets lined with shops, galleries, and cafes. One of our favorite apparel stops there is One Ocean One Love maker of some very cool hand-printed surf-inspired clothing – plus, they donate 5% of their net profits to cleaner oceans!

Despite the obvious presence of the fishing industry on the peninsula, Bearskin Neck is also where you really get the sense of Rockport as an artists’ colony, where you’re just as likely to see someone painting at an easel as unloading lobster traps. Browse work by local artists and take in charming views of the harbor and ocean, as well as the legendary fishing shack known as Motif #1 – said to be one of the most photographed buildings in the US.


photo courtesy of the New England Historic Society

Main Street and Dock Square

You won’t see any chain stores in downtown Rockport – only small boutiques and businesses owned and operated by locals. Browse the impressive array of French imported tablecloths, dinnerware, and clothing at La Provence. Check out the handmade cards, whimsical gifts, toys, and books at The Paper Mermaid, a local favorite for over 17 years. And don’t leave without popping in to Tucks’s Candy and Gifts, a Rockport institution since 1929 (we personally can’t handle the fudge). If you love local art, the Rockport Art Association and Museum on Main Street always has an interesting show mounted, along with their impressive permanent collection. 


Rockport is at its heart a fishing village, and the local cuisine reflects that. There are a bunch of great seafood places, all casual and fun with standard local fare – standouts include Nate’s at Front Beach, Top Dog, and Roy Moore Lobster Company. If you don’t mind driving a bit out of the town center, the Lobster Pool offers a unique, picnic-style setting right on Ipswich Bay. Always busy but moves fast. BYOB.

Getting There

Unfortunately, Rockport’s charm means big crowds in the summertime. Your best bet? Ditch the car at the Cape Ann Transportation Authority parking lot and take their free shuttle into town.