How to Spend a Day in Rockport

Rockport, MA is a charming little village nestled within the bustling fishing city of Gloucester on Cape Ann. While Gloucester is seemingly all about business, Rockport is all about play. And it is the perfect place to spend a summer day, from dawn until way after dusk. Here’s how to spend a day in Rockport.

Have breakfast at Helmut’s Strudel

I’ve been visiting Helmut’s since I was a very little girl and so it is always a treat when we stop in for some delicious chocolate croissants and some tea or coffee. If you get there really early you may be lucky enough to nab a table on the back porch with a view of Motif #1 (see below). 

Soak up on the Sun on Front Beach

After you’ve had your fill of amazing pastries, walk down to Front Beach and grab your spot on the sand for a morning of fun and sun. The beach is just off the main street, making it easily accessible and there are restrooms right there so you can easily change in and out of your suit.

Enjoy lunch at Roy Moore Lobster Co.

You’re bound to work up an appetite with all that swimming and sunbathing, so after you pack up your beach supplies and store them in your car, make your way back down Bearskin Neck to Roy Moore Lobster Co. It may seem a little like dining in the rough, but once you taste their sumptuous lobster rolls you will be glad you made the decision to “rough it.”  

Hit the shops on Bearskin Neck

A visit to Rockport would not be complete without a stop in at the Bearskin Neck General Store. As a child, I just loved filling up a bag of the penny candy and playing the player piano. When we made our most recent trek north to visit, Arielle’s favorite thing was to put the quarter into the piano and then dance through the whole store! 

You also must pick up a chunk of the toll house fudge from the Rockport Fudgery. For unique items, check out The Floating Lotus and The Blue Lantern. And you’ll find beautiful silver jewelry at The Village Silversmith. If you want to venture off the neck, visit Sand Castles for women’s and children’s clothing, as well as housewares and toys. Strut Boutique and Wicked Peacock have a great selection of trendy pieces, while La Provence is the place to find gorgeous gifts imported from the south of France.

Take a few pictures of Motif #1 during Golden Hour

I had no idea but Motif #1 is one of the most photographed and painted landmarks in the world. I mean, who knew? This large red icon is actually a re-creation of the original fisherman’s shack and it does make for some amazing pictures.

Grab Dinner at My Place by the Sea

This picture was taken just steps away from My Place by the Sea and as you can imagine, the view from this award-winning restaurant is stunning. In fact, it was named one of the ten best destinations for oceanfront dining on the Massachusetts coast, according to Zagat.

Finish off your day with an ice cream 

I don’t know about you, but I always need to end my meals with a sweet treat. So if you don’t have any fudge left from earlier, or you’d rather take it home and indulge in something else, make sure to complete your day at Sunday’s Ice Cream or  The Ice Cream Store. You’ll thank me later.

Have you been to Rockport? What’s your favorite thing to do there?