48 Hours in Rockport, Massachusetts

Historic Rockport, Massachusetts is a seacoast village located on the tip of Cape Ann. I recently spent 48 hours exploring this old, salty gem of a North Shore town. It is a perfect New England getaway. Just an hour from Boston, it is a place to escape the city yet still be close to home. It’s most famous claim to fame, the often painted and photographed Motif. No 1, is the centerpiece of this still active fishing village. That magical light in the harbor attracts many to see the well known scene, but you’ll want to stay a few days to enjoy the great dining, an array of beaches, and to walk the old streets laden with shops and galleries.

Here’s how we spent our 48 hours in Rockport…

We arrived in Rockport early in the afternoon and checked into our accommodations for our visit. We stayed at the Addison Choate , which is a charming boutique hotel. From this hotel, it is just a short five minute walk to Dock Square, Motif No. 1, and Bearskin Neck. You can even walk or bike to a few of the beaches easily from here. The hotel is a great mix of old time charm with a fun, modern twist. They offered a great breakfast with our stay, which was the perfect fuel for our explorations.


Click here to read my post about our stay at Addison Choate

After freshening up, we walked ourselves right down to the historic district. First stop…

Motif No. 1

I had to make this our first stop on the Rockport tour! The afternoon light was divine and we took our time walking around this spectacular scene. I think I might have to dedicate a post just to Motif No. 1, because I took so many photos and the whole area surrounding it is full of delicious coastal details that my eye kept spying. My kind of place!

It’s great to visit it in different times of the day too. The harbor is ever-changing with activity and the light is unique at all different hours. Honestly, we visited this area at different times all three days we were here. It was a photographer’s dream and a great walking area in the morning and late evening. The afternoon light was my personal favorite.

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Bearskin Neck

This is the historic street of shops and galleries that call old fishing shacks home. We loved all the art galleries. To see it before the streets were bustling, we went early and took our time exploring every nook and cranny. There are so many great spots to enjoy the morning light with water views too. You can grab coffee at the Bean & Leaf Cafe to enjoy on your stroll.

Once shops open, it’s fun to walk around and visit them. Honestly, I was more into the art galleries, but I couldn’t resist buying a handmade candle from the Rockport Candle Company as a souvenir. There’s a lot of touristy souvenir shops along Bearskin Neck which is great if you want a shirt or souvenir mug.

One store to mention that is just up Main Street in the historic district is the John Tarr Store. It hit all my preppy-loving coastal buttons for outfitting.

There are several restaurants in this area too. You must get lobster at Roy Moore Lobster Company —you have to if you are in Rockport. If you want something different, it’s fun to go to Top Dog which has just about every kind of hot dog concoction you could dream up. There are several ice cream shops along this stretch too, but the Ice Cream Store is by far the cutest and has a great selection.




Walk Out on the Jetty

If you walk to the end of Bearskin Neck, you have access to a jetty that looks out on the Atlantic and Rockport Harbor. You can get a faint view of Straitsmouth Island Light on a clear day. It’s a good spot to sit with a take out meal or drink and enjoy the ocean views.

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Visit the Area Beaches & Coves

The town beaches like Front Beach and Back Beach fill up pretty quick on a hot summer day. They are good for quick dip and to cool off, but I really enjoyed the quieter beaches. At the recommendation of our inn keeper, we took our Jeep and headed out to Loblolly Point and Cape Hedge Beach (which is right next to the more popular Long Beach.) These more off the radar spots were just my speed and at Loblolly Point you can see all three lighthouses in Rockport. The Twin Lighthouses on Thatcher Island really stand out from the lookout point. It’s quite the view and I highly recommend it if you are looking for more than just a swimming hole.

Click here to see my post on the quieter beaches & coves in Rockport, MA

Listing of all Rockport beaches here.


Eat Lobster & Other Treats

There were so many restaurants and treat shops to choose from that we stuck to the most popular ones this trip since it was our first time here. These are the ones we ate at while we visited and they all had great food.

  • Roy Moore Lobster Company– Pick up window for a classic lobster dinner and other options. Small seating area in the back.

  • The Blue Lobster Grille– Seafood and American fare and had a decent outdoor seating area.

  • Top Dog– We grabbed some dogs and chips and ate by Motif No. 1. Fun stop for kids too and very inexpensive.

  • The Ice Cream Store– Classic ice cream options and tons of flavors.

  • Sundays– Another ice cream shop and has a great view of Motif No. 1 with its lawn seating in back. We grabbed a sorbet here in the heat of the day and it was a nice treat.

    I was told there are some great lobster joints just a short 10-15 minute drive from Rockport too. Next time, I want to venture out a bit and try a few while I’m exploring.


Between walking and photographing around Motif No. 1, shopping the historic district, visiting a few beaches, trying the eats, and our walks to explore every nook and cranny around town— our 48 hours flew by here!

I definitely want to come back in the fall. I just have a feeling it is wonderful that time of year to visit too. I’ll be sharing more on Instagram and I will be posting here to the blog soon with more Rockport goodness.

Until next time,



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