Don’t get me wrong, I love the snow, but I equally love a sunny, summer weekend by the beach and this snowy, cold New England week has me dreaming of summer vacations past. With that in mind, I wanted to look back at one of my favorite trips we were able to take last summer, our weekend in Rockport, Massachusetts.

When you think of what makes up a quintessential New England seaside town, Rockport checks all the boxes. Picturesque ocean views, adorable fishing shacks, art galleries, and incredible lobster! We drove, but you can also take the Commuter Rail from Boston, which drops off just a short walk from downtown. As soon as we got close, we could feel the excitement and vibrance of Rockport immediately. There was a steady stream of masked-up vacationers strolling down Main Street and beyond them and the adorable storefronts were breathtaking views of the harbor. I was immediately smitten.

We stayed at Captain’s Bounty on the Beach, where every room has a private balcony and an incredible ocean view. We even slept with the sliding door open, so we could fall asleep to the sound of the waves crashing. With friendly staff, immediate access to the beach, and an unbeatable location right in town, I cannot recommend this place enough!

The weather for our weekend did not turn out to be the perfect beach weather that we had hoped for, but honestly, I think that worked out for the best. Instead of lounging the day away at the beach, we were able to explore the town. Both mornings we woke up early before the crowds of tourists arrived from the city and walked unbothered down Main Street to Bearskin Neck (I know it’s a strange name, you can read more about its name and history here) where the merchants prepared for the day. During the day, we shopped at the art galleries and other shops along Bearskin Neck, often having the opportunity to chat with the store owners or artists themselves. Between shopping, stops for ice cream, and the ocean views, it was pretty much a perfect weekend.

It was one of those trips that you just do not want to end. I was so close to booking another night. Instead, we decided to extend our trip by heading down to Gloucester for lunch and a stroll along the Harbor and then by driving the long way home, winding our way through all of the beautiful seaside towns in Essex on Scenic Route 127.

My Top Picks for a Trip to Rockport

1. Bearskin Neck

Bearskin Neck and its adorable fishing shack shops seem to be the heart of Rockport. There is so much to see for such a tiny area. Artist galleries, darling shops, and restaurants line the narrow streets. If you are up for it, at the top of Bearskin Neck you can carefully walk out along the harbor’s breakwater to get a fantastic view of Rockport Harbor.

2. Motif No.1

Motif No.1 is a red fishing shack adorned with lobster buoys that stands proudly at the end of Bradley Wharf in Rockport Harbor. It also just happens to be known as the most painted building in the world. It really is just a simple red fishing shack, but between boisterous red color and proximity to other colorful fishing shacks and boats in the harbor (which inspired my logo), it becomes the focal point of a spectacular scene.

3. Roy Moore’s Lobster Co.

Roy Moore’s Lobster Co. on Bearskin Neck is the perfect spot to get your seafood fix. My husband and I got the works – lobster, lobster rolls, clam chowder, and oysters! It was fantastic and the experience was even more fun. You can take your food to go or venture down a narrow gap between the Fish Shack and the Shore Thing next door to get to a small back deck that holds a few picnic tables for you to wait for and then enjoy your food. It is also BYOB so if that’s your thing bring something to imbibe with your delicious seafood.

4. Dinner at the Emerson Inn

Just a mile north of town sits the beautiful Emerson Inn that has welcomed guests for over 150 years. On our first night, we enjoyed cocktails and a lovely dinner at the hotel's restaurant, Pigeon Cove Tavern. We ate on their large front porch that sits on a bluff overlooking the ocean. It was a blissful spot to view the changing color of the sky as dusk arrived. The Emerson is the perfect spot for a quiet weekend away, with quick access to all that Cape Ann and Rockport offer.

Sandro (my husband) enjoying fresh lobster from Roy Moore's Lobster Co.

On the Wish List for My Next Visit

1. Shalin Liu Performance Center

Along Main Street is the stunning Shalin Liu Performance Center. From the street, you can see down into the auditorium, where the stage’s stunning backdrop is a floor to ceiling window overlooking the ocean. It looks like an incredible place to watch any musical performance. Sadly, because of COVID-19, the Performance Center closed for in-person events during the summer of 2020. I hope to go back and see a performance there very soon!

2. Halibut Point State Park

Just north of Rockport, Halibut Point State Park, a former granite quarry, is now an outdoor recreational area with trails, tide pools, and beautiful views. Because of COVID-19 restrictions, we were not able to find a parking spot and therefore didn’t go this time, but we’ll be back!