Cape Ann: A Vintage New England Getaway

My husband and I just got back from a quick trip to Cape Ann in Massachusetts. It was our first time to Cape Ann and it definitely will not be our last.

Cape Ann is less than an hour north of Boston. It offers so many different activities that people of all ages can enjoy the quaint New England beach towns Cape Ann has to offer.

While visiting we checked out the towns of Gloucester, Rockport and Essex.


Our first stop was in Gloucester. We learned during our visit this town is home to America’s oldest working seaport. Gloucester offers beaches, hiking trails, artist studios and more. While we drove through we saw a beautiful beach shoreline.

Some of the beaches you can visit in Gloucester include:
Good Harbor Beach
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This beach provides a view of Thacher Island, home of the Twin Lights. Visitors can also enjoy swimming and beach combing. Additionally, at low tide you can walk out to Salt Island.

Wingaersheek Beach
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On this beach you can explore tidal pools, climb the large rocks on the beach. Go at low tide to have access to a large sandbar for additional beach combing.

Cressy’s Beach at Stage Fort Park
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This rocky beach has views of Gloucester Harbor.

Half Moon Beach at Stage Fork Park
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This is a quiet, crescent-shaped beach that is surrounded by a rocky hill.

Pavilion Beach
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This beach is popular for beach combing and boat watching. It’s close to downtown Gloucester.

Points of Interest in Gloucester

Cape Ann Museum
This museum provides you with the history, culture and art of Cape Ann. The collections at the museum include: artifacts from the granite and marine industries, two historic homes, a sculpture park, art and textiles. For more information, visit

Hammond Castle Museum
This castle and museum is like nothing you have ever seen before. First of all, I had never heard of John Hays Hammond, Jr., but apparently he was a well-known inventor. He built this home for his wife during the 1920s as a medieval-style castle, however when going through the castle you will see architecture designs from medieval England and Renaissance era France and Italy.

These are some photos of the outside and inside of the castle.

The most interesting part of the inside of the castle is the courtyard Hammond created to look like a 1500s era French village. There is even a pool in the center. He created controls in this indoor courtyard so that when guests came over he could make it rain, be foggy, nighttime or daytime. Below are some photos from views inside this amazing courtyard.

Besides the actual building, outside of the castle there is a breathtaking view of the Atlantic Ocean. The castle is well-worth the visit. View more information here.

Here is a photo of the ocean view from the castle.

The inn we picked to stay at was located in Rockport. I had gotten a deal on Groupon for the Emerson Inn, which is located on the water in the Pigeon Cove area of Rockport. The outside of the Inn was beautiful. An expansive porch surrounds the back of the Inn, which allows you to either sit in a rocker or sip a cocktail at a table that overlooks the ocean. There is also a pool that looks out onto the water. The best part of staying at the Inn was having breakfast on the porch in the morning and looking out at the glistering water while enjoying blueberry pancakes and a cup of coffee. Below are photos of the Inn and the amazing view we had at breakfast.

After settling into the Inn we decided to take a drive to downtown Rockport. It takes less than five minutes to drive from the Inn. It is about a two mile walk.

We absolutely loved the look and feel of the downtown area. There are dozens of quaint shops, art studios and restaurants that overlook the water along Broadway, Main Street, Dock Square and Bearskin Neck. If you walk all the ways down the street at Bearskin Neck you will arrive at a beautiful view overlooking the water. Below are some photos of the amazing harbor views and docks and the shops at Bearskin Neck.

Shops in the area range from homemade candy, gift shops, art studios, jewelry stores, clothing shops and more. Ice cream shops, hot dog stands and seafood restaurants scatter the area as well. The evening that we were in Rockport all of the restaurants were packed, so I suggest arriving early for dinner. We ended up eating at this great seafood place called Roy Moore’s Fish Shack Restaurant. They offer fresh seafood. We opted to get the crab cakes, which tasted amazing. They had just enough flavoring and crab and not too much breading. We also ate the boiled lobster (which happened to be $20 for a 1 1/4 lb lobster the night we were there, which we thought was a bargain compared to the price of lobsters at home (Connecticut). The food was amazing and the service was great too. The best part is the restaurant has large glass windows that overlook the water, so you can enjoy great seafood and see an amazing view in the comfort of air conditioning throughout the summer.

Beaches in Rockport

Front Beach
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This beach is great for swimming and sunbathing. It is close to the downtown area so you can walk to restaurants and shops. Paid on-street parking is adjacent to the beach.

Long Beach
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This beach is about one -mile long and offers views of Thacher Island’s twin lighthouses. This is a good beach to go for a walk and beach combing. Parking is available in a privately operated lot.

Other Points of Interest in Rockport

The Paper House

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The walls and furniture in this house are made from approximately 100,000 newspapers that took a 20-year period to assemble.

Thatcher Island/Twin Lights

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On Saturdays you can take a boat shuttle to his national landmark from T-Wharf in Rockport. The island contains two lighthouses that were built in 1771. On the island there is a museum, trails and a campground.


The last town that we visited on our trip was Essex. This small New England town is filled with antique chops and treasures to be picked. Many call the town America’s Antique Capital, with more than 25+ antique and collectible shops in the town. We stopped at several of the antique stores and found a wide array of items, but the theme throughout the stores was coastal antiques. It was fun to rummage through the collectibles to see what we would find.

Photos from some of the antique shops in Essex.

Besides all of the shops there are also several seafood restaurants scattered across Main Street in the downtown district with fresh seafood right off the boats.

There is so much more to see at Cape Ann. We were only there for two days, so we didn’t nearly have enough time to see everything. There are plenty of opportunities for hiking and beach combing, restaurants, art displays, fishing charters and you can even go whale watching. It is a good location to go for a day trip if you are local or a weekend getaway. It’s a tourist location that is great for all ages, couples and families. If you haven’t been, I highly recommend checking it out—you will not regret taking the trip.

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