Gloucester, Massachusetts Day Trip
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I recently took a day trip to Gloucester, Massachusetts, which is a historic fishing town located on Cape Ann. This town is known as America’s oldest seaport. It has a rich maritime heritage and it’s home to the famous Gloucester Fishermen’s Memorial. The city’s rugged coastline, scenic beaches, historic homes, and thriving arts scene make it a popular destination for tourists and artists alike.

Getting There – Where is Gloucester, MA?
Gloucester is located on the northeastern coast of Massachusetts on Cape Ann in Essex County. It is about 30 miles northeast of Boston. The city is part of the North Shore region and is easily accessible by car or commuter rail from Boston.
A Full Day In Gloucester
I left my house as the sun rose to spend the full day in Gloucester. I live about two hours and thirty minutes from the town. Since I left so early, I was able to avoid all traffic and get to town at 8:30 in the morning.
Breakfast
I started my trip by stopping at Cape Ann Coffees for breakfast. This was such a cute little coffee shop. I got a small hot chocolate and a bacon, egg, and cheese sandwich on a plain bagel. They had a lot of baked goods that looked delicious, but I knew I wouldn’t have room for both, so I decided not to get a baked good. I didn’t want a pastry just sitting in my car for hours.

My food came out super quickly, which was awesome! I’m pretty picky about eggs, but I loved this egg sandwich. The eggs were cooked well and the bacon on the sandwich was nice and crispy. My hot chocolate with a dash of vanilla was also super good! I’d definitely go back to this spot if I ended up in the area again.

Hammond Castle Museum
After breakfast, I headed to the Hammond Castle Museum. This medieval style castle was the private residence and laboratory of the inventor John Hays Hammond. The castle was built between 1926 and 1929. When I arrived at the castle, it really felt like I had been transported to somewhere in Europe! It was hard to believe this castle was in Massachusetts.

Since it was raining, we decided to tour the castle as soon as we got there. We checked in at the gift shop since we had already purchased our tickets online. There were both guided and self-guided tours available, but we had opted for the self-guided.
The self-guided tour gave us flexibility to get to the castle between certain hours, which was nice because we were coming from a couple hours away and you never know if you’ll hit traffic. I also just prefer going through houses at my own pace. While I do love learning about the history of the houses I tour from docents, I prefer not being in a group.
This castle is extremely interesting to tour. There are a ton of artifacts from around the world on display here, so it’s both a house museum and kind of like a history museum. It was definitely unique!
I had a couple favorite features in the house. The first was the Great Hall. I felt like I had stepped into a historic church. There were high, vaulted ceilings, stained glass windows, and it was just grand in size. I stood in that room for quite some time admiring the space.

My second favorite feature was the courtyard. The courtyard was located just off of the Great Hall. The courtyard featured lush plants, a square pond, and some benches to enjoy it. It felt like stepping into a courtyard in the middle of a town.

There were a lot of rooms that were off of this and they had windows looking into the courtyard. There were bedrooms upstairs that had windows overlooking the courtyard and it was just so stunning. As I admired the courtyard from the second-floor guest bedroom, I imagined what it must have been like to stay in such a unique room.
Outside, there are some gorgeous water views. When I was there, they seemed to be setting up for an event in the back of the house, so we weren’t able to go down there to overlook the water from a bit lower. But, we did enjoy the water views from the level where we entered the castle.

All in all, I thoroughly enjoyed my visit to the castle! I could have spent hours there looking at all of the different objects in the house and the details. I’ll likely go again in the future.
Beauport, the Sleeper-McCann House
Since I really love historic houses, I decided to check out Beauport, The Sleeper-McCann House. This house is located on a road that is labeled as a private road. Don’t be deterred by this, you’re allowed to go down the road to visit the mansion. I simply had to check in with a security guard at the end of the road. I just let him know I was going to that house.
This is a Historic New England property, which I have a membership for. Unfortunately, they didn’t have any spots available on tours until 1:30pm, which wouldn’t work for us since we had a lighthouse cruise scheduled for 2:30pm. Since I am a member, I will likely make a trip up here again to actually tour the house.

Despite not being able to tour the inside of the house, I was able to walk the grounds of the property. The grounds weren’t large, but they were beautiful. There were some gardens, patios, and a small yard in the back that overlooked Gloucester Harbor. I am so glad that I was able to walk the grounds!

Mass Audubon’s Eastern Point Wildlife Sanctuary
This spot is also located on the private road. There are a lot of signs that suggest that you can’t go down here, but you can continue down the road. At the end of the road is Eastern Point Wildlife Sanctuary. This spot has very limited parking and there is a $10 admission fee. I paid cash, but I think there was an option to pay with your card or with your phone. However, if you are a member of Mass Audubon, admission is free.
While we did see some coastal birds here like gulls, cormorants, and barn swallows, the main reason why I chose to visit this spot was because of the lighthouses. You can view Eastern Point Lighthouse easily from this spot. Since this is still an active lighthouse owned by the Coast Guard, it is fenced off and you can’t get right up next to it. But, you can get pretty darn close.

There is a jetty here that you can walk down as well to get to another lighthouse. This other lighthouse is known as Dog Bar Breakwater Lighthouse. I’ll be honest, it does not look like your typical lighthouse. But, it is still cool to see!

In addition to the two lighthouses, this seems to be a popular spot for fishing. While I was there, I saw multiple people fishing along the breakwater.
Lunch
After we left Eastern Point Wildlife Sanctuary, we decided to head back into downtown to grab lunch before we needed to check in for our lighthouse cruise. We ended up grabbing a quick bite to eat at Stones Pub and Eatery. This spot had a nice casual vibe. They had an assortment of games that you could bring back to your table to play, which I thought was really cool. It definitely seemed like a nice place to relax with friends.

Cape Ann Lighthouse Cruise
Since I love lighthouses, I booked a lighthouse cruise with Harbor Tours of Cape Ann. This was a two-and-a-half-hour narrated cruise out of Gloucester. On the cruise, we would see six different lighthouses as well as other points of interest. I will be honest, the water was really rough, but the captain did great and so did the crew to make sure everyone was doing well throughout the trip!

The first lighthouse that we saw was the Annisquam Harbor Lighthouse. This lighthouse was built in 1897 to replace the previous wooden frame. The lighthouse is 41 feet tall.

The second lighthouse of the trip was Straitsmouth Island Light Station. In 1835, the first lighthouse was built on the island to mark the entrance to Rockport Harbor and the dangerous reefs of the Salvages and Avery’s Ledge. The current lighthouse that you see on the cruise was built in 1896 and is 37 feet tall.

After, you will see the Thacher Island Twin Lights. Each lighthouse is 124 feet tall. They are constructed of solid granite on the outside with brick inner walls. The lighthouses were completed in 1861. These lighthouses are the only two operating twin lighthouses in America.

Next, you’ll see Eastern Point Lighthouse. I had seen this lighthouse earlier in the day from land. Despite this, it was nice to see it again from the water. Being on a boat gave me a completely different perspective, which was great! This lighthouse was established in 1832, but the current tower was built in 1890.

The last lighthouse you’ll see on the tour is Ten Pound Island Lighthouse. This cute little lighthouse was established in 1821. It was built to help mariners find their way into Gloucester inner harbor while avoiding dangerous ledge to the southwest of the island.

Other Points of Interest On The Cruise
While this was a lighthouse cruise, there were some other points of interest along the way. I’ve included some pictures below!






Dinner in Downtown Gloucester
After the boat ride, we went back into downtown to grab a bite to eat. We went to Minglewood Harborside. It was a casual spot to grab a bite to eat, which was perfect since we had just spent two hours out on the rough water.
Since the water was pretty rough, I wasn’t feeling too hot. I ended up getting something safe because while I knew I needed to eat something, I was still feeling a bit queasy from the boat ride. I got some chicken tenders without any of the delicious sauces they offered. I had a two-and-a-half-hour ride ahead of me, so I didn’t want to make myself feel worse. The chicken tenders were good and I’d love to go back to this spot to get something else off of their menu.

Is Gloucester Worth Visiting?
I’d say so! I spent pretty much a full day there and there was no shortage of things to keep me occupied. And since I was only there for a day trip, I had only scratched the surface of things to do and places to eat.

If I were to go back, I’d definitely tour the inside of Beauport, the Sleeper-McCann House. I’d also like to do a whale watching tour out of Gloucester.
The town has so much history and gorgeous views. You’ve got historic houses, historic lighthouses, and miles of shoreline to discover. It’s definitely a great spot to visit in coastal Massachusetts!
This looks like a fun day trip and the town of Gloucester seems absolutely charming. I love that the highlight of a wild life sanctuary was the light houses. The seafood must be amazing. Looking forward to hearing about your second trip.
It definitely is charming! And, it definitely is a great spot to grab seafood.
Your photos are stunning! I’ve not spent much time on the east coast, and feel inspired to change that asap.
Thank you! The east coast is charming and worth exploring 🙂
Wow, those lighthouses look so dreamy. It’s great that they have a cruise as an easy way to see them all. Gloucester wasn’t even on my radar but it looks like a great day trip!
It’s definitely a great spot for a day trip! And it was nice to see so many lighthouses and other sites from the water. It’s always fun getting a different perspective from the water.
This guide makes Gloucester sound like the perfect coastal getaway! I’d love to explore the Hammond Castle and enjoy some fresh seafood by the harbor. Thanks for the inspiration!
It’s definitely a great spot for a coastal getaway!! I’d love to spend some more time there in the future.
I did not know there were cute little towns like Gloucester in the USA! Both the castle and the lighthouse look stunning!
We have a lot of cute little towns like this throughout New England 🙂