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.

A tall, ornate clock tower rises above historic brick buildings on a cloudy day, with parked cars and trees lining the street in the foreground.
Photo credit: Kailey MarcAurele.

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.

A glass bakery display case filled with assorted pastries, cookies, muffins, and croissants; tea boxes are lined up on a shelf above the case.
Display case with baked goods at Cape Ann Coffees. Photo credit: Kailey MarcAurele.

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.

A breakfast sandwich with egg and cheese on a bagel is cut in half on wax paper, next to a takeaway coffee cup on a mosaic table.
My bacon, egg, and cheese sandwich and hot chocolate. Photo credit: Kailey MarcAurele.

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.

A woman with long hair walks towards the entrance of a stone castle, crossing a small bridge flanked by two lion statues.
Outside of the castle. Photo credit: Kailey MarcAurele.

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.

Two photos show interior views of a gothic-style church with arched ceilings, stone walls, stained glass, and wooden pews, illuminated by soft lighting.
The Great Hall at the Hammond Castle Museum. Photo credit: Kailey MarcAurele.

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.

A stone courtyard features a small chapel with an arched doorway, a statue above the entrance, plants, and a pond in the foreground.
The Courtyard in the Hammond Castle Museum. Photo credit: Kailey MarcAurele.

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.

Stone ruins with five arched windows overlook the sea; four benches and a round stone planter sit on gravel in the foreground, surrounded by greenery.

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.

A large, dark brown and stone house with arched windows, wooden shutters, and a turret, surrounded by a lush garden and a birdbath in front.
Front of the house. Photo credit: Kailey MarcAurele.

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!

A brick house with a shingled roof overlooks a bay, with a green lawn, tall shrubs, and partly cloudy skies in the background.
Back of the house. Photo credit: Kailey MarcAurele.

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.

A weathered white lighthouse with attached buildings sits on a rocky hill under a partly cloudy sky. A chain-link fence runs along the base of the lighthouse.
Eastern Point Light. Photo credit: Kailey MarcAurele.

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!

A small metal lighthouse stands on stilts at the end of a rocky pier extending into the water, with cloudy skies overhead.
Dog Bar Breakwater Lighthouse. Photo credit: Kailey MarcAurele.

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.

A white bowl filled with macaroni and cheese sits on a white plate with a metal spoon and a napkin.
Cup of mac & cheese at Stones Pub & Eatery. Photo credit: Kailey MarcAurele.

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!

A red and white fishing boat docked by a waterfront, with brick buildings and a clock tower in the background under a cloudy sky.
View of Gloucester from where the boat tour departed. Photo credit: Kailey MarcAurele.

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.

A white lighthouse with a black railing stands on rocky terrain near the water, with an American flag and a small building nearby under a cloudy sky.
Annisquam Harbor Lighthouse. Photo credit: Kailey MarcAurele.

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.

A white lighthouse with a black top stands on a rocky shore near the water, with a wooden walkway and cloudy sky in the background.
Straitsmouth Island Light Station. Photo credit: Kailey MarcAurele.

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.

Two stone lighthouses stand on a rocky island, with several small buildings nearby, under a cloudy sky by the water’s edge.
Cape Ann Light Station. Photo credit: Kailey MarcAurele.

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.

A white lighthouse with a red roof stands on a rocky shore, surrounded by grass and weathered buildings under a cloudy sky.
Eastern Point Lighthouse. Photo credit: Kailey MarcAurele.

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.

A white lighthouse with a black top stands behind green shrubs and large rocks, with seagulls flying nearby under a cloudy sky.
Ten Pound Island Light. Photo credit: Kailey MarcAurele.

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!

A red brick industrial building labeled "MANUFACTORY ESTABLISHED 1867" stands by the waterfront, with a tall chimney and cloudy sky in the background.
Tarr and Wonson Paint Factory. This company improved the concept of copper-based paint to combat marine life that drilled through the wooden hulls of ships. Photo credit: Kailey MarcAurele.
A bronze statue of a fisherman standing at a ship’s wheel, mounted on a stone base with the inscription “THEY THAT GO.” Trees and a building are in the background.
Gloucester Fisherman’s Memorial. This was built to celebrate the city’s 300th anniversary and honor the lives of its fishmen who were lost at sea. Photo credit: Kailey MarcAurele.
A large stone mansion with castle-like architecture stands near a rocky shoreline, surrounded by trees, with a white event tent on the lawn.
The backside of Hammond Castle Museum. Photo credit: Kailey MarcAurele.
Large stone mansion with multiple chimneys sits on a rocky shoreline, surrounded by trees, viewed from across the water.
Beauport, the Sleeper-McCann House from the water. Photo credit: Kailey MarcAurele.
A steel arch bridge spans over a river, with trees and houses visible on both banks under a cloudy sky.
Bridge going over the Annisquam River. This is the bridge you’ll likely go over as you make your way into Gloucester. Photo credit: Kailey MarcAurele.
White waterfront building with nautical decor and dock, situated on a rocky shoreline with greenery and a US flag in front.
Unique boat house along the river. Photo credit: Kailey MarcAurele.

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.

The entrance to a building with a rustic wooden sign reading "MINGLEWOOD" above double glass doors and a window, with plants and a paved walkway in front.

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.

Fishing boats docked at a wooden pier with lobster traps, brick buildings, and a clock tower in the background under a cloudy sky.
Gloucester, MA. Photo credit: Kailey MarcAurele.

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!

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10 Comments

  1. 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.

  2. 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!

    1. 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.

  3. 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!

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