Blake Walsh

25 Best Things to Do in Gloucester, MA

  • Published 2023/03/29

Gloucester is a beautiful coastal city amidst Cape Ann in Massachusetts.

It is a famous city with a significant number of tourist attractions.

From beautiful parks to lighthouses boasting stunning views, this city has got it all.

On top of that, there are so many beaches for you to visit in Gloucester.

At the beaches, you can relax, go swimming, get a tan, and play beach games like Frisbee and volleyball.

That’s just the tip of the iceberg, too.

Are you interested in finding out more about this bucket-list-worthy destination?

Here are the best things to do in Gloucester, Massachusetts:

Go Swimming at Good Harbor Beach

Waves crashing on the shores of Good harbour beach

MG photos /

Good Harbor Beach is a compact and beautiful white sandy beach with incredible waves.

The beach is clean and well-maintained, with crystal clear and cold water.

It boasts silky sand, deep intermittent tide pools, and some excellent rolling concessions.

The tides are usually low, making this beach perfect for swimming.

Families swimming at Good Harbor Beach

James Kirkikis /

The view of the lighthouse is very pleasant, and you can see the gentle descent into the ocean.

You can spot a lot of seagulls here.

You can take a dip in the chilly waters and swim around.

Picturesque sunset at Good Harbor Beach

Jeff Piraino /

They allow dogs off-leash in the off-season, so you can take your dogs at that time.

You can find seashells or crabs at the beach and explore around.

Spot Stunning Sea Creatures at Wingaersheek Beach

Lighthouse at Wingaersheek beach

ND700 /

Are you wondering what’s unique about Wingaersheek Beach?

This beach has a long soft stretch of sand, great views all around, and a quaint and relaxing atmosphere.

There are rocks to climb on and sand dollars everywhere.

You can find a lot of lobsters and a ton of marine life.

Mouldy rocks at Wingaersheek Beach

Ted Pendergast /

The water is crystal clear, and the sand is powdery, just like in Cape Cod.

The whole vibe of this beach is beautiful and relaxing.

There are loads of rocks to climb, and the beach also provides a stunning view of a small lighthouse.

The whole beach is very picturesque in the evening, with so many creatures to find in the tide pools.

The sunset here is incredible.

Aerial view of Wingaersheek Beach

Wangkun Jia /

The boulders are scattered all along the shoreline, which makes the place even better.

You’ll find hermit crabs and shells in the water, but the water is clear and mostly free of seaweed.

So, do visit this beach for a calm and serene experience.

Watch the Gorgeous Sunset at Plum Cove Beach

Plum Cove Beach is best known for having the prettiest sunsets over the water.

You can spend hours watching the hermit crabs here.

The tide pools are great, and the rocks are covered in seaweed at low tide.

The sunsets here are simply breathtaking.

There is a gorgeous little area where you can take a break from daily life and spend some time with your partner while watching the sun and making art with the sky and the water.

The beach is very romantic and is neatly tucked in between two ridges that border Plum Cove.

Its waters are calm and quiet, perfect for swimming, scuba diving, and observing marine life such as crabs or small fish.

The presence of the hills on one side and the mainland in the distant background give this beach the most aesthetically pleasing view of the sunset, perfect for gazing, photographing, or even painting.

Take Your Kids to Half Moon Beach

Trees around Half moon beach

Nhatchimai8, CC BY-SA 4.0, via Wikimedia Commons

As beautiful as its name sounds, Half Moon Beach is a lovely small beach with a lot of rocks to climb.

It is located at Stage Fort Park, so there is plenty of space to explore around the area.

You can visit this beach with your family, as kids are going to enjoy climbing the huge rocks that go out into the ocean.

Sea weed covered rocks at Half Moon Beach

John Hoey from Framingham, MA, United States, CC BY 2.0, via Wikimedia Commons

This secluded beach in the middle of the historic Stage Fort Park is great, and the rocky beach to the right of Half Moon is also amazing.

Overall, it is a lovely beach with lots of rocks to jump into the water from and lots of areas to explore.

Go Hiking at Ravenswood Park

Boulders at Ravenswood park

Philip Mowbray /

Ravenswood Park is a beautiful nature preserve in the west of Gloucester.

It is home to a great deal of flora and fauna.

The beautiful park boasts diverse and interesting trails for you to go hiking, walking, or bike-riding.

Ravenswood Park is a great place to have picnic dates.

There are a lot of clean and well-maintained trails and a lot of friendly dogs all along the way.

What is better than cute little pups and beautiful sunsets?

This park is worth a visit if you are in the city.

Admire the Displays at Cape Ann Museum

Entrance of Cape Ann museum

M2545, CC0, via Wikimedia Commons

Cape Ann Museum is a small beautiful museum with local flavor.

It is well-built, clean, and well-maintained.

The museum is exceptionally well-curated and focuses on the artistic heritage of the Cape Ann region.

Interior of Cape Ann Museum

Daderot, CC0, via Wikimedia Commons

It exhibits fine art and sculptures related to the history and artists of Cape Ann.

The whole exhibition in the museum is unique and beautiful.

It is a great place to learn about the history and culture of Massachusetts.

Ancient lamp at Cape Ann Museum

Daderot, CC0, via Wikimedia Commons

They have a wonderful collection of materials and artifacts on local industries, major figures, and artists.

This museum is a must-visit for people who are interested in local history and art.

Join a Whale-Watching Cruise

Whale watching in Gloucester

Wangkun Jia /

You will probably be seeing a lot of water in Gloucester, so why not make it as fun as possible?

Cape Ann Whale Watching and 7 Seas Whale Watch are two amazing cruises that give you the best whale-watching experience.

The cruises take you deeper into the sea, where you will get to see a school of whales playing and swimming around.

Whale at Gloucester

KarthikMani /

In addition to whales, you also get to watch the dolphins, ocean birds, and different types of seals.

The Capp Ann cruise will take you to a marine preserve, which is really great.

They also have a cute little gift shop near the center by the shore where you can get some souvenirs for your friends and family.

Pictures of whale captures from a cruise

Zimneva Natalia /

The tour offered by the 7 Seas Whale Watch Cruises is no different; it is informative, educational, and scenic.

This could be the perfect romantic getaway you have been planning with your partner.

The best time to go whale-watching is at sunset when everything around is extremely gorgeous.

You are sure to have an amazing experience.

Enjoy the Views from Eastern Point Lighthouse

Field of grasses around Eastern point lighthouse

Richard Cavalleri /

Eastern Point Lighthouse is a beautiful and historic lighthouse situated on Cape Ann.

The scenic beauty of this place is fantastic.

You can get a view of the beautiful river, fishermen catching fish, and kids playing around during the sunset.

Bird's eye view of Eastern Point Lighthouse

Wangkun Jia /

The whole vibe and beauty of this place are not going to disappoint you.

If you love nature photography or like watching sunsets from beautiful spots, this lighthouse in Gloucester is truly unmissable.

Stone path leading to Eastern Point Lighthouse

Allan Wood Photography /

Pay Your Respects at the Gloucester Fishermen Memorial

Statue at Gloucester fishermen memorial


The Gloucester Fishermen Memorial is a fantastic place to walk and enjoy the view of Gloucester Harbor.

With a beautiful boardwalk, well-maintained bushes, and a great view of the water and neighboring houses along the water, this park is truly a must-visit.

It is perfect for a day trip and especially for taking pictures.

Aerial view of Gloucester Fishermen Memorial

Wangkun Jia /

The whole vibe of this park makes it a very serene place.

In this park, you can find a beautiful memorial consisting of plaques in honor of Gloucester sailors who got lost at sea.

Waves crashing on the fence at Gloucester Fishermen Memorial

Danae Abreu /

Even when it’s covered in snow during the winter, the boardwalk remains well-maintained for enjoying a walk and visiting the memorial.

The Gloucester Fishermen Memorial’s spectacular views and historical importance make this place a must-visit.

Have a Picnic at Stage Fort Park

Boulders at Stage Fort Park

Paul Mozell /

Stage Fort Park is another very beautiful and serene park in Gloucester.

The park is perfect for watching the sunset over a nice picnic or hiking and riding your bikes.

Gazebo at Stage Fort Park

Robert J. Bradshaw /

You can find both rocky and sandy beach areas to enjoy, as well as a great ice cream stand on site.

The beach is well-maintained, and the ocean is beautiful to gaze at.

The park is dog-friendly, so you can bring your pets, meet cute dogs, and have a great time with yourself or with your family and friends.

Calm waters at Stage Fort Park

Paul Mozell /

Take Inspiration from Beauport, the Sleeper-McCann House

Exterior of Beauport House

Elisa.rolle, CC BY-SA 4.0, via Wikimedia Commons

The historic Beauport, the Sleeper-McCann House is also known as Little Beauport or Henry Davis Sleeper House.

This house was built by Henry Davis Sleeper, a famous interior decorator of the time.

Beds at Sleeper-McCann House

Alizada Studios /

Inside, you’ll find displays of beautiful and unique interiors, art, architectural artifacts, and much more.

It is a very creative and cool place to visit in the city.

Living room at Sleeper-McCann House

Alizada Studios /

The views of the ocean from this house are spectacular!

Overall, this artistic home is a fun place to pay a visit.

Experience Gloucester’s Rich Maritime Heritage

Maritime Gloucester is a unique maritime museum, aquarium, and working waterfront all in one place.

They’ve worked hand-in-hand with Gloucester Public Schools for 18 years to offer a way for students to learn about science and the environment.

They utilize Old World techniques and methods to teach aspects of watermanship across their working waterfront to educate anyone and everyone about the maritime sciences.

The museum is especially interested in helping introduce students to science at an early age and connect that knowledge to the local marine environment.

They do this by trying to excite students by learning more about their oceans and what they can do at an early age.

This is to foster a better sense of community when it comes down to the safety, preservation, and upkeep of the marine ecosystem.

Create a Photo-op Moment of Ten Pound Island Lighthouse

Ten Pound Island Lighthouse in Gloucester

Wangkun Jia /

Ten Pound Island, nestled at the eastern end of Gloucester’s inner harbor, derives its name from the amount of money and/or the number of sheep pens that it used to house.

First maintained as a light station in 1821, Ten Pound Island Lighthouse was erected simply to keep mariners well-guarded during their navigation into Gloucester’s inner harbor.

It’s somewhat of a mystery as to why Winslow Homer (1836-1910) spent the summer of 1880 on this island out at sea.

From what’s been gathered, he painted over 50 pieces of Gloucester Harbor while here.

And other artists also seem to have painted images of the same place, such as Fitz Henry Lane, a.k.a. Fitz Hugh Lane.

The U.S. Coast Guard owns Ten Pound Island Light and is maintained as a Federal aid to navigation.

The island itself will be closed to guests, but visitors can enjoy an excellent view of the lighthouse from several points on the Gloucester waterfront.

Catch a Light Southwesterly Breeze with Schooner Thomas E. Lannon

Schooner Thomas E. Lannon sailing in ocean at Gloucester

Wangkun Jia /

Imagine yourself walking onto the deck of this gorgeous 65-foot schooner that is heading out of Gloucester harbor while catching a light breeze from the southwest.

The ship was built in Essex, MA, back in 1997 and came to Gloucester many years later to berth at the historic Seven Seas Wharf.

They offer two-hour sails during the spring, summer, and fall months.

Sail around the beautiful coastline of Gloucester, MA, and take in all the sights and sounds that come along with it.

A lot of Lannon’s weekend special events feature music.

They offer great group rates for these unique sailing experiences.

There are private charters for weddings, corporate entertainment, team building, and more.

Captain Heath Ellis and his crew will make all your sailing dreams come true.

Go Rock Climbing at Red Rocks Conservation Area

Located along Forest Lane lies one of the more underrated nature spots in Gloucester: Red Rocks Conservation Area.

It’s a haven for technical rock climbing and bouldering, making this a niche place for people who are avid enjoyers of those hobbies.

However, you can also experience Red Rocks Conservation Area the easier way; it’s a nice place to do some trekking if you’re experienced in nature exploration.

With moderate-to-difficult hiking trails, it can be a bit daunting for beginners, so it’s best to add this to your itinerary if you’ve had prior experience.

Still, you’ll be rewarded with amazing nature trails and lush forests that you can observe at varying elevations.

One of the most picturesque nature spots in Gloucester, Red Rocks Conservation Area is a neat addition to your itinerary.

Take Scenic Photos at Rafe’s Chasm Park

Found along Hesperus Avenue lies a hidden coastal gem in Gloucester: Rafe’s Chasm Park.

While Gloucester is famous for its iconic beaches and state parks, Rafe’s Chasm Park should be more known because of its overall aesthetic.

It has huge rock formations where you can see the waves crash, giving this a magical vibe that makes you feel like you’re at the end of the country.

You’ll also gain access to the cliffs here, which is a great photo opportunity—just remember to be careful!

Beautiful and awe-inspiring, Rafe’s Chasm Park is a great addition to your itinerary if you’re all about coastal photography.

Eat in an Igloo at Mile Marker One Restaurant

Mile Marker One Restaurant is one of the most famous dining establishments in Gloucester because of their food and igloo gimmick.

If you’re traveling during the non-summer months, Mile Marker One Restaurant has heated private “igloos” overlooking the water—it’s a nice place to be in with lovers and a small group of people.

The igloos are obviously not real, but the scenery here that overlooks the neighboring marina is something worth experiencing.

When it comes to the food, Mile Marker One Restaurant is atop of its competitors, serving amazing lobster rolls and a bunch of other seafood like haddock and scallops.

Find Mile Marker One Restaurant along Essex Avenue—one of the prettiest spots in Gloucester.

Have a Fun Time at Cape Ann Lanes

Cape Ann Lanes doubles as a pub and a bowling alley, making this a great stopover to enjoy with friends and family.

Besides their neat bowling alley, Cape Ann Lanes also has arcades that are highlighted by their addicting pinball games.

The atmosphere here is fun and lively, and they serve underrated burgers and pizzas.

The selection of beer is also robust because Cape Ann Lanes is also a brewery, making this a fun hangout spot for the adult crowd.

You can find this awesome bowling alley and pub along Gloucester Avenue.

Do Gallery Hopping at The Cultural Center at Rocky Neck

The Cultural Center at Rocky Neck is one of the more interesting things you can add to your itinerary if you’re looking to diversify it.

Rocky Neck is a collective of artists with a diverse range of artistic skill sets—many of their members are skilled in painting, pottery, and textile design.

Inside The Cultural Center at Rocky Neck, you’ll be able to see the artworks with a chance to purchase them; it’s a neat way of having a memorable souvenir from Gloucester.

Operating well over 100 years now, The Cultural Center at Rocky Neck is both an artistic and historical experience to boot.

Start your gallery hopping at Wonson Street.

Other Things to Do Nearby

Take a Day Trip to Singing Beach

Sunset at Singing Beach

Oen Casey /

This beautiful beach in Manchester-by-the-Sea is most known for its unique sand, which is extremely hot and soft.

Singing Beach is just a 15-minute drive away from Gloucester, making it an ideal day trip destination.

The walking trail by the entrance is well-maintained and clean, and the water at the beach can get extremely chilly.

Waves crashing on the rocks at Singing Beach

Scott Terrasi /

There are lots of restaurants and food shops nearby, along with many shopping markets near the beach.

From mouth-watering food to delicious beverages, this beach will satisfy your hunger cravings.

The beach is super dog-friendly, so you can take your pets to play around or meet other dogs.

Singing Beach on a sunny day

CO Leong /

The views are very beautiful, and there are a lot of blankets and sunbeds available for you to use.

The best thing about visiting Singing Beach is getting to enjoy stargazing nights and candlelit dinners on the sand.

It is the perfect beach for a serene calm experience.

Spend a Relaxing Day at Halibut Point State Park

View of the ocean at Halibut Point state park

FotoRequest /

Are you interested in checking out more of Gloucester’s neighboring areas?

This fantastic park is located in Rockport and is a 15-minute drive away from the city.

Halibut State Park has everything in store for you, including beautiful ocean views, sunbathing experiences, hiking trails, and plenty of space for picnics.

You can get the most stunning view of the ocean from the top point.

Quarry at Halibut Point State Park

quiggyt4 /

The park gives you the experience of hiking near a real quarry, which is a truly memorable experience.

The trails here are well-marked, and the view from above the quarry is breathtaking.

There are a couple of places to climb down to the water line, which provides another great perspective.

Shoreline of Halibut Point State Park

Sven Naser /

You can climb around the rocks and watch the waves in the ocean crash against the huge rocks.

The scenery and the beautiful sounds of the crashing waves are beautiful and soothing to see and hear.

The trails in this park take you to the most beautiful views.

Explore the Breathtaking Misery Islands

Aerial view of Misery Islands

travelview /

Located 15 minutes away from Gloucester, Misery Island is a nature reserve and an uninhabited piece of land in Beverly.

The place is quite the opposite of its name, as it brings positivity and calmness to the soul.

The water is crystal clear, and the scenery is beautiful.

It’s the perfect place for taking Instagram-worthy pictures.

The island holds a lot of interesting history and is a must-visit attraction.

Visit the Fascinating Paper House

This tourist attraction in Rockport, Massachusetts, is a folk art site with lots of unique and amazing machines, tools, furniture, and more on display.

It is called Paper House for it displays different kinds of paper and newspapers all around the place.

You can take a self-guided tour of the museum and enjoy the classic displays.

The hike up to the museum is a fun feature to add to your experience.

The place is clean, well-maintained, and beautiful.

There is a charming cottage right beside Paper House, which is a must-visit if you’re there.

Overall, this unique place near Gloucester is a spot you must add to your itinerary.

Final Thoughts

If you’re in the market for a traditional seaside community, then Gloucester is the place to be.

It has everything from charming streets filled with history, culture, and spectacular sights to beachside fun without ever stepping foot into the water.

Make sure your itinerary includes these top must-sees!

© All rights reserved.