Blake Walsh

20 Best Things to Do in Rockport, MA

  • Published 2022/10/23

At the very edge of Cape Ann’s sandy shores, you’ll find Rockport, one of its most popular coastal towns.

It originally went by Sandy Bay until 1840, then officially became Rockport after the break off from Gloucester.

The little town, which owes its name to its quarries, was famous for its quality of granite, which had been distributed all over the country.

It is also a proud place that has reaped a reputation for its timber used in shipbuilding and fishing.

The scenic Rockport offers gorgeous ocean beaches.

When you’re looking to get away from it all on your next romantic date, a trip to the North Shore on the outskirts of Boston is sure to set you up for success.

In Rockport, you can enjoy a variety of dining and shopping options, as well as quiet afternoon drives through the charming seaside town.

Whatever your reason for visiting Rockport, Massachusetts, here are the 20 best things to do when you get here:

Stroll to the Rockport Breakwater for Stunning Views

View of Boats at Rockport Breakwater

James Kirkikis /

One of the favorite places of many Rockport tourists and locals where you encounter nature is the 1/8 mile long Breakwater at Rockport.

It’s just a short walk from downtown.

The views of Cape Ann and out toward Gloucester, Massachusetts, are beautiful.

It’s flat enough to walk on during most times of the year and is surrounded by water on three sides, which is perfect for viewing Motif #1, the harbor, and sailboats.

View of Boats at Rockport Breakwater

James Kirkikis /

Or it’s great for just enjoying nature on its own terms (and wanting some exercise.)

The water and sky look different depending on weather and time of day, so take your camera with you and be sure to check it out several times during your visit.

If you’re lucky, you’ll catch a glimpse of seals swimming near shore or gray whales migrating past during early spring and late fall.

Sailboats at Rockport Breakwater

LI Cook /

Visit The Art of David Arsenault Gallery for a Timeless Cape Ann Experience

Once you visit The Art of David Arsenault Gallery, you will experience what it feels like to be at peace while taking in the surrounding scenery through unique perspectives.

The next time you’re in Rockport, stop by the art gallery at 8 Dock Square and say hi to David.

He’ll love to show you around his adventure in the world of oil painting with his wife, Sue.

Visit each room of their home studio for intimate renditions of their favorite Cape Ann memories.

Whether that’s to experience the sense of freedom with their ‘Going Towards The Light’ or gaze at the sailboats gently bobbing in the water with their ‘Harbor Masters,’ there are always captivating colors everywhere you look when they capture the essence of the region.

Walk Along a Secluded Rockport Beach in Old Garden Beach

When it comes to secret spots that are definitely worth sharing, there is no better news than discovering the virtually undiscovered coastline of Cape Ann.

Whether you’re into shell hunting on the beach or spending hours tracing your footfalls through the sand, the family-friendly Old Garden Beach is a great place for you to get back to nature without getting lost.

East of the Old Garden Beach, a public footpath meanders among the homes and provides views of Straitsmouth Island and Twin Lights.

To the west, there is another path that leads to Headlands.

The views in this area are exceptional!

Experience the Scenic Beauty of Halibut Point State Park

Scenic Beauty of Halibut Point State Park

Milan Kolovrat /

Make your way over to Halibut Point State Park, which offers some of the most breathtaking scenery on New England’s south coast.

Here, you can walk along some of Cape Ann’s best beaches and enjoy unparalleled views of the Atlantic coastline.

There are multiple hiking trails throughout Halibut Point State Park, offering visitors views of some of Massachusetts’ most scenic landscapes; some paths even lead right down to the shore.

Scenic Beauty of Halibut Point State Park

Sven Naser /

At Halibut Point State Park, visitors can look out over the ocean and across the horizon to see Mount Agamenticus.

Offshore, you can catch a glimpse of the Isles of Shoals.

Here, you can find stunning views of sunrise and sunset while feeling embraced by the sea’s extraordinary nature.

Scenic Beauty of Halibut Point State Park

SewingForce /

Take your time exploring all that Halibut Point has to offer during your next trip to Rockport.

Be sure not to miss out on visiting Halibut Point State Park if you’re looking for something fun and relaxing to do while visiting coastal Massachusetts!

Head to the Headlands

Hidden along a romantic side street in downtown Rockport is an inspiring scenic view called the Headlands.

Confusingly located off of Bearskin Neck but easily identified due to its views of appealing coastline options, it makes for an excellent chance to take a relaxing stroll free from technology.

Though it may take some time to reach the rocky outcropping, it has become known to residents as one of the best great escapes around.

Just south of the granite bench, you can spot a lighthouse on Straitsmouth Island.

Granite benches allow you to sit and be entertained by what it has to offer.

The view of the island is spectacular, especially when the sun shines brightly in the sky.

As you walk around this section of town, you’ll notice how others walk towards Old Garden Road, heading anywhere from north to south only to turn back around.

You can join them if you so choose, but be sure to stay on Atlantic Avenue, where you got your start so that your trip back home will be shorter than your trip here.

Go on a Bike Ride With Addison Choate

Looking for a peaceful and relaxing way to spend your time when you visit Rockport, Massachusetts?

It’s possible to see the best of the area by renting a bicycle and exploring different places around town.

Enjoy the breathtaking scenery of the East End along with a leisurely ride on newly furnished bicycles, courtesy of Addison Choate.

Located in a scenic residential area less than 5 minutes from Sandy Bay/Front Beach, this cozy bed and breakfast will let you explore all that Rockport has to offer.

While cycling down Bearskin Neck, you’ll want to stop into The Harbor Ice Cream Store for your favorite scoop.

While you’re here, check out the beautiful coastline or marvel at historical amenities like Motif #1.

If you’d prefer not to ride but still want to explore the area without getting exhausted, you can just admire the landscape from Halibut Point or stop by The Lobster Pool or the delightful shops at Bearskin Neck.

Experience the Power of Music at Shalin Liu Performance Center

Outside View of Shalin Liu Performance Center

Wangkun Jia /

Rockport contains the gorgeous Shalin Liu Performance Center, where some of the world’s greatest artists gather.

It’s arguably one of the most beautiful stages on the East coast.

The stage’s backdrop is made of glass and peers out onto Rockport harbor in the distance, allowing for one of the most breathtaking views you can imagine when it’s sunset time.

Inside View of Shalin Liu Performance Center

Photograph by Peter Van Demark, (c) Rockport Music, CC BY 3.0, via Wikimedia Commons

But what makes this place so welcome to performers and audiences alike is the incredible acoustics that comes with such a location — it almost sounds like you’re inside an expensive recording studio.

This venue has hosted numerous local events, including the Rockport Celtic and Jazz Festivals and the Rockport Chamber Music Festival.

Outside View of Shalin Liu Performance Center

Alizada Studios /

Here in this lovely town, you’ll find something for everyone who enjoys excellent tunes.

It doesn’t matter if one prefers classical music, jazz, folk, or even pop music; you can enjoy all kinds of concerts throughout the year right in the middle of Main Street.

Inside View of Shalin Liu Performance Center

User:Magicpiano, CC BY-SA 4.0, via Wikimedia Commons

Check Out Rockport Quarries Hike

Quarry at Rockport

quiggyt4 /

The Rockport Quarries Hike will take you through beautiful woodlands and along breathtaking views of the town of Rockport.

The hike starts at Rockport Train Station, where one can arrive by train from Boston’s North Station.

It is roughly a four-hour walk and boasts an almost eight-mile journey, and it culminates with a visit to World Famous Motif #1 on the way back into the train station on the other side of town.

Here, you’ll see quarries like Carlson Quarry, Flat Ledge Quarry, and Johnson’s Quarry.

Exploring all these incredible slate quarries together makes for a fun family day trip — a great opportunity to learn more about this beautiful rural area.

Visit Rockport Brewing Company and Taste Their Most Popular Beers

If you want to get an authentic taste of what makes Rockport so special, stop by one of its many famous craft breweries.

For example, if beer is your thing, head straight to Rockport Brewing Company, a microbrew adopted by the Pickup family and created for the people.

Located in Rockport, MA, Co-founders Jordana and Ray dreamt it up while sitting on Long Beach, reminiscing about the small town that used to feel like home (and still does).

Their passion for creating high-quality beer embodies the heart of the consumer experience they plan for everyone.

Their fan-favorite Cape Hedge — an exceptionally crisp, clean-tasting hybrid-style ale fermented with ale yeast at lager temperature — is a straight-up tasty introduction for any traditional beer drinker.

Browse Bearskin Neck for the Best of Cape Town

View of People in Bearskin Neck

MBCF, CC BY-SA 4.0, via Wikimedia Commons

When visiting the picturesque coastal village of Rockport, Massachusetts, you will find one of the most scenic locations in all of Massachusetts, Bearskin Neck.

This charming vista sits in the heart of the town and extends out towards the harbor while offering a truly unique panoramic view.

It’s no wonder that visitors are drawn to Bearskin Neck.

View of People in Bearskin Neck

Adavyd, CC BY-SA 3.0, via Wikimedia Commons

There are so many small, independently-owned businesses lining the roads.

Here, you can find one-of-a-kind artistic treasures, meet friendly shop owners who are part of the local community, become acquainted with the local history, and even make a few new acquaintances in this welcoming Cape Ann town.

View of People in Bearskin Neck

John Phelan, CC BY 3.0, via Wikimedia Commons

Bearskin Neck is known for its fishing spots and Motif Number One, a small red-colored shack used as a storehouse to store fishing gear.

Because of that, it has become something of an icon in the town and has been involved in multiple artistic endeavors, such as painting or photography.

Swim at the Front Beach

Front Beach during sunset

Robert J. Bradshaw /

On warm summer days, if you want to relax and venture out to the beach without having to drive too far from Rockport, Front Beach may be your destination of choice.

Its proximity to Rockport’s charming town center makes it accessible to visitors who want to enjoy an idyllic getaway without sacrificing the rich cultural offerings of a larger city.

Because it’s very close to several restaurants, eateries, and shops, you can enjoy some time on the beach or at the restaurant or whatever it is you’d like to do.

Families enjoying at Front Beach

James Kirkikis /

In the summer months, lifeguards hover over the beach at Front Beach.

Front Beach looks especially beautiful against warm summer days, bright winter mornings, and throughout the fall season.

It’s no wonder why so many visitors and locals alike love this beach so much.

Enjoy Arts and Culture at the Rockport Art Association & Museum

The Rockport Art Association & Museum is a charming gallery found hidden among the shops in the heart of Rockport.

The Rockport Art Association & Museum has got on offer everything for the avid art lover.

Here, you’ll find lovely native artists’ work showcased in its beautiful light and airy interior.

It’s always nice to browse for presents here after perusing the shops nearby to purchase all of your favorite “Coastal living” gifts (no pun intended!)

When you walk through the galleries at your leisure, friendly staff are on hand to answer any query you might have about the art or any other associated matters.

The association is also a place to stop by, where you can enjoy the artistic flair of culture enthusiasts — with talks, demonstrations, workshops, and special functions dealing with light-hearted topics.

A great environment to discover wonderful art pieces by all kinds of artists that boosts your overall creativity if you’re an artist yourself!

Explore the Historical Sewall-Scripture House

View of Historical Sewall-Scripture House

John Phelan, CC BY 3.0, via Wikimedia Commons

The Sewall-Scripture House is a museum and National Historic Landmark found at King Street, Rockport.

The Federal-style building constructed in 1832 is a granite structure that’s 2.5 stories high.

The home’s owner, Levi Sewall, made a lot of money as the owner of a successful quarry and a successful builder and contractor.

When Sewall died, he left the house to his family, who continued to live here until 1957, when the Historical Society acquired it.

Its front and side walls are built with dressed stone blocks that are timber width (roughly 0.3m2 ) by approximately 1m high.

The rear wall is more rustic, built with coursed random rubble topped with some squared ones.

Visit the Paper House

The Paper House in Rockport, Massachusetts, is a house built from paper!

Over eighty years old, the building architect Elis F. Stenman began his project in 1922 with a timber frame, floors, and a roof!

But Stenman didn’t want to make the walls purely out of wood.

He chose to build it with something different but still very versatile: newspaper.

Indeed, the contents of this quaint abode were made entirely from recycled newsprint.

Roughly 100,000 sheets of this recycled paper were used to construct 215 layers worth of 1-inch thick panels for the house’s doors, walls, and other furniture.

Every single item in the room, from the desk to the chair to the clock, is crafted out of paper.

There’s a piano and a fireplace, but they’re not entirely made out of paper.

Visit Feather and Wedge and Try Their Jungle Juice

Feather and Wedge is a stellar restaurant and bar located on Main Street Rockport.

It offers good food – sourced from local products and prepared with care – and is a great place to stop by and enjoy the town’s past.

They serve a menu of dishes and cocktails strongly oriented towards international flavors in a chic, modern setting with a hint of natural light.

Their ever-changing menu will feature dishes from different regions worldwide; its roots sprinkled with a dash of local flair here and there.

There’s a lovely ambiance; the dining room is pleasant.

The prices are the perfect fit, the food is cooked to perfection, and there’s a fine selection of drinks to choose from if you’re in the mood for something refreshing.

In fact, their signature Jungle Juice drink may just become your go-to drink when you want to unwind after work or have a weekend getaway with friends.

Discover History at James Babson Museum

During the initial Babson family gathering in July 1931, Roger W. Babson unveiled the modest stone building now known as the James Babson Museum for the first time.

The little stone house is packed with an assortment of tools and relics spanning almost three centuries of craftsmanship or commerce activities when it opened in 1931.

Roger turned the space into a single-room museum.

A remarkable assortment of wooden and metal devices, ranging from butter churns to oxen yokes, are on sight and tools for producing barrels.

Visit the Babson Museum to explore the over 200 tools and artifacts that make up the museum’s collection.

You’ll find equipment used in the cooperage industry, which was the stone building’s original use.

Barrels constructed by James Babson were taken to the neighboring Good Harbor Harbor, loaded with fish, and then delivered to England, the West Indies, and other countries worldwide.

Shop and Stroll around the Pewter Shop

Exterior view of Pewter Shop

James Kirkikis /

Lewis Whitney and Blanche Whitney founded the first gift store in Rockport, Massachusetts, The Pewter Shop.

The Pewter Shop opened its doors to the public in 1935.

The Whitneys were inspired to pursue their trade by the thriving community of fishermen, boat builders, painters, and other craftspeople surrounding them.

Name board of Pewter Shop

quiggyt4 /

It wasn’t long before the business was filled with up to seven artisans hand-hammering plates, bowls, and other objects.

You may walk to nearby restaurants, art galleries, shops, and beaches.

Take in the Peaceful Atmosphere in My Place by the Sea

My Place by the Sea, a restaurant with an unmatched romantic atmosphere viewing the Atlantic Ocean and top-ranked New American cuisine, is situated in the center of Rockport, Massachusetts.

Numerous prestigious newspapers have published My Place by the Sea and received numerous honors.

It is among the top 10 seaside eating locations in Massachusetts.

When they took over this classy waterfront restaurant in 2000, renowned Chef Kathy Milbury and co-owner Barbara Stavropoulos produced a unique food experience.

Rockport’s history has been expertly reflected by Kathy’s enthusiasm for local, sustainable food and Barbara’s eye for design.

The ideal setting for feasting on food and drinks and celebrating indoors and out is the multi-level sitting spaces that give stunning views of Rockport’s rugged New England shoreline.

Search for Products to Keep at Floating Lotus

The mission of Floating Lotus is to provide a handcrafted, fair deal, and ethically sourced goods from all corners of the earth.

Karin & Justin, the proprietors, spent considerable time living and working as teachers in Southeast Asia.

Twenty years of travel and adventure have influenced their passion for world art and culture.

They feel privileged to offer their extensive collection of items, which includes clothes, jewelry, textiles, wood sculptures, and musical equipment.

To produce beautiful goods for Floating Lotus, artists and families formed enduring partnerships with Floating Lotus.

Through conversations and connections that are constructive and mutually helpful, their goal is to unite individuals from different cultures.

Book a Night in Beech Tree Bed & Breakfast

The 1860 Greek Revival building that houses Beech Tree Bed & Breakfast was lovingly renovated to combine old-world elegance with contemporary comfort.

It is located in the center of Rockport, Massachusetts’s Historic Seaport Village, close to the coast, beaches, art museums, restaurants, and specialty stores.

The best accommodations and facilities are available to all visitors at Beech Tree Bed & Breakfast.

Unwind and feel at ease in luxurious bedding, plush Turkish towels, spa bathrobes, and a full bath with a rainforest shower.

Utilize the room’s air conditioning, ceiling fan, flat-screen TV with DVD player, and blow dryer.

As you enjoy your weekend trip at Beech Tree Bed & Breakfast, stay in contact through their free WiFi and prepare for a laid-back day and night.

Final Thoughts

It’s hard to describe the sheer beauty of Rockport, MA.

There is a wide variety of things to do and places to visit for everyone and every taste.

The gorgeous beaches and captivating sunsets coupled with friendly people make this charming fishing village like no other!

Check out this list of top spots so you won’t miss any hidden gems during your stay!

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