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If you are thinking about a summer spent enjoying the New England coast, visiting the charming town of Rockport, Massachusetts, should be high on your list. Rockport is nestled on the shores of the Cape Ann Peninsula in Essex County, less than an hour from Boston and two hours from Cape Cod, another popular New England seaside town.
Founded in the 1600s by a granite cutter, Rockport was known as a thriving fishing port and exporter of timber and granite. It was a dry town from 1856 up until 2005 when alcohol was allowed to be served in restaurants.
Today, Rockport is known as a lovely resort town with beautiful summer homes, a small fishing village, quaint shops, and friendly locals. Along with its picturesque scenery, rich history, and vibrant art galleries, Rockport and its surrounding areas offer many fun things to see and do, perfect for solo travelers, couples, and families of all ages.
Keep reading for 50 of the best things to do in Rockport, MA.
See the Coast on a Boat Tour of Cape Ann
A boat tour is a fantastic way to see the coast from a unique perspective. There are many tour options available, from guided history tours to hop on hop off harbor tours. You’ll have the chance to admire the cliffs, coves, bridges, lighthouses, and natural formations that make this area so distinctive. Cape Ann Harbor Tours offers the only tour that encircles the entire cape.
Enjoy Gloucester Harbor Walk
If you like to walk, the Gloucester Harbor Walk is a stunning area to enjoy some of the best coastal views, showcasing Gloucester’s beauty and maritime heritage. Along this paved trail are over 40 optional pit stops, including historical sites, museums, and public art. In summer, you can enjoy the colorful flower gardens that line the walkway along Western Ave near the USS Constitution Replica Cannon. It’s a beautiful way to immerse yourself in the coastal charm of Gloucester while enjoying the outdoors.
Enjoy Views of the Eastern Point Lighthouse
This historic lighthouse was established in 1832. It has an iconic look with a white tower, a black lantern, and a two-story keeper’s quarter. The lighthouse represents the maritime heritage of Gloucester and the New England region, adding to the town’s historic charm. It’s closed to the public, but the walkable breakwater around it offers fantastic views.
Walk along the Rockport Harbor Breakwater
The Rockport Breakwater Walk, also known as the Rockport Breakwater, is a unique and popular attraction in Rockport, Massachusetts. It offers a scenic and enjoyable walking experience, allowing visitors to walk out into the Atlantic Ocean along a massive granite breakwater, enjoying stunning panoramic views of Rockport Harbor and the coastline. The walk is just under .5 miles round trip and allows for a glimpse of the Straitsmouth Island Light Station.
Catch a Wave
Rockport might not come to mind when thinking of the best surfing spots on the east coast, but it is a perfect activity for anyone interested in combining surfing with the picturesque coastal charm of Rockport. With fewer crowds and smaller waves, Rockport offers a unique and charming surfing experience that can be enjoyed by beginners, intermediate surfers, and those looking for a delightful and rewarding experience. Cape Ann SUP + Surf offers surfing lessons of all kinds in two different Rockport locations. Grab your wet suit and enjoy this unique coastal experience.
Test Your Balance at SUP Yoga
If you want to take stand-up paddle boarding to the next level, try a SUP Yoga class. Cape Ann SUP + Surf host yoga workshops and classes weekly during the summer. It is a great way to get out on the water, have some fun, test your skills and improve your strength. Classes are around 90 minutes long and cost $40 per person.
Hike the Abandoned Dogtown Common
Dogtown Common, located in Gloucester, Massachusetts, 15 mins from Rockport, is a unique and historical hiking area with a fascinating backstory. It’s a destination that appeals to history enthusiasts, nature lovers, hikers, artists, and those seeking a unique and off-the-beaten-path experience in Massachusetts. Now named a historical site, its laybrinth of trails and historic ruins from a 17th and 18th centuries settlement along with its rustic beauty, picturesque environment and mysterious aura make it a wonderful thing to do in Rockport, MA.
Visit the Rockport Art Association & Museum
The Rockport Art Association & Museum (RAA&M) is an organization that serves as a hub for visual arts, creativity, and cultural engagement. Founded in 1921, the RAA&M is one of the oldest and most prominent art associations in the United States. It plays a significant role in promoting the arts, preserving local artistic history, and fostering a vibrant arts community in the town of Rockport.
Enjoy the RAA&M’s gallery and museum space that features rotating exhibitions and permanent collections of various art forms, including paintings, sculptures, drawings, photography, and more from local and regional artists, as well as artists of national and international acclaim.
Gloucester Waterfront Festival
This annual family-friendly festival has a lot to enjoy, from over 150 artists’ booths to live music, gourmet delights, and delicious local food. The festival takes place in mid-August and showcases the best local talent and American-made crafts, including clothing, candles, fine jewelry, pottery, leather accessories, pottery, and decorative art.
Rockport, Massachusetts, offers several excellent bird-watching spots, thanks to its coastal location, diverse habitats, and natural beauty. The mix of coastal habitats at Halibut Point State Park make this park a top location for bird watching. For forest-dwelling species, including songbirds and woodpeckers, head to Andrews Woods Conservation Area. Make sure to bring binoculars, a field guide, and comfortable walking shoes. The best bird-watching times are during the early morning and late afternoon when birds are most active. Different seasons can bring different species, so be sure to visit during migration times to observe a wide range of birds.
Enjoy the Coast from a Sailboat
Sailing is a great way to enjoy the picturesque Cape Ann coastline, offering a combination of natural beauty, cultural heritage, relaxation, and recreational activity. Whether you’re a seasoned sailor or a beginner looking for a unique experience, the coastal waters of Rockport provide a captivating and rewarding setting for your sailing adventure. Many sailing companies offer private sailing charters and sailing lessons from Rockport Harbor, Harbor Cove, and State Fish Pier.
Explore Pigeon Cover Harbor
Another great area to explore in Rockport, Massachusetts, is the historical and picturesque Pigeon Cove Harbor. This harbor exudes small-town charm with a less commercial atmosphere. Its cultural identity, historic importance and scenic beauty contribute to Rockport’s unique character and serene coastal environment. It is a beautiful place to go for a leisurely stroll or enjoy a relaxing small boat or kayak tour, admiring the scenic rocky coastline along the way.
Go Scuba Diving
While Rockport itself may not be as well-known for scuba diving as some other coastal locations, there are opportunities for diving enthusiasts to explore unique underwater sites along the Cape Ann coastline. Join a dive boat and a guided tour to swim through underwater rock formations and see vibrant marine life and ecosystems at work. Folly Cove, Back Beach, Font Beach, Straightsmouth Island and Thatcher Island are popular dive sites near Rockport, MA hosting a variety of sea life including crabs, lobster, tautog, bluefish and schools of scup.
While Rockport, Massachusetts is better known for its beautiful coastal scenery and maritime heritage, there are still opportunities for enjoyable snorkeling experiences. The waters off Rockport’s coastline tend to be cooler and rockier compared to some other snorkeling hotspots. However, Back Beach and Front Beach offer easy entry and diverse marine life. Folly Cove is another great snorkeling spot when the tide is in.
Discover a hidden gem: The Paper House
This historic property, built in 1922 by inventor Mr. Elis F. Stenman, is truly one of a kind. He initially started building his summer house as a hobby, using layers of newspaper as insulation between the wooden house frame. But he didn’t stop there; his curiosity and knowledge as an engineer continued into furniture. He built a Grandfather Clock, desk, chairs, lamps and tables entirely out of rolled varnished newspaper. After he moved out in the 1930s the well-preserved home became a museum. Enjoy a self guided tour paying close attention to the furniture made entirely out of news clippings with headlines that can still be read today.
Take in a show at the Shalin Liu Performance Center
From opera, jazz, folk and pop, the summer sounds of Rockport Music come alive at the Shalin Liu Performance Center. This historic building, host to the Rockport Music Association, is situated on the shoreline with stunning coastal views of Rockport Harbor. The company strives to inspire and teach the understanding of music through live performances and creative learning opportunities. Their summer calendar is full of curated shows, music festivals and film screenings. You can view their calendar of events and purchase tickets to any show on their website.
Admire the iconic Motif Number 1
Motif No. 1 is an iconic red fishing shack on Bradley Wharf in Rockport Harbor, often called “the most painted building in America” (the reason for its name). This historic structure, built in 1840, has inspired countless artists and is one of Rockport, Massachusetts’s most iconic things to see.
It has been featured in Finding Nemo as a nod to the director’s home town of Rockport and as the real life town of Sitka, Alaska in the Proposal with Sandra Bullock, Betty White and Ryan Reynolds. Although the original Motif No. 1 was destroyed during a 1978 blizzard, the community rallied to rebuild the historic structure back into its full glory. Make sure to bring a camera and enjoy a sunset overlooking this picturesque harbor icon.
Walk through Downtown Rockport
A visit to Rockport wouldn’t be complete without a stroll through its charming downtown area. Filled with historic buildings, quaint shops, and local eateries, downtown Rockport offers visitors an enjoyable experience.
This art colony is a paradise for art enthusiasts – check out the over 30 art galleries in Rockport’s Cultural District, showcasing local and international artists’ works. Local favorites include The Art Nook and John Caggiano Art Gallery.
The Rockport Art Association and Museum, founded in 1921, is a non-profit organization dedicated to promoting and supporting the visual arts in Rockport. The association features rotating exhibitions of contemporary and traditional art, as well as educational programs and workshops for all ages.
For a dose of nature, explore Millbrook Meadow, a four-acre park nestled in the heart of downtown Rockport near Front Beach. This lovely park has a winding brook, a frog pond, and a stone bridge, making it a great place to walk around or relax outside.
Enjoy the Sandy Beaches
Rockport is home to several beautiful beaches, each with its own unique charm. Located near Thatcher Road, Long Beach has lifeguards on duty and is one of Rockport’s best places to swim. From this beach, you can see the twin lighthouses in the distance on Thatcher Island. A retaining wall also backs these waters, while the shore is lined with beautiful summer cottages.
Known for its soft sand, blue water, and stunning ocean views, Front Beach is a calm oasis with minimal waves, making it perfect for families and beachgoers of all ages. Just a short walk from downtown Rockport village, Front Beach is easily accessible from nearby inns and hotels. During the summer months, lifeguards are on duty, ensuring a safe and enjoyable beach experience for everyone.
With an array of restaurants, eateries, and shops in close proximity, you can effortlessly combine a day at the beach with shopping and dining.
Pebble Beach is a hidden gem that offers visitors a unique and tranquil coastal experience. Just a stone’s throw from Route 127, this aptly named beach is covered in smooth, rounded rocks, which create a stunning landscape for visitors to enjoy.
As you relax on the shore, you might be lucky enough to catch a glimpse of local divers exploring the ocean floor or even playful seals frolicking in the surf. When visiting Pebble Beach, I recommend bringing a chair and beach shoes for comfort, as the pebbles can be a bit challenging to walk on.
Cape Hedge Beach
Located about 2.5 miles from Rockport’s Dock Square, this unique beach is nestled between Long Beach and Pebble Beach, providing a more serene and quiet atmosphere for those looking to escape the bustling tourist areas.
The beach is not your typical sand and water destination; it’s mostly made up of pebbles, creating a striking and humbling sight as the ocean water has smoothed them out over time. However, the closer you get to the water, the more likely you are to find some sand!
One of the intriguing places to visit in Rockport is Back Beach, a unique and beautiful stretch of shoreline located off Route 127, just north of the Village area. While it isn’t your typical swimming beach, it’s an ideal spot for scuba diving enthusiasts and those looking for a peaceful place to sit and enjoy the ocean breeze. This small beach is mostly rocky with a few sandy areas, but you’ll definitely need a beach chair while you’re here.
Old Garden Beach
The beach features a sandy shore near Rockport Harbor, and just a short walk from downtown Rockport, this charming destination is perfect for a relaxing oceanside stroll. To the east of the beach, you’ll find a public footpath that takes you behind some lovely seafront homes, offering scenic views of Straitsmouth Island.
In addition to its natural beauty, Old Garden Beach is also a popular training site for New England divers. The Old Garden Beach Association works to maintain the area’s quality and foster a sense of community among beachgoers.
Good Harbor Beach
This beautiful beach offers white sand, crystal clear water, and scenic views, making it a perfect destination for a relaxing day by the shore. During low tide, visitors can walk out to Salt Island or explore the nearby Annisquam River, providing ample opportunities to discover the diverse marine life in the saltwater estuary.
The beach is well-equipped with restrooms, showers, and an on-site concession stand offering snacks, drinks, beach toys, and more. Good Harbor Beach is also handicap accessible and has lifeguards on duty from Memorial Day weekend through Labor Day, ensuring a safe and enjoyable experience for all visitors.
Note that parking spots go fast at this beach! If you don’t have a resident parking pass, you’ll need to make a parking reservation up to ten days in advance.
Spend the day at Halibut Point State Park
Visiting Halibut Point State Park is one of the best things to do in Rockport, Massachusetts. This beautiful park on Cape Ann features hiking trails, picnic areas, and an old granite quarry. From this park, on a clear day, you can see Mount Agamenticus, about 40 miles away in Maine. You can also view the Isles of Shoals in the distance, off the coast of New Hampshire.
This 67-acre park has a small visitor center and museum dedicated to the area’s natural history and granite quarrying industry. Whether you want a dose of history or outdoor relaxation, this state park has something for everyone.
Take a tour of Thacher Island
Thacher Island has a rich history – it was the place where both major and minor naval confrontations occurred during the American Revolution.
Accessible by private boats, kayaks, or seasonal guided tours, about 3 miles from Rockport Harbor, Thatcher Island is home to the historic Cape Ann Light Station also known as the Thacher Island Twin Lights. These were the first lighthouses to mark a hazardous location rather than an entrance into a port. They are closed to the public but can be viewed from a Cape Ann Lighthouse Tour or seasonal island tour aboard the Thatcher Island Launch.
Once you get to the island, you can explore the trails, birdwatch, and take in the scenic views of the Atlantic Ocean. This island has three miles of trails, and one of the best hikes is Anne’s Way Walk, leading to the island’s south end.
Go on a Whale Watching Tour
One of the most popular things to do in Rockport, Massachusetts, is whale watching – the best season to do so is between May and October. With several companies offering whale watching tours, including Cape Ann Whale Watch and 7 Seas Whale Watch, you’ll have the opportunity to see these majestic creatures up close in their natural habitat. Tours typically last a few hours, and expert guides will share informative insights about the whales and their behaviors. Bring your camera, as you’ll undoubtedly want to capture these memorable moments!
Drive or Bike down the Essex Coastal Scenic Byway
For an unforgettable road trip along the North Shore of Massachusetts, look no further than the Essex Coastal Scenic Byway – one of my favorite things to do in Rockport, MA. This 90-mile roadway links 14 coastal communities, starting in Lynn, Massachusetts, and ending in Salisbury, Massachusetts.
This scenic drive offers breathtaking views of the Atlantic Ocean. Rockport is located at the midway point of this road, which also happens to be one of the most beautiful areas of the drive. As you drive along this path through Rockport, Cape Ann, Essex, and Gloucester, you will surely enjoy the salt marshes, tidal rivers, and rugged granite shoreline.
Take in some History at the Sewall-Scripture House
Owned by the Sandy Bay Historical Society, the house serves as a museum of Rockport antiquities, showcasing a variety of antiques, period artifacts, and items of local history. Built in 1832 by Levi Sewall, a successful contractor and granite quarry owner, the Federal-style building was constructed using granite sourced from Rockport’s quarries. The house is listed on the National Register of Historic Places, preserving a unique piece of Rockport’s heritage.
Today, the Sewall-Scripture House Museum offers visitors a glimpse into the past, with its classical decor and numerous artifacts from when it was built. Among the items on display are an antique piano and an extensive collection of photographs and other historical materials related to the Rockport area. Visitors can explore the house and learn about the life and times of the Sewall family, as well as the history of Rockport and its surrounding communities.
Open to the public from June to September, the museum charges a small admission fee for adults. It welcomes history enthusiasts of all ages to explore this charming and significant piece of local history.
Get out on the Water
Head to the North Shore Kayak Outdoor Center to spend time on the water. Offering guided kayak tours, this is a fantastic way to explore the beautiful coastline of Rockport and the surrounding areas. Paddle through calm bays, rocky coves, and scenic marshes while learning about the local flora and fauna from knowledgeable guides. You can choose between seal and birding tours, or island tours, depending on your preference. No experience is necessary, as the center caters to both beginners and experienced paddlers.
Eat Some Authentic New England Lobster Rolls
If you went to Massachusetts and didn’t have a lobster roll, did you really go to Massachusetts?
One of the best places for incredible lobster rolls near Rockport is Jeff’s Variety, a no-frills deli with a variety of sandwiches. While the Italian subs are great, the lobster rolls are the real highlight. Served on a hot dog bun with mayo, these rolls are all about the meat-no fillers!
Another lobster shack, Roy Moore’s Fish Shack, is one of the most popular spots in Rockport, and for good reason! This quintessential New England fish house has some of the freshest lobster in New England – it comes right off the boat and in through the back door! They also offer fresh New England clam chowder, and oysters on the half shell.
Lobster Pool is another great spot in Rockport for a lobster roll. This hidden gem is located just past Halibut Point, has excellent food, and it’s also a great place to enjoy views of the bay.
Although a lobster roll can set you back $28-$38, it makes a great splurge when enjoying a summer on the New England coast.
Make a Hole-in-one at the Rockport Golf Club
If you’re a golfer, you won’t want to miss out on the opportunity to play a round at the beautiful Rockport Golf Club, located on the tip of Cape Ann. This charming nine-hole course offers fantastic views of the surrounding area and a fun challenge for golfers of all skill levels. After your round, relax at the clubhouse and enjoy a meal or a drink with fellow golfers.
Search for Hidden Gems Along the Antique Trail
Just a few miles outside Rockport, you’ll find the Antique Trail in Essex, Massachusetts. With over 25 antique stores within a one-square-mile area, this little town on the North Shore has become a popular destination for those who appreciate the beauty and craftsmanship of vintage and antique items. Each antique shop in Essex has its own distinct character, housed in 18th and 19th-century buildings, offering a diverse selection of high-quality antiques in close proximity.
One must-visit shop on the trail is Perim Lang Antiques. This store has been recognized in Boston Common Magazine’s “Luxe List” and was awarded Best of Boston in 2019. Perim Lang Antiques offers an exceptional collection of Essex antiques, making it a must-see destination for any antique enthusiast.
Another noteworthy stop in this area is the Essex Exchange, situated right on Route 133. While the store does carry antiques, it positions itself as an upscale resale shop. The Essex Exchange features a diverse array of goods from various sellers, including furniture, lighting, flatware, sculptures, paintings, restored items, and a variety of ephemera at reasonable prices.
Enjoy window shopping along Bearskin Neck
Named after a local fisherman who saw a bearskin drying on the rocks, this popular tourist area in Rockport Harbor is home to countless local shops and boutiques oozing with small-town charm and a historic feel. It is the perfect place for some retail therapy.
From trendy fashion boutiques and handmade jewelry to sweat shops, fish shacks, yoga studios and souvenir stands, there is plenty of variety to keep everyone in the group entertained. The neighborhood’s most popular local businesses include Rockport Candle Company, The local General Store and SeaBags, among many others!
Snap a photo of the Straitsmouth Island Lighthouse
The Straitsmouth Island Lighthouse is a beautiful and historic landmark located on the 31-acre Straitsmouth Island, just off the coast of Rockport, Massachusetts. Originally built in 1835, the lighthouse has a long history of guiding mariners to safety and warning them of dangerous shallows and rocky coasts. Over the years, the lighthouse has undergone various renovations and updates, with the most recent major renovation occurring in 2013.
This 37-foot-tall structure is situated on an island owned by the Massachusetts Audubon Society and serves as a wildlife sanctuary. In addition to the lighthouse, the island also features a keeper’s house, an oil house, and other structures that have been restored over the years.
The best way to see the lighthouse is from the water on a boat tour or a kayaking trip as the lighthouse and accompanying island is closed to the public. From dry land, you can catch a glimpse of the lighthouse from the end of Bearskin Neck street in Rockport Harbor.
Sip some Brews at the Local Breweries
Rockport has a surprising number of excellent breweries – stop in and unwind after a day of beach-going, shopping, and sightseeing. Riverwalk Brewing Company is one of the best breweries in the area, offering a trendy atmosphere, pizza, and a great beer selection.
Great Marsh Brewing is another good option – enjoy the covered outdoor beer garden, the spacious and chic interior, a vast selection of food, and a variety of fantastic beers.
Visit the Crane Estate
This mansion will make you feel as though you stepped into the pages of The Great Gatsby. Nestled in the charming town of Ipswich, Massachusetts, the Crane Estate is a breathtaking historical landmark that showcases the opulence and grandeur of the 1920s. Built between 1926 and 1928 as a summer home for Mr. and Mrs. Richard Teller Crane, Jr., this 57,000 square foot Tudor Revival mansion sits atop Castle Hill, a 165-acre drumlin surrounded by sea and salt marshes. The estate is a testament to the luxurious lifestyle of the wealthy during the early 20th century and offers visitors a glimpse into the past.
Today, the Crane Estate encompasses more than 2,100 acres and boasts three distinct properties: Castle Hill, a National Historic Landmark that houses the Great House, making it a spectacular venue for weddings and corporate events; the winding salt marshes and miles of barrier beach, offering picturesque views and tranquility; and the surrounding landscape. The estate is open to visitors, providing guided tours of the house and the opportunity to explore the stunning grounds.
Explore a Medieval Castle
Immerse yourself in the area’s rich history by visiting the enchanting Hammond Castle Museum. Built in the late 1920s by scientist, inventor, and art connoisseur John Hays Hammond Jr., this European-style castle sits high on a bluff overlooking the Atlantic Ocean. This castle is a stunning blend of art, architecture, and culture, with innovative technological features integrated seamlessly into its design.
Devour a Sweet Treat
Bearskin Neck abounds not only in shops, restaurants, and boutiques, but also in ice cream stores! If you’re here in the summer, sampling the local ice cream is a must. Stop into the Ice Cream Store, Bearskin Neck’s first-ever ice cream parlor. Down the street, you’ll find Sundays, offering hand-dipped flavors and harbor views. Gifford’s is another excellent place to grab a cone, boasting a variety of flavors and toppings. No matter which spot you choose, you can order your ice cream and enjoy a view of the harbor and the nearby fishing boats.
If fudge is your first choice, try the hand made fudge at the Rockport Fudgery. They have been creating their famous fudge since the 1960s. With tons of flavors like Maple Walnut, Penuche, Oreo Crunch and Triple Chocolate, it’ll be hard to choose just one!
Visit the Cape Ann Museum
The Cape Ann Museum is a prominent cultural institution that focuses on preserving and showcasing the history, art, and culture of Cape Ann. The museum’s collections include a wide range of artworks, artifacts, documents, and photographs that highlight the area’s maritime heritage, fishing industry, artistic legacy, and local history. It features works by notable artists associated with the region, such as Fitz Henry Lane and Winslow Homer, who were inspired by Cape Ann’s scenic beauty.
Take a Day Tour
If you have seen it all and still have some time to spare, Rockport’s coastal location offers easy access to a variety of interesting day trip destinations.
Known for its rich history, especially the Salem Witch Trials, a day trip to Salem offers museums, historic sites, and a vibrant downtown area with shops, restaurants, and waterfront views.
About an hour’s drive away, Boston is a hub of culture, history, and attractions. Visit landmarks like the Freedom Trail, Fenway Park, and the Museum of Fine Arts.
Plum Island, Newburyport, MA
This barrier island offers wildlife refuges, bird watching, and beautiful beaches. Newburyport’s downtown area has charming shops and restaurants.
Cross the state line into New Hampshire and visit Portsmouth, a charming town known for its historic sites, waterfront dining, and cultural attractions.
If you’re up for a longer day trip, Portland is about a two-hour drive. Explore this lively city with its renowned food scene, waterfront, and arts culture.
Whether you’re interested in art, nature, history, or simply soaking up the sun, Rockport offers a wide range of activities to enjoy during the summer months!
I can’t wait for a return trip back to Rockport. The last time I went it rained the entire weekend, but I still had a great time walking the Bearskinneck, eating plenty of fresh seafood and ice cream, and enjoying Rockport’s neighboring towns like Manchester-by-the-sea and Gloucester. I can easily spend hours driving around the villages admiring the charming homes and Inns. Rockport is one of my favorite small towns along the East Coast, and I am sure, after a visit to this iconic seaside village, you will easily agree!
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