Summer Day Trip to Rockport, MA
Few coastal towns manage to fit in quite so much charm. Here’s what to do on a summer day trip to Rockport, MA, including where to eat, shop, and more.
By Bethany Bourgault|Jun 29 2022|
Motif No. 1 | The Story Behind the Little Red Shack
Photo Credit: Bethany BourgaultRockport, Massachusetts, is a popular New England coastal town known for good food, creative shopping, and seaside charm. It’s the perfect place to relax by the ocean, browse the works of incredible artists, and enjoy a lobster roll. Ready to join me on a day trip to Rockport?
Photo Credit : Bethany Bourgault
There’s something special about Rockport. In all of my New England exploring, I’ve yet to encounter a place that captures the essence of coastal life quite like it. After all, Rockport is the inspiration behind so many works of art (it’s been an artists’ haven for almost a century — most notably thanks to Motif No. 1, pictured above) that it’s no wonder Rockport is the physical embodiment of our ideas of life by the water. And with its next-door neighbor to the north, south, and east being the Atlantic Ocean, I can’t help but feel like Rockport would rather be a part of the sea anyway.
As the tip of the Cape Ann peninsula, Rockport is located in historic Essex County. It began as part of the nearby town of Gloucester, and together, these areas got their start in the fishing business. Pine harvested from the vicinity was used for shipbuilding, and locally quarried granite (they didn’t call it “rock”port for nothing!) was shipped up and down America’s east coast. It wasn’t until much later that tourism appeared on the local economy’s radar, but now that it has, there are plenty of dining, shopping, and cultural experiences for the sea-seeking explorer to enjoy.
Summer Day Trip to Rockport
I arrived in town just before noon — just in time to visit one of my favorite seafood restaurants, Roy Moore’s Fish Shack. I remember eating here with my family as a little girl, and trust me, the menu looks just as delicious now as it did back then. Roy Moore’s has two locations in the Bearskin Neck area to suit the preferences of all lobster-lovers. One, a sit-down nautical-looking restaurant at 21 Dock Square, is perfect for dinnertime or taking a break from the outdoors, and the other, a more casual eatery at 39 Bearskin Neck, is a great option for diners on the go.
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Ocean-side dining complete, it was time to head to the shops and galleries, where you can find everything from prints, pottery, and photography to original paintings, hand-crafted jewelry, and more. Most of these are concentrated on Bearskin Neck itself, though several have spilled over to the adjoining streets. Wear your walking shoes! Here’s a quick sampling of some of my favorites.
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Of course, Rockport’s main attraction is the ocean that surrounds it. Every turn showcases the great blue Atlantic from a different angle, and each breeze carries the refreshing, salty air characteristic only of oceanic proximity. Several beaches dot the Rockport coast, so dip your toes in the water at least once before going home. Or, take a moment to stand at the end of Bearskin Neck to take it all in. After all, everyone needs a breath of ocean air once in a while.
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Photo Credit : Bethany Bourgault
Have you ever visited Rockport, MA?
This post was first published in 2016 and has been updated.
SEE MORE:
10 Prettiest Coastal Towns in New England
15 Best New England Lobster Shacks
25 Best Beach Towns in New England
Rockport is an absolute gem and you did a great job presenting it. My cousin was an artist, god rest his sole, and did several paintings of motif # 1 and other sites around the area. Haven’t been for a while and thanks for the memory. My wife and I will be coming soon.
Cannot wait to go back.
My claim to Rockport fame: my beautiful Elegant cane, guiding each step, came
from Rockport, MA.
I grew up in Woburn MA and spent many weekends in Rockport. My friends and I had the greatest times going thru the stores and enjoying the ocean! Thanks for all the great pictures they brought back many memories!
Wonderful article and beautiful photos. I felt like I was there again sailing with my sister Lori who lived there for several years. She passed away in 2009.
Taking a trip from our home in Florida to New England in September. Will now seriously consider stopping here. Thanks????
I have been to Rockport many times in the past,always nice to go down memory lane again. I live in Arizona now and miss New England very much.
One of the most wonderful towns in the USA!…Have been there many times, especially back in the 60’s and 70’s!!! Miss Oleana’s, and the original CHRISTMAS DOVE! The live Christmas Pageant is not-to-be-missed!!! Of course, the OCEAN is magnificent! I have the privilege of meeting prople from all over the world in my businesses, and I always encourage them to go “north” to visit Rockport (and Gloucester – and Salem)!
I miss Oleana’s and the Christmas Dove too! We ALWAYS ate at Oleana’s when we went to Rockport when I was a child. I live less than an hour away so my husband and I go there fairly often for day trips. Everywhere you walk, including beyond the area where the shops are, is full of interesting sights. We do often go on non-weekend days or in the off-season, which has the advantage of no problems parking at all, but it can mean that some of the shops are not open. There always seems to be some places open though, and the buildings and seascapes are perhaps even better when not crowded.
Just back from a very short week in Rockport. I was born in Gloucester and my grandfather sold vegetables from a horse drawn cart (Soteros Vrachos) in the 1920s-50s. I have so many memories of Cape Anne… Each time I cross that bridge, I really feel like I am home.
A story on Rockport which doesn’t mention the spectacular Shalin Liu Performance Center! Like talking about Lenox without mentioning Tanglewood.
Yes! It used to be a clothing store called The Madras Shop which was very popular w/the girls in town, at least in the 80’s! The SL center is drop dead gorgeous, what a transformation!
From the time I was a child our family went to Rockport. My Mother was an artist, also my Uncle. they both did many paintings of Motif#1 and all around Rockport. It is still my favorite place to vist, as I now live in CA. There isn’t anything about the town that I don’t love and oh the fantastic memories. Hope to be there in Oct.
Spent a lot of years as a kid on Bearskin Neck with a family from Worcester. In 1965 I was in the Navy and we pulled into Boston. One of my shipmates from Brooklyn, NY asked if I would take him to Rockport which I did with two others via train. Well, when the four of us walked into town you would have thought we just liberated Rockport from the Germans. I took them right to right to my friends house and she and her family paraded us all over town and took us to Oleanders for lunch and absolutely made their day. Love Rockport.
A visit every trip to New England must include Rockport. From New Jersey, we sesrch out homes for sale yearning to make it our new home. You’ll not only find a watercolor of Motif #1 in my portfolio, but also one of our photos adorns our credit card. See you in October!
You missed the number one desert store on the neck, Bella and Harvey! ????
Sundays Ice Cream Store, second building on right as you enter the Neck. Not only do they have great ice cream (about 40 flavors) but have a relaxing yard in back where one can sit and enjoy the view of the harbor, including Motif #1, the most photographed and painted picture in the country.
Love Rockport. Visited many times in years past. We stayed several times at a wonderful B&B by name of The Captain’s House. Is it still there? One year we visited in winter and actually met Sven Ohrvel Carlson, a Rockport painter whose poster of Motif #1 is hanging in my home. Though I now live in St. Louis, MO, I try to visit Rockport whenever I go “back home”!
Very nice intro to downtown Rockport … I hope you do a follow-up and include the wonderful Shalin Liu, our many sandy beaches, Halibut Point State Park, the Paper House in Pigeon Cove, and the Lobster Pool Restaurant for waterfront dining in or out…. 🙂
I wondered if that Fishing Shack, as remember someone calling it, should be renamed Motif 1a, as a winter storm essentially destroyed it. The restoration captured the style of the of the original structure.
John Clark
I have wonderful memories of Rockport – in the summer and also at Christmas time. There used to be a little restaurant on Bearskin Neck that sold the best clam chowder – and don’t forget Helmets – the best strudel ever !
We love Rockport. Roy Moore’s two locations are reason enough to visit. Also hike around at Halibut Point and see the granite quarry. Plenty of good places to eat from quick and easy to eclectic. We enjoyed the hospitality at Seven South Street Inn (B&B) — the included breakfasts are really good and it’s an easy stroll to Bearskin Neck. Or drive through the charming residential neighborhoods and dream of which seaside home you’d buy if you win the Lottery. As an aside, visit Gloucester, a short drive south and go on one of the whale watch excursions. Rockport, you are special!
My mom absolutely loved Rickport and took us there yearly. We also fell in love with the town! One of the best whale watches we ever went on, departed from Bearskkn Neck! Great memories.
I grew up in Reading, and summer trips to Rockport were regular excursions for us! So many memories. We always went as a family with Dad in the lead! Loved being there on 4th of July, too! Just such a wonderful place and so glad it was part of my childhood!
My grandmother was from Rock[ort, my grandfather from Gloucester. He was a quarryman. After doing some family research I have found a lot of relatives there and I may even be a cousin of Roy Moore-my fav place for lobster! I feel at home every time I visit Rockport, like I belong there. I cant wait to visit again soon!
Rockport is just about perfect. My favorite time from past visits was getting up before dawn, wrapping in a quilt and watching the fishing boats head out from my porch at the Yankee Clipper Inn.
I’ve been to Rockport several times, but it’s been well over forty years since the last time I was there. I used to live in Wakefield, Massachusetts, but live in Utah now. It looks like much has changed over the years for the better. Sure would like to visit again. I loved your article. It reminds me of home and what I’m missing.
I too am from Wakefield, MA and am returning for my 40th High School Reunion from Atlanta, GA. With my husband, we will round out our trip with a stay in Rockport. I look so forward to this special time. Upon my return, I will provide a complete post of my visit.
Rockport is one of my favorite places to visit. Being an artist, I have painted this scene of Motif #1 more than once and can smell the sea air every time I look at the painting! I would love to visit there again. Thank you for bringing back such wonderful memories.
We were lucky enough to vacation in Rockport at the end of June. We were guests at the Seafarer Inn, a quintessential New England coastal property. We ate at Tom Moore’s, enjoying local steamed and fried clams and lobster rolls. Loved Bearskin Neck and enjoyed an evening of Music on the Beach. Proximity to Salem and Gloucester made them easy day trips. Loved Rockport and look forward to returning.
EACH DAY IN MANY WAYS I AM LUCKY TO KNOW THIS SPECIAL TOWN AND ITS GREAT PEOPLE….COME VISIT…
I loved Rockport and thoroughly enjoyed your article. What was missing was any mention of the beautiful lighthouses around the area! ????
My grandfather and his family came from Rockport and when I was a child we would go there for family gatherings. My great grandfather Emerson Haskell used to have an out door eating place at Lob Lolly. It is a very beautiful area
I moved to Rockport in 1967 as my stepdad’s family had simmered there since the 30’s. My dad gave me a wonderful treasure when he took mom and me to live in Rockport. My dad, Thomas F. Murphy is also buried in the Rockport Cemetary. After learning how to sail, living in a wonderland, and spending the best of my teen years in Rockport, Thomas Frances Murphy was killed in a head on collision on Rt. 128 by a drunk driver. Rockport has grown as the years pass but Rockport will always be a place I call, my home.
My family and I just returned from Rockport. It is my absolute favorite place to be. My son and daughter in law joined us from Ohio. My son and husband thoroughly enjoyed (each) a 2 1/2 lb lobster at Roy Moore Fish shack. We also love the strudel at the German bakery (can’t remember name). Everything is wonderful and the views are amazing. We usually stay at Captain Bounty right on the beach. ❤️
The strudel place is Helmuts! I grew up there, have since moved away but when I go back to visit, I always stop there. Yum!
Your article was great and captures the highlights of our special town. My husband and I decided on a change of lifestyle from Boston city living and moved to Rockport four years ago. It’s like a dream to live in this wonderful community. Other favorite spots we’ve enjoyed here are Halibut Point State Park, which has a beautiful quarry alongside spectacular ocean views, the Shalin Liu, which has some great musical guests tour through it, the Rockport Art Association, which hosts gatherings of all sorts, including an art show honoring a renowned local artist who passed away. What makes Rockport accessible is that it’s on the commuter rail line for anyone else who wishes to escape the hustle and bustle of the city, even if it’s for just a day or two. 🙂
I’m lucky to live in Rockport. Beyond the simple tourist attractions it is a village with a great sense of community. The Shalin Liu center provides access to music in a beautiful hall, and nature provides more than enough inspiration for artists. In winter it is equally inspiring. The Sandy Bay Yacht club is a great resource for both local and transient sailors. Trains running to Boston provides a means for Boston residents to escape to the seaside and Rockport residents an alternative to driving to and parking in Boston. Watching the power of a winter Noreaster breaking on the granite of Rockport is quite a sight.
I loved to visit Rockport but lately there is a big parking problem. They made parking very difficult and sparse. It is too bad.
There is a parking lot as you come into town, no fee. Then there is a trolley that takes you downtown, making many stops. Small fee for the trolley. You’ll never have to worry about parking again!
Love Rockport,during my working days took a long weekend every year,now every other year.As I sornd the winters in Fla.I found a huge old oil painting of Motif #1 snd I proudly have it in my dining room and enjoy Rockport every day!
Visited Rockport after the whale watching trip in Gloucester. Walked in Rockport, loved the setting, delicious seafood at Blu Lobster Co with the Motif No.1 views.
Worked three meals a day at the Turks Head Inn in Rockport in 1951. We lived up stairs in a red barn behind the Inn. Went with my best childhood friend.
Also, the Mooring Stone Guest House is a great place to stay if you are going for more than one day – nice location within walking distance to shops but slightly off the beaten path at the same time, so not noisy in the evening.
Two clear omissions: Helmuts German Bakery for the to-die-for strudels; and the wonderful array of art galleries featuring some very fabulous and high quality art works for the patron who may wish to take home more than a mouthful of cavities from their trip to bearskin neck lol!!
All your pictures and stories really making me homesick. Moved away more than thirty years ago Miss it every day Nothing beats NE weather in the summer and all quaint Rockport has to offer
My wife and first visited Rockport on our honeymoon. That was 50 years ago. We have been vacationing there every year since. Many of the artists there were good friends of my father in law, who was also an artist. We befriended them over the years. It was like going home every year, and visiting family. Sadly all have passed now, but going back always brings back fond memories of our get togethers. I never fail to find new things to draw and paint each year. Rockport is so inspirational.