Thinking about visiting the quaint coastal village of Rockport, Massachusetts but not sure what to do when you visit? You’ve come to the right place!
There is so much to explore in Rockport, Gloucester and the Massachusetts north shore that you could spend the whole spring, summer, fall and winter here and not even scratch the surface!
In this article, we’ve provided a list of some well-known things to do and some things that are under the radar. But we’ve tried to create a comprehensive list that truly has something for everyone.
So, without further ado, here is our guide to 40 things to do in Rockport, MA.
The little red fishing shack in Rockport Harbor loving known at Motif #1 is basically the symbol and heart of the town.
Originally built in the 1800’s it’s worth a visit to see the shack that inspired so many artists over the years. And, let’s be real, it’s incredibly photogenic and social media gold.
Motif#1 has been captured in so many different settings, weather conditions, light and somehow, it never gets old. Want to learn more about Motif? Check out this Beginner’s Guide to Motif #1
Got the pic? Perfect! You now have documented proof that you actually made it out of the house. Now let’s get some grub.
No trip to Rockport would be complete without dining on the local delicacy: lobster. They are as ubiquitous as pubs in Southie.
There are some fantastic spots to grab seafood in town including Roy Moore’s, The Lobster Pool, Blue Lobster Grill, and Feather and Wedge and some other classic seafood shacks across Cape Ann.
If you are on the hunt for the perfect lobster roll, take a closer look at the journey we took over the spring. The Hunt For The Perfect Lobster Roll On Cape Ann.
We love convertibles, we love motorcycles but there is something about riding a bike on the coast that brings out the inner child in everyone.
There are some incredible scenic vistas around Cape Ann and riding on two wheels is the perfect way to enjoy and connect with the scenery in an intimate way that just cannot be touched by motorized vehicles.
If you are need of a bike, we rent them here at Addison Choate. Learn more: Bike Rentals in Rockport, MA.
Rockport is famous for being an active art colony. With 30 galleries featuring works of over 400 artists there is never a shortage of art to explore and the local artists are all happy to discuss and share their work and their journey.
It’s a pretty special dynamic that is unique to Rockport. Not sure which galleries to check out? Well, you can just take a walk through Dock Square and Bearskin Neck and find some great galleries. But here are some of the galleries in the area that we enjoy: 7 Great Rockport Art Galleries
The north shore of Massachusetts has an incredible trail system that is perfect for taking your bike off road or getting in that Sunday long run that you have been putting off.
From Rockport to Gloucester to Essex and Beverly the trails are definitely worth checking out.
To get a closer look at what’s available we think that All Trails is a fantastic resource: Search Trails Near Rockport, MA
Getting out on the water is essential when visiting coastal communities and one great way to explore is by kayaking out of Rockport Harbor.
There are many places to drop your kayak in and much to explore along the craggy coastline where you can view historic lighthouses, seals, and some incredible birdlife.
Embrace your inner-Cousteau and dive into the cool Rockport waters.
Back Beach has legendary diving and you can also dive off of Old Garden Beach and Folly Cove in Gloucester. Take a look at what lies in the murky deep and discover lobsters in a habitat other than a tank or a pot.
Here is a great write up on diving at Back Beach: Diving In Rockport, MA
One of the natural treasures of Cape Ann is the impressive whale population. You can get out on the water and see some of the largest mammals on the planet! On your whale watch excursion you can expect to see the Humpback whale, Minke whale, and Finback whale.
In fact, our guests here at Addison Choate love it so much that we have partnered with Cape Ann Whale Watch to offer our guests a discounted excursion. Gloucester Whale Watch Discount.
Rockport has some classic New England Beaches to explore. Some beaches in the area that we love include: Long Beach, Cape Hedge Beach and Front Beach. When Summer heats up there is no better place to be than with your toes in the sand looking out on the ocean and some historic lighthouses.
For additional details on local beaches and their differences you can check out our article on the Top 5 Beaches in Rockport, MA.
A beautiful reservation at the tip of Cape Ann, Halibut Point was previously a working quarry. You can walk around the picturesque water-filled quarry and out on the low coastal shelf overlooking some impressive surf.
It’s a great place for a picnic and enjoying some of the beautiful scenery of this coastal village. Learn more about Halibut Point and read some reviews on Trip Advisor.
Just down the road from Rockport you will find the town of Essex, Massachusetts. With over a dozen antique shops within a few miles of each other, it is a destination for Massachusetts antique lovers.
If you are feeling like a treasure hunt, browsing these shops is just what the doctor ordered. You are bound to come across a treasure that you simply cannot live without!
Here is our guide to the Essex, MA Antique with some of our favorite stops: Antiquing in Essex, MA.
Perhaps it’s a rainy day and you’re looking for some indoor fun or a sunny day and you’re looking to beat the heat. You can always hit up Cape Ann Lanes, just down the road in Gloucester.
The new owners Nic and Caitlin Pszenny have breathed new life into these historic 1959 candlepin lanes and now offer a variety of video games, food, and even a new brewpub. So, unless you’re observing Shabbos there is always a good reason to lace ‘em up and let ‘em roll on Cape Ann.
Escape the trials and tribulations that plague landlubbers with a cruise on the beautiful 65 foot schooner Thomas E. Lannon.
Berthed at Seven Seas Wharf in Gloucester, the schooner offers visitors 2 hour sails and private charters from May through October. Step back to a simpler time when these beauties roamed the harbors of Cape Ann.
Rockport has a rich quarrying past that dates all the way back to the first settler of the Sandy Bay Colony, Richard Tarr, who was a granite cutter himself.
The Rockport quarries became a major source of stone during the Industrial Revolution and many of the city streets were lined with granite from the Rockport quarries.
Many of the quarries in Rockport are no longer active and serve as the perfect Summer getaway for a nice cool dip or a leap of faith for adrenaline junkies.
Hop aboard the boat at Tuna Wharf on Bearskin Neck and take a scenic cruise around Sandy Bay where you will see harbor seals, cormorants, historic lighthouses, scenic islands and dramatic shorelines.
The boats depart daily from May to October at 11:30am, 1:30pm, and 3:30pm.
Just off the coast of Rockport is the famous Thacher Island. The island has an incredible history including shipwrecks and even serving as home of a mafia hitman turned informant.
You can get to the island via boat or kayak, explore the scenery and even camp on the island from June 1st through September 15th. To learn more about Thacher Island you can take a peek at our Blog Post on Thacher Island.
Looking for some training on the dark arts so that you can pass Severus Snape’s course? Well, look no further than Salem, MA. A national historic treasure, Salem is home to some incredible architecture, history, and, of course, witches.
You can acquire all of your potion needs and even enjoy a delicious bite to eat at Turner’s Seafood or maybe Howling Wolf Taqueria. The town really gets hopping in October and a great way to visit is by staying in Rockport and taking a short commuter rail jaunt down to Salem.
While in Salem be sure to check out the House of Seven Gables, Witch Museum, the Peabody Essex Museum (a fantastic little museum) and maybe even head over to Salem Willow’s for some old time arcade action on the water.
A can’t miss stop when visiting Cape Ann is a tour of Hammond Castle. Former home and laboratory for eccentric inventor John Hays Hammond Jr., the father of radio control.
Hammond Castle is a fun romp for anyone interested in technology, history, architecture or artifacts. The great hall houses artifacts from the Renaissance that were collected by Mr. Hammond as well as a giant pipe organ.
But perhaps, the most enjoyable part of the tour is learning about some of the mischief Mr. Hammond got into around the home.
If you are coming to Rockport, do yourself a favor and take a peek at the Shalin Liu Center schedule. It’s well worth taking in a performance at this stunningly beautiful venue.
The performance center features a floor to ceiling glass backdrop overlooking Sandy Bay and the intimate 300+ seat venue has an impressive draw with acts such as Branford Marsalis, John Scofield, Tom Rush, Arlo Guthrie, Adam Ezra, and Del McCoury to name just a few!
Within walking distance to town, you can grab some food and drink at Brackett’s Oceanview or Feather and Wedge and walk a couple doors down to the performance. It’s almost too convenient.
If you’re heading up to Rockport for a few nights and are looking for an evening activity, consider purchasing tickets to a show at the North Shore Music Theater.
Located 20 minutes down the road in Beverly, the North Shore Music theater features theater “in the round.” Recent productions include: The Music Man, Little Shop of Horrors, 42nd Street and the annual performance of A Christmas Carol.
Gloucester Boat Rental has 5 boats that you can choose from to rent for the day! Rentals include a 19 foot Sea Pro, a couple of 19’ Grady White’s a 20’ Hydra Sports and a 21’ Striper.
They also offer rods and lures so that you can embrace your inner angler out on the historic Cape Ann waterfront that has been worked by professional fishermen for centuries.
But be careful out there by the Cut Bridge or you may end up living in infamy as a Cut Bridge Kook!
If you’re in need of some retail therapy, it doesn’t get much more classic than shopping on Bearskin Neck in Rockport. Here you’ll find a number of locally owned stores and a landscape that is almost like a time capsule. Take a leisurely stroll down the neck to the jetty and enjoy the fresh salt air.f
From clothing to food, sweets & ice cream to souvenirs and art, Bearskin Neck truly has it all. Take a closer look at some of our favorite shops.
One of the best things about the north shore of Massachusetts is the number of incredible beaches within a short drive.
While you’re up in Rockport you can take an excursion to visit some of the other local beaches such as Singing Beach in Manchester, Crane Beach in Ipswich, or Good Harbor and Wingaersheek in Gloucester.
In addition to beaches, the north shore of Massachusetts is home to some incredible breweries! Here in Rockport, we now have our very own brewery: The Rockport Brewing Company! You can find their beers in local shops like Sea and Cellar and Whistlestop Market.
Here is a closer look at 8 fantastic breweries on the north shore that you can visit: https://addisonchoate.com/blog/the-best-north-shore-brewery-our-top-8-favorite-microbreweries/
Looking for that coveted first edition Leaves of Grass? Or perhaps some early work from Sir Arthur Conan Doyle? We have you covered!
There are some fantastic bookstores in the Rockport area including Art Longwood Books, Manchester By The Book, Dogtown Books and the new Susie’s Stories on Bearskin Neck!
Learn more about the incredible independent bookstores on Cape Ann here: Best Independent Bookstores on Cape Ann.
Down off of Atlantic Ave in Rockport you will find a rocky outcropping referred to as The Headlands. It’s a great spot to visit to enjoy an al fresco lunch and relax for a bit. The views are spectacular and include Bearskin Neck, the jetty, and Rockport Harbor.
Watch the fishing boats come in and out of the harbor and the sailboat lessons while enjoying the refreshing coastal breeze and the warm sun.
Is there anything more quintessentially summer than enjoying an ice cream cone oceanside? We submit that there is not!
There is no shortage of delicious ice cream options on Bearskin Neck. Refreshing summer treats can be found at the Ice Cream Store, Robin’s Nest Gelato and Sundays Ice Cream. Grab a cone find a view and enjoy!
Speaking of views…Perhaps you want to ease into the day with the Sunday Times and tea with a view. Well, how about this gorgeous nook wedged between The Ice Cream Store and Bean and Leaf Café? Grab some tea or coffee and ease into the day with watching the birds over of the ocean.
What better way to relax and unwind then getting that lactic acid moving on a massage table. There are some fantastic massage studios in the Rockport & Gloucester area such as Salt Water Massage and The Well.
Services at Salt Water Massage include everything from deep tissue to cupping, hot stones, and CBD massages. While The Well offers deep tissue, acupuncture, reiki and craniosacral therapy.
The perfect ending to the perfect day is enjoying a cocktail and a delicious meal on the deck at My Place By Sea overlooking the water as the sun goes down. My Place is definitely a Rockport treasure that is worth checking out. But, be forewarned, getting a reservation can be a challenge. They only accept reservations same day starting at noon.
Ok take a time machine trip back to childhood and visit Rockport’s adorable fudge shop located on Bearskin Neck. Here you can embrace your inner Augustus Gloop!
Watch them make fudge the old fashioned way right on site and indulge in a variety of delicious flavors. Trust us, you’re not getting out of here without a tasty snack to fuel your travels!
If you’re thinking of heading over to Crane Beach, why not make a day of it and stop by The Crane Estate. Built by Chicago industrialist Richard Crane, this hilltop mansion sits on 2,100 acres overlooking the Atlantic.
In August and December, you can even embrace your inner Gatsby at the Crane Estate’s roaring 20’s parties! Go on old sport and head over to the estate, it’s worth a visit.
Cape Ann is home to some hallowed fishing grounds including Stellwagen Bank, Jeffries Ledge, and Straw Hat. If you’re ready to embrace your inner angler we’ve got you covered with some deep sea fishing!
Depending on your level of commitment you can head out for a half day, 3/4 day or full day.
One of the great things about staying in Rockport is that there are no Holiday Inns or Best Westerns in sight! Almost all of the inns, bed and breakfasts, motels and hotels are family-owned and offer the highest levels of hospitality, cleanliness and care.
If you’re going to visit Rockport, treat yourself to a stay in one of the many historic homes in town such as Addison Choate, Sally Webster, or the Seafarer. Learn about the history of the area and stay in a home that has housed generations of Rockporters.
Rockport takes Christmas seriously. From a live nativity pageant to shopping nights, festivals, and Christmas performances at the Shalin Liu you can’t help but get into the holiday spirit in this coastal village. Plus, you can catch old Saint Nick breezing into town on, what else but, a lobster boat. So you can come feel the warmth of the Christmas season in Rockport where Christmas is still celebrated the way it used to be.
Sea glass, beach glass, or mermaids tears, is glass that had been softened, and worn by the persistence of time, sand and the ocean. And, there is no shortage of this this treasure is certainly located on the shoreline of Cape Ann.
If you’re in the mood for an excursion, sea glass can be the perfect catalyst to get you off the couch and out in the wild. A few beaches to consider for your quest: Front Beach in Rockport, Pavillion Beach in Gloucester and Niles Beach in Gloucester. Happy hunting.
It’s no secret that Rockport is filled with some incredible makers. From painters to potters, glassblowers and everything in between! While in town you can try your hand at some crafts such as candle making at Rockport Candle Company! Or perhaps you are looking to improve your painting ability, you can always try out an online course from the Rockport Art Association. Based on how Saturday mornings went with Bob Ross, we are going to explore other hobbies.
Dogtown was an area of Gloucester that was created as a safe haven that was located away from the ocean front. It was primarily populated with the wives and widows of seamen and the dogs that protected them.
By the early 1800’s it was only elderly women, who were believed to be witches. When the population waned, all that remained were their dogs and their wild descendants.
Long after the last inhabitant passed, Roger Babson created a trail with 30 massive boulders etched by local masons with inspirations sayings. You can hike the trail, view the boulders and think about the storied history of the area.
Looking for something outside the box for a fun group outing? How about a scenic river excursion on on the Essex River! From May to October you can take an informative narrated cruse along the Essex River.
They offer a food and drink menu, including a bar, and they also have private charters for group outings, rehearsal dinners etc. They even offer clambakes on the beach! Learn more here.
Perhaps the best thing to do in Rockport is just to relax, unwind, and breathe in some of that good ocean air. Maybe its time to catch up on a book or two that you have been meaning to read or just spend some time with friends and family. Either way, Rockport offers the perfect setting.
We hope that you enjoyed our list of 40 fun things to do in Rockport, MA. And, more importantly, that you found some things to do that will help make your next trip to this coastal enclave more enjoyable.
If you have any questions about what to do on your next trip, our team here at Addison Choate would be more than happy to help point you in the right direction!