Ten Things to Do In & Around Rockport, Massachusetts

There is something about the northeastern coast that I love. The rocky coasts and clapboard houses, the old lighthouses and lobster traps offer a dose of old-world charm that you won’t find just anywhere. I’ve been lucky enough to visit a number of the towns that dot the coast from Boston to Bar Harbor. One of my favorites is Rockport on Cape Ann.

Located about 40 miles northeast of Boston, Rockport is the easternmost town on the cape.   The harbor still has an active fishing fleet, and visitors can watch lobstermen hauling their catch.  Unlike the more commercial fishing town of Gloucester (Think Gorton’s.), Rockport is more laid back and artsy.  Summer is an active time in Rockport, and there are many activities in both the town and immediate area.


Walking is relatively easy, free, and fun. I recommend finding a place to park in town and using your feet for transport. The Rockport Chamber of Commerce has a guide that outlines seven (SEVEN!) scenic walks that will take you everywhere from Bearskin Neck to Dogtown to Cape Hedge, along the Atlantic Path,  and through Halibut Point State Park.   Enjoy the scenery and breathe in fresh coastal air.

One of Rockport’s beaches


If you are a swimmer, check out Rockport’s two public beaches. Close to the downtown area, both are free to the public.  The water is calm, and the beaches are clean and not as crowded as I would have thought.  When I was there, I noticed that, in addition to swimmers,  people were sitting on the large granite boulders  just enjoying the sun on their faces.


If you love to be on the water, renting a kayak or boat might be just your thing.  You’ll find places all over Cape Ann where you can rent kayaks, take a lesson, paddleboard, etc.  Personally, I like the bigger boats where I can just relax and enjoy the sites as we pass by.  There are options that will take you around the area, and one or two that are shuttles around Gloucester.  One of the boats, the Ardelle, is an historic schooner.


I’m quite taken by these large creatures, and there are a number of companies that do whale watch tours out of Gloucester.  I didn’t have time to take one, but I overheard a number of people talking about how much they enjoyed their tours.   If you’re lucky, you’ll see seals, puffin, and a variety of whales.


You have to figure that if an area is popular with commercial fishermen, it must have good fishing.  If you like deep sea fishing, there are a number of companies that will take you out for half- or all-day fishing adventures.  Yankee Fleet offers everything from half-day to marathon fishing events.


There are, believe it or not, a number of museums on the cape that you can visit.  You’ll find everything from the Shipbuilding Museum in Essex to The Paper House in Rockport, from the Manchester Historical Museum to Maritime Gloucester, and more.


The cape hosts a number of festivals all summer, so if you’re lucky, you’ll time your visit for one of them. I had planned to go to a festival (St. Peter’s) in Gloucester while I was in the area, but after I drove around for almost an hour trying to find a parking spot, I gave up and went back to my hotel.  Moral?  Time your arrival so that you can actually find a parking spot and attend the festival.


Shop the boutiques

Let’s be honest. You can’t go to a town like Rockport and not shop in the eclectic mix of stores that line Bearskin Neck and the harbor.  I found that a good majority of the businesses I visited in Rockport and Gloucester are local businesses. Yes, there are a few chains, but for the most part, the boutiques and stores are locally owned.


As you would expect, there are seafood restaurants throughout Rockport and the cape. While I don’t like fish, I’ll eat some seafood (as long as it’s not staring at me from the plate….whole lobster or crab, for example). Roy Moore’s Lobster Company, a small walk-up restaurant on the main drag in Rockport, called out to me, and I did try a lobster roll.  Full of lobster covered in melted butter (not mayonnaise!), the sandwich was delicious.

The perfect lobsta roll

Christine Cutler

Writer. Photographer. Editor. Guide. Teacher. Traveler. Ohio Native. Nevada Resident. World Citizen. That’s me wrapped up in a less-than-neat yet ever-changing package. I live in Las Vegas with my husband and our crazy Welsh Terrier, but I can't sit still very long. I'm always ready for my next adventure. When I’m on the road, I post to my blog daily, and the rest of the time, I publish 3-4 times per week with reviews, interviews, and travel advice. Follow me at www.coldpastaandredwine.com