If you are looking for an easy and fun family road trip in the Boston area, definitely consider a drive to Rockport, Massachusetts. I’d lived in Massachusetts for over a decade before visiting this seaside town, but now we try to go at least once or twice a year. It’s a great day trip option in the Boston area and is a short drive.
It’s such a fun, quaint place to visit, and has lots of great things to do. This past Labor Day weekend, we headed out for one more summer afternoon in Rockport. Here are some of my favorite things to do in Rockport, Massachusetts.
Disclosure: This post contains affiliate links, including on the embedded map. Purchasing and/or clicking on some of the links may result in a commission paid to us. All opinions are our own. We attended a complimentary press trip to the area several years ago but have visited many times on our own.
Things to Do in Rockport MA
Like most outdoor destinations in Massachusetts, the small town of Rockport is best visited in the spring, summer, and fall months. Some of the shops and activities are seasonal, while few are open year-round. If you want to visit the beach, summer is really the best option, when there are plenty of things to do.
Location of Rockport MA
Rockport Massachusetts is a little town located on the Cape Ann peninsula, which is north of Boston on the north shore. It’s less famous than the more famous Cape Cod in MA, but is still beautiful with lots of great things to do, especially in the summer.
You’ll find both Rockport and Gloucester on Cape Ann within Essex County, MA. These towns are located on the tip of Cape Ann.
Bearskin Neck is the name of the downtown area of Rockport. This is definitely one of the places you’ll want to visit. When visiting Bearskin Neck, it’s best to park in one central location and then walk around. You’ll find public metered parking spots along the main street, as well as paid parking lots.
Go to the Beach in Rockport, MA
We don’t go to the beach in Rockport, but there are several options, including Front Beach, a small beach located right by downtown Rockport. I probably wouldn’t spend a whole beach day there, but it’s a nice spot to look at the water and enjoy a quick dip. There’s also Pebble Beach, which is lined with smooth pebbles.
Long Beach, another popular spot, is located in both Rockport and Gloucester. This beach offers lifeguards, and guests can see the twin lighthouses which are on Thatcher Island.
There are also several great beaches in nearby Gloucester. They would be great to visit if you are planning on staying in Rockport overnight, or plan to get up early and drive in for a beach day.
Our favorite sandy beaches in Gloucester are Wingaersheek Beach and Good Harbor Beach, which are perfect for a family. These beaches are very popular in the hot summer months, so I’d recommend going early to make sure you are able to get parking in the lots, especially on a sunny day.
Places to Eat in Rockport MA for Delicious Food
Seafood fans definitely won’t want to miss out on eating delicious, freshly-caught lobster in Rockport. Lobster rolls are probably the most popular entree in the area, but all of the local seafood, including the clam chowder, is delicious.
The most famous of the local restaurants in downtown Rockport MA is Ray Moore Lobster Co, which usually has a long line out the door. I love the lobster roll at Roy Moore’s. On one of our trips, we opted to eat at their sister restaurant, the Roy Moore’s Fish Shack Restaurant, which has indoor seating.
Our food was wonderful, and they have several kid-friendly options too. Save room for dessert though, because there are lots of cute ice cream shops within walking distance. Grab a cone from a local ice cream shop, and walk over to the Rockport harbor waterfront to take in the scenic views.
Other popular restaurants in Rockport include the Red Skiff Restaurant, the Whale’s Jaw Cafe, and the Blue Lobster Grille.
Shopping in Rockport MA
My favorite thing to do in Rockport, Massachusetts is shop. Bearskin Neck, which is the downtown area of Rockport, has lots of cute gift shops and boutiques. I often take the opportunity to buy unique gifts while I am in Rockport because there are so many different things that you just can’t find elsewhere.
My favorite of the Bearskin Neck Shops is the Pewter Shop, pictured above. It’s so quaint, and I always find great gifts there. It’s definitely worth walking through, especially if you are in the market for a gift.
The area also features art galleries. It’s a wonderful place to purchase from local artists, including painters, potters, and jewelers. On my last trip, I purchased a beautiful clay seashell filled with colorful blue resin.
Take Photos in Rockport, MA
Downtown Rockport is home to Motif no. 1, a red fishing shack that many claim is the #1 painted building in the US. The current building is an exact replica of the original.
With the waterfront, the fishing boats, and the quaint buildings, Rockport is a great place to take pictures. If you are an amateur photographer or have kids that like taking pictures, it’s the perfect spot for a photo walk. Even in the winter, the harbor is just so picturesque.
For those who want to explore the water a different way, Northshore Kayak offers rentals and tours. They are open from June through Labor Day. Kayaking would be a great way to enjoy a nice day on the water. They offer a variety of different options, including a kayak tour that includes a camping overnight.
Take a Walk
Right beyond Bearskin Neck are the Headlands, a short walk from downtown. There you can take a walk down a path to a rocky area where you’ll get to see fantastic views. It’s not a strenuous walk, but it’s a good idea to wear comfortable shoes.
Visit A State Park in Rockport, MA
Drive to Halibut Point State Park where you’ll find a visitor’s center and observation tower. On a nice, clear day, you may be able to see Mount Agamenticus in Maine and the Isles of Shoals in New Hampshire.
This former granite quarry also offers tours where you can learn about Rockport’s granite history. There’s a parking fee from May to October. Swimming is not allowed in the quarry.
Go on a Whale Watch
If you want to see whales, there are several options for whale watches in Cape Ann. These whale-watching trips depart from Gloucester and are generally about 3-4 hours long. One of the most popular whale watching companies is Cape Ann Whale Watch, but there are some other options. You can also book fishing charters in Gloucester, where you can enjoy ocean views and catch fish.
Tour the Paper House
As you drive out of Bearskin Neck, it’s worth a short detour to the Paper House if you are interested in quirky little roadside stops. This house, which was built in 1922, is made with paper walls and furniture. It’s a fun, unique tourist attraction, and is a quick stop.
It’s tucked away in a residential neighborhood and often operates on the honor system for the admission fee ($2 for adults and $1 for kids). Although it just has two rooms, my kids enjoyed seeing the layers and layers of paper. It’s open from 10 am to 5 pm through the spring, summer, and fall.
See lodging options on the map below and click to book (affiliate links)
Things to Do in Rockport in Winter
Most of the Rockport activities are best in the summer, but it’s still fun to visit Rockport in the off-season. While many of the restaurants and businesses do close seasonally, there are still some places open. It’s also much less busy and so easy to park.
A few years ago, we were invited to Rockport to attend their New Year’s Eve celebration, New Year’s Rockport Eve. This event features music, entertainment, and other activities. It’s a popular event, and most people in the area attend.
Have you been to Rockport, Massachusetts? What was your favorite thing to do?
Tuesday 13th of September 2016
Omigosh, I love Rockport SO MUCH! I went to college in Wenham, about a half hour away. I used to babysit for a family that had a home overlooking the ocean in Rockport. It was AMAZING. Such a cute little town to visit too. This post brings back happy memories.