Rockport Massachusetts 15+ Family Things To Do

15+ Family things to do in Rockport, Massachusetts. Things to see, places to visit and other travel trips for a great family getaway.

Visiting back home we always try to find a happy medium between visiting with family and showing our kids where we use to grow up. Sadly, we don’t get to visit as much as we’d like but hopefully in the future that will change.

On our last trip home my husband and I each choose a few special places we wanted our kids to see. Places like Maudslay State Park, Hampton beach and my favorite, Rockport, Massachusetts.

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This seaside village is known for its rocky beaches, small boutiques, fishing boats and art galleries but growing up it was just where we use to visit on a Saturday afternoon.

After a picnic lunch at Halibut State Park, we’d journey off to the rock quarry and us kids would explore the large boulders along the Atlantic coast and find tide pools filled with tiny creatures. After a tiring afternoon at the park, we’d continue our adventure to the popular spot of Bearskin Neck for a little shopping and ice cream.

Here we’ll cover some of the best places to visit, explore, and photography while visiting this charming New England town of Rockpork, MA.

Shopping at Bearskin Neck, Rockport, MA.


Halibut Point State Park

Located on the northern tip of Cape Ann, Halibut Point State Park is a great place to stop and stretch your legs. This state park offers a well maintained walking path to a beautiful visitors center where you can learn more about the park. At the visitors center you’ll also find picnic tables and a large quarry in front of you that was in operation until 1929.

Halibut Point visitors center.
Quarry at Halibut Point State Park.

The path will continue down to the ocean where you can explore along the rock shelf and take a moment to view the tiny creatures in each tide pool. -View trail map-

Be sure to check out the scenic vista overlook where, on a clear day, you can view all the way to Mount Agementicus in Maine!

Trail to the ocean at Halibut Point State Park.
Walking along the rock shelf.

Travel Tips- You’ll want proper footwear once you get down to the rock shelf. These rocks are a lot of fun to walk around but they are large and can be slippery when wet.

Parking- Pay to park at kiosk. (no cash) There are 70 parking spaces available. If they do happen to run out of parking they will close the parking lot for 2 hours. In which case you can explore other parts of the town.

  • MA resident $5
  • Non-MA resident $20 (determined by vehicle license plate.)
  • Vehicles with Disabled Veteran, Purple Heart plates, and disability Placard/plates park for free with both MA and non-MA plates.
  • Displayed Senior Citizen Pass
  • You may also be able to check out a day pass at your local library -View more information about parking, here-

Bearskin Neck

Visiting Bearskin Neck is like taking a trip back in time to those little shops and boutiques you can only dream of. The streets are lined with rustic storefronts including a country store, several boutiques, restaurants, toy stores and so much more.

Bearskin Neck in Rockport Massachusetts.
Shops lining Bearskin Neck in Rockport Massachusetts.

At first, you may just need a moment to take it all in. But once you gather yourself together you’ll want to visit every single shop and art gallery you come across.

Pro tip- Inside the Country Store you’ll find an old piano and one man band behind a display glass that will play you a catchy toon for a few quarters. You’ll also find a wall of penny candy along with other old time favorites, so be sure to stop in for a look.

There are many popular shops along the way including The Pewter Shop, Floating Lotus Rockport, and Happy Whale Toys and Games, just to name a few. Since you’re walking down the street to the end of a peninsula, you can also stop in on your way back through town.

Stores lining the streets of Bearskin Neck, Rockport.
The Floating Lotus and other stores.

Be sure to check out some of the great restaurants and coffee shops in town also. Some favorites being the Bean and Leaf Cafe, the Ice Cream Store, Tuck’s Candy Factory and Roy Moore Lobster Company along with several other great spots.

Rockport Breakwater

Rockport breakwater is located at the end of Bearskin Neck peninsula. These giant, relatively flat, boulders create a pier that is roughly ⅛th mile long. With the proper footwear, you are able to walk out to the end of the breakwater and see the harbor from a different point of view.

View of the harbor from Rockport Breakwater.
Sailboats along the harbor.

Note- Although you are allowed to go to the end of the breakwater, there is a sign warning to proceed at own risk. This area is not for young children.

Rockport breakwater pier.

Photograph Motif Number 1

Located on Bradley Wharf, Motif Number 1 is said to be “the most often painted building in America.” And with good reason. This weathered red fishing shack was a favorite among those in the art community and has been painted and photographed many times over the years.

Motif Number 1 Rockport

The original structure was built in 1840 but was later destroyed by a blizzard in 1978. A replica was constructed that same year and people have been enjoying this building that encompasses the beauty of a New England fishing village.

How to get there- You can view this building from two different locations. The first location is off of Bearskin Neck where you’ll see a red store called The Pewter Shop. At a 90° angle is a small road to the right called Bradley Wharf. From there you can walk to the back of the building and see Motif Number 1.

View of Motif Number 1 from the Sandy Bay Yacht Club.

Another great spot to see this building is across from the Sandy Bay Yacht Club located at 5-T Wharf, Rockport, MA. As you head out of Bearskin Neck take a left onto Mt. Pleasant St. along with another left onto T-Wharf. From there walk to the end of the road and you’ll see this stunning red building on the lefthand side.

Rockport Art Association and Museum

The Rockport Art Association was formed in 1921 and is open to the public. Being located right on Main St. it is within walking distance from Bearskin Neck and a great place to spend a quiet afternoon. There is a small admission fee to enter but seniors and children are free.

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The Shalin Liu Performance Center

The Shalin Liu Performance Center is a concert hall like you’ve never seen with music ranging from classical, jazz, folk and everything in between. Not only does this hall offer great music, they also have one of the best views you could ask for while enjoying your evening.

Docked boats along the bay with the Shalin Liu Performance Center in the background with large windows.

Behind the stage is a wall of glass with the ocean and shoreline creating art behind the performers themselves. Crashing waves, beautiful sunsets, and music you’ll love make this one evening you won’t soon forget. You can view the Shalin Liu Performance Center calendar here.

The Paper House

The Paper House is a bit of a quicker stop but an interesting one nonetheless. Built in 1922, by Elis F. Stenman, this house started as a hobby and became much more along the way. The framework is wood along with the floor and roof but the walls are layers of paper that have been varnished to keep them waterproof.

Inside you’ll find interesting pieces of furniture made of of rolled paper logs. Furniture such as a piano, clock, desk with chair and several other pieces you’ll just have to see for yourself. The Paper House is open from the spring until the fall and does have as a small admission of $2.00 per adult and $1 for children 6-14. -View directions and admission here-

North Shore Adventure and Outdoor Center

You can find North Shore Adventure right on Bearskin Neck located just past the Fudgery. Here you can rent kayaks, bikes, stand up paddle boards and more. They also offer guided island tours and have knowledgeable guides for even the novice kayaker.

North Shore Adventure storefront at Bearskin Neck.

If you’re looking for even more adventure check out their package deals with other local companies to include stand up paddle boarding and a brewery.

Captain Jim Seaventure Lobster Tour- Take a lobster tour with Captain Jim where he’ll share his knowledge of catching lobsters while you pull in some lobster traps and enjoy the waters around you. If you’re lucky you may even spot a whale on the horizon.

Thacher Island Twin Lighthouses

Thacher Island is a small island off Cape Ann that is made up of 54 acres. On the island are two lighthouses also knows as twin lighthouses. This island is named after Anthony Thacher and his wife who survived a shipwreck in the Great Colonial Hurricane of 1635. Sadly, their 8 children died along with everyone else on board.

This island has taken many victims over the years and in 1771 they constructed two lighthouses. Only a few years later in 1775 the lights were destroyed by a group of townspeople who felt that the lighthouses were helping the British fleets but were later rebuilt in 1861.

Rocky beach along Rockport.

Today you can visit the island and they even offer camping from June 1st-September 15th and have three miles of walking trails. Kayaking to the island is not recommend for beginners but you can catch a tour with one of the companies in town. -View more information on hours of operation and how to get there, here- You can view Thatcher Island and their lighthouses from the shores of Pebble Beach or Cape Hedge Beach.

Rockport Beaches

There are a few Rockport beaches you can enjoy on your day trip but several of them have very limited parking or require a resident sticker. Some of the easier ones include Front Beach and Back Beach.

Front Beach- Front Beach is a beautiful sandy beach to enjoy some ocean therapy and is within walking distance to shopping and restaurants on Bearskin Neck. Paid on street parking is available both in front of the beach and on the streets nearby.

Front beach in Rockport, Massachusetts.

Back Beach- Back Beach is a favorite among scuba divers and also close to downtown shopping. Here you’ll find paid on street parking. -More information on beaches and parking, view here-

Other beaches include:

  • Old Garden Beach- Restricted parking. Limited on street parking nearby.
  • Pebble Beach- Restricted parking. Limited parking available on Penzance Road.
  • Cape Hedge Beach- Parking lot restricted to residents. Limited non-resident parking on South Street.
  • Long Beach- Parking lot restricted to residents only. Private lot available seasonally accessible from Rock-Port Road in Gloucester.
Kayaks in the harbor with sailboats in the background.

PRO TIP: Parking in downtown Rockport can be tricky. You may get lucky with on street paid parking but if you happen to come when it’s a bit more busy, try taking the Rockport Shuttle. The shuttle bus has conviant parking areas and drop off locations and is affordable at only $1 per ride. -More bus information here- Note: Exact change needed when boarding.

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Castle Hill On The Crane Estate-

Tour the great house and gardens on the beautiful Castle Hill On The Crane Estate in Ipswich, MA. This gorgeous estate sits on 365 aches of manicured gardens and feels like it is straight out of a fairy tail. Advance ticket purchase is recommended but they do offer tickets on site on a first come first serve basis. -View more information here-

Hammond Castle-

Hammond Castle is a European Castle that sites on the shores of New England and is nothing like you’ve seen. It was built in the late 1920’s by John Hays Hammond Jr. and overlooks the Atlantic ocean. Here they offer both guided and self guided tours. There is a general admission fee but you can visit a portion of the grounds without a ticket. -View more information here-

Motif Number 1 with lobster traps lining the pier.

Rockport Massachusetts is a seaside village that is second to none. With it’s rich history, historic buildings and family friendly environment, there is truly something for everyone in this breathtaking town.

So take the trip and discovery some of your own favorite things to do in Rockport, Massachusetts.

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