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Located at the tip of Cape Ann, Rockport is literally at the end of the road, the epitome of “can’t get there from here,” with its dramatic, on-all-sides shoreline and incredible ocean views. 

That special “land’s end” feeling also gives Rockport its unique magic. There’s its world-famous sunlight, which has attracted plein air artists for decades; the iconic red fishing shack, Motif Number 1, known as the most-painted building in America; and the compact and walkable Bearskin Neck peninsula, which juts into Rockport Harbor and always manages to feel like a quaint fishing and artists' village, no matter how busy it gets in the summertime. 

“It almost feels like a town that you would see in a Norman Rockwell painting,” says Karen Koretsky, executive director of the Rockport Art Association and Museum. “I think, for people who come from other parts of the world, it’s what they imagine New England would look like. And then you’re beside the ocean to boot, which is incredible.”

Artists have long been inspired by Rockport’s natural beauty, and one of its most special places is Halibut Point State Park, a former granite quarry and WWII barracks that now provides one of the town’s biggest “wow” factors with a view over Ipswich Bay, says Ramona Latham, visitor services supervisor there. Because Halibut Point curves out with the Cape Ann peninsula, its views are of the Massachusetts, New Hampshire, and Maine coasts, including Mount Agamenticus in York, Maine, on a clear day.

“It’s a ‘wow’ view that is pretty spectacular and unique because you’re looking westerly and you can see the eastern coast,” Latham says. 

Halibut Point State Park | Photograph by Shutterstock

The 52-acre state park abuts other conservation land and includes roughly two miles of trails; a visitor center that tells the story of the land, including the Rockport granite industry; and a WWII gunfire tower. The spot is also popular with winter birders who flock to see wintering seabirds like the vibrantly colored harlequin duck.

Plus, the park’s entrance and entry trail are newly ADA compliant. 

“It has just added so much to the park to be able to encourage all abilities to come and get that wow view,” Latham says. “It’s an amazing little park with a great cultural history.”

Rockport also has options for people who want to explore the ocean itself. There’s Front Beach for those who’d rather stay on land instead of boat. North Shore Adventures offers kayak and bike rentals and kayak tours for people of all skill levels, from those who want to learn out on the water and stay close to the shoreline to those who want to explore some of the islands off the coast of Cape Ann. 

Photograph by Jared Charney

“Our most popular island is Straitsmouth Island,” says North Shore Adventures owner Clayton Kern. It’s about a 30-minute paddle and has a lighthouse that visitors can climb when it’s open in the summertime. Other popular spots are Thatcher Island, which is farther out to sea and has two lighthouses, and The Salvages, a set of rocks that’s home to a gray seal colony. 

Although kayak rentals are great for those who just want to get onto the water, taking one of North Shore Adventures’ tours offers a chance to learn kayaking, biology, history, and more with a guide. North Shore Adventures also partners with other local businesses to combine kayaking or biking with other activities, a tour with North Shore Brewery Tours, or a lobster boat excursion with Rockport’s Captain Jim’s Rockport Seaventure.

Shalin Liu Performance Center | Photograph by Jared Charney

Nature is naturally imbued into Rockport’s art and music culture, too. 

Rockport Art Association and Museum combines art and nature with its new set of historic walks and talks called “ramblings.” There are also new weeklong, nature-themed summer programs for kids, as well as free, drop-in family programs in gallery spaces “where families can make art surrounded by art,” Koretsky says. In addition, Rockport Art Association and Museum will host several art receptions this summer with food, live music, and a chance to gather with creative people and featured artists. 

Karen Koretsky | Photograph by Jared Charney

And, of course, there’s Rockport Music and its magnificent Shalin Liu Performance Center, which boasts the ocean as a backdrop for many of its concerts and shows. The annual Rockport Chamber Music Festival, running from June 9 to July 9, is just one of the many incredible events happening there this summer, says Karen Herlitz, Rockport Music’s director of marketing. It’s also hosting Rickie Lee Jones, the New England Brass Band, Tom Rush, Alicia Olatuja, Grace Kelly with Strings, and many other artists.

Rockport “has such a love of all the arts, and it draws people who are interested in that,” Herlitz says. “It feels like you’ve gotten the full mini vacation, even if it’s just a day trip.”