Despite having close ties to the South Shore of Massachusetts, the mister and I have developed a real love for the North Shore as well. I’m bringing you a mini series featuring guides to some of our favorite places up there, written by residents and fellow bloggers of each seaside town! We’re kicking off with Jen (@rockportgirl)’s weekend guide to Rockport– a town that really deserves more than a day trip if you can swing it…

At the tip of Cape Ann, often called “the other Cape,” lies the quaint New England seaside village of Rockport…

DAY 1

Start your day in the heart of the town at Brothers Brew for coffee and “Cape Ann’s Best Donuts.” From there you are centrally located to enjoy all of Rockport’s many boutique shops and art galleries– most of which are independently owned and many multi-generational.

Bearskin Neck, the narrow piece of town that juts into the ocean, provides the perfect stroll for sightseeing, people watching, and shopping. At the beginning of the Neck, stop into Wicked Peacock for the most unique jewelry and accessories. Further down, you can watch local artists at work in their studio and gallery at The Art Nook. At the historic Pewter Shop, you’ll find everything from locally made charms and ornaments to kitchen accessories. Bearskin Neck Leathers features leather shoes and other goods for men and women. The end of the Neck provides spectacular views of Sandy Bay– take a seat on a granite bench and enjoy the breeze.

Up for a quick kayak or paddle boarding around the harbor? North Shore Kayak on Tuna Wharf just off Bearskin is open 7 days a week.

Head back down the Neck for lunch in the rough on the back deck of Roy Moore Lobster Company where the special of the day is always lobster (BYOB and a lobster cracker for those in the know!).

Save some room for ice cream at The Ice Cream Store, housed in an old fishing shack and quite possibly the world’s cutest ice cream store with the best view.

Next, onto the very tip of Rockport and Halibut Point State Park. You’ll the history of Rockport’s famous quarry industry while taking in the amazing ocean views and walking trails around the quarry.

Yes, there is an abundance of seafood to be had in Rockport and you will want to get your fresh lobster fill! But few places have the sunset location like The Lobster Pool. Located just around the corner from Halibut State Park on the Gloucester border, this is a BYOB, picnic table, sunset viewing haven.

Tucked away on the shore between town and Halibut State Point is the historic grand hotel the Emerson Inn by the Sea. With oceanview rooms, it’s a quiet reprise from the day’s events.

DAY 2

Up for a sunrise? The Headlands, located at the end of Atlantic Ave, is a rocky outcropping overlooking the harbor downtown. Watch the boats sailing out for the day and an artist or two set up to paint the stunning view.

Fuel up at Helmut’s Strudel Shop back on Bearskin Neck with an iced cappuccino and a piece of warm strudel while seated on the outdoor deck overlooking the harbor.

A fixture in town since 1929, Tuck’s Candies has two locations, doubling your chance to stock up on homemade saltwater taffy and all sorts of chocolate-covered goodies.

Spend the day at one of the town’s most accessible beaches, Front Beach, a small crescent beach just outside of town. Calm water (and actual bathrooms!) make this beach popular with families and tourists. Swim out to the floating raft for views of town.

Right across the street from Front Beach is Nate’s. Step up to the surf shack-like takeout window where you can order everything from fried clams to cheeseburgers. For a break from the sun, take your lunch into the adjoining Millbrook Meadow and dine on the grass by the stream. After lunch, stroll through this hidden gem of a park and check out the dam and old Mill House.

Back to the Emerson for a quick shower and then its off to dinner before your show at the Shalin Liu Performance Center. A stay in Rockport is not complete without a show at this stunning recently-opened building. Acoustically perfect and with a stage that features a wall of windows with the ocean behind it, the center was built especially for summer night concerts.

TIP // Rockport is still a “dry town,” (no liquor stores), but a few places in town are BYOB, so stock up in Gloucester on your way in!

NOTABLE EVENTS

Hump Day Parties at My Place by the Sea, every Wednesday 5-9pm

FREE Rockport Cultural District Walking Tours, every day at 10am– meet in Dock Square

Rockport Farmers Market every Saturday 9am-1pm in Harvey Park until October

 You can find Jen sharing gorgeous photography and additional Rockport tips and to-do’s on Instagram at @rockportgirl. Stay tuned next week for more North Shore travel!

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