Experience Peak New England Charm in This Coastal Massachusetts Town
Rockport is a prime example, full of storybook houses, sandy beaches, and winding streets—it’s as New England as you can get.
Boston is considered the heart and soul of Massachusetts to many visitors, but the Bay State is brimming with seaside towns that are often unjustly overlooked. Only an hour North of Boston, Rockport is a prime example, full of storybook houses, sandy beaches, and winding streets—it’s as New England as you can get.
At the tip of the Cape Ann Peninsula, Rockport is surrounded by the Atlantic Ocean on almost all sides, making it a seafood-lovers paradise. It’s definitely worth a visit year round, but spring and summer is when Rockport truly comes alive. With small fishing vessels circling, seagulls roaming the skies, kayaks along the shore, and the air full of the smell of freshly caught lobster, it’s the perfect spot for those looking for a little rest and relaxation while delving into the excellent food scene and outdoor activities.
One or two coffee shops, artist hideouts, antiques, quaint restaurants, and a few bars—it’s almost reminiscent of Stars Hollow (for those in the know). “We often describe Rockport as Rockwellian,” explains Marshall Tulley, owner of Addison Choate Hotel. “It has a classic American small-town vibe that is very special. All of the shopkeepers and artists will welcome you into their stores and galleries and tell you their story. The historic buildings give the town a feeling like it is frozen in time.”
Here’s how to make the most of your trip.
Travel time:
52 minutes from Boston
10 minutes from Gloucester
If you don’t do anything else: Browse the local art galleries and stroll along historic Bearskin Neck
Bearskin Neck is no doubt Rockport’s central hub. It takes about 10 minutes or so to walk the entirety of the charming street—but you’ll definitely need more than that to thoroughly explore the pedestrian-filled road. Quaint storefronts on either side with sneaky views of the ocean between each building, the narrow street leads directly to a gorgeous rock-wall along the water that makes for a perfect escape after the hustle and bustle.
If you’re a fan of local artwork, you’re in for a treat. Home to over 30 galleries with works of art depicted by over 400 artists in the area (many of which are on Bearskin Neck and Main Street), Rockport’s art scene is just as ‘small-town vibey’ as the town itself—every artist seems to know one another. Incredibly friendly, artists will beckon you in to explore their creations and tell you their story. Most of the artwork in the area draws inspiration from Rockport’s surroundings—but no two are ever the same. That’s the fun thing about the art scene here. You can wander up and down the streets as many times as you want, and still find a piece you haven’t seen.
Fill your days:
Beaches near Rockport
You can’t visit a beach town without doing a little beach hopping. After doing a little shopping and lobster roll sampling, you’ll want to head over to Front Beach. Just a short walk from Bearskin Neck, this local spot is a cozy alcove with views of the town. Sandy shores mixed with rock formations make it an incredible beach to bring the family for some exploring.
Though not as popular as its neighbors, Back Beach is a short walk away and is a quarter-mile stretch of shore that often disappears during high-tide. Though a little rockier than most, Back Beach is actually home to one of the most popular dive sites in Massachusetts. Speaking of diving fun—Old Garden Beach is another popular training site, so it can get quite busy on weekends. Close to the town, it’s not necessarily the best sunbathing beach, but it’s definitely worth the visit.
Outdoor activities near Rockport
Whether you have a car or simply want to walk and explore, the beauty of Rockport won’t disappoint. Sure, the New England architecture, narrow streets, and galleries are a draw. But there’s a whole other side of Rockport that is often overshadowed by its beaches and charm.
Surrounded by the ocean in almost all directions, Rockport actually has some of the best outdoor activities and hikes. The infamous Halibut Point State Park is a unique coastal seascape with sprawling views as far as Crane Beach. The drive from Rockport town is a mere eight minutes, while walking will take a little over an hour. Though both viable options, one of the best ways to see Rockport and its surrounding landscapes is definitely by bike.
As mentioned above, Back Beach is one of the best dive spots around. Juvenile flounders, lobsters, and squid. Rockport doesn’t earn the reputation of some of the best seafood in Massachusetts for nothing. If being underwater isn’t your thing, then on top of it may be better. Believe it or not, MA is home to many species of whales (and sometimes sharks)—so a whale watch is a good bet. Depending on the season, if you leave from Rockport you’re likely to see Humpbacks, Finbacks, and Minke Whales.
“One of our favorite adventures is going out on the Rockport SeaVenture Lobster Boats pulling traps, visiting the seals, and learning about the history of the town and islands. There are two islands with lighthouses just off the coast, Thacher Island and Straitsmouth Island. You can take shuttles or kayak out to them, tour the grounds, and even visit the lighthouses,” says Addison Choate owner, Marshall Tulley.
Eat, drink, and sleep:
Restaurants & bars in Rockport
Ocean vistas, wandering gulls, and the smell of sea salt at every turn, it’s pretty impossible not to crave seafood when you’re visiting Rockport. If you’re strolling along Bearskin Neck, don’t forget to visit Roy Moore lobster Co. The tiny shack catches lobster and serves them up right there and then—you won’t find anything fresher. If you want something slightly cheaper, Bearskin Neck Bistro has plenty of seafood too.
Head on over to Feather and Wedge at night. Not only will you find good cocktails and delicious bites, there’s a wrap-around bar that makes it surprisingly easy to chat to the locals and fellow travelers. Bean & Leaf Cafe is incredibly cute for grabbing a coffee by the sea, and the Ice Cream Store serves as a treat for a midday snack. Yummy year-round, Helmut’s Strudel hits a little differently during the cooler months.
Where to stay in Rockport
From seafront hotels to cozy inns and campgrounds, you won’t run out of options of places to stay in Rockport, but be sure to book in advance if you’re traveling during peak season (June-August) as they tend to get booked quite early.
Hospitality and coziness can be found at family-owned boutique hotel, Addison Choate. Limited rooms on site make for a truly intimate stay. Owners Marshall and Courtney Tulley have done a superb job renovating the central property and making it a welcoming place for all. The warmth of the hotel is noticeable upon arrival, with a wrapping veranda laden with hanging flowers. Inside you’ll wonder if you’ve stepped into someone's home or a hotel.
No two rooms are alike. Pops of color, communal spaces, and quirky finishings—there’s a small nook for everyone. You’ll find a maze of rooms on the first floor filled with art, trinkets, and all the furnishings expected in a family home. Breakfast is also delivered in the morning.
With sprawling Ocean views and nautical-inspired rooms, The Cove at Rockport is another option if you want to be directly along Front Beach. Rockport Inn and Suites and Seafarer Inn are also near town. Rockport Inn is a short walk from the center, with ample outdoor space and an indoor pool perfect for families. Seafarer is slightly off-the-beaten-path, near Gully Point Cove and Gap Cove.