Rockport, Mass: A Bright and Funky Seaside Town

By Devinne Zadravec

Home for me has always been Massachusetts, and yet there are still so many incredible places within New England and even my own state that I have yet to explore!

So, naturally, when the chance to visit the iconic Massachusetts town of Rockport came my way, I jumped at the opportunity.

I knew very little about Rockport before my trip. I had seen paintings and pictures of the iconic red fishing shack, adorned with colorful buoys, and posed against a backdrop of the ocean. I had heard that it was a very “artistic” town, though I didn’t know if this referred to the setting or community.

I also knew it was once a historically dry town—meaning that no alcohol was served within the town borders– and a small part of me believed that a town with a ban on alcohol might be a bit old and stuffy for a young twenty-something like myself.

Heading for the Coast

Braced with my preconceptions, my friend Kaylyn and I headed off for the coast. It looks… nice, was my first thought as we entered the town. Lots of old colonial houses, cute storefronts, plenty of seafood restaurants.

As my old car chugged up a hill towards our bed and breakfast, I caught a beautiful glimpse of the ocean in the spaces between some of the old homes.

Our lodging was at the historic Seven South Street Inn, a charming B&B situated a mere quarter-mile from downtown and that offered a sumptuous 4-course breakfast every morning.

We were very comfortably lodged in a first-floor suite with its own private entrance, a queen bed, bathroom, television, and some very fluffy bathrobes at our disposal. Eager to begin exploring the town, we dropped our bags and made our way back to the reception area to beg a professional opinion of what we should check out first.

A Path Through Town

Our gracious host Jim was more than accommodating, providing us with a map of the town and outlining a favorite path to take down into town that passed through a little park perched on an overlook of the harbor.

As promised, this truly was the scenic route into town. We passed through a couple of quiet residential streets, immaculately kept houses both new and old lined gracefully on either side of the road, and within a couple of minutes, we emerged onto the main drive that ran parallel to the ocean.

Something about travel, beautiful weather, and a salty sea breeze just does wonders for one’s spirits, and we found ourselves rather giddily stepping onto the hidden park path our friend at the inn had shown us.

“Today is just perfect!” I called over my shoulder, inhaling deeply in appreciation of the warm sea breeze. I didn’t turn around but I knew that Kaylyn was in agreement and equally content with our surroundings.

Picking our way carefully over rocks and some muddy spots on the trail, we soon stepped out onto a large rocky outcrop, the overlook park that stood sentry over the harbor.

The views were stunning, both of the ocean and the town, and we quickly agreed to return to this same spot later in the evening to watch the sunset and take some photos. The trail picked up again on the other side of the cliffs and put us out on the road that bordered one side of Rockport Harbor.

Just across the water, we caught our first glimpse of the weathered red fishing shack, the famous “Motif No. 1”, adorned with brightly colored buoys just like I had seen in paintings.

Plenty of Photographers

Boats bobbed gently in the current as I snapped a few pictures, and I noticed I wasn’t the only one who has stopped to take in the view. On our small stretch of pier alone were three other photographers, all boasting impressive equipment and snapping photos with the practiced and confident air of someone who takes photos for a living. It was obvious that we had entered the artistic part of town, Rockport’s true claim to fame.

At this point we tucked away our map and continued navigating our way down town like true tourists, pausing in every store window to admire the displays and scouting every restaurant menu as a possible lunch destination. Our first official stop was the Bean and Leaf Café, where we would be meeting one of Rockport’s locals for a tour.

We hadn’t so much as crossed the threshold when a friendly-looking woman with a small daypack waved to us from the corner of the front stoop. “Are you Devinne?” she asked at the same moment I said, “Are you Sue?”

It was enough of an introduction. We all broke into smiles and offered up handshakes, and then went together into the café.

Our meeting spot was also our first stop on our tour, and as a self-proclaimed coffee connoisseur, I was quite excited to sample the local offerings. The shop itself was the definition of seaside quaint, the walls all done in shades of pastel blue and green, and large windows in the back offering an unparalleled view of the cove.

The café served a variety of drinks and foods, from traditional coffee and espresso to juices and smoothies, from pastries to salads and sandwiches. I opted for an iced coffee and a butter pecan pastry, both of which were delicious.

Walking Rockport

Thusly nourished and caffeinated, we headed back out onto the street to begin our walking tour of Rockport. While not particularly sprawling, there are plenty of shops, restaurants, galleries, and other attractions all within walking distance of downtown Rockport.

Rockport is a town immensely rich in both history and culture. It was officially founded as a town in 1840 and gained prevalence as a seaport through its thriving granite industry. Even after the demand for Rockport’s granite diminished, before the turn of the century,  it remained established as a thriving artist colony.

Sue explained how this legacy is what brought her and her artist husband to Rockport in the first place. “Rockport’s location is what makes it so special for artists,” she said. Located on the Cape Ann peninsula, the town is surrounded on three sides by water—and receives light like almost no other location in the country. “The light here is beautiful, any time of day. That’s what draws in so many of our artists,” Sue said.

Artists of all kinds have made a home out of Rockport. We witnessed painters, jewelers, potters, photographers, their galleries all proudly displaying works inspired by Rockport and the surrounding area.

Performing artists, too, have flocked to the town, and we stopped along one sunny stretch of sidewalk to admire Rockport’s famous Shalin Liu Performance Center.

Concerts at Shalin Liu

The hall holds a variety of music concerts throughout the year and is renowned for its beauty and design. Peering through the windows, we could see the concert chamber, done almost exclusively in soft wooden tones and its entire back wall a giant window overlooking the sea. It was too easy to see how this small and intimate venue was a special point of pride for the town.

We continued traversing the streets, admiring old colonial homes and views of the ocean, and Sue continued to dot our conversation with interesting historical anecdotes.

My personal favorite of these was the true story of Rockport’s dry town heritage, a policy that was created when a group of local women banded together to destroy spirits in town that were excessively consumed by the men during the harsh winter months when they could not set sail to fish.

It was all too easy to imagine this band of women, armed with hatchets to take apart any keg of liquor they could find, storming around town and taking matters into their own hands.

At every turn, Rockport was a surprising gem of a town, and I found myself engaged in every historical anecdote, enthralled with every sprawling ocean vista, and enjoying every funky art gallery we toured.

I was also duly impressed by just how friendly everyone was– shop and gallery owners greeted us and our guide personally everywhere we stopped, and even random passersby would wave and offer a friendly greeting.

Bear Skin Neck, Rockport

Our tour finished on the end of Bear Skin Neck, the long wharf that houses the densest area of downtown Rockport. We made our way slowly down the strip, popping into any store that caught our eye and chatting with the locals.

Taking a recommendation from our guide, we also stopped for a bite in Rockport’s famous Roy Moore fish shack, a simple and immensely popular seafood joint downtown. Even at the unconventional hour, we chose for lunch, it was obvious that this was one of Rockport’s top eateries, and the waterfront out back was lined with people of all ages enjoying the fresh seafood.

After lunch, we wanted a change of pace for our afternoon explorations, so we walked back to the inn to collect the car and drove to Halibut State Park. The drive was short but scenic, following a winding road along the coastline, and we arrived within ten minutes from leaving downtown.

Hiking by the Quarry

We found ourselves occupied with the many hiking paths and hidden viewpoints for the rest of the afternoon. The terrain was accessible for people of all ages and varied from wooded paths, coastal treks, and a loop around one of Rockport’s famous quarries.

Wind from the sea made us glad for our jackets, but we spent nearly three hours comfortably exploring and admiring the views from the many vantage points within the park.

We finally made our exit, leaving only to find a place to eat dinner but wishing we had more time to spend exploring the paths of Halibut.

We were not, however, quite yet ready to forgo the beautiful scenery, and so rather than dining in a restaurant we order a surprisingly good pizza from Seaside Pizzeria and enjoyed our slices as a picnic at the overlook we first stopped at leaving our B&B that morning.

With the sun slowly setting over the harbor, it was a beautiful evening and the perfect way to end our day of exploration.

Four-Course Breakfast

A great night’s sleep had us ready and refreshed for our final day in Rockport, and it began with a decadent breakfast served at our inn. The four-course meal is the Seven South Street Inn’s claim to fame, and we were served everything from tropical smoothies, to fresh pastries, and fluffy french toast.

Other guests at the inn joined us at the communal table for breakfast, and we enjoyed the opportunity to chat with other travelers as we enjoyed our food together at the single large dining room table.

And while we wished for more time, when we left we also felt like we had experienced enough in our full day there to make it a memorable trip, and are both eagerly awaiting another sunny summer day when we can return.