The small town of Rockport, Massachusetts is located about 40 miles (64 km) northeast of Boston at the tip of the Cape Ann peninsula. This charming New England town has a population of less than seven thousand but invites tens of thousands of tourists from the United States, Canada, and other parts of the world every year.

Main Street and Bearskin Neck

Rockport, MA is surrounded on three sides by water. The main street going through town, called Bearskin Neck, has dozens of quaint shops. Bearskin Neck is named after a legendary skirmish between man and beast, in which a menacing bear was slain and skinned with a knife.

There are plenty of seafood restaurants in the vicinity, including the famous Roy Moore Lobster Company (I recommend getting the lobster roll here. There are actually two locations in Rockport: Roy Moore's Fish Shack is at 21 Dock Square, Rockport, MA 01966; Roy Moore Lobster Company is at 39 Bearskin Neck, Rockport, MA 01966).

Photos from my visit to the fishing village of Rockport, MA are below.

Rockport, MA preparing for the Independence Day celebration.

Views of flowers on Main Street, Rockport.

A storefront with flowers and glassware for sale.

A gravel-lined walkway to a gallery on Bearskin Neck in Rockport, MA.

View of the main street in Rockport, MA: Bearskin Neck.

With street names like "Tuna Wharf," you know you've made it to a fishing village.

One of the many galleries in Rockport, MA.

Helmut's Strudel in Rockport, MA. The delicious smells wafting out of this quaint shop were hard to resist!

An entrance to a store on Bearskin Neck.

The summer months are interesting in the New England area: weather can fluctuate rapidly. On this particular day, the day began with rainfall and was cloudy throughout the morning. However, by mid-day, the sun was shining bright.

Exploring the Headlands in Rockport, MA

One of the must-see detours in Rockport, MA is a walk along an area known as the Headlands. The Headlands are outcroppings of rock on the other side of the town, allowing you to take in beautiful views of the town.

To get to the Headlands from Bearskin Neck (Main Road), walk south on Mt. Pleasant Street and then turn left on Atlantic Avenue. (NOTE: Atlantic Avenue is a one-way road, so if you drive to the Headlands, take the next street south, Norwood Avenue and then look for parking on Old Garden Road near Old Garden Landing). If you are walking on Atlantic Avenue, there will be a sign marking the trail to the Headlands from the last house on the street on Atlantic Avenue.

Map of Rockport, MA. To get to the Headlands (blue icon on the upper right), walk from Bearskin Neck via Pt. Pleasant Avenue and Atlantic Avenue. There will be a sign marking the trail to the Headlands from the last house on the street on Atlantic A… — Map of Rockport, MA. To get to the Headlands (blue icon on the upper right), walk from Bearskin Neck via Pt. Pleasant Avenue and Atlantic Avenue. There will be a sign marking the trail to the Headlands from the last house on the street on Atlantic Avenue.

A few photos from the Headlands exploration are below.

Detail from a house on Atlantic Avenue. I suppose one of the men working for Rockport's Fire Department lives here.

Approaching the Headlands on Atlantic Avenue in Rockport, MA.

Rockport, MA as seen from the highest point in the Headlands.

Waves crashing on the rocks in the Headlands.

Enjoying the views at the Headlands in Rockport, MA.

Native daisies growing near the Headlands in Rockport, MA.

Wider view of the Atlantic Ocean and native daisies growing in Rockport, MA.

Old Garden Landing and Old Garden Beach

If you continue southeast from the Headlands, eventually you will approach Old Garden Landing and Old Garden Beach, a small sand and stone beach with an adjacent municipal park. This area offers an expansive view over Sandy Bay. There is a cozy grassy area at the Old Garden Landing and there are picnic tables to enjoy a breakfast or a picnic lunch.

Views from Old Garden Beach in Rockport, MA.

Views from Old Garden Beach toward the center of Rockport, MA.

A view of Rockport, MA in the distance from the Old Garden Landing.

Walking in Rockport, MA

Rockport, MA is quite wonderful to epxlore by foot. From the Old Garden Beach, I took some of the other streets in town to get back. I took Harraden Avenue, Clark Avenue, and Norwood Avenue to get back into town center.

A few photos from that stroll are below.

Another house seen in the "suburbs" of Rockport, MA. The patio overlooks the Atlantic Ocean.

By mid-afternoon, the sun was shining bright and this mailman was feeling the heat.

Harbor Views and Motif Number 1 in Rockport, MA

One of the most interesting facts about Rockport, MA is the structure known as Motif Number 1. Located on Bradley Wharf in Rockport, this structure is a replica of a former fishing shack well known to students of art and art history as "the most often-painted building in America." Motif Number 1 was built in the 1840s during the time that Rockport, MA was becoming a home to a colony of artists in the area. This shack (or barn, if you want to call it that) became a favorite subject of painters because of its favorable composition against the water. Motif Number 1 endures as a symbol of maritime life.

As for how Motif Number 1 got its name? Legend has it that the name is derived from an impulsive exclamation by the painter Lester Hornby. During his summer seasons in Rockport, Hornby noted that many art students chose the dilapidated shed on the edge of the inner harbor. Its prominence and its simple but interesting proportions made it a natural model for sketches and paintings, good and bad. One day when a student brought for criticism a pencil drawing of the house, Hornby exclaimed, "What! Motif No 1 again!" It has been called that ever since.

The original Motif Number 1 was built in 1840 but destroyed in the great blizzard of 1978. However, the structure was rebuilt in the same year. Today, Rockport takes pride that Motif Number 1 is the most painted building in the world.

Fun fact: in the animated film Finding Nemo, the dentist's office has a picture of Motif Number 1 hanging on the wall (see screenshot I captured from the film here), a tribute by director Andrew Stanton to his hometown of Rockport, MA.

Harbor view with Motif Number 1 in the background. Motif Number 1 is known as the most painted building in the world.

A shed directly across from Motif Number 1 reminds you that you're in a fishing village.

Rockport, MA is definitely worth visiting on a day-trip from the Boston area. The pedestrian friendly streets, plenty of shops and restaurants, and gorgeous views have something for everyone. If you don't want to drive, there is always the option of taking the commuter rail from Boston's North Station. Rockport is the last stop on the Rockport line.