Travel Guide: Rockport, Massachusetts

Only an hour drive from Boston, Massachusetts, the quaint seaside town called Rockport is a mecca of artwork and artists themselves. Rockport has more than thirty art galleries and has one of the oldest art colonies in the United States. The streets are filled with art galleries, souvenir shops, curated boutiques, and a variety of dining establishments. Besides, being absolutely stunning the area was also the backdrop for the majority of the movie The Proposal while filming. 

Best Time to Visit: The best time to visit is in the summer. Since I am not from New England, I did not realize that at most summer hotspots the majority of establishments open after Memorial Day. It was a surprise to see that most places are still closed in late May. Once summer hits, weekday visits will yield less crowds as most people travel to these hotspots for weekend visits. 

Parking: There is metered parking located around the town. Make sure to download the Passport app before visiting. The Passport app allows you to pay for parking directly on the app. Love this app since I have been to different places where the pay kiosk does not work or is a mile away from my car. 

Things to Do:

Motif Number 1: The most famous landmark in Rockport is Motif Number 1, which is a classic red fishing shack with a variety of buoys attached. Motif, a French term for a repeating feature or idea, was coined since many artists favored painting or drawing this particular fishing shack. This shack was built in the mid 1840’s, however the building succumbed to a blizzard in 1978. The town realized its significance and built a replica. We took many photos of the Motif Number 1 in which you can grab a variety of angles of the structure around the harbor. 

Rockport Art Association & Museum: The Rockport Art Association was founded in 1921. Dedicated to the advancement and preservation of all phases of the visual arts. One can find members of the association's works of art in two separate historical homes. It is free to visit, but a small donation is kindly recommended.

Bearskin Neck Shopping: A historic street of shopping, galleries, and dining which juts out into Rockport Harbor. At the end of the shopping center there is a beautiful view of the harbor and many boats docked. Shopping is walkable from Motif Number 1. All shopping is locally owned, and listed below are some of my favorite stores for shopping around Rockport.

1.) The Pewter Shop: Opened in 1935 and is the oldest gift shop in Rockport with a long history of making pewter items. All items are hand made, so it is worth a stop inside the store.

2.) Rockport Candle Company: I was disappointed since this store was closed when we visited because it was on my list of places to visit. This store has a DIY candle bar. You can create your own custom blend scent as you are guided through the candle making process. Plan ahead. It does take one hour for the candle to cure and harden before you are able to take your candle home.

3.) Bearskin Neck Country Store: I love a good country store. I find there is always a variety of local items that make the best souvenirs. This store also has a candy store inside. Don’t miss the freshly popped popcorn YUM.

Beaches: The popular beaches for a summer retreat are Front Beach and Back Beach which are very popular during the prime of summer. A quieter, more peaceful beach is Cape Hedge Beach.

Lighthouses: Visit Thacher Island three miles from Rockport Harbor on a day excursion. Here you can visit the Thacher Island Twin Lighthouses. Once on the island, you have the ability to climb the lighthouses, with only 156 steps to the top on each lighthouse. You can even kayak at this lighthouse for a $5 landing fee per person.

Loblolly Cove: This cove gives you a great lookout point of Thacher Island where you can view Thacher Island Twin Lighthouses from Rockport. Truly impressed since I have never seen twin lighthouses before. It is also a great spot to grab a to-go dinner to view the sunset since there is a single picnic table overlooking the gorgeous backdrop of the ocean and lighthouses.

Boat Tours: Cape Ann Harbor Tours offer a variety of boat tours leaving Rockport, which make for a great day trip if you are in the area for an extended time. Some of the tours include a lighthouse tour, lobster/harbor tour, and Annisquam River Trip featuring the waterscape of the area and an array of birdwatching. Linking this charter company here

Outfit Deets: I bought this dress awhile back from Sailor-Sailor. Linking similar ones from their site here and here. The dress has moisture wicking capabilities. Perfect escape from the summer heat. My favorite part is the dress contains UPF 50+ for sun protection. Being fair I burn easily and this is a great dress to sport for all occassions without worrying about placing sun block on continously. Linked below similar dresses as well! Tried and true I have been wearing Sperry's since grade school. A shoe that is timeless and comfortable. 


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