Things to do in Rockport, MA: a day trip from Boston

Things to do in Rockport, MA | PACK THE SUITCASES

I wanted to put together a little post on some things to do in Rockport, MA because it was my absolute favourite day of my holiday to Boston, USA. Rockport is the perfect day trip to do on the train from Boston. The train goes down the coast (although I use the term ‘train’ loosely…) for just over an hour to get there (more on that further down).

The picture-perfect town of Rockport itself is on Cape Ann, a headland/promontory at the top of Massachusetts Bay. I didn’t really know what to expect from it but it was just beautiful – a total gem. There are loads of colourful wooden buildings, independent shops, fresh seafood and magnificent sea views from sandy beaches. It reminded me SO much of North Berwick in Scotland, which is a similar perfect day trip from Edinburgh on the train too – only with Scandinavian wooden buildings. Scotland + Scandinavia = my dream!

Don’t let the name ‘Rockport’ put you off if you’re a UK visitor. Those horrendous shoes of the same name that were really popular with people being hard in the 90s were 100% nowhere to be seen. 

So here are some things to do in Rockport, as well as what to eat and how to get there from Boston on the train…

Things to do in Rockport, MA | PACK THE SUITCASES

Explore the art shops and galleries in the town

It’s no surprise that Rockport is a bit of a mecca for artists and creative types in Massachusetts. There’s even a music performance centre in the town, although we didn’t have time to go to it.

I know I’ve just said Rockport reminded me of North Berwick, but the quality of the light for painting and the general artiness actually reminded me of Kirkcudbright (known as the artists’ town of Scotland and my favourite childhood place FYI!). 

According to Google, Rockport has over 30 little art galleries as well as an art association. I can’t say we made it to many of the galleries as it was such a nice day I didn’t want to be indoors too much and of course we had a lot of eating lunch to do… but we did pop into numerous art shops along the main road.

If you have enough room in your suitcase, there were lots of lovely paintings of the town and the coast which would make good souvenirs. 

Things to do in Rockport, MA | PACK THE SUITCASES

Stroll along Rockport’s pretty beach

Known as Front Beach, the main beach in Rockport that you can walk to is to the west of the main headland with all the shops on.

It wasn’t straightforward to get onto/off from what I remember. I think we walked along it to the end and ended up emerging from behind a shop wondering if that was actually meant to be a proper route or if we’d end up in someone’s garden. 

On a nice day, it’s a lovely place to sit on a well-placed rock and watch the waves lapping. It was also fairly quiet as it was May, so not peak tourist season yet. We had the whole beach to ourselves at one point.

Things to do in Rockport, MA | PACK THE SUITCASES

In the words of J-Lo, don’t be fooled by the rocks that I got. There is still plenty of beautiful sand, too.

Things to do in Rockport, MA | PACK THE SUITCASES

Eat fresh seafood

Rockport had so many lovely-looking restaurants and cafés full of pescatarian-friendly food. I was actually quite disappointed to only be able to have lunch there.

The most popular gaff in town seemed to be Roy Moore Lobster Company (it was in our Lonely Planet book too). But there was a queue when we got there and I was on the edge of death from actual starvation so we ended up at Red Skiff Restaurant.

We shared a gorgeous lobster roll with chips and a clam chowder with bread. Clam chowder is a New England speciality: a very thick and creamy soup. I’m not sure a cosy soup was entirely appropriate for a sunny spring day, but whatever. No regrets. The lobster roll is the even more local speciality and that was amazing too.

Like everywhere in the USA, the portion sizes were on the larger size of average. But I think this was the one meal I managed to entirely eat. Something the waistband of my jeans can vouch for.

Things to do in Rockport, MA | PACK THE SUITCASES

Spend too much money in cute shops

I was dangerously on the edge of my luggage allowance. But as ever, I pretended everything would be fine if I squeezed a few more things in.

Rockport has some really, really good independent shops. Okay, there were a few tourist tat ones as well, but I was very impressed with how many nice gift shops and boutiques there were.

We went in quite a few but I can’t remember all the names. I did note down a few though.

Things to do in Rockport: shopping

If you’re doing a day trip to Rockport, keep your beadiest of eyes out for:

  • Wicked Peacock – If you’re a regular reader on here, you’ve probably got sick of seeing photos of me with a beige-coloured backpack traipsing round Europe and Japan over the last year. That little beauty came from here! I’ve absolutely got my money’s worth out of it and it’s been all over the place with me. As well as really nice bags, they also did lots of unusual jewellery.
  • Strut Boutique – I got a really nice necklace from here although I really wanted a dress and a blouse. But even I know my suitcase’s limits and I didn’t want to pay an extra baggage fine. Again.
  • Rockport Fudgery – Chris got some fudge for his parents from here and apparently it was a good one. I’m not a fudge fan so can’t comment on that but I did buy a coaster for my dad of the Bear Skin Neck sign (see further down this page!).
  • Carol Lee’s Cottage – This is the perfect shop for buying pretty gifts to take home. It was fully of floral, pastel bits and bobs (most would fit in a suitcase too). We were in there ages talking to the friendly owner, who was everything I adore about Americans – SO chatty and warm. She’d been to England so we got talking and I think I ended up giving her a business card for the blog (yes, I’ve become that person) and she gave me a lipbalm that I still carry around in my handbag now. Lovely!

Things to do in Rockport, MA | PACK THE SUITCASES

Things to do in Rockport, MA | PACK THE SUITCASES

Visit Motif #1

Motif #1 seemed to be the symbol of Rockport and the main photography spot too (hence this photo being in this blogpost twice because I was so pleased with it!). It was once a fishing shack (in the 1840s) and has since been a meeting place and artist’s studio, before finally becoming a monument and landmark of the town.

Apparently it’s also the most painted building in America – as in, painted in pictures by artists, not literally given coats of paint. Although I bet it’s had a few of those over the years too. 

If you’re into photography, set aside a bit of time to get some good shots at Motif #1. There’s something very pleasing about the composition, light and colours.

Things to do in Rockport, MA | PACK THE SUITCASES

Enjoy the colourful seaside houses

Aside from Motif #1, there are loads of other gorgeous houses and shops that scream ‘seaside’. Lovely weathered, wooden and colourful facades line most of the streets.

Honestly, Rockport is incredibly pretty and (although I hate this word) charming.

I particularly loved this one below with its turquoise door and gate. I wonder how much a holiday cottage would be around here…

Things to do in Rockport, MA | PACK THE SUITCASES

Walk to the end of the town and along the breakwater

At the top of the headland, there are a few benches for a sit and a stony breakwater that you can go to the end of.

The nicest thing about Rockport being on a headland is that you can almost always sea the sea. If you can’t, it’s only a turn or a few steps until it pops up from another angle.

While we were there, we saw a lot of eerie thick fog sat in a clump across the horizon. This didn’t spoil the otherwise clear blue skies and sea, but apparently you can usually see a lighthouse from here and it was having none of that.

It’s a good spot for having an ice cream and watching the sea (or people watching, naturally).

Things to do in Rockport, MA | PACK THE SUITCASES

Find the Bear Skin Neck sign

‘Bear Skin Neck’ is the name given to a little jutting-out bit of Rockport, because of a bear who drowned there in 1700 🙁

It’s also where the first dock was built, so they have this little plaque to mark it. Not something to go out of your way to find, but mildly interesting if you’re passing it.

Things to do in Rockport, MA | PACK THE SUITCASES

Useful information: Things to do in Rockport, MA: a day trip from Boston

How to get there (and away)

This was a day trip from Boston, so we got the train that runs along the coast. It takes just over an hour. Commuter trains to Rockport leave regularly from Boston’s North Station. The trains themselves are interesting. If you’re used to Europe and Asia, be prepared to be patient. They are SO slow. They’re also ancient and clunky. But they get you there! Once you arrive at the station in Rockport, you’re only a five-minute walk from Rockport’s ‘downtown’ (the town centre).

Where to stay

We didn’t stay over in Rockport as we just did it as a day trip from Boston, but it would be such a lovely place for a weekend. And it looks like there are plenty of nice hotel options within walking distance of the centre. I like the look of this one or this one (sorry, both are over £100 a night but the USA is proper expensive for hotels!).

How to get around

Once you’re there, everything is very walkable.

When to go

We went in May. It was sunny but cold. May was a decent time to go though. Not too many tourists, but everything was open and bustling to a nice degree.

Save and share: Things to do in Rockport, MA

If you enjoyed this post on things to do in Rockport, MA, why not hover over the image below and pin to your Pinterest board?

Things to do in Rockport, MA | PACK THE SUITCASES Things to do in Rockport, MA | PACK THE SUITCASES

If you’d like an email alert when I publish a new post, subscribe using the box at the side (if you’re on a laptop) or at the bottom (if you’re on a mobile or tablet).

You may also like


  1. Another funny post Caroline, love your writing! I’ve been to Boston but missed this little gem

    Looks amazing


  2. Thanks for sharing these beautiful photos…I will surely go there…it’s very nice place. My tour planers will help me out in my travelling. Thanks a lot for this article.

  3. Hi , just completed your day in Rockport! Amazing blue sky day and completely agree – In comparison, Salem was just not in the same league. Thanks for the recommendation, without it we would never have ventured out of the City.

Leave a reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.