8 lovely things to do in Rockport, MA: a pretty seaside town

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Here are some lovely things to do in Rockport, MA, a very pretty seaside town in New England, USA. The town is located on Cape Ann, a headland/promontory at the top of Massachusetts Bay. I didn’t really know what to expect from it when I visited, but it blew me away. A total gem. It’s overflowing with bright and colourful wooden buildings, unique independent shops and fresh local seafood. There are magnificent views out onto the ocean from surrounding sandy beaches and you’re never far from being able to see the sea even in the town centre. It reminded me very much of North Berwick in Scotland, another picture-perfect seaside town.

Rockport is the perfect day trip to do on the train from Boston. The train goes down the coast for just over an hour to get there (more on that further down).

Side note: For my (mostly) UK-based blog readers, don’t let the name ‘Rockport’ put you off. Those horrendous shoes of the same name that were really popular in the 90s are nowhere to be seen!

So here are some nice things to do in Rockport, MA, and some details on how to visit the town as a day trip…

8 lovely things to do in Rockport, MA

1. 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. It’s almost like the town was designed to be painted, it’s so beautiful. According to Google, Rockport has over 30 little art galleries as well as an art association. You’ll find plenty of art shops along the main drag and if you have enough room in your luggage, there are lots of lovely paintings of the town and the coast which would make good souvenirs to take home. 

I know I’ve just said Rockport reminded me of North Berwick in Scotland, but the quality of the light for painting and the general arty vibes also reminded me of Kirkcudbright, which is known as the artists’ town of Scotland. Perhaps that’s why I like it so much.

I read in one of the galleries that the famous American realist painter Edward Hopper stayed on Cape Ann in the 1920s and visited Rockport to work. He’s the chap who painted ‘Nighthawks‘, an image of a very sparse pub with a few people standing in it. You’ll recognise it if you see it. The paintings he did while visiting Cap Ann helped him to get established as an up-and-coming artist at the time, which is interesting.

Some of the shops and galleries I enjoyed browsing when I visited Rockport, MA, included:

• Rusty and Ingrid Creative Company – This is my favourite! I really wanted to buy a print when I visited but my luggage allowance was already on the brink. Really reminded me of the kind of retro travel posters that are so popular at the moment, but much more tasteful.
• The Art Nook – Lots of bold and bright local art here, and you can really see the colours of the local area reflected in everything. 
• Tusinkski Gallery – This one has so many striking and attractive canvases but also glass vases and bowls in beautiful pastel colours.

There are lots more though – that’s just a selection. You could spend all day popping in and out of them just browsing.

2. Stroll along Rockport’s pretty beach – one of the best things to do in Rockport, MA, on a sunny day

Known as Front Beach, the main beach in Rockport is to the west of the main headland (the road with all the shops on it). It’s a small beach, mostly sandy but with a few rocky areas.

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

On a sunny day, Front Beach is a lovely place to sit on a well-placed rock and watch the waves lapping. There’s quite a bit of sea glass about so if you’re into that, you’ll enjoy poking around.

3. Eat fresh seafood, especially lobster rolls – one of the best things to do in Rockport, MA, for foodies

Rockport had so many restaurants and cafés in a small space, you’ll be spoilt for choice. It’s mostly focused on seafood so if you’re not into that, I’d recommend doing your research to find alternatives. The local speciality in Rockport is definitely a lobster roll, often served with chips (‘fries’) and a side salad. 

The most popular gaff in town seems to be Roy Moore Lobster Company. Getting some lobster rolls from there is clearly one of the best things to do in Rockport, MA, for foodie visitors to the town. There’s always a queue outside. Even the Lonely Planet guidebook to the area mentions it.

If you’re in a rush or don’t want to queue, I highly recommend Red Skiff Restaurant as an alternative. The lobster rolls here are gorgeous, as is the clam chowder. Clam chowder is a New England speciality: a very thick and creamy soup. I’m not sure a cosy soup is entirely appropriate for a sunny seaside day, but whatever. When in Rome! Like everywhere in the USA, the portion sizes at Red Skiff are on the larger size of average… But I think this was the one meal of my USA trip that I actually managed to finish. Something the waistband of my jeans can vouch for.

4. Spend too much money in Rockport’s independent shops

Rockport has some really good independent shops. Okay, there are a few tourist tat ones as well, but that’s only to be expected with a seaside town and you can easily spot the wheat from the chaff.

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

• Wicked Peacock – If you’re a regular reader on this blog, you’ve probably got sick of seeing photos of me with a beige-coloured backpack traipsing around Europe and Japan over the last couple of years. That little beauty came from Rockport! 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 do 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… Definitely a good one to browse for clothes.
• Rockport Fudgery – I’m not a fudge fan personally but I have friends and family who love the stuff. This is a good place for some small and edible souvenirs. You can also buy coasters of the Bear Skin Neck sign (see further down this page for more on that).
• Carol Lee’s Cottage – This is the perfect shop for buying pretty gifts to take home. It’s full of floral bits and bobs (most would fit in a suitcase too). When I visited, I spent 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). She gave me a lip balm that I still carry around in my handbag now. Lovely. Definitely worth a visit.

5. Put your photography skills to the test at the iconic Motif #1 – one of the best things to do in Rockport, MA, if you want some great Instagram shots

Motif #1 is the symbol of Rockport. It’s also the main photography spot in the town (hence this shot being in this blogpost twice because I’m so pleased with it!).

Perched in Rockport’s inner harbour, at the end of Bradley Wharf, Motif #1 started its life as a humble red fishing shack in the 1840s. Since then, it’s been a meeting place and artist’s studio, before finally becoming a monument and landmark of the town. The shack is actually a replica of the original structure, which was destroyed in a blizzard in the 70s, but locals constructed an exact replica.

Apparently, Motif #1 is 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. It even features in Finding Nemo, in a painting hanging in the dentist’s office. The director added it as a tribute to his Rockport-based roots. I really need to re-watch the film and look out for it now.

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. You can get it from several angles, but the one I’ve gone for below seems to be the classic choice.

6. Enjoy the colourful seaside houses

Motif #1 isn’t the only brightly coloured building in Rockport. 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. Of all the things to do in Rockport, MA, just wandering around taking in its beauty is the most memorable. I particularly love this gorgeous house below with its turquoise door and gate. I wonder how much a holiday cottage would be around here…

7. Walk to the end of the town and along the breakwater

At the top of the headland in Rockport, there are a few benches for a sit and a stony breakwater that you can walk to the end of to enjoy that bracing sea air. The nicest thing about Rockport being on a headland is that you can almost always see the sea. If you can’t, it’s only a turn or a few steps until it pops up from another angle. From the breakwater, you can normally see some lighthouses, as long as you don’t have a foggy day.

This a good spot for having an ice cream and watching the sea (or people watching, naturally). Pick up some cones at The Ice Cream Store, which is a cute little shop that does local ice cream or frozen yoghurt. The scoops are very generous.

8. Find the Bear Skin Neck sign

‘Bear Skin Neck’ is the name given to a little jutting-out bit of Rockport on the headland. It got this name because of a bear who drowned there in 1700. Poor bear. It’s also where the first dock was built, so they have this plaque to mark it.

This is not something to go out of your way to find, but mildly interesting if you’re passing it. You can find it at the entrance to the headland.

Useful information: things to do in Rockport, MA

How to get there

I visited Rockport as a day trip from Boston on the train that runs along the coast. The journey 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 trains 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

I just did Rockport as a day trip from Boston, but it would be such a lovely place for a weekend. It looks like there are plenty of accommodation options within walking distance of the centre so I’ve done a bit of research. Just bear in mind that this area and the US as a whole are very expensive for hotels.

Here are a few options for you. I’ve listed the prices below with all of the taxes and so on included, which Booking.com will also do for you. All prices are correct at the time of writing. 

• Treat yo’self: If you want to really splurge, you can do so at the boutique hotel Addison Choate (about $291 a night).
• Mid-range: A nice middle option is the stylish Sally Webster Inn (about $200 a night). 
• Budget: The most affordable one is Bearskin Neck Motor Lodge (about $170 a night). It’s still not what I’d normally class as ‘budget’ on here, but the US is expensive for hotels generally and doesn’t have cheap chains like Motel One or Premier Inn. 

How to get around

Once you’re there, everything in Rockport is very walkable. You won’t need to hire a car unless you want to go further afield.

When to go

I visited in May. Spring in Rockport is sunny but cool and fresh, which I think is perfect for exploring. There won’t be too many tourists, but everything is open and bustling to a nice degree. So I’d recommend that as a good time to plan a trip.

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