How To Not Spend A Day In Rockport, MA

Rockport is a small, quaint town on the North Shore of MA. I have visited multiple times in my younger years but only had scattered memories of it. All I could recall was that it was very cute and that the movie The Proposal was filmed here. As we are gearing up to move to London very soon, I’ve been enjoying exploring all the little towns in MA. Rockport has been a place I’ve wanted to visit again, so I decided to take a little trip with the kids. In full transparency, I would have done our day slightly differently had I had more intel, so I’m sharing what we did and what I think we should have done differently during the trip to help you plan your day here better.

WHAT NOT TO DO:

Let’s just jump right into it, shall we? Rockport is very small, so unless you plan to hike or go to the beach, you only need to spend a few hours in this little town. So I do not recommend treating this as a full-day trip if you are coming from far away.

I also do not recommend getting breakfast here. We did not find many good options downtown, so I would opt for lunch or dinner instead as the options are more robust.

Lastly, I do not recommend arriving too early unless, as mentioned, you plan on going hiking or to the beach. The parking meters do not start running until 10 am, and many shops do not even open until after 10 am. The town has a very relaxed vibe, so if you come too early in the morning, you will just be strolling through a ghost town. I would say to arrive around 9:30 am if you are coming during a weekday in the summer. If you come on a weekend, taking the commuter rail might be a better way to visit the town without having to worry about parking at all, as it does get quite busy and the streets are very small and littered with pedestrians.

WHAT TO DO:

Ok, onto some positive news. If you are traveling from far away, I would recommend visiting another North Shore town to make the trip worthwhile. Some cute towns nearby include Salem, Newburyport, Marblehead, Gloucester, and Manchester-by-the-Sea. 'You can pop into Rockport for a bit and then head to one of these other towns. If you are not from MA and are visiting this state, my recommendation is to visit Salem, as it is rich in history and offers many sights and great museums.

In Rockport, I also highly recommend walking around, taking in the views, and popping into the cute little shops without a set itinerary. It’s definitely a town to stroll and just discover things. You can walk the whole area in 15 minutes without stopping, making it the perfect place to just take your time and enjoy.

WHERE TO PARK:

Parking right in the heart of Rockport can be tricky, as spots are limited. You can find parking on the streets, or our favorite place to park is the lot right at the end of Bearskin Neck, which also has the most gorgeous view. It’s also situated near all the shops, making it the ideal spot to start your day. You can park there early, but the meters do not start running until 10 am, and you cannot pay early, so you either have to wait until 10 am to pay or run back to your car at 10 am to make sure you pay in time. The lot also only offers 11 spots, so it can fill up quickly. It does have a 4-hour limit, though, which gives you more than enough time to explore the area. To guarantee a spot, I recommend arriving before 10 am, but be mindful that many shops do not open until after 10 am, and some even closer to 11 am-12 pm. So I recommend heading to a cafe first, then walking through the shops afterward. Street parking is typically 2 hours max, while lots are 4-5hours. Parking in a lot is preferable so you do not have to move your car, and 3-4 hours is more than enough time to see the main sites of downtown Rockport and grab lunch.

If you want to avoid parking altogether, you can ride the commuter rail using the Newburyport/Rockport line, getting off at Rockport Station. It's a 0.5-mile walk from the station to downtown.

WHERE TO GO:

There are some places we visited that I would say you could skip altogether, and some I would say you can not miss. First, we’ll start with the places we love that you should definitely visit on your trip to Rockport.

ALL DOUGH

All Dough is a little cafe that offers quality drinks and an assortment of pastries and light bites. There is no seating inside (aside from window benches), and it can get crowded and, at times, they run out of items. It was barely 10:15 (they open at 9), and we got the last 4 croissants on the menu. It didn’t seem that busy to already be running out of food, so I’m assuming maybe they got a rush as soon as they opened or they only had a very limited quantity. The croissants were nothing to rave about, and I didn’t see any fresh pastries laid out on display, nor did I smell anything freshly baking, so I would skip the pastries and food and just get the drinks. The matcha I ordered was delicious.

BROTHER’S BREW

Next, we headed to Brother’s Brew intending to get breakfast, but we quickly pivoted once we arrived and were told they only had egg patties. With that information, I knew it was premade, and I definitely did not want to serve my kids microwaved egg patties, so we ended up skipping breakfast here and instead ordered some doughnuts to go, which this restaurant is actually famous for. We ordered the cinnamon sugar, blueberry, and old-fashioned flavors, and they were all incredible. They serve some of the best doughnuts I have tried, not too sweet, very flavorful, and cakey. They were a big hit; it was worth the visit just for these sweet treats.

THE ICE CREAM STORE

The Ice Cream Store is an absolute must-visit. This little shop is tiny but mighty. It offers homemade ice cream in an assortment of flavors. The girls and I got the salted caramel truffle flavor, and it was fantastic. Rich and decadent yet light and creamy. Some of the best ice cream I have had in New England. They have a small indoor seating area and outdoor tables and chairs overlooking the water, where you can enjoy your ice cream, but it’s best to take it to go and continue exploring the town. I would come back to Rockport just for this ice cream. There are many ice cream options along the way, and though I can only attest to this shop, I wouldn’t try anywhere else before visiting this iconic ice cream shop first.

FLEUR CUISINE

We were really excited about Fleur Cuisine, a Caribbean fusion restaurant in Rockport, of all places. The ambiance is nice and simple, and they have outdoor seating overlooking the harbor. The food is good and flavorful, and, given the other nearby food options, you will find the most interesting and diverse menu here. It’s a great spot for lunch or dinner. I do recommend making a reservation to guarantee outdoor seating, as that is the most appealing area to dine at this restaurant.

If you love Lobster rolls (a classic New England cuisine), then you may want to pay a visit to Roy Moore Lobster Company, a restaurant specializing in this iconic New England sandwich. They are quite popular, with a line out the door throughout the day.

WHERE NOT TO GO:

The next part of our list are places we were either underwhelmed by or flat out disappointed in. I always implore people to experience things for themselves, as I may love something you hate and vice versa, so by all means, if you want to do these things, please do, and just use this guide for context.

DELISI’S RED SKIFF

Delisi’s Red Skiff is a restaurant serving breakfast all day, within easy walking distance of all the downtown attractions, and it offers indoor and outdoor seating. However, we were very disappointed in the food. Though the pricing is great for the area, the food was basic, unflavored, and lackluster. It's not horrible, just plain, and if you are coming all this way, it's a bit disappointing not to love the restaurant you choose. The only appeal of this restaurant was that the placemats are meant to be decorated, and the kids loved coloring them; they even hung their pictures on the wall afterward. But honestly, that's no reason to endure lackluster food. If you’re going to trek out to Rockport, I recommend going to a restaurant with a view. At least if you don’t love the food, you'll enjoy the nice scenery. My Place By The Sea is at the tip of Bearskin Neck and offers a more upscale menu with a gorgeous view (It's also a great spot to grab a drink if you want to skip the food).

MOTIF #1

Motif #1 is a famous landmark in Rockport on Bradley Wharf. It's an old fishing shack turned monument and now an iconic part of this little town. It is also very much only a photo opp. I wouldn’t say to skip it altogether, but you can just make a pass by it as you stroll around, take your photo, and move on. There is not much else going on the wharf, so it's a quick stop, and right in the heart of everything, so you don’t have to go out of your way to see it. But that’s all you do: just see it and go.

We left a tiny bit underwhelmed by Rockport, only because we treated it as a full-day trip; and as mentioned, you don’t need to spend a whole day in downtown unless you plan to buy or pursue art at the many galleries littering the streets. If you're going to be in the area or plan to visit another North Shore town, spending a few hours in Rockport makes for an idyllic part of your day.

The optimal way to enjoy this area when traveling with small children is to browse the shops and sights, have a nice lunch by the water, enjoy some ice cream, and grab doughnuts to go. Then head to another town nearby. Or, if you want to stretch the day, head to Halibut Point State Park for some hiking and views, or to Front Beach, a family-friendly beach located within walking distance of the shops.