Family Trip Destinations: Rockport, Massachusetts

While many are packing up, getting ready to head off on a spring break getaway, before you know it summer will have arrived. (The current Montreal temperatures certainly have us feeling that way at least!) And as we all know, it’s never too early to plan for that next family trip. Chalets on the lake Up North are getting booked, beach houses in Ogonquit, Maine have been reserved since last summer. So I wanted to share one of our family’s most favourite nearby destinations to add to your list of options.

I started visiting Rockport, Massachusetts when I was a kid. We would travel there every summer with different families and my memories of this little quaint, fishing town are ever-lasting. We’ve been going back since Hannah was just 18 months old,  creating family memories of our own.

About a five hour drive from Montreal (we split ours up with a stop in Stowe, Vermont) this is a do-able destination with kids in the car. Here are my top picks to make your family trip to Rockport a great one:

where to stay

We always dream about having a house of our own on the beach and have even visited a few in anticipation of future visits. But year after year we keep coming back to the Rockport Inn & Suites. For me, it means no laundry, dishes or cleaning up. For the kids it means swimming in a pool and getting to use fun cereal machines at breakfast (their only chance during the year to eat Fruit Loops). A typical motel, we opt for a suite room which includes a den on the main floor with pull-out couch, microwave and mini fridge. Upstairs, mom and dad (and more recently Leo) have our own loft with a vaulted ceiling and a skylight.. It’s just the right amount of separation for a family trip. With on-site tennis courts, an indoor pool for when it’s too hot or rainy and a hot tub, the hotel amenities are exactly what we need. Prices for suites are around $200USD/night when you book early. The hotel is pet-friendly too with lots of green space. We’ve never brought our dogs along since we spend most of our days out.

where to eat

Lobster rolls with a view at The Lobster Pool

It took us a good four years to discover The Lobster Pool and now a trip is not complete without a visit to this casual restaurant on the water. The food is good but the views are even better. Come for sunset and you’ll be eating a lobster roll next to one of the most beautiful scenes ever. There are plenty of options for the kids but be warned: vegetables are a bit hard to come by. The Lobster Pool is also BYOB.

A short drive away from Rockport is the town of Gloucester is The Market Restaurant. The husband and wife chef team received their training at Chez Panisse and serve farm to table fare in a beautiful setting. While the restaurant is on the fancier end for kids, we like to go for breakfast or brunch and sit out on the terrace over the cove.

A few of our other favourites include Top Dog of Rockport for super casual hot dogs with lots of topping options, authentic Italian subs and salads at Virgilio’s Bakery in Gloucester and ordering pizza on the beach from Mike’s Place (my mouth waters just thinking about their Melenzane pizza with eggplant, ricotta and caramelized onions.) For a good cup of coffee and doughnuts for the kids, go to Brother’s Brew Coffee Shop, about a 15 minute lovely morning walk from the hotel.

Iced coffee and donuts from Brothers Brew Coffee Shop

where to play

The bridge to Good Harbor Beach

The main reason we keep going back to Rockport is the beach. The ocean may be too cold to swim in when we typically travel in late June but a sandy beach is my family’s happy place. Click here for a complete guide to the area’s beaches. Our most favourite beaches include Good Harbor, Wingaersheek and Half Moon in Stage Fort Park. The first two are large family-friendly beaches. Good Harbor is wide and open with beautiful lighthouse views while Wingaersheek is long and narrow with tons of rocks to climb on as an additional source of entertainment. Half Moon is a tiny cove great for a quick taste of the beach and shell hunting.

One of our favourite Gloucester beaches

beach tip 1:

Pack your own lunch. While plenty of healthy options are available at the snack shacks, lunch for a family of five can get expensive. we bring our own and then let the kids get a treat.

beach tip 2:

Plan one of your beach days for the evening. By arriving after 4pm you will avoid the crowds and parking fees. Pack dinner or order pizza and watch the sunset.

what to do

Brothers swinging at Stage Fort Park

On non-beach days there are plenty of other activities to keep your family entertained. We recently discovered the Maritime Gloucester where you can learn about sea life and boats. They have a small aquarium featuring local marine life and even offer drop-off programs for older kids.

Walk through Bearskin Neck to experience Rockport’s local artists, see Motif No. 1 the famous, photo-worthy red building adorned with colourful buoys and watch salt water taffy being made at Tuck’s Candy.

My kids adore the playground at Stage Fort Park which has a combination of new equipment like a climbing wall and older attractions like a lighthouse and wooden ship. Sign up for a whale watching tour, visit the nearby Salem Witch museum or make the 20 minute drive to the nearby Target in Danvers, you know you want to! On a rainy day, the Children’s Museum in Boston is another great option. It’s about a 45 minute drive away.

Every year we plan our trip so that it coincides with Gloucester’s St Peter’s Fiesta. It’s a traditional Italian festival celebrating the infamous local fisherman with a full-on carnival with rides and games. The Greasy Pole contest features brave daredevils who attempt to walk on a  greased pole out over the harbour. It’s quite a comedic site to watch. The 2018 festival takes place from Thursday June 28 to Sunday July 1.

A good old fashioned family fair takes place every June.

So there you have it. The makings of an amazing family trip this summer. And please note. I do keep calling it a family trip for a reason. Travelling with younger kids is never really a vacation. It will be tiring and there will be temper tantrums and lots of arguing in the back seat, so you won’t get to really rest. But you will be creating a lifetime of memories.

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