What to Do in Gloucester with Kids: Our Top 5 Fabulously Fun Family Activities Gloucester, MA!

Bonjour, my chic mamas and little adventurers! If you’re wondering what to do in Gloucester with kids for an unforgettable family getaway, you’ve landed in the most stylish spot on the web! Gloucester, MA, that charming jewel of Cape Ann, isn’t just for seasoned sailors and art aficionados; it’s a veritable playground for families, brimming with delightful family activities Gloucester MA offers that will have your little ones (and you!) utterly enchanted. We recently had the most divine time exploring, and I’m simply bursting to share our favorite finds!

1. Conquer the High Seas (of the Playground!) at Stage Fort Park

Oh, darlings, Stage Fort Park is an absolute must! This isn’t just any park; it’s a wonderland for children of all ages. The playground is simply magnificent, and the pièce de résistance? A glorious pirate ship jungle gym that had my little ones shrieking with delight, imagining themselves as the chicest buccaneers on the seven seas! What I adored, as a mama needing a moment’s reprieve, was the ample shade and plentiful benches where one could relax and watch the joyful chaos unfold. It’s the perfect spot for an afternoon of imaginative play and perhaps a stylish little picnic.

Also for those heading to the area in June, you’ll be able to catch the reenactment of the Battle of Bunker Hill here (being held at Stage Fort Park due to spacial issues at the original battle site in Charlestown and Boston). 

2. Make a Splash (Figuratively!) at Maritime Gloucester

For a touch of education wrapped in a whole lot of fun, you simply must steer your crew towards Maritime Gloucester. While the entire institution is fascinating, the undeniable highlight for any little oceanographer-in-training is the touch tanks! Getting up close and personal with sea stars, crabs, and other local marine life is such a wonderfully tactile and memorable experience. It’s a fantastic way to spark curiosity about the big blue, and honestly, even I was utterly captivated! Also the staff is so kind and informative. We could have spent the entire day exploring!

3. Storm the Castle (Carefully!) at Hammond Castle

Now, for a dash of medieval glamour, Hammond Castle is a sight to behold. Perched dramatically overlooking the Atlantic, it feels like stepping into a fairytale. A little note for my fellow mamas of tiny tots: no carriages are allowed inside. This did make the logistics a tad tricky with my sweet Aurora still needing to be expertly corralled, but let me assure you, the breathtaking architecture, the stunning views, and the sheer romance of the place make it so worth a little extra planning. The girls were wide-eyed with wonder!

4. Strike Gold (or Pins!) at Cape Ann Lanes

Darlings, prepare yourselves, because Cape Ann Lanes might just have been the absolute highlight of the trip for my little Arielle! And honestly, it was a blast for all of us. This isn’t your average bowling alley; it’s a retro-chic haven of family fun. What I particularly adored was how incredibly accommodating they were for even the tiniest bowlers. They had a special guide so even Aurora could actually bowl – and it was dinosaur-shaped, no less! Too cute!

It’s candlepin bowling, so the balls are smaller and easier for little hands. And here’s the genius part: you can opt to bowl with or without bumpers, and the bumpers go up and down per player! So, if your littles need that extra help (like ours did!), the bumpers pop up for their turn. But if you have a bowling pro in the family (or just a surprisingly coordinated adult), the bumpers can go down for their turn. We opted to have the bumpers up the entire time, and thank goodness we did – the girls ended up gleefully taking over our turns for most of the evening!

And for a little bit of pop culture sparkle, this very bowling alley was recently featured in an Ed Sheeran music video for his single, “Old Phone”! How fabulous is that? It’s owned by a wonderfully charming husband and wife team. The husband is the brilliant brewer behind the Laneside Brewery, which is right there! You can also check out the pub, which is so cleverly designed with tables and a bar made from repurposed bowling lane wood, and old locker doors adorning the walls. They also have a lovely outdoor beer garden.

But the detail that truly sealed the deal for this mama? Potty training seats in the bathroom stalls! It’s these thoughtful touches that make a place truly family-friendly. Cape Ann Lanes, you have my heart!

5. Beach Bliss: Good Harbor & Beyond

While our recent visit was so packed with adventure that we didn’t quite make it for a proper beach day this time around, no guide to Gloucester with kids would be complete without mentioning its stunning coastline. We absolutely adore visiting Good Harbor Beach, with its soft sand and gentle waves, perfect for little paddlers and aspiring sandcastle architects. There are several other beautiful beaches in the area too, each offering its own unique charm. A day spent by the sea is always a day well spent, wouldn’t you agree?

So there you have it, my dears! A little peek into the fabulous family activities Gloucester MA has waiting for you. It’s a town that effortlessly blends history, natural beauty, and good old-fashioned fun, making it a truly special destination for families looking to make some stylish memories.

For more on where to stay, make sure you check out my post on our Atlantic Vacation Homes property. And for what to wear, I have all kinds of suggestions here!

A great big thank you to Discover Gloucester for hosting us! 

Until our next adventure!