A Kid Friendly New England Summer In Gloucester Massachusetts

A town where lobster shows up in your breakfast, lunch, and dinner is already a strong start but Gloucester, Massachusetts delivers way more than seafood. Kathleen interviews Melissa about a June family trip to Cape Anne that feels like pure New England summer: salty air, kids in sweatshirts on the beach, and that relaxed rhythm you only get when your rental house is steps from the water.

We get specific about what actually works with kids, from flying direct into Boston and driving to Gloucester, to choosing a calm, protected beach like Niles Beach for early mornings. Melissa shares the surprisingly magical entertainment of sea glass hunting, how to turn it into games, and why Good Harbor Beach is the “party” beach option with iconic lighthouse views. Kathleen also drops a practical tide primer, because the dramatic tidal swings up north can turn into chaos fast if you don’t plan where you set up.

Then we hit the main event: St. Peter’s Fiesta, the citywide celebration tied to Gloucester’s fishing community and the infamous Greasy Pole. Picture a long telephone pole greased up over the harbor while competitors sprint, slip, and wipe out trying to grab the flag. We talk about where to watch, why a boat view is unbeatable, and how it becomes a true core memory for all. Finally, we wrap with the real essentials: lobster roll restaurant picks, daily ice cream stops, a “driving nap” parenting hack, and a quick Rockport side trip to Bearskin Neck plus a souvenir tradition that somehow had to be a lobster.

Subscribe, share this with your favorite travel planner, and leave a review if our Gloucester family travel tips helped you map your next New England summer trip.

Restaurants: 51 Rocky Neck, The Lobster of Gloucester, Surfside Subs, Lobsta Land

Charter: Lyla Rose Charters

Clothing: Nuuly

Transcript

Lobster Filled Cold Open

Melissa 0:00

Lobster Benedict, lobster rolls, lobster pasta. So much lobster. Lobster everywhere.

Kathleen 0:06

Did you get sick of it?

Melissa 0:08

No. Never. Never, never, never.

Why Gloucester Feels Like Summer

Melissa 0:21

Hi, we're Kathleen and Melissa, and welcome back to another episode of Organized Chaos.

Kathleen 0:27

So today I am going to be interviewing Melissa. We're gonna change it up a little bit. And I have been waiting for this episode because this trip, the photos, the videos, the vibes, it is giving me peak New England summer. Glou Gloucester Glou Gloucester? Okay, how do you say it?

Melissa 0:45

Well, I'm not from New England. I kept calling it Gloucester, and then everyone corrected me, so I think it's Gloucester.

Kathleen 0:53

Okay, we're gonna go with that. Gloucester. So Melissa is going to talk to us today all about taking your kids to Gloucester over the summer.

Kids 1:02

Welcome to Organized Chaos!!!

Melissa 1:15

It really was everything I would imagine if someone said, close your eyes and picture the East Coast in the summer. That was Gloucester.

Kathleen 1:25

We're talking salty air, kids in sweatshirts on the beach, lobster rolls every day. I'm salivating.

Melissa 1:32

Every single day I ate a lobster roll, it was a dream.

Kathleen 1:38

And honestly, a festival involving grown men running on a greased telephone pole over the ocean... were they wearing shirts?

Melissa 1:47

Some were wearing costumes, some were shirtless. It kind of ran the gamut.

Kathleen 1:52

Should some of them have been wearing shirts?

Melissa 1:55

Probably. That whole situation deserves its own documentary. We'll have to get into it a little bit later in this episode. We went to Gloucester in June with my in-laws and my kids. I think it was the sweet spot for New England travel. It wasn't too hot, it wasn't too crowded yet, but there was still a ton of summer energy and kind of all the vibes you would think you would get.

Flights, Car Rental, And Potty Stops

Melissa 2:23

Tell me how you get to Gloucester from Southern California. We flew direct from LAX in and out of Boston. Always a huge win if you can book a direct flight.

Kathleen 2:32

Always. Always direct if you can make it work.

Melissa 2:35

And then from Boston, we had a rental car and we drove to Gloucester. It's about a 45-minute drive or an hour and a half if you're us and you're traveling with three kids and four adults and lots of potty breaks and snack breaks and, "Oh my seatbelt's hurting me" and all that stuff.

Kathleen 2:54

So for some long drives, we bring that porta potty, but I'm guessing that you didn't gate check that at the airport.

Melissa 3:03

No, we didn't. We would just stop at a rest stop if needed.

Kathleen 3:07

Don't you love a gas station rest stop for potty breaks?

Melissa 3:10

Oh, do you want to know my favorite thing is when you do a potty break with one kid and then you say, "Okay, everybody else go potty." And then they all huff and puff, and sometimes you can get them to go. And then you get back in the car, and then 20 minutes later, another kid has to go potty. Oh, so fun.

Kathleen 3:28

That that is like my nightmare on Earth. I I do not like to stop when we're driving. I would prefer to blow right through and get the drive over. I can't imagine how annoying it is for a 45-minute drive to take an hour and a half.

Melissa 3:43

It was a little bit annoying, but you know, we kept the vibes high. It was good. It was also a really easy drive, and the scenery was beautiful. So you can't really complain too much.

Where To Stay Near Niles Beach

Kathleen 3:56

Moving on, we know how you got there. So tell us where do you stay when you get to Gloucester?

Melissa 4:02

We stayed at a rental house right on Niles Beach, which honestly set the tone for the entire trip being right there by the beach.

Kathleen 4:11

That's so nice.

Melissa 4:12

It really is. And Niles Beach is a really quiet, protected beach. It's tucked into the bay, so the waves were really small, which was great for the kids. It just felt calm and safe, and it was a lot less crowded than some of the other beaches nearby. I think that's because the parking is really limited there. It might even be residents only, but we were able to walk on so we didn't have to deal with the parking situation.

Kathleen 4:40

That's so nice, especially when the kids get up early in the morning, that you can just leave the house, have them run around, get their sillies out early in the morning and not wake the rest of the house.

Melissa 4:51

Yeah, that was one of the biggest perks. Once the kids woke up and had breakfast, it wasn't too hard to convince them just to kind of put your shoes on, get the towels, and let's go. And then anyone who else who wanted to sleep in and stay at the house, they were able to do so. So it just made for a relaxed situation in the mornings for the kids and everyone else we were staying at in the house.

Kathleen 5:13

Sometimes I feel like that's one of the hardest things, not only on vacation but in life, is getting everyone out of the house. Like getting the shoes, getting the towels, getting the snacks, and just getting out the door. So it makes it so much more convenient when you don't really even have to go far. And if you forget something, you can go right back to the house.

Melissa 5:33

Yes, I totally agree. And Niles Beach was just so perfect.

Sea Glass Games And Crab Hunting

Melissa 5:38

It was also really exciting to the kids for one main reason, and that was seaglass.

Kathleen 5:44

Oh my gosh, I'm obsessed. Tell me more about that.

Melissa 5:48

Having sea glass was a totally new beach experience for my kids. They would spend hours hunting for seaglass, and we would turn it into different kinds of games for them.

Kathleen 5:59

Okay, tell me about these competitive games. I feel like you are always creating games with your family. It's one of my favorite things about going on vacation with you guys.

Melissa 6:07

We do kind of make everything a game. It's one of the things I've kind of done my whole life with my family. So maybe that's just something that I've brought into, you know, my family now that I'm a parent. But yes, so the seaglass games. It was who can find the biggest piece? Who can find a green one? Who can find an orange one? Who can find one shaped like a heart? Like any kind of category you could come up with, or who can find the most. And just keeps the kids focused on something so they have, so they have a purpose or a reason for why they're hunting for the seaglass, but also it's just fun.

Kathleen 6:40

It does sound fun. It's a certain kind of vacation magic that I'm sure they're going to remember for the rest of their lives. It's simple, free entertainment for the kids as well. The thing I despise the most is when my kids come up to me on vacation and say, "I'm bored." So this sounds like a great way to keep them occupied. Yes.

Melissa 7:00

And full credit to my mother-in-law for the sea glass games. Shout out to BeBe.

Kathleen 7:05

We love a BeBe moment.

Melissa 7:06

The kids also love picking crabs right out of the water. It was very New England core.

Kathleen 7:11

Were these big crabs or little crabs?

Melissa 7:14

They were, I would say like two to three inches. There were some big ones, but they didn't pick those ones up.

Kathleen 7:22

And they weren't scared?

Melissa 7:23

They were not scared, no. I think the boys love all that. And since Hannah has older brothers, she tends to be a little bit more tougher of a kid, I guess. So yeah, they weren't scared of the crabs.

Kathleen 7:34

So Niles Beach sounds amazing. Tell me about some of the other beaches that you explored while

Good Harbor Beach And Big Tides

Kathleen 7:40

you were there.

Melissa 7:40

So another beach that we loved was Good Harbor Beach. This was the opposite vibe of Niles, though.

Kathleen 7:47

Which one did you prefer?

Melissa 7:49

They were different. As we were saying, Niles was really good for that slow morning where we're just trying to get the kids out of the house and you just get the wiggles out before we were starting the adventures for the day. Good Harbor was busier. You walk across the super cute footbridge, and then you're suddenly on this clean white sand, no pebbles, hardly any seaweed, but it was a vibe. It had volleyball nets, tons of people. It was, I would say, more like a party atmosphere, not like a crazy party, but it was a busier beach. It depended on the vibe that we were going for for the day. It also had these really nice views of 10 Pound Island and Twin Lighthouses.

Kathleen 8:33

Okay, and what I was reading about, the internet mentions something about tides. The tides there were wild.

Melissa 8:42

They would go out so far, and so you'd be like really, really deep into the middle of the ocean to get to the water, and then suddenly, like in a snap, there'd be a huge swing, and then the tides would be coming in really fast, way up a high in the sand. It was very dramatic, but fun.

Kathleen 9:05

So marine biologists coming in here with a science lesson. For everyone who's wondering about the tides, the further north you go from the equator, the more dramatic the tides become. And that's because of the gravitational pull. Basically, if you go all the way up to the Alaska or the Northwest Territory, it can be miles that the tide comes in and out. And it can be quite dangerous. So if you're going to a place with really extreme tides like this beach, just make sure you're aware of when they come in and out. So you can be prepared to move your beach stuff and not lose all the sand toys. So

Melissa 9:44

We should have had you there to give that science lesson to my kids because they said, "What's going on?" And we said, "Ah, we don't know. Run!" But yes, good reminder to move your stuff or make sure you're aware of where you're putting your stuff so that you don't get caught in a big dramatic tide change.

Kathleen 10:01

I wonder if the locals at Gloucester take bets on tourists coming and like what will there's gotta be like a polymarket betting scam for like Gloucester residents where they say, "How many plastic buckets will be lost on this day from the tides," right?

Melissa 10:20

Oh my goodness. If they don't, they should start because it is probably pretty good people watching just to watch everyone freak out and move their stuff.

Kathleen 10:27

Right. Let's talk about why lots of people go to Gloucester in June.

St Peter's Fiesta And Greasy Pole

Melissa 10:34

The main event there is St. Peter's Fiesta, which is the annual celebration that's tied to the feast day of St. Peter. It's sponsored by the Italian American fishing community. And over time in Gloucester, it's become this huge citywide celebration. There's parades, statues, paintings, rowing races, and the blessing of the fleet. It is a huge carnival.

Kathleen 11:02

I think you're burying the lead here.

Melissa 11:05

Yeah, so the biggest thing is the greasy pole.

Kathleen 11:09

I would say it's infamous.

Melissa 11:12

Yeah, so anyone unfamiliar with the Greasy Pole event, just picture a 40-foot-long telephone pole suspended over the water horizontally, completely slathered and greased. And then men in costumes, some just in their swim trunks, but a lot of them are in costumes, try to run across this pole and grab a flag that's at the end.

Kathleen 11:38

And tell me how that went.

Melissa 11:41

So for the majority of them, they're falling, there's a like flipping off. It's all very dramatic, especially if they fall in like a weird way or you know, on their private parts or something like that. Our kids were cracking up, so were we watching it. It was hilarious. And then the person who wins ultimately gets hoisted onto the crowd's shoulders and is paraded through town in full glory, and they're sort of like the king of the festival, it seems like at the end.

Kathleen 12:18

Is there like a monetary prize or like a trophy, or is it just that you won?

Melissa 12:25

Maybe there's a trophy or something, but it's the glory and the storytelling and saying you're the one who won. So there would be an announcer over the loudspeaker, and they would have these stats on the people. So it'd be like, "oh, this person won back in 2025", or "this person won three years ago". This person..., so it's your badge of honor if you live there, it seems like.

Kathleen 12:48

And Brook didn't want to participate in the greasy pool run?

Melissa 12:52

He absolutely would have done it, but it's legit, and you have to sign up, you have to qualify. There's all these kind of pre-qualification events and things like that. I'm not even sure if you can do it if you're not a local. I really don't know the rules, but regardless, he didn't do it, but I think he was pretty jealous. The kids and I we were saying we're kind of egging them off. Like, do it, just get out there, do it. Just get out there.

Kathleen 13:16

I bet that there's those rules in place to prevent drunk tourists from injuring themselves in the process. It seems kind of dangerous.

Melissa 13:25

It seems super dangerous. You could see these people walking around afterwards, and some of them would definitely be really banged up.

Kathleen 13:31

Oh no.

Melissa 13:32

Also, I do think some of them were drinking alcohol before. By the tone of the celebration.

Kathleen 13:41

Getting liquored up to get greased up.

Melissa 13:43

Yeah. Yes.

Kathleen 13:45

Okay, so where do you watch this from? Is it from like grandstands or a boat? What did you do?

Melissa 13:52

There's kind of two different places you can watch it from, or three. You it's broadcast all over the TV. In every bar, or restaurant you're in, and all over the local news, they are showing the greasy pole event. We watched it from the shore on one day. So you just stand on the shore and watch it. You can also watch it from a boat. So we did both. This event goes over multiple days. So on the second day, we went out on a boat. Shout out to Matthew at Lyla Rose Charters. That was a really fun experience. He drove us all around. We got to see the coastline. And then he got us up real close to the greasy pool. So we had a front row seats. It's a core memory for the kids and myself.

Kathleen 14:38

That sounds awesome. So boat or shore?

Melissa 14:42

I would say if you can get on a boat, watch it from the boat. Because then you get the boat experience too.

Kathleen 14:46

That sounds awesome.

Summer Outfits And The Nuuly Plug

Kathleen 14:48

Okay, a quick interruption. I remember following you along on social media, and I need to say peak New England summer outfitting. How did you get so summer chic?

Melissa 15:01

Oh, thank you, thank you. Nuuly!

Kathleen 15:03

This is a shameless plug here, you guys. Melissa and I are definitely part of the Nuuly crew.

Melissa 15:10

Kathleen introduced me to Nuuly, and I'm pretty obsessed with it.

Kathleen 15:15

It's just a great way to freshen up your outfits for a vacation or a summer trip or a different season, and things that you might wear for one season you might not wear for the next. So it's a guilt-free way to keep your closet fresh.

Melissa 15:32

So Nuuly, we're huge fans. Sponsor us, please.

Kathleen 15:35

We're waiting in the wings.

Lobster Roll Restaurants Worth It

Melissa 15:38

So now on to the food. I think I already said this, but I ate a lobster roll, at least one lobster roll every single day.

Kathleen 15:46

Is it like I read everywhere where everything has lobster in it all the time?

Melissa 15:52

Yes. There is lobster as part of the options on basically everything: lobster benedict, lobster rolls, lobster pasta. So much lobster. Lobster everywhere.

Kathleen 16:04

Did you get sick of it?

Melissa 16:06

No. Never. Never, never, never. We had a rental house, so most of our breakfasts were eaten at home, but for lunch and dinners, we went out.

Kathleen 16:18

Okay. Tell me about some of the restaurants you would recommend.

Melissa 16:22

The Lobster of Gloucester had fresh lobster. It was great for groups. My husband and his cousin split this huge seafood platter, which was honestly the size of a small child. Other places that we ate and would recommend were Surfside Subs. Again, all of my recommendations are gonna be about lobster rolls, but we ate at Surfside Subs where they had the best lobster rolls, too. It was really more like a takeout kind of situation for us. So we did that. 51 Rocky Neck was really good. They had live music, they had this wraparound bar, the oysters there were delicious. And then Lobstaland we went to and it had the best views. It like we ate dinner at sunset time, and there was just this beautiful sunset over the marsh. They had live music. I had a lobster roll. It was great.

Kathleen 17:18

I feel like the theme of this is lobster roll.

Melissa 17:21

That should be the title of this episode.

Kathleen 17:23

Okay, so I'm salivating. I know we're recording right now and it's close to lunch, but I'm hungry. So with kids, did they like the lobster? Were they willing to try it?

Melissa 17:36

Yes, they were. And then you always get fries on the side, so

Kathleen 17:40

everybody was happy.

Melissa 17:41

Everybody was happy.

Ice Cream Stops With Kids

Kathleen 17:42

Okay, and then also with kids, you cannot forget the sweet treat after dinner. I feel like a vacation staple is always ice cream. Were there any particular places that you'd recommend?

Melissa 17:53

Yes, New England summer days demand ice cream. We went to the Ice Cream Gallery, which was the super adorable little pink cottage with a ton of different ice cream flavors. And then also Surfside Subs had a huge selection of flavors. I think we ate ice cream every day, as well as me eating lobster rolls every day.

Kathleen 18:11

It sounds like it was a really low calorie trip.

Melissa 18:14

Oh yeah, totally. It was perfect for summertime. Calories don't count on vacation.

Kathleen 18:19

No, they don't. I don't even what are calories?

Rockport Driving Nap And Souvenirs

Kathleen 18:22

Okay, so let's talk about driving, napping, Rockport. Tell me about that part of your trip.

Melissa 18:30

We were staying in Gloucester, but we did do a driving nap to Rockport one day.

Kathleen 18:36

Okay, I don't know that you have explained the driving nap to our listeners yet.

Melissa 18:40

All of my kids, and honestly me, we all fall asleep instantly in the car. So sometimes we'll plan slightly longer drives on purpose in order to get everyone to have a midday nap.

Kathleen 18:55

This, in my opinion, is a genius parenting hack if your kids will sleep in the car. So go on. Tell me about Rockport.

Melissa 19:02

My youngest daughter still always naps. My older two sons don't nap in just sort of our typical day-to-day lives. But sometimes when you're on vacation, you're just using a lot of energy. You're trying to get the kids to stay up late so that you can have more of a nice dinner out or something like that. So you kind of gotta force the nap a little bit. And it's just like a nice reset for everyone. So the driving naps work great. And so we did a driving nap. We went to Rockport. It's a quaint classic New England town. Bearskin neck is full of shops, restaurants, and art galleries.

Kathleen 19:41

Okay, so this is news to me. You guys have an ornament tradition?

Melissa 19:45

I try to always buy a Christmas ornament on vacation as a souvenir. And then it's just like a nice thing to kind of remember your trip by when it comes Christmas time and you're reflecting on all the fun that you had in the year. So this is where we got our New England Christmas ornament.

Kathleen 20:01

What did you buy? A lobster?

Melissa 20:03

It was a lobster. That wasn't even a teed-up joke. It was a lobster. That was a good guess. So we also we grabbed fresh oysters to go and we walked around with the kids there. So yeah, bearskin neck, it's great. Rockport, it was great.

Kathleen 20:23

I did a little research on Rockport. Fun fact uh Mermaids was filmed there, and so was The Proposal, which love both those movies.

Melissa 20:33

Yeah, I really do feel like it's just exactly like what you expect or picture when you're thinking of a little New England town.

Kathleen 20:39

Right, like idyllic, oceanside, lobster rolls.

Melissa 20:43

Absolutely. So that was our trip to

Dedication to Nana And Where To Follow

Melissa 20:47

Gloucester. Before we wrap up, I do want to dedicate this episode to someone very special.

Liam 20:53

This episode is dedicated to Nana.

Beckham 20:56

I love you, Nana.

Hannah 20:58

I miss you, Nana.

Melissa 21:00

And that's Gloucester.

Kathleen 21:02

Thanks for listening, and don't forget to subscribe and leave a review if you enjoyed today's episode.

Melissa 21:08

Until next time, happy planning and safe travels.

Kids 21:12

Thanks for listening. See you on our next adventure.

Kathleen 21:25

One more note if you want to reach out to us online, you can visit our website at ourorganized chaos.com.

Melissa 21:33

And then on socials, we're on Instagram at our.organized.chaos And then on TikTok with the same handle, our.organized.chaos So follow along.