Weekend in Portland, Maine with Kids

Weekend in Portland, Maine with Kids


Weekend in Portland, Maine with Kids

This past summer we decided to finally visit the last state in the Northeast that we had yet to as a family. We spent 3 nights in Portland, Maine with kids as a long weekend trip. This was our last road trip of the summer and luckily the shortest amount of time in the car. The 4.5-hour trip turned into closer to 6 hours because of Friday evening traffic. But luckily the girls had plenty to keep themselves busy and food to keep them happy in the back!

Where We Stayed

Our family stayed at the Hyatt Place in the Old Port area of Portland. We love staying at a Hyatt Place when we can because the room setups work great for our family of four. Also, the prices are typically great for quality. The hotel couldn’t have been in a better location. We were right smack in the middle of restaurants and shopping. We parked in a garage just a short walk from the hotel entrance. There was plenty of parking available in the garage. However, the only problem was that the garage locks at night and the one morning we tried to leave early for our whale watch they weren’t open to unlock it until 8 AM. Luckily we JUST barely made it to the whale watch on time!

What we Did

Whale Watching

Our first day we got up early and drove just over an hour to get to Boothbay Harbor. We chose Cap’n Fish’s Whale Watch for its decent reviews online and this way we got to visit a different town in Maine on our trip. The whale watch started at 9:30 and we were out on the water for about 3.5 hours. The ride out of the harbor was so beautiful and was interesting to learn about all of the islands we were passing by. Our girls (ages 2 and 6 at the time) were not very into this part and just wanted to see some whales.

Once we got a little further out in the harbor, we saw the whales come to the surface quite a few times, which the girls truly enjoyed seeing. Because you could only see their backs or a fin come to the surface, the girls had to be very patient to spot them. After seeing the whales a few times the girls were ready to head back to Boothbay Harbor. A quick tip: dress in layers and to bring sunscreen! We ranged from freezing cold to sweating all within our 3-hour boat ride. Also if you have little kids bring snacks and stuff to occupy them. Whales are awesome, but not guaranteed to be an action-packed viewing experience every trip.

After the whale watch, we spent some time walking through some gift shops in Boothbay Harbor. The town is very easy to walk around, and there are many small shops and restaurants.

L.L. Bean Flagship Store

On our way back to the Hyatt Place in Portland, we stopped in Freeport, Maine to visit the L.L.Bean flagship store. It was very chaotic here, but that shouldn’t have been surprising for a Saturday afternoon in  August. We took a while to find a parking spot and spent about 2 hours wandering around the L.L.Bean store and then in and out of other outlet stores. We probably would have spent even less time doing that if it weren’t for our 2-year-old passing out in the stroller. It made for a perfect place for her to take a nap while we shopped.

Maine Craft Breweries

Okay, so this part was not intended to be kid-friendly in the slightest. My husband is a total beer snob and likes to seek out great craft beer anywhere new we head to. So he had a little list of breweries that he wanted to visit during our short time in Maine. Some of the breweries that we visited included: Maine Brewing, Lone Pine Brewing, Battery Steele, Liquid Riot, and Bissell Brothers.

Obviously, this is not a kid-friendly activity but you would be surprised that the kids didn’t hate it. The breweries were all very friendly and had games for kids and adults. When we go to a brewery with or without the kids, we typically get a flight to split and then buy a bunch of cans of whatever beer we really liked. We don’t spend a lot of time in each one, but the fact that they all had something for the kids to “do” made it so much more fun for them!

Portland Head Lighthouse

About a 15-minute drive south from Portland you will find the iconic Portland Head Lighthouse. We went down after brunch on our second day of the trip and when we got there it wasn’t very busy at all. We parked in the lot closest to the lighthouse which was a quick walk to see it.

After walking around the actual lighthouse we walked along the water’s edge on a trail. The view of the water and the lighthouse from the trail were awesome. Along the trail, there were some paths down to the water where people were walking on the rocks. We chose the skip that with the kids but would have loved to check it out if they were older. At the end of the trail, it dumped you onto a small rocky beach. The girls could not resist putting their feet in and splashed around in the cold water!

The park also offered a playground and a few food trucks including one offering lobster rolls. We skipped the food since we had a big meal before but grabbed drinks for our walk back to the car!


On our last day on our way home, we stopped in Kennebunkport, ME, which was about a 40-minute drive south of Portland. Okay, so we mainly stopped here for a lobster roll. But we figured we had time to spare before our drive home so time in a picturesque Maine town was necessary. When we got to Kennebunkport, we drove out to a small beach so the kids could get out and explore before lunch. We found a perfect spot for them to see and experience the water, but they also got to check out some tide pools and these rocks full of barnacles.

After exploring the beach we went into town where we got lobster rolls and other seafood for lunch. We spent a few more hours in and out of gift stores and local shops before we got on the road to drive home.

What We Ate

Checking out new restaurants is one of my favorite things to do when visiting a new area! The food in Portland, Maine did NOT disappoint. There were so many options it was hard to narrow it down for our three-day trip. With lots of research and advice from some locals, we picked a few places to try out. Our other requirement besides awesome food at restaurants this trip was no place with a dress code and options that were kid friendly.

Empire Chinese Kitchen, Portland, ME

We came here the first night we arrived in Portland. Check out my other blog post on Empire Chinese Kitchen!

Eventide Oyster Company, Portland, ME

After our long day whale watching and then checking out Freeport, Maine we came back to the hotel, freshened up and headed over to Eventide before it got too busy. Check out my other blog post on Eventide Oyster Company.

The oyster bar at Eventide Oyster Company – Portland, Maine

Hot Suppa, Portland, ME

We got brunch at Hot Suppa on the one morning before we went to Portland Head Lighthouse. They did not accept reservations so we tried to get there as early as we could to avoid a long wait. We still had a short wait, but it was definitely worth it!  My girls split a waffle and my husband ordered the BBQ Pulled Pork Eggs Benedict. I ordered the Mother Clucker which was amazing and I was beyond stuffed for the remainder of the day. They also had great mimosas and Bloody Mary’s!

Taco Escobarr, Portland, ME

We went to Taco Escobarr for our last night in Portland. We called in advance to see if they had a wait to get a table and they said it was wide open. It was a bit of a walk to get there and even slower with our 2 and 6-year-old, so by the time we got there the restaurant was quite busy. They had one available table which was, unfortunately, a high top. Sounds fine but with our crazy two years old it is like living on the edge, literally. We were hungry and didn’t want to wait so we took the high top and sucked it up for the meal. The restaurant was packed and loud, which was perfect for with kids. We split a bunch of apps and tacos on the menu between the four of us and my husband and I consumed way too many margaritas, hence the quality of the photos I had to choose from (see below).

Mount Desert Island Ice Cream, Portland, ME

Okay yes, this is the first of 3 ice cream shops we went to. This is a vacation thing. Must get ice cream every night. Mostly we get 1 or 2 scoops to split between the 4 of us… mostly. Mount Desert Island Ice Cream had lots of unique flavors of which I can not remember (we came here right after Taco Escobarr… lol). Somehow my older daughter walked out with the most boring flavor they offered because she is not a super adventurous eater!

Gorgeous Gelato, Portland, ME

This yummy gelato shop was right across the street from our hotel, how convenient!

The Gelato Fiasco Old Port, Portland, ME

This was the one place that we went to a few times. Mostly due to the fact that my husband found one flavor of gelato he was obsessed with and needed to get it each night before we went back to the hotel for bed!

Holy Donut, Portland, ME

Before our whale watch, we fueled up on donuts at The Holy Donut. See more on my post all about The Holy Donut!

The Clam Shack, Kennebunkport, ME

This was our last stop of the trip before we hit the road to head home. The Clam Shack opened at 11 and we got in line promptly then!

We all split a lobster roll and some shrimp and fries. The lobster roll was awesome – although I would just prefer the lobster straight up, it was so good. There were some benches to eat at right outside the walk-up food stand and the tables were made from lobster traps!

For such a short trip, we had a blast visiting Maine this summer. I think my husband and I would agree it was the best food of all the summer trips. The girls always love getting to put their feet in the ocean, even if the water is freezing cold. We are however thinking next time we take a trip to Maine that we will head up more north and explore the Bar Harbor area! I totally plan on using this article: What to do in Bar Harbor with Kids when we explore north of Portland!

Pin it for later…

Related Posts

Weekend in The Hamptons with Kids

Weekend in The Hamptons with Kids

Where we Stayed Because we were only staying in the area for 2 nights we decided to get a hotel that was a good value. Many properties to rent require longer stays in the peak season. So we stayed at the Hyatt Place in Riverhead, […]

Seattle CityPASS Review

Seattle CityPASS Review

Seattle CityPASS Review On our first visit to Seattle, we bought a Seattle CityPASS in order to visit a bunch of our “must-see” Seattle attractions. Being that we had never visited the city before, we wanted to be sure we saw all the best things […]

9 thoughts on “Weekend in Portland, Maine with Kids”

Leave a Reply