The Best Family Day Trip to Beautiful Kennebunkport, Maine

by | Family, Travel

Kennebunkport, ME and the southern Maine area is full of special places! Check out the hightlights of our family day trip through this beautiful area!

It has been just over 18 years since I visited Kennebunkport, Maine for the first time.  Robb and I spent some time in this sweet town during our honeymoon!  What a delight to make it part of our family’s New England Fall Trip!

It was just as charming and quaint and beautiful as I remembered!

We even grabbed a quick picture by the former Captain Lord Mansion, the bed and breakfast where we stayed.  Our 13-year-old photographer did a pretty good job, even though no editing will make me look as young as I did in 2003!

We spent some time strolling through the downtown, checking out the beach, and browsing a few of the amazing antique shops that run through “Antique Alley” along Route 1.

Here are a few highlights from our family day trip through southern Maine and Kennebunkport!

Antique Browsing through Southern Maine

You may not believe me, but it’s true.  I purposely did not spend time researching antique places for any of our New England stops.  This trip was really all about our family and I didn’t want to find any “must stop” places and then be disappointed if it didn’t work out!

I decided that I would be perfectly happy if we happened upon any fun places to stop and even happier if it worked out to browse.  Some did and some didn’t.  But Southern Maine was full of them on a morning when we had time to stop!

Our kids are pretty used to a family day trip that includes an antiques stop or two.  For the most part, they enjoy it too!

Tip for antiquing with kids: My kids love to do an alphabet scavenger hunt.  They have to find something that starts with every letter of the alphabet and they have to go in order!

If you know me well, you know my favorite vintage things are almost always large in size, such as old signs, architectural salvage, and that type of thing.  There were so many pieces that I loved but couldn’t get home.  It was still super fun to browse!

I am always so interested to see antiques in different parts of the country.  So different than our Florida or even southern state antique stops!

One super fun find was this antique marmalade jar.  They can be super pricey online and I’ve never seen one in person that I was willing to pay the steep price for.  But this jar was tucked into a random little shop for only $12!  Score!

I’ll set it on my shelf or tuck a flower stem into and fondly remember our morning of browsing whatever little shops we came upon that family day trip!

My friend Ann from Dabbling and Decorating has some great blog posts with suggestions for thrifting and antiquing in New England.  If you’re headed to the area, make sure to check her blog.  I was excited to see that we ended up stopping at several places on this post!

You can find my favorite tips for vintage hunting and antiquing, no matter what part of the country, here!

Scenic Views on Our Family Day Trip


Maine, quite simply, is beautiful.  We enjoyed a drive along the coast in Kennebunkport, Maine, as well as some time climbing around the rocks that overlook Walker’s Point.


Harrison, especially, would have stayed here all day just climbing around and having fun.  They thought it was pretty awesome how different the beach is there compared to our Florida beaches!


No doubt, this is a great spot to get out, enjoy the coastal air, and get some great pictures too!  I was able to get some great pictures of the kids out of this stop and Payton even grabbed a snapshot of Robb and I too!


It was really beautiful to see the signs of fall all around, while still overlooking the ocean.  People who live along the New England coast may take that uniqueness for normal, but it was especially beautiful to me.

Of course, we had to collect a few of the beautiful, freshly fallen leaves!


Around the Town in Kennebunkport, Maine

It really is just the cutest downtown!  After exploring the coastal scenery, we drove back into the downtown and enjoyed an afternoon and evening of browsing the shops, enjoying the leisure time, and of course, enjoying some great food!

Not to be critical of our Florida pumpkin patches and displays, but they just can’t measure up to New England.  Let’s just say, it isn’t South Florida’s strength.  Haha!

Of course, I couldn’t pass up the chance to grab a family picture by this fun pumpkin display at the end of the downtown area!

Kennebunkport has adorable little shops and we all loaded up on some pullovers, hoodies, and souvenirs.

Travel Tip: We love to collect a Christmas ornament from places we travel.  It is so fun to pull them out at Christmas, one by one, and remember all the fun memories.  I choose them in neutral colors so that no matter the colors we want to use, they will always mix in!

The Best Food on our Family Day Trip

No family day trip is complete without some yummy food, right?!  We decided to forego the nice restaurants and eat at a little stop overlooking the boats.

We convinced two out of three kids to try the lobster and they loved it!  Clam chowder was a favorite for Harrison and is one of mine too.  It is safe to say that we thoroughly enjoyed our waterside, seafood dinner in Kennebunkport!

Addy decided that we should have ice cream in every state on our New England trip.  It took zero arm-twisting for her mom and dad!

We finished our evening in Kennebunkport with some yummy ice cream!  I loved the creative focal wall of this little stop and it made a great backdrop for documenting our ice cream.

Even if we were all a bit tired and tired of taking pictures at this point!  Ha!

Kennebunkport, you were a highlight of our New England fall vacation!  It was the perfect family day trip and we can’t wait to visit again!

For more fun stops on our fall road trip, check out these pictures from our trip to Woodstock, Vermont,America’s Most Beautiful Town”.

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