Take a Virtual Trip to the Charming Town of Kennebunkport, Maine

Whenever I go on vacation, I struggle with whether or not to share my photos here on the blog. I’ve heard some people complain about people who share their vacation photos. But then I figure, if you’re like me, seeing photos helps you decide if that’s a place you’d like to visit. Vacation brochures always show the best spots but don’t always portray an area accurately. So without further ado, I’m sharing photos from around the charming town of Kennebunkport, Maine.

I think this iconic “Welcome” sign has to be the most photographed thing in town. I saw several people take photos of it and when you Google “Kennebunkport,” this sign always pops up. The red building behind it is a souvenir shop of sorts and is where I bought three Kennebunkport hoodies! Two were on sale so I don’t feel bad about it.

Welcome to Kennebunkport


While on the bridge where I took the photo above, you can see more interesting sights along the Kennebunk river. I believe the river is the dividing line between Kennebunkport and Kennebunk. I found out some of the locals don’t like it if you confuse the two.

The bay between Kennebunkport and Kennebunk


For this post, I’m going to focus on the Kennebunkport side of the river. The front of these shops face the main drag through town.

Downtown Kennebunkport, Maine


lobster buoys on Maine house


And there are plenty of charming little shops to visit. Every time we passed The Candyman, I couldn’t help but think of the song Sammy Davis Jr. made famous in the Willy Wonka movie. Needless to say, that song was stuck in my head.

Candyman Store in Kennebunkport


You’ve probably seen photos of the famed Dock Square in the center of Kennebunkport, Maine.

Dock Square in Kennebunkport


Here’s another view of Dock Square, which is really more of a circle in the very middle of it.

Dock Square in Kennebunkport


We didn’t really venture inside a lot of the stores, but they were cute and photo worthy on the outside.

Antiques store in Maine


The seaside architecture gives a sense of the town’s vibe, which is utterly charming and beautiful. Honestly, we never saw a run-down section while visiting, and we explored quite a bit.

Downtown Kennebunkport


A few blocks from Dock Square are more interesting buildings, like the Kennebunkport Historical Society building with its grand pillars.

Kennebunkport Historical Society


Here’s the quaint public library which isn’t very big.

Public Library in Kennebunkport


And the Cider Mill Press which is just around the corner.

Cider Mill Press book publishing


Another yellow building is of The Captain’s Collection which is one of four historic Kennebunkport homes once owned by leading sea captains. You can book or room or enjoy a fine meal.

The Captains Collection - lodging in Kennebunkport


Kennebunkport, Maine is equally charming at night as it is during the day. Maybe more so because there’s less people milling around. We didn’t go to Ben and Jerry’s because we stumbled across Rococo Ice Cream first, on the other side of the river in Kennebunk. Best ice cream in town (my fave was the Whoopie Pie flavor), although Ben and Jerry’s is pretty good, but I can get that here at home.

Ben and Jerry's ice cream


The Congregational Church was especially pretty all lit up at night.

Kennebunkport Congregational Church


I hope you enjoyed this virtual trip to Kennebunkport’s downtown area. I’ve still got some historic homes to share with you, but I’ll spread those out over time so you’re not inundated with Maine (although I don’t think you can ever have too much of Maine).


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  1. Thanks, Jennifer, for sharing these memories of your vacation! PLEASE don’t stop posting lots of travel pics–I love your blog. My husband went to UofM/Orono, but I’ve only been to ME a few times (not enough!). We had dreams of retirement adventures there, but health issues are preventing that right now. So keep your photo-heavy posts coming!

  2. Thank you for sharing this inside look at Kennebunkport, Maine. The reader was able to see the charm it offers!!!

  3. What a pretty place and the buildings are wonderful. I was surprised it was very colorful. Usually the NE is bland when it comes to color. I can’t wait to see the homes. Thank you.

  4. Heading there next week! Thanks for the great pics. Hope you have more coming including the flowers, especially hydrangeas, and Bush info.

  5. Thank you SO much for sharing these wonderful photos. I added this charming destination to my “Travel Dreams” board on Pinterest.
    Your lovely giveaway book arrived safe and sound. I created a flat lay for an Instagram post that will go live this afternoon ((I’ll tag you) and will feature it on tomorrow’s Sunday Smiles post on my website, Decor To Adore.

  6. Fun to see a sneak preview. Love Kennebunkport and that entire area. Going to be visiting this week. And btw in originally from Hinsdale IL so fun to see your blog of great homes in that area too !

  7. Ok that does it- I need to go to Maine! I’ve always wanted to and now it’s confirmed. Thank you for the lovely photos!

  8. Hi Jennifer ~ I love your CURATED selection of travel photos. And that is the key to sharing them, isn’t it?! We went to Kennebunkport a few years ago but only had a few hours to spend in the area. Returning is high on my bucket list priorities! I love what you post every single day and am inspired by all that you share. Thank you for this beautiful blog.

  9. Don’t ever quit showing your vacation photos, because you make them so interesting. I love spending a few minutes seeing all there is. Thanks and have a great day.

  10. I love your vacation photos. I love the state of Maine but have never been to Kennebunkport. Would love to visit there.

  11. I lived in NE for a few years, in NH as well as ME. I absolutely love New England and dream about having a permanent address in ME. Thank you so much for sharing your Kennebunkport pics. I can continue to dream about one day.

  12. We went there for our first time. The houses on the way to Kennebunkport from Kennebunk were some of the most beautiful houses we’ve ever seen, anywhere in New England. Wonderful restaurants as well. This vacation made us wish we lived in this beautiful town.