Weekend Travel Guide to Kennebunkport

Kennebunkport Travel Guide: What to do in Kennebunkport: A weekend travel guide to Kennebunkport, Maine.

There’s nothing quite like New England in the fall. After this Texan had her treat of fall foliage and crisp & cool weather, she’s thinking she’s going to have to make the trip up north each and every autumn!

Okay, now back to first person. đŸ˜‰ Kennebunkport was definitely the highlight of our recent trip to Maine. This tiny town was settled in the 1600s and today boasts adorable boutiques, authentic lobster shacks, delicious local food, gorgeous old sea captain mansions converted to inns & a rich history of lobstering.

The highlights of Kennebunkport can definitely be knocked out in 36-hours. So I’m sharing a weekend guide to Kennebunkport in the fall: where to eat, drink, sleep & sightsee. Oh, and where to apple pick too! Because what’s fall in Maine without apple picking!?



Day 1: Friday

Start with lunch at Arundel Wharf

If the weather is nice, be sure to request a table on the patio. The view of the port is straight out of your dreamiest New England imagination.


Explore the shops of downtown Kennebunkport

From cozy wool sweaters, scented pine candles and kitschy beachy souvenirs, the many shops clustered about will occupy you for hours!



New England Babymoon Ideas: A Stay at Lodge on The Cove in Kennebunkport, Maine.

Check into your Hotel

We stayed at Lodge on the Cove, and loved every single second of our experience here! You can read all about our stay in this post.

Seraphine Maternity Swe


Dinner at Toroso

When Patrick and I travel, we love to try as many different new & unique dishes as we can. Toroso is a newer restaurant in the area and offers tasty tapas inspired by local ingredients. The braised octopus was divine!

The pineapple ketch lobster tour review, in Kennebunkport, Maine.

Day 2: Saturday

Kick off the day with a lobster boat tour!

(After coffee, of course.) We spent two hours aboard the Pineapple Ketch, a restored 38 ft. boat with burgundy sails that locals refer to as the port’s very own pirate ship.


Be sure to cozy on up! I wore like five different layers under my wool fisherman sweater, and was still a bit chilly.


But the views of the coast were worth any sort of chill & splash from a wave below.


I kindly asked our captain if we could extend the tour a few more hours, as I never wanted to leave!

Sadly, he had to decline my request – as they were transporting a bride to her wedding venue later that day. Talk about making a fabulous entrance!


Walker’s Point, the Bush family’s vacation compound, was one of the highlights of the water tour. That and learning all about the art of lobstering.

I’m convinced Patrick and I could move up here, live in a cabin & be lobster fishermen. I mean … maybe for like a day!? đŸ˜‰



Lunch at Salt + Honey

After our morning at sea, we walked on over to Salt + Honey to fill our bellies with delicious traditional New England-style comfort food. From lobster tacos to chicken biscuit sandwiches and bloody marys, we were quite content! (As it was our babymoon, a virgin bloody mary for me was in order!)




Happy Hour at Ramp Bar & Grill

We headed a few miles east of Kennebunkport to Cape Porpoise to explore the cape at low tide. We then cozied up at a table inside Ramp Bar & Grill to watch a catch up on Saturday football (for Patrick) and to snack on nachos (for me!) A pregnant girl has got to eat!

The views and the nautical scenery over here made this spot stand out. Colorful lobster buoys decorated every corner of the restaurant, both inside and out.


Visit Goose Rocks Beach

A very popular destination in the summer months, Goose Rocks Beach is still just as much fun during the fall. Three miles of sandy beach is protected by a barrier reef called goose rocks, which can be visible at low tide.



We made our way up there at 4:00 in the afternoon and the tide was extremely low. With even more beach to explore thanks to the low tide, we were able to walk for almost an hour, strolling past the calm waves and chatting about life + our baby to be. It couldn’t have been a more perfect afternoon!



Dinner at The Tides Beach Club

Our dinner spot that evening was located conveniently across the street from Goose Rocks Beach at the Tides Beach Club. With classic architecture and modern touches, we felt as if we were truly dining at the Sea Captian’s house who once owned the place.


And dinner was absolutely deeeeelicous! With a wedge salad followed by lobster ravioli, I couldn’t have been happier.


Day 3: Sunday

Visit the Walker’s Point Overlook on Ocean Ave. 


Forget the Bush compound, Walker’s Point, the views of the sprawling seaside mansions and the rocky coast lining this drive are worth the trip alone! Tourists can stop and park their cars at the end of the drive on a small rocky overlook giving onlookers the perfect view of the Bush family’s gorgeous estate.


While Walker’s Point was a sight to see (picture below)  I was more in awe of the natural beauty of the area, watching wave after wave crash against the frigid coast.



Me probably saying, “But I’m not ready to leave yet!!!!”


Apple Picking at Spiller Farm

Just about 15 minutes outside of Kennebunkport lies a fall lover’s playground, Spiller Farm. Guests can stroll through the orchards picking apples to their delight, or head to the other side of the farm to pick their perfect pumpkin.


Cows, a flock of geese and even a rabbit or two will greet you during your visit.



This being our first time in an apple orchard, we were naturally overly excited.


We filled my bag with a few apples to go and made sure to grab some fresh apple cider donuts to munch on on our way out town.

Capping off our fall weekend in Kennebunkport with a visit to an apple orchard was like icing in the cake!  Maine, I am absolutely smitten with you and I can’t wait to come back and visit again soon!

If you’re planning a trip to this area down the road and have any questions, feel free to shoot me an email! I’d love to chat travel tips with you! As always, thanks for stopping by the blog. Don’t forget to follow Lone Star Looking Glass on Instagram, as I’m always sharing what I’m up to outside the blog here.



  • Kennebunkport is the cutest! Love your pics, lady!

  • WOW! This looks amazing! And what a great guide… Definitely adding to my Wanderlust list! xo

  • Kelsey H

    This looks amazing! I’ve always wanted to go to Maine! Def on my bucket list!

    xo Kelsey | http://www.chasingcinderellablog.com

  • This looks absolutely amazing!!! I have never been to Maine but want to so badly!! Such a great post, lady and you are SO adorable with your cute little baby bump! đŸ™‚

  • I’ve only ever been to Maine in the summer, but it looks beautiful in the fall. It seems like you had a great trip!



  • I have been wanting to visit Maine for the longest time. It looks absolutely beautiful. I will definitely be using your recommendations when I eventually visit!

  • Nicole Leffew

    All of your outfits are so cute and everything you did sounds so fun!

  • It sounds like such a fun trip! I’ve never been to Maine but it looks beautiful!
    By Lauren M

  • Adaleta Avdic

    All the photos in this post are absolutely BEAUTIFUL, and I seriously want to visit Maine so bad. I’ve heard some of the most amazing things! xx adaatude.com

  • Sara Oberton

    Maine is on my bucket list for sure! This trip looked amazing.

  • Oh so fun! Love all of your fab pics. I feel like I got to go with you! Maine is gorg this time of year. You covered a lot while you were there. I know the sea food was amazing! The apple orchard looks so fun too!!

  • Ah! This seriously looks like something straight out of a movie. The scenery is so perfect!! And your looks were perfect!