A Week in Bailey Island, Maine

Rocky Ridge Orchard, Maine

Vacation with a toddler is different. It can be a lot of fun, but relaxing isn’t a word that comes to mind. We’ve taken a lot of great trips since Milo was born. Most notably to Japan, Bermuda, Portugal and France, but none that have been super restful.

This fall, we have enjoyed staying close to home and taking in the beauty of New England. People travel here from all over the world to experience the fall. It can be easy to forget how special this season is in our own backyard! Last week, we piled in the car and headed 2.5 hours north to Bailey Island, Maine for a week of ocean air, seafood, and island life. I was really excited to get off the grid and enjoy time outdoors letting Milo run around barefoot. I certainly wasn’t expecting to feel so relaxed or head over heels in love with Bailey Island.

It often takes me a few days, if not the entire vacation to feel at ease and really ready to relax. Only after a few hours, I could sense my shoulders dropping and just a little more space between each breath. There are certain places in this world that just seep into your bones and put you in a state of peace. This island is a special place, and I almost immediately felt its magic.

Jaquish House, Bailey IslandJaquish House, Bailey IslandMilo in Maine Quiet Morning on Bailey Island

We partnered with The Gills Group for this trip, and stayed in the stunning Jaquish House and Cottage. Without a doubt, our stay in this beautiful home was 99% of why we felt so at ease and “at home” while on Bailey Island. Renovated in 2015, the home possesses so much character but is also comfortable, luxe and modern. I honestly could have moved right in and stayed forever. No detail was overlooked and I was constantly taking notes for how to recreate a home like this in Boston.

Matt and I stayed in the incredible master suite that had massive windows looking out onto the bay. At night, we would keep the windows open and it felt like we were drifting to sleep on a boat. The master bathroom was insane, too, with a giant soaking tub looking right out onto the water. Spectacular views everywhere you looked!

Our friend, Meg and her two little pups joined us for a few days as well as Matt’s brother. The house sleeps 10 and the nearby cottage sleeps another 2, so we had plenty of space to stretch out. Suffice to say, Weber and Milo loved exploring every crevice indoors and outdoors.

The front yard looked out onto Casco Bay. There were so many places to sit and enjoy the sweeping views and soft sounds of the tide. I especially loved cozying up on the front deck, sitting in the hammock, or sprawling on the lawn out front. Milo loved climbing on the wooden picnic tables (I perhaps should have stopped him but it was too cute) and collecting rocks.

Homemade Apple PieJaquish House, Bailey IslandBailey Island, MaineJaquish House KitchenJaquish House

In addition to the main house, where we stayed, there was a little cottage just across the lawn. The 1 room cottage was adorable and had the tiniest little bathtub! Matt worked most of our trip (grateful that he can work from wherever) and the little cottage was the perfect spot. Milo loved running over and saying hi through the screened door.

Milo in Bailey Island, Maine

Milo isn’t great at taking naps in the crib, so after lunch I’d pop him in the stroller (this is the one we have and love) and we’d wander down to Land’s End (the house is located on Jaquish Lane which is literally the last street on the island — so peaceful) and the sound of rocks and dirt road under foot would put him right to sleep. I’d wander back up to the house and he’d sleep soundly thanks to the salty and humid breeze drifting in through the stroller. During this time, I’d sit back down with my coffee on the ridiculously comfortable couches (which I am now looking to purchase for my own living room — they were that comfortable) or outside with my feet in the grass. Perhaps I’ve been living in the city too long, but the feeling of grass against the bottoms of your feet is so grounding.

Bailey Island with a ToddlerJaquish House - The Gills Group
Natalie and Milo - Bailey Island

The main house had four bedrooms, one of which had two sets of bunk beds. It was so fun, and I wish we had more kids with us so they could have had a big sleepover! I love the idea of having a kids room, and since we have limited space in our Boston condo, it’s neat to live out that dream if only on vacation. The room had lots of books and adorable puppets of animals that you’d likely find in Maine like a bear and fox. Milo loved them.

jaquish house

One afternoon we accepted the property manager, Dave, up on his offer to take us out on his lobster boat. Dave grew up on the island and his own father was a lobsterman. He was a captivating storyteller and I loved hearing his anecdotes of a place that already felt so near to my heart. We took a beautiful ride around the bay and when he asked if we had a little more time to catch some lobsters, we of course said yes. It was so fun to see him in action and lobster has never tasted so good.

The boat ride happened to be during Milo’s nap, but luckily I brought my Lillebaby carrier. I can’t remember the last time he snuggled up and fell asleep against me. It’s so exciting to see him grow up and really become his own little person, but I cherish the moments that he just wants to be next to his mama.

The island has three restaurants. We lucked out since they were all closing for the season the following week. If you visit Bailey Island, here are some things that I recommend doing:

– for groceries, stop at Morning Glory Natural Foods in Brunswick. It’s like an expensive mini Whole Foods where the only options for eggs are cage-free local eggs. Everything is delicious and fresh. We came here on several occasions. They also sell wine and beer. If you are looking for wine and beer closer to Bailey Island, I’d recommend stopping in to Black Sheep Wine Shop. It’s a tiny store, but they have an impressive amount of wine and some really great local beer options.

Morse’s Cribstone Grill is the first restaurant when you drive on to the island, and it was always crowded. We enjoyed dinner there one evening and everything was delicious, but I’d definitely recommend the fried haddock. (We saw this amazing sunset one evening from Morse’s.)

Sunset on Bailey IslandBailey Island SunsetSunset in Harpswell, Maine

– hike Devil’s Back on Orr’s Island and the Cliff Trail where kids make fairy houses.

– you’ll likely drive through Brunswick a fair amount since that is how you get onto the island and where you’ll find the grocery store, gas station etc. We didn’t actually walk around much, but the main street is really cute and if you were looking to spend some time there, it looked like there were plenty of cute shops and restaurants.

– if you are in the area during the fall like we were, I’d recommend checking out Rocky Ridge Orchard to pick apples. We had a wonderful afternoon and we had the orchard to ourselves, which never happens in Massachusetts. The apples were delicious and so were the homemade apple cider donuts. Milo loved seeing the orchard from a wagon!

Apple Picking in MaineRocky Ridge OrchardRocky Ridge Orchard Maine

– if you love antiques like I do, definitely pop into Cabot Mill Antiques in Brunswick. There are many antique shops in the area, but this one had over 160 vendors. I left empty-handed but there was lots of nice furniture.

If you are interested in staying at the Jaquish House (or one of the other properties by The Gills Group), please send Dave an email at dave@thegillsgroup.com or check out the listing on VRBO. I’m already looking at dates for next year…. if not sooner. And if you go, please invite me! This place is so, so special.

bailey island maine
Jaquish House Bailey Island Land's End Harpswell Jaquish House Bailey Island

Man, what I would do to be back here right now! Thank you to Dave and Carter for a wonderful trip. Can’t wait to be back on Bailey Island again soon.

Thank you to The Gills Group for providing us with a complimentary stay. All opinions are my own.

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