Bailey Island, Maine Vacation
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Bailey Island, Maine Vacation

by Jen
(Nashua, NH)

Peaceful Cove in Bailey Island, Maine

Peaceful Cove in Bailey Island, Maine

Three years ago my mother in law called me up and told me that for her birthday she was renting a cottage for a Bailey Island, Maine vacation. She was inviting us up to spend the weekend with her, naturally we accepted...

...who doesn't want to spend the weekend relaxing on the ocean.

I started asking for details about where we were supposed to go and other details and she really didn't have any answers.

She told my she put a check in the mail for the amount of the whole week and the owner told her just show up and it will be unlocked. He said just clean up after you leave and don't leave any trash behind.

I instantly got suspicious thinking she just got ripped off. So we pack our bags quietly hoping there was a cottage at the end of our 3 1/2 hour drive.

Upon our arrival we found an amazing little island with just a few roads covered in trees surrounded by the ocean. It was like heaven, the woods and the ocean all in one. What more could you ask for in a vacation destination.

As for the cottage, it was there and unlocked and absolutely perfect. It was a little cottage with a wraparound porch surrounded by grass and then a drop off directly to the ocean.

You see, Bailey Island is kind of like stepping back in time.

On the island everyone talks to one another, trusts one another. You sit around on the docks and talk to the fishermen as they unload the days catch.

They have a little restaurant called the Giants Stairs restaurant where all the locals talk about what's going on around town.

You just get a sense of belonging here, not of being a tourist.

There are plenty of accommodations for vacationing though. You will find quite a few places to stay on the island from the quaint little Cook's Motel to the picturesque Sea Escape Cottages.

There are a few attractions to see, Lands End, the end of the island, and the Lands End gift shop. The Giant Stairs is a great little hike to a formation of stone steps leading into the ocean. They are not steps you can walk they are giant- hence the name the Giant's Steps.

You can also find some cruises leaving from Cooks Lobster House restaurant at the pier.

There is not much in the way of a swimming beaches, at high tide the locals swim at the boat launch. However, the main reason for a Bailey Island, Maine vacation is to sit and relax in the ocean air and watch the fishing boats come in and out every day.

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Bailey Island, Maine Vacation

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Visiting Bailey Island, Maine
by: Liz

Hi Jen, Although I have never taken a Bailey Island, Maine vacation, I have visited the island on many day trips. I can only imagine how much fun it would be to rent a cottage on Bailey Island and stay for a few days.

I discovered this area by accident...

A friend invited my husband and me to join him in a fishing tournament, just off the coast of Yarmouth, Maine. It turned out to be a steamy, cloudless day, so I decided that while everyone else fished, I explore that part of the Maine coast in the comforts of an air conditioned car.

I drove as far north as Wiscasset and turned to head back. As I came through Topsham I saw the sign for Bailey Island, and something in me just said that I had to go.

The island is simply gorgeous, and as you say...

"Bailey Island is kind of like stepping back in time."

After spending time climbing around on the rocks at Lands End I drove back to Cooks Lobster House (I didn't discover the Giant Steps until a subsequent visit!) and sat eating an awesome lobster roll, totally mesmerized by the scenery.

The following year I introduced my husband to Bailey Island, and we have not missed an annual visit since. It's a great addition to our summer time Freeport outlet shopping spree!

Did you visit nearby Cundy's Harbor? It is Maine's oldest commercial fishing village and is located just off Route 24 as you travel out the Harpswell peninsula toward Bailey Island. It's a wonderful side trip - talk abuot going back in time!

I am sure you must have noticed the Bailey Island Cribstone Bridge that connects Orrs Island with Bailey Island.

The bridge is on the National Register of Historic Places and is said to be the only one in the world built as a cribstone bridge.

Granite slabs are placed one on top of another, and secured only by the paved surface. This allows for the ebb and flow of tides and for minimal current disruption. Major refurbishing work was completed on it in November of 2011.

If anyone reading this is considering a Bailey Island, Maine vacation and would like to rent a cottage, you may be interested in...

...Bailey Island vacation rental

Thanks for sharing your story, Jen.




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