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©2018 by Two If By Sea. Joyfully created by Suzzanne

Chebeague Island, MA - pink sky at night, a sailors delight


Finding Chebeague (pronounced "sha-big") Island was not easy! The fog was very dense and at times we couldn't see past the front of our boat. Not only are there other vessels and small islands to watch for, but thousands of lobster pots. Ryan and Molly were amazing at monitoring the radar screen for Tad.


Located in the Casco Bay, an inlet of the Gulf of Maine, Chebeague Island is the largest island not connected by a bridge, and one of the twelve major islands of the Calendar Islands, a name coined by Wolfgang William Römer in the 1700s after stating, "there are as many islands as there are days in the year."


Chebeague Island is also known as "Great Chebeague," as it is not always a single landmass. The nearby island of "Little Chebeague" is accessible on foot, via a sandbar that appears at low tide. Little Chebeague is about 3/4 of a mile long, is uninhabited and mostly dense shrub and forest. It was used during World War II as the Fire Fighters School of the Portland Naval Training Center.


Photo by my son, Ryan Freeborn!

Starting at the southern tip of Deer Point, we took a beautiful morning bike ride around the 3.5 miles of land. The Island actually has a total area of 24 square miles, but 21 square miles is inland water, thus giving it its native name "Chebeague" meaning "Island of many springs".


The year-round resident population in the 2010 census was 356.


A Bit of History

It is believed the Native American's never inhabited the island, rather they would arrive by canoe to fish and gather shellfish for the winter months. The early white settlers arrived around 1746, the first being Zachariah Chandler. Other early settlers Ambrose Hamilton and Deborah Soule Hamilton, had fourteen children and seventy-two grandchildren, almost all settling on Chebeague. Holy smokies, Batman!


Early commerce on the island developed around fishing, farming, and the construction of "stone sloops," use for the building of breakwaters, lighthouses, and set navigational markers.

By the late 19th century and throughout the early 20th century, tourists began to arrive by steamboat from Portland, Maine. Five hotels, such as the Chebeague Island Inn were built to accommodate the new industry of tourism.


What to do. What to see.

Nestled high upon a hill overlooking the harbor is the last of the island's five hotels, the Chebeague Island Inn. They offer small craft dockage and mooring buoys, and we moored overnight for a mere $25 bucks! It was easy to see the inn was a beauty in its day, but sadly, it is starting to show heavy wear and is in need for some updating.

We enjoyed dinner on the veranda of the restaurant which overlooks the harbor. The food was very good, the sunset was spectacular!


The next morning Tad and Ryan played 9-holes at the Chebeague Golf course on an adjacent hill from the inn. The 99 year-old course was originally a family homestead from the early 1800s.

Just off the clubhouse, respectfully encased with a stone rock-wall is the family burial plot with tipping headstones, no longer aligned side-by-side and washed blank by the elements of time.

Although only a nine-hole course, it held its unique challenges such as the signature seventh hole where you tee off from the Stone Wharf dock, over the Casco Bay to an even more challenging green.


Probably my slightly "off" sense of humor, but another attraction was the small grocery store where we biked to buy a few things. Onesie-twosie items on old metal shelves and a hovering scent of a burnt-bottom pot of yesterday's chili made for a fun and entertaining visit! Chebeague Island has its own post office and library. It also has a historical museum run by the Chebeague Island Historical Society which is open during the summer months.


Another beautiful sunset....

Chebeague Island Inn Moorings

The inn offers eight free moorings and launch service if you’re coming by your own boat (or a boat club boat).  These moorings are available on a first-come, first-serve basis, and the launch drivers are on channel 9. 

There is limited transient town dock space that is also available on a first-come, first-serve basis for a minimal dockage fee ($5.00/hr Mon-Thurs and $7.00/hr Fri-Sun). They charged us a flat $25.00 for the overnight stay. Fortunately, the bay is perfect for anchoring as well, and their water taxi is happy to come and get you!