Orr’s Island Village (Harpswell Town), a settlement of attractive summer homes, lies along a low ridge sloping to the shore. Deep-sea fishing is among the popular summer sports here. The transition from the mainland to the islands, lying in the northeastern part of Casco Bay, is hardly noticeable because of the narrowness of the channels; the road runs through a growth of pines that spread a carpet of tawny needles to the edge of the road. South of the village the highway crosses Will Straits on Bailey Island Bridge, which spans the narrowest part of the channel, then curves to follow the line of a thin spit to solid ground. The rocky ridges along the highway terminate in ledges at the southern tip of Bailey Island.  –Maine: A Guide Down East (WPA, 1937)


WILL’S GUT – Harpswell, Maine

There is something in you that tells you where you belong… it’s your gut. My wife and I returned to our native state of Maine recently to escape an emotional roller coaster, which is trying to sell a 2-bedroom house in a Connecticut community that will only tolerate a 3-bedroom home. Replacing a septic tank and a rotted, termite-infested beam has to date not been enough to extract ourselves from these circumstances.

Without a lot of planning we ended up on Orr’s Island, which is connected to Bailey Island by their historic Cribstone Bridge, the only one of it’s kind in the world. For a long time the residents of Bailey Island pleaded with their town of Harpswell to build a bridge connecting their island to Orr’s. Since 1892 the town continually turned down their request until a bridge was finally built in 1928.

Design of the bridge was complicated because of the powerful tides surging back and forth between what’s known as Will’s Gut. They decided to build their unique crib-stone bridge with 10,000 tons of giant granite slabs quarried between Yarmouth and Pownal. The stone slabs were considered heavy enough to withstand wind and wave while the open cribbing allowed the ebb and flow of water without increasing tidal pressure.

Besides that, there is not a lot of robust island history to mention, outside of change of title. And maybe that’s its charm… its simplicity – its lack of human imprint. I imagine the locals have plenty of lore to share, but for a community this small there was little I could dig up while I was there besides a simple listing of families and relatives that had originally settled there.

After the earliest European settlers in the 1600s, the first settler was William Black aka Black Will, a freed slave from Kittery, Maine who moved across Will’s Gut to what was then known as Newaggin Island (named by the Abenaki Indians), in 1727. It then became Will’s Island and the most colorful part of the island’s history is perhaps that Will purportedly sold his island to Reverend Timothy Bailey in 1742 for one pound of tobacco and a gallon of rum. Will moved back to Orr’s and from then on Will’s Island became Bailey Island to this day.

I spent intermittent time on these islands as a young kid sightseeing with my family and later as a restless teen escaping my nearby hometown of Brunswick, and ultimately getting arrested with a friend by the lone sheriff policing Harpswell. My post-prom party took place in an old buddy’s house here, and prior to that we’d often drive the roughly 10 mile stretch from Brunswick down to these islands to park the car and inconspicuously walk through the sloped, pine-laden woods to the shoreline, where we’d sit on rock ledges and sip beer while we watched the fishermen come back to port with occasional seals trailing them. The thick pinewoods were like a dark loden blanket shielding our backs.

Back then we were escaping the pressures of high school and teen-life. This past weekend I was attempting escape of real life, so I dragged my wife down through the same pine-thick woods to the same rocky ledges and we watched nothing but the bluest sea rise up while the sun fell down. These brine-weathered islands were an escape back then and a Godsend now. I could use a gallon of rum while I await our return to Maine, but I’d never trade a single acre of this state for anything.


Guide to the Northeast, Brett Klein pines for Maine. See his website, Tumblr and Instagram for more of his work.



“omg im crying, my dad came in to see if I was okay” -Times Magazine ★★★★★

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Parents Upset When Book About A Transgender Child Is Read To Class -- Reality Too Much For Them

Parents Upset When Book About A Transgender Child Is Read To Class — Reality Too Much For Them

Bigotry is learned, love is innate. It is really as simple as that.

An elementary school in Kittery, Maine, was attempting to be all-inclusive, as they should be, but parents got their Underoos in a bunch when they found out their kindergartners were being read a book about a transgender child. Children that do, in fact, exist.

Parents however, wanted to be informed if such a book were to be read…

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