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Cundy's Harbor, Harpswell

I remember when friends started buying second homes, get-away’s, not for their children when they were in the midst of raising their families, but as the next stage – looking toward their own fulfillment and retirement years. I remember feeling happy about it, satisfied. Not old. Not mixed. Just happy and curious to see what friends were choosing.

Purchased close enough to travel to on weekends, still working during the week, they bought at Bayside in Northport, Boothbay Harbor, Rangeley, and Little Sebago Lake. And one life-long friend bought and introduced us to Cundy's Harbor in Harpswell.

Harpswell is just beyond Brunswick, a town with the longest coastline in Maine at 200 miles. It comprises Bailey Island, Eagle Island, Haskell Island, Orrs Island, Harpswell Center, West and South Harpswell, North Harpswell and the village of Cundy's Harbor on Great or Sebascodegan Island.

Cundy's Harbor lies in East Harpswell on the southeastern portion of Sebascodegan Island, sandwiched between Ridley Cove and the mouth of the New Meadows River. Most of the dwellings in Cundy's Harbor were constructed in the 19th century, traditionally a fishing village and truly a working waterfront.

Edna St. Vincent Millay, a poet I learned about at The Telling Room, lived with her husband on Ragged Island in Harpswell in the 1930’s. Arctic explorer Robert Peary maintained a summer home on Eagle Island which we pass often in summer as we boat to Dolphin’s Marina. Author Elizabeth Strout (Olive Kitteridge) grew up in Harpswell, once working at Bailey’s store, I’ve heard.

Bowdoin College’s Coastal Studies Center is located on Orrs Island, hosting a research facility and nature trails open to the public. The town of Harpswell provides The Harpswell Guide to town-owned and Harpswell Heritage Land Trust areas at They include miles of short hiking trails, open spaces, and nine nature preserves managed by the Land Trust. Doughty Nature Preserve, accessible only by water across Gurnett Narrows from Prince’s Point, is a 42-acre peninsula of forest where Ospreys nest.

Our friends bought the tiniest little 2-bedroom cottage and completely, and adorably, renovated it. We were invited to an afternoon visit and early dinner late in February. Although the sky and land were stark and gray and cold at that time of year, it made the cottage even sweeter with its light inside colors and beach theme. We sat in rockers, looking out their front window, across the porch to the cove just out front, wisps of snow blowing over the frozen land.

Walking to Holbrook’s Wharf and peeking at the closed-up gift shop had us tightening scarves and blowing on cold fingers but undeterred from basking in this quaint, seaside community. Taking a walk in the cold, up and down the hills, pausing on the wharf, made the delicious meal with friends taste even better. Naturally, we told stories of old times, laughed heartily, and toasted to our futures. One couple’s son was about to marry another couple’s daughter. We reminisced about our own weddings, decades ago. Life in a small town, the closeness of community.

The drive out to Cundy's Harbor, especially in spring when wildflowers are coming back to life in vast meadows along the way, is a sweet one. The country roads and views of the ocean along the fingers of Harpswell are quintessential Maine – not in a showy way, but in a humble, working, living-life way.

Our friends love heading north to their little slice of coastal-village-living every Friday afternoon until the time comes when jobs end, kids are far away, and this couple settles back into a quiet life with one another – now a little grayer, a little slower moving, but relishing, still, their beautiful life.

We’re grateful to have shared it.

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