Kenneth Walsh is one of Westport native Don Willmott’s favorite bloggers.
Kenneth lives in Manhattan. But he has a strong Westport connection, through his late grandmother.
He visited here over Thanksgiving, to look into the places she lived. Then he posted photos from his tour.
Willmott calls it “a great, somewhat epic saga of family dysfunction: Westport ‘behind closed doors,’ with lots of before/after photos he took thanks to the cooperation of generous current residents.”
Kenneth and his husband Damian “rented a quirky guest house in Westport, with plans to recharge, see a couple friends (everyone we know is moving that way so we’ve become ‘Connecticut curious’),” then went on a “family-history spree” to see where his maternal grandmother spent the last chapter of her life, before dying by suicide shortly after her 50th birthday.
His long story about his family history — fascinating to people with an interest in such things — is sprinkled with photos from decades ago, and how they look today. They include Hillspoint Road opposite Old Mill Beach, and Drumlin Road.

Kenneth Walsh (right) in front of his grandmother’s former Drumlin Road house (left) …

… and 240 Hillspoint Road.
Kenneth also writes about his grandmother’s neighbor (a former colleague of Albert Einstein), the drinking culture of the town at the time, and more.
He gives a shoutout to the restaurants he and Damian visited (Basso, Spotted Horse, The Cottage, Rive Bistro), and to the “welcoming” Westport Pride rainbow crosswalk on Jesup Road.
It’s an intriguing look at our town, from an outsider who appreciates his inside connections.

Kenneth Walsh and his husband at Old Mill Beach. Decades earlier, Kenneth’s grandmother and her husband posed at the seawall there.
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