Matthew Houskeeper

Matthew Houskeeper Jan. 12, 1965 – Aug. 14, 2024
Matthew Charles Houskeeper, of North Bennington, Vermont, passed away unexpectedly from a cardiac event while kayaking on Sherman Reservoir on August 14, 2024. He was 59 years old.
He is survived by six loving brothers and sisters: Jeanne Chisamore of Manchester, Vermont; Bernadette Dooney of Hopewell Junction, New York; Peter Houskeeper (Claudia) of Poughkeepsie, New York; Robert Houskeeper (Jamie) of Encinitas, California; Margaret Ohrn (John) of Newburyport, Massachusetts; and Erica Houskeeper (Dave) of Burlington, Vermont – and ten nieces and nephews.
Matt was predeceased by his parents, James Robert Houskeeper and Elizabeth O'Leary.
Born in 1965, Matt grew up in Putnam Valley, New York, a rural community one hour north of Manhattan in the Hudson Valley. Matt's family relocated to Manchester, Vermont, when he was 14. He attended Burr and Burton Academy in Manchester before enrolling at the University of Vermont, where he graduated in 1988 with a bachelor's degree in geography.
Matt lived a life of many interests. He was an avid reader and loved both baseball and politics, but his truest passion was the sea.
A skilled sailor and yachtsman, he spent his life navigating the Atlantic Ocean from Florida to Cape Cod. Long Island Sound was always his favorite. It was there that Matt's father first introduced him to boating. Matt soon began working as a deckhand at Cove Marina in Norwalk, Connecticut. Before long he graduated to captain, handling large vessels for clients while still only a teenager.
After college, Matt worked as a stockbroker in San Diego and passed his Series 7 exam. He transitioned to residential and commercial construction after returning to New York in his early thirties. He bought a sailboat, which he kept at City Island, New York, before relocating to Saybrook, Connecticut. It was during this time that Matt started Soundbounder, a blog in which he shared stories and photos of his life on Long Island Sound.
Matt eventually returned to Southern Vermont, where he worked as a bartender at Bromley Mountain, Firefly Restaurant in Manchester, and Kevin's Sports Pub and Restaurant in North Bennington. He also continued to work on the water, operating boats of all sizes up and down the East Coast. Perhaps fittingly, Matt's last assignment came only days before his passing, when he transported a vessel between Block Island and Cuttyhunk.
To know Matt was to have a friend. Kind and personable, his easy manner, quick wit, and soft smile drew people in. Friendships and shared history were important to him. He connected with people in a lasting and meaningful way. There was nothing superficial about Matt. He lived life on his own terms. A wonderful sailor, brother, and friend, he was first and foremost a good man.
Matt's brothers and sisters would like to extend their tremendous gratitude to the Vermont State Police Search and Rescue and Underwater Recovery Teams; the Vermont Department of Fish and Wildlife; the Massachusetts State Police; New England K9 Search and Rescue; and Rescue Inc. Their professionalism, dedication, and hard work are greatly appreciated.
The family would also like to thank Stephen C. Gregory and Son Cremation Service of South Burlington, Vermont.
Please join us for a celebration of life held in Matt's honor at Kevin's Sports Pub and Restaurant in North Bennington on Saturday, October 19 from 11 a.m. to 2 p.m.
Donations in Matt's memory can be made online to Save the Sound (https://www.savethesound.org) or by mail to Save the Sound, 127 Church Street, 2nd Floor, New Haven, CT 06510.