Welcome October in Dutchess County, where the days are filled with pumpkin and apple picking, hayrides, and harvest festivals, and nights come alive with costume parades, trick-or-treating activities, and haunted parties. Discover Dutchess County’s best October events.
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With a noticeable chill in the air and leaf colors changing, it’s clear that fall is here. Make the most of it in Dutchess County, with plenty of harvest festivals, corn mazes, scenic colorful hikes, cozy outdoor movie nights, pumpkin picking, and so much more to get yourself into the colder-weather spirit.
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For more than 100 years, the Morgenthau family’s Fishkill Farms has celebrated fall with pumpkins, apples, cider, donuts, and festivals.
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Troutbeck’s estate in Amenia debuts four River Cottages with Champalimaud interiors, local furnishings, and art, accommodating up to 12 guests.
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Built in 1804 by Janet Livingston Montgomery, this Red Hook estate features Alexander Jackson Davis architecture, historic orchards, and gardens now stewarded by Bard College.
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Owned by artist William Harris and sensory innovator Mindy Yang, Silverbrook Manor combines regenerative farming, wellness gatherings, and creative collaboration across 54 acres in Millbrook.
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Dover Plains artist Cannon Hersey photographs and sculpts Hiroshima’s survivor trees, exploring “future memory,” inherited history, and his grandfather’s legacy.
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Dutchess County offers a wide range of schools, including college preparatory boarding academies, Montessori programs, faith-based academies, and specialized programs for students with learning differences.
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This fall, Wethersfield Estate & Garden in Millbrook hosts four equestrian events, from hunter paces to traditional Millbrook Hunt meets.
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DASSAI BLUE in Hyde Park celebrates three years with an October 3–4 festival of tours, food markets, and Japanese culture.
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