September 2026 - Dutchess Magazine

25 Fall Things to Do in Dutchess County

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.

Fishkill Farms: The Great Pumpkin Patch

For more than 100 years, the Morgenthau family’s Fishkill Farms has celebrated fall with pumpkins, apples, cider, donuts, and festivals.

Four New Cottages at Troutbeck in Amenia

Troutbeck’s estate in Amenia debuts four River Cottages with Champalimaud interiors, local furnishings, and art, accommodating up to 12 guests.

Living History; Montgomery Place

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.

Earthly Work, Lofty Ambition; Silverbrook Manor

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.

Cannon Hersey; The Art of Memory

Dover Plains artist Cannon Hersey photographs and sculpts Hiroshima’s survivor trees, exploring “future memory,” inherited history, and his grandfather’s legacy.

Dutchess County’s Complete School Guide

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.

Wethersfield Estate & Garden Fall Equestrian Activities

This fall, Wethersfield Estate & Garden in Millbrook hosts four equestrian events, from hunter paces to traditional Millbrook Hunt meets.

Dassai Blue Sake Brewery Turns Three

DASSAI BLUE in Hyde Park celebrates three years with an October 3–4 festival of tours, food markets, and Japanese culture.

Harlem Valley Rail Trail; Twenty-Three Miles of Color

Stretching 26 miles from Amenia to Copake Falls at Taconic State Park, the Harlem Valley Rail Trail offers scenic autumn views for cyclists and walkers.