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A bluegrass band performing at the Country Living Fair, which will be held at the Dutchess County Fairgrounds in Rhinebeck Oct. 2-4, 2026.

Country Living Fair at the Dutchess County Fairgrounds in Rhinebeck (Oct. 2-4)

October 4
Dutchess County Fairgrounds
A man sitting in the grass playing a rainbow-colored percussion instrument at the Beacon Flow Music and Wellness Festival. Photo by Alejandro Lopez.

Beacon Flow Music and Wellness Festival

October 10
Pete & Toshi Riverfront Park
A horse and rider jumping over an obstacle at the Silo Ridge Masters Horse Show at Keane Stud in Amenia

Highlands Cup Horse Show at Keane Stud in Amenia (Oct. 9-11)

October 11
Keane Stud
Oblong Friends Meeting House, Quaker Hill, Pawling

2026 Dutchess County Quaker Meeting House Tours

October 11
A young woman wearing a wool sweater smiles as she holds a sheep in her arms at the New York State Sheep and Wool Festival at the Dutchess County Fairgrounds in Rhinebeck

New York State Sheep and Wool Festival at the Dutchess County Fairgrounds (Oct. 17-18)

October 17
Dutchess County Fairgrounds
Madam Brett Homestead-Beacon

First Public Ghost Hunt at Madam Brett Homestead in Beacon with Full Moon Paranormal

October 17
Madam Brett Homestead
Oblong Friends Meeting House, Quaker Hill, Pawling

2026 Dutchess County Quaker Meeting House Tours

November 8