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Group of ladies at oktoberfest

Oktoberfest at Hunter Mountain Resort

Usually in September
Hunter Mountain Resort

I Hate Hamlet

October 9
Elmwood Playhouse

Bear Mountain Inn Family Fall Festival & Craft Brew Garden

October 10
Bear Mountain Inn

I Hate Hamlet

October 10
Elmwood Playhouse

Bear Mountain Inn Family Fall Festival & Craft Brew Garden

October 11
Bear Mountain Inn
Meadowbrook Farm Catskills Bachelorette at tulip walk

Beer, Bacon & Bourbon Festival

Usually in October
Meadowbrook Farm Catskills
Oblong Friends Meeting House, Quaker Hill, Pawling

2026 Dutchess County Quaker Meeting House Tours

October 11

Bear Mountain Inn Family Fall Festival & Craft Brew Garden

October 12
Bear Mountain Inn

The Phoenix Festival: Live Arts in Nyack Returns!

October 16
Nyack
The exterior of Washington Irving's Sunnyside home.

Legendary Tours of Washington Irving’s Sunnyside

October 16
Washington Irving’s Sunnyside
The Headless Horseman bridge alight with carved pumpkins.

The Great Jack O’Lantern Blaze

October 16
Van Cortlandt Manor
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