Arts
Rhinebeck Crafts Festival (Summer)
Dutchess County Fairgrounds, Rhinebeck
(845) 876-4001
One of the premier fine crafts festivals in the Northeast, featuring more than 200 juried artisans. Admission charged. Annual event held since the 1970s.
Arts
Hudson Valley Shakespeare Festival
Boscobel House & Gardens, Garrison (nearby)
(845) 265-9575
Outdoor Shakespeare performances with a Hudson River backdrop during the annual summer season.
Sports
Poughkeepsie Regatta
Hudson River, Poughkeepsie
Annual rowing regatta on the Hudson River.
Ongoing
FDR Library Lecture Series
4097 Albany Post Rd, Hyde Park
(845) 486-7770
Monthly public lectures on American history and the Roosevelt legacy.
Fair
Dutchess County Fair
Dutchess County Fairgrounds, 6550 Spring Brook Ave, Rhinebeck
(845) 876-4001
The largest county fair in New York State. Held annually since 1842, with rides, livestock shows, entertainment, and food. Admission charged.
Food & Wine
Hudson Valley Wine & Food Fest
Dutchess County Fairgrounds, Rhinebeck
Annual celebration of Hudson Valley wines and cuisine, with more than 50 wineries and restaurants.
Food & Wine
Millbrook Winery Harvest Festival
26 Wing Rd, Millbrook
(845) 677-8383
Annual harvest celebration at Millbrook Vineyards.
Food & Wine
Hudson Valley Wine & Food Fest
Dutchess County Fairgrounds
More than 50 Hudson Valley wineries and restaurants, with live music and chef demonstrations.
Arts
Rhinebeck Crafts Festival (Fall)
Dutchess County Fairgrounds, Rhinebeck
Fall edition of the premier crafts festival, featuring more than 200 artisans.
Festival
Beacon Sloop Club Pumpkin Festival
Beacon Waterfront
Annual family festival celebrating the fall harvest, with pumpkins, music, and food. Free admission.
Sports
Walkway Marathon & Half Marathon
Walkway Over the Hudson, Poughkeepsie
Annual race across the world’s longest elevated pedestrian bridge.
Festival
Beacon Sloop Club Pumpkin Festival
Long Dock Park, Beacon
Free family festival with pumpkin decorating, live music, local food vendors, and Hudson River views.
Festival
Millbrook Harvest Festival
Millbrook Village
Annual fall festival in the village of Millbrook with crafts, food, and entertainment.
Arts
Hyde Park Drive-In
4114 Albany Post Rd, Hyde Park
(845) 229-4738
One of the few remaining drive-in theaters in the Hudson Valley, with fall horror and classic film screenings.
Arts
Dia:Beacon Fall Programming
3 Beekman St, Beacon
(845) 440-0100
Special fall exhibitions and events at the world-class contemporary art museum.
Ongoing
Rhinebeck Farmers Market
61 E Market St, Rhinebeck
Local produce, artisan goods, and live music. Free admission.
Ongoing
Beacon Farmers Market
Beacon Train Station area
Local vendors, produce, and crafts.
Ongoing
FDR Library & Museum
4097 Albany Post Rd, Hyde Park
(845) 486-7770
Permanent exhibitions on Franklin and Eleanor Roosevelt. Admission charged.
Arts
Bardavon 1869 Opera House
35 Market St, Poughkeepsie
(845) 473-2072
Concerts, theater, and dance performances throughout the year.
Ongoing
Dia:Beacon
3 Beekman St, Beacon
(845) 440-0100
World-class contemporary art museum. Admission charged.