September and October in the Hudson Valley are packed with crisp air, colorful leaves, and some of the region’s most iconic celebrations. From Oktoberfest steins and grape stomping to garlic feasts, apple picking, and lantern-lit nights, there’s no shortage of ways to embrace the season. Whether you’re looking for family-friendly fun, local food and drink, or arts and culture, the Hudson Valley has a fall festival for everyone.
Here’s your guide to the can’t-miss events this September and October 2025
September 2025
September 6–7 – Oktoberfest – Germania Festival Grounds, Poughkeepsie, NY
Raise a stein and enjoy live music, traditional German food, and family-friendly festivities at this classic Oktoberfest celebration.
September 6–7 – Hudson Valley Wine & Food Festival – Rhinebeck, NY
Over 300 vendors showcase New York wineries, cideries, distilleries, breweries, gourmet specialty foods, as well as fine arts and crafts.
September 12–November 16 – Great Jack O’Lantern Blaze – Van Cortlandt Manor, Croton-on-Hudson, NY
Experience thousands of illuminated pumpkins in creative displays, perfect for a magical autumn evening stroll.
September 20 – Skywalk Arts Festival & Rip Van Winkle 90th Anniversary – Rip Van Winkle Bridge, Catskills, NY
Celebrate local artists and the iconic Rip Van Winkle story with live art, crafts, and cultural performances.
September 20–21 – Moon Festival – Port Jervis, NY
Honor the harvest season with lanterns, music, and community festivities at this vibrant celebration of moonlight and tradition.
September 21 – Sleepy Hollow Street Fair – Sleepy Hollow, NY
Featuring over 145 arts and crafts vendors, food, and local shops, plus entertainment for the whole family.
September 20–21 – Benmarl Harvest Grape Stomping Festival – Marlboro, NY
Get hands-on in the winemaking tradition with grape stomping, tastings, and live entertainment.
September 27–28 – Hudson Valley Garlic Festival – Saugerties, NY
Savor garlic-inspired dishes, local crafts, and live music at this flavorful celebration of one of the Hudson Valley’s most beloved crops.
October 2025
October 4 – Town of Tuxedo Fall Festival – Tuxedo Park, NY
A day of seasonal fun featuring crafts, pumpkins, face painting, hayrides, food trucks, and community activities.
October 4–5 – Hudson Valley Apple Festival (Barton Orchards) – Poughquag, NY
Pick fresh apples, enjoy hayrides, and savor apple-themed treats at this family-friendly harvest celebration.
October 4–5 – Handcrafted Oktoberfest – Dutchess County Fairgrounds, Rhinebeck, NY
Celebrate artisanal foods, local beers, and Oktoberfest traditions in a lively, handcrafted setting.
October 5 – Warwick Applefest – Warwick, NY
A beloved annual tradition featuring apple tastings, live music, and fall activities for all ages.
October 10–12 – O+ Festival – Kingston, NY
Experience a unique blend of art, music, and community wellness at this creative cultural festival.
October 11–13 – Harvest Festival Weekend (Barton Orchards) – Poughquag, NY
Enjoy seasonal produce, pumpkin picking, and family-friendly farm fun over a festive weekend.
October 11–12 – Sugar Loaf Fall Festival – Sugar Loaf, NY
Discover local artisans, live music, and seasonal crafts in the charming village of Sugar Loaf. Trick-or-treating for kids included!
October 11 – Coxsackie Fall Festival at The Grange – Coxsackie, NY
Celebrate autumn with live entertainment, local vendors, and community activities in historic Coxsackie.
October 12 – SUP Witches of Sleepy Hollow Festival – Kingsland Point Park, Sleepy Hollow, NY
A spooky and fun event combining paddleboarding on the Hudson with a Halloween twist.
October 12 – Nyack Famous Street Fair – Downtown Nyack, NY
Featuring over 300 exhibitors across four states with arts & crafts, home decor, unique gifts, food, and entertainment.
October 18–19 – Hudson Valley Sheep & Wool Festival – Rhinebeck, NY
Meet local shepherds, explore fiber arts, and enjoy hands-on demonstrations at this beloved agricultural and craft festival.
October 19 – Rosendale International Pickle Festival – Rosendale, NY
With over 100 vendors, this festival features pickle-inspired eats, baked goods, crafts, and the famous Pickle Triathlon with contests and games.
October 26 – Nanuet Fall Festival – Lake Nanuet Park, Nanuet, NY
A family-friendly event with pumpkin decorating, live music, vendor booths, and a Trunk or Treat celebration.
Ongoing Fall Events
September & October – Fall Harvest Festivals – Fishkill Farms, Fishkill, NY
Pick apples, taste cider, and enjoy seasonal treats at this scenic farm throughout the fall.
September & October – Harvest Festivals at Bethel Woods – Bethel, NY
Enjoy corn mazes, hayrides, farm and craft vendors, and food trucks.
Through October 4 – New York Renaissance Faire – Tuxedo Park, NY
Step back in time with costumed performers, jousting, and artisanal food at this lively Renaissance Faire.
September 12–November 16 – Great Jack O’Lantern Blaze – Croton-on-Hudson, NY
A magical pumpkin spectacle lighting up the fall nights with intricate designs and themed displays.
September 19–November 1 – Mystic Moon at Harvest Moon Farm – North Salem, NY
Experience illuminated gardens, mystical installations, and seasonal enchantment at this evening festival.
Plan Your Hudson Valley Fall Adventure
With so many festivals and seasonal events, September and October are the perfect months to experience the magic of fall in the Hudson Valley. Whether you’re looking for apple orchards, cultural celebrations, or family fun, there’s a festival waiting for you. Grab your calendar, pack your sweater, and get ready to make unforgettable autumn memories.