Hudson Valley Events
Halloween & Haunted
Sleepy Hollow After Dark Twilight Village
02
OCT
10/2 - 10/31
See event link
See event link
Philipsburg Manor becomes a twilight Halloween village with local legends, odd encounters, fortune telling and a night market. Spooky without the full chase-you-through-the-woods treatment.
Sleepy Hollow, NY
Family & Fall
Dogwood Acres Pumpkin Party
02
OCT
10/2 - 11/1
See official site
Sat–Sun 11 AM–6 PM
Pumpkins • Farm activities • Family fun
Hayrides, a corn maze, farm animals, pumpkins and plenty of room to wander turn a simple pumpkin stop into the kind of fall outing that quietly eats an afternoon.
Dogwood Acres Family Farm
Middletown, NY
Family & Fall
Autumn Glow Festival
02
OCT
Fri - Sun through 11/1
From $16.99 • Ages 0–2 free
6:30–10 PM • Last entry 9 PM
Illuminated trail • Fall displays • Free parking
Glen Island Park glows after dark with hundreds of lanterns, huge illuminated creatures and a waterfront full of color. A very different visual language for October.
Glen Island Park
New Rochelle, NY
Halloween & Haunted
The Great Jack O’Lantern Blaze
01
OCT
9/18 - 11/8
From $24 • Free parking
Timed admission • Hours vary
Hand-carved pumpkins • Illuminated trail
Thousands of hand-carved pumpkins take over a historic Hudson Valley estate after dark. Book the timed ticket, grab a jacket and let the scale of it do the rest.
Van Cortlandt Manor
Croton-on-Hudson, NY
Arts & Culture
Armonk Has Heart
21
SEP
8/26 - 9/27
Free to view
Auction closes Sep 27 at 5 PM
Public art • Local artists • Community auction
Follow a trail of artist-designed heart sculptures through local storefronts, turning an ordinary stroll into a playful public-art hunt. Every heart has its own personality, every stop supports a larger community effort, and the finale gives the whole experience a meaningful pulse.
Armonk Square and local businesses
Armonk, NY
Jazz Festival
JazzFest White Plains
23
SEP
9/23 - 9/27
Free Events + Ticketed Shows
Hours Vary by Performance
19 Performances • 5 Days
A whole city becomes a jazz club. Catch celebrated artists, rising talent and local players across intimate rooms, outdoor stages and major halls, then build your own perfect run of shows. Serious jazz credentials, zero pressure to be an expert.
Downtown White Plains
Multiple Locations
White Plains, NY
Shopping & Markets
Taconic Antiques Fair
26
SEP
9/26 - 9/27
$10 weekend admission
Sat 9 AM–5 PM • Sun 10 AM–4 PM
100+ dealers • Antiques • Vintage finds
The hunt is half the fun at this dealer-packed antiques fair. Expect vintage finds, furniture, art, oddities and the thrill of spotting something with real history before someone else does. Come with an open mind and a way to get your treasure home.
Columbia County Fairgrounds
Chatham, NY
Juried Art Show
Armonk Outdoor Art Show
26
SEP
9/26 - 9/27
Adults $18 • 18 & Under Free
10:00 AM–5:00 PM Daily
160 Artists • Family Activities
An open-air gallery filled with exceptional juried work, live artist conversations, family fun and the distinct possibility of finding the piece that changes a room. Come browse, meet the makers and see why collectors return year after year.
North Castle Park
205 Business Park Drive
Armonk, NY
Food & Drink
Hudson Valley Garlic Festival
26
SEP
9/26 - 9/27
Advance adults $10 • Gate $15 • Under 12 free
Sat 10 AM–6 PM • Sun 10 AM–5 PM
Garlic food • Growers • Crafts • Entertainment
A full-scale garlic pilgrimage where chefs, growers, food vendors, crafts and entertainment turn one ingredient into an entire weekend. Come ready to taste the unexpected, stock up on local goods and leave with the kind of glorious culinary confidence only garlic can provide.
Cantine Field
Saugerties, NY
Food & Drink
Naples Grape Festival
26
SEP
9/26 - 9/27
See official site
10 AM–5 PM
Grape pies • Wine • Arts and crafts
The Finger Lakes grape harvest gets the full celebration treatment with local wine, food, art, music and the legendary grape pie that has people planning their visit around dessert. Come hungry and save room for the thing everyone will tell you not to miss.
Naples High School and Memorial Town Hall
Naples, NY
Food & Drink
Whiteface Oktoberfest
26
SEP
9/26 - 9/27
See official ticket page
Sat 10:30 AM–6 PM • Sun 10:30 AM–5 PM
German food • Live music • Fall scenery
Raise a stein, eat something hearty and let the mountain backdrop do its thing. German food, live music, festival energy and early fall color make this a seriously fun excuse to spend a weekend at elevation.
Whiteface Mountain
Wilmington, NY
Festivals & Fairs
Saratoga Giant PumpkinFest
26
SEP
9/26
See official site
Time to be confirmed
Giant pumpkin weigh-off • Fall fun
Watch giant pumpkins push the limits of what seems physically reasonable, then enjoy a fall celebration built around their ridiculous size. The weigh-off is the main event, but the crowd reaction alone makes this a great day for anyone who loves gloriously weird traditions.
Saratoga Farmers’ Market / High Rock Park
Saratoga Springs, NY
Festivals & Fairs
Great Adirondack Moose Festival
26
SEP
9/26 - 9/27
See official site
2026 schedule pending
Moose-themed activities • Townwide festival
A whole Adirondack town leans into moose season with themed activities, local character and plenty of reasons to make a weekend of it. Come for the wildlife obsession, stay for the small-town fun and mountain-country atmosphere.
Route 28 and locations throughout town
Indian Lake, NY
Festivals & Fairs
New York Renaissance Faire
26
SEP
8/15 - 10/4
Adults $60 at gate • Children $28
10 AM–7 PM
Jousting • Live shows • Artisan marketplace
For one glorious day, ordinary life gives way to jousts, wandering nobles, bawdy comedy, music, artisan wares and food designed for eating with both hands. Dress up or do not, but come ready to play along. This is full-scale escapism with a very enthusiastic court.
New York Renaissance Faire
Tuxedo, NY
Outdoor Recreation
Bicycle Sundays
27
SEP
9/13, 9/20, 9/27
Free
10 AM–2 PM
Car-free parkway • Cycling • Walking
A whole stretch of parkway becomes your personal playground. Bike, walk, skate or simply cruise without traffic beside you, then remember how ridiculously good a familiar route can feel when cars are taken out of the equation.
Bronx River Parkway
Westchester County, NY
Festivals & Fairs
Bethel Woods Harvest Festival
27
SEP
9/6, 9/13, 9/20, 9/27
Free admission • Parking $5 advance/$7 day
11 AM–4 PM
Market vendors • Live entertainment • Family fun
A Sunday market with more soul than your average errand run. Browse regional makers, catch live entertainment, let the kids burn some energy and take in the storied grounds. It is an easy way to make a simple fall afternoon feel unexpectedly complete.
Bethel Woods Center for the Arts
Bethel, NY
Festivals & Fairs
Country Living Fair
02
OCT
10/02 - 10/04
$28 - $150
10:00am - 5:00pm
275 vendors • Music • Food
Country Living Fair turns the fairgrounds into a full-on celebration of collecting, making, and good old-fashioned browsing. Explore 200+ handpicked vendors, meet designers and tastemakers, catch folk, bluegrass, and Americana on the Americana Music Stage, and get inspired in hands-on workshops. Come for the treasure hunt, stay for the creative energy, cider donuts, and finds you will be talking about all fall.
Dutchess County Fairgrounds
6636 US-9
Rhinebeck, NY
