Pumpkins, Apples and Beer: New York’s Best Fall Festivals

These are the best autumn festivals to attend upstate.

Get out of the city to take in the best of the fall festivals. LightRocket via Getty Images

Let us raise a venti pumpkin spice latte and make a toast to the warm fuzzy glories of autumn. It’s a nostalgic, sunny but also almost-chilly time bursting with foliage, apples and late-night viewings of Hocus Pocus. And while melancholy songs like “Autumn In New York” muse about the wonders of fall in the city, why not really enjoy the splendid season by getting out of town?

There’s no better way to experience the best of autumn than exploring the festivals that mark the last, comfortable gasp of outdoor activities while dressed in mere light layers. There are a bushel of options to enjoy in upstate New York, from small-town charmers (Windham’s Autumn Affair) to the rowdy (Oktoberfests) and the quirky (Hudson Valley Garlic Festival). 

Here’s your guide, weekend by weekend, of where, exactly, to celebrate the awe-inspiring sights of an autumn getaway. 

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Image: Welcome sign at the Hudson Valley Garlic Festival.
Hudson Valley Garlic Festival. Hudson Valley Garlic Festival

Hudson Valley Garlic Festival

Cantine Memorial Complex, Saugerties, NY 12477
September 29 & 30
Admission: $10 in advance, $15 at the gate

It’s a sprawling homage to the humble garlic clove. Located in the Ulster County town of Saugerties, New York, the Hudson Valley Garlic Festival is a massive annual bacchanal devoted to everything garlic. Along with fresh cloves of it from all over the Northeast, its many vendors also hawk everything from garlic burgers, to garlic chowder and even garlic chocolate. 

If that’s too much for you, there’s also cuisine-spanning grub and dozens of vendors hawking wares ranging from woodworking to clothing. Throw in a variety of talks and performances for kids and adults and you have a quintessential country festival. Just maybe chew some gum afterwards. 

Oktoberfest. Courtesy Hunter Mountain

Hunter Mountain’s Oktoberfest

64 Klein Ave, Hunter, NY 12450
September 30, October 1, 7, 8, 14 & 15
Admission: Free

Proust! Make believe you’re somewhere in the mountains of Germany at this long-standing upstate New York hallmark. Occurring just as the glorious Catskill Mountains around you absolutely explode with color, Oktoberfest takes over the ski and snowboard mecca of Hunter Mountain with all of the libations and treats one would expect at the celebratory bash. 

Along the way, revel in keg rolling competitions, live performances and maybe even take a journey on the Skyride gondola to the top of the mountain. Revelers have three separate weekends to check out the action, which is ideal considering how temperamental autumn weather can be.

Image: The Great Jack O'Lantern Blaze fall festival.
The Great Jack O’Lantern Blaze. Bryan R. Smith/AFP via Getty Images

The Great Jack O’Lantern Blaze

525 S Riverside Ave, Croton-On-Hudson, NY 10520
Daily throughout October
Admission: Varies

The famed Great Jack O’Lantern Blaze was voted New York State’s best fall festival by Travel & Leisure and considered one of the most iconic fall getaways in the country at large. This festival boasts a whopping 7,000 carved and glowing pumpkins, along with sound and light displays. 

This year’s confab boasts what they’re dubbing a pumpkin ferris wheel and a spooky circus sideshow. Even better, the price of the admission goes toward a local nonprofit specializing in education. 

Windham Autumn Affair. Windham

Windham Autumn Affair

Main Street, Windham, NY, 12496
October 7 & 8
Admission: Free

Back for what will be its 29th annual iteration, the ski town of Windham, New York turns into a fall-fueled block party during the cutely-named Autumn Affair. 

A celebration of the businesses that make up the picturesque town, it’s a laid back gathering of fifty vendors, including food and crafts. It’s the kind of festival that’s straight out of a Hallmark movie, so here’s hoping the plot of yours has a happy ending.

Montauk Fall Festival

Montauk Village Green, 742 Montauk Highway, Montauk, NY 11954
October 7 & 8
Admission: Free

Since its inaugural event back in 1981, this Long Island autumn bacchanal has morphed into a multi-pronged celebration of the season with a farmer’s market, live entertainment and lots of booze. 

What sets it apart are the regional touches, including a food-eating contest that puts the Nathan’s Hot Dog Eating Contest to shame. Here, contestants are in competition to slurp down cups of clam chowder, which sounds even more stomach-turning than Coney Island’s buns and franks. If you’d rather not partake, revelers will also find fresh oysters and clams on sale to eat at your leisure, too. 

Image: Entrance sign at Peace, Love, and Pumpkins at Bethel Woods Center, NY.
Peace, Love, and Pumpkins. Peace, Love, and Pumpkins.

Peace, Love and Pumpkins 

200 Hurd Rd, Bethel, NY 12720
Every Friday, Saturday and Sunday from October 13-29
Admission: Varies; Night Market admission is free

Peace and love, peace and love! Ringo Starr’s famous saying gets the seasonal treatment here at the singular Peace, Love and Pumpkins. Set among the expansive Bethel Woods Center for the Arts (which was the site of the original Woodstock Music and Arts Festival), the area turns into a glowing wonderland of carved pumpkins which depict everything from rock and roll stars to other eye-popping and inherently Instagramable scenes. Elsewhere, the venue’s Night Market boasts unique vendors, delicious grub and live entertainment. 

Town clock with autumn decorations in sleepy hollow
Sleepy Hollow. LightRocket via Getty Images

Tarrytown Halloween Parade and Sleepy Hollow Haunted Hayride and Block Party

Patriots Park, Route 9, Tarrytown, NY 10591 & Sleepy Hollow Village Hall, 28 Beekman Avenue, Sleepy Hollow, NY 10591
Halloween Parade: October 28
Hayride: October 20 and 21
Admission: Parade is free, hayride varies

Halloween history rides a quick train ride north in two quaint towns to the east of the mighty Hudson River. Made famous the world over by the writer Washington Irving, who set his terrifying tale of the Headless Horseman in the area, both Sleepy Hollow and nearby Tarrytown go all out with multiple events and festivals in October. 

From a haunted hayride and block party in Sleepy Hollow, to a Halloween parade on October 28th which begins in Wiley’s Swamp (where the Headless Horseman was first seen by protagonist Ichabod Crane), it all makes for the ultimate seasonal escape. Don’t forget to visit Sleepy Hollow Cemetery as well, where scores of people visit to pay their respects to the final resting place of the late author.

Pumpkins, Apples and Beer: New York’s Best Fall Festivals