Top 10 Things to Do in the Hudson Valley this Fall

Fall foliage with the words overlaying the image saying "Ten Things to do in the Hudson Valley in the Fall"

With the leaves changing color and the crisp cool air, to all the farms opening their doors to the public for pick-your-own apples and pumpkins, the Fall in the Hudson Valley is unlike anywhere else. There is SO much to do, dozens of places to see, and tons of events to attend… it’s a good thing we compiled a list of our top 10 things to do here in the Hudson Valley this Fall.

A group of people in front of a movie screen that says "Woodstock Film Festival"

10. Woodstock Film Festival. October 2nd – 6th. Woodstock, NY Rhinebeck, NY. 

Founded in 2000 as a grassroots arts organization driven by the sheer love of film and community, the Woodstock Film Festival has grown into one of the premiere independent film festivals in the US, bringing together thousands of filmmakers and film lovers over the years. They will celebrate the 20th anniversary of the Woodstock Film Festival this Fall. Also marking the 50th anniversary of the legendary Woodstock Festival, as well as the 100th anniversary of Woodstock as America’s oldest colony of the arts.

Films, panels, parties and the Maverick Awards Ceremony during the Woodstock Film Festival generate large, enthusiastic audiences, news headlines, social media exposure, and a gamut of other promotional opportunities for all of our supporters. Their success is linked to your generous support. Here is your chance to be a part of what actor Paul Rudd (Rhinebeck resident) calls “a great festival… what a film festival should be, which is really independent films and showcasing the work of filmmakers you might not know about.”  –

Image of the Headless Horseman on his horse being used as a flyer for the Headless Horseman Haunted Hayrides in Ulster Park, NY

9. The Headless Horseman. Friday – Sunday evenings from September 21st to November 2nd and October 24th & 31st. Ulster Park, NY.

The 250 year-old farm incorporates over sixty-five acres of naturally landscaped property including foreboding woods, surreal ponds, fruit orchards and more. Headless Horseman Hayrides and Haunted Houses is a unique, immersive experience with a theme that changes each Halloween season. Featuring a theatrical one-mile hayride, a corn maze, and 8 haunted attractions:

  • The Lunar Motel
  • Glutton’s Diner & Slaughter House
  • The Horseman’s Tomb
  • Dark Harvest Corn Maze
  • Mama Rose’s Swamp Shack
  • Night Shade Nursery & Greenhouse
  • Dr. Dark’s Black Spider Circus Sideshow
  • The Feeding presents “The Pain Killer”
  • Two Raven’s Manor, with skilled stunt actors and a magic-illusion side show starring Ryan Dutcher.

In addition, the creators of Headless Horseman Hayrides and Haunted Houses are proud to present a new concept of interactive, immersive entertainment. A real life escape experience Headless Horseman Escape Rooms” – a first for the Historic Hudson Valley.

Headless Horseman continually evolves with unusual monsters, amazing illusions, stunning special fx, unique and original costumes, makeup, animations and frightening detail created by our sister company American Made Monster Studios. Only the courageous will survive the intense encounters with the infamous Headless Horseman.

The attraction also includes line actors, four themed gift shops: Magic Moon Gift Shop, Scare Ware, Fear Gear, and Phantom Photo, and five food options: Evil Eatery, Witch Hazels, Croaked Crow, and Deadly Donuts. They employ over 350 actors and staff trained to provide a memorable and enjoyable evening for the whole family.

Headless Horseman Hayrides and Haunted Houses has received numerous awards and honors:

  • Named #2 Haunted Attraction for 2019  by USA Today 10 Best Readers’ Choice Travel Award
  • America’s Scariest Haunted House in the Northeast by MTV
  • #1 in America two consecutive years by HauntWorld Magazine
  • #1 Hallow Scream by The Weather Channel
  • World’s Best Haunted Hayride by AOL News
  • #1 on the Planet by New York Daily News
  • “One of America’s Best Hometown Haunts” by Fangoria Magazine
  • #1 Outdoor Attraction by American Airlines
  • #1 Scream Park and Hayride in America by HauntWorld Magazine
  • #1 by USA Today

In addition, Headless Horseman is consistently named in the Top Ten Haunted Attractions by CNBC and AOL. It has been featured on The Travel Channel, Comedy Central, Emeril Live, Good Morning America, Nightline, CBS Evening News, The Today Show’s segment “Sara in the City” and several national magazines. –

A photo of groups of people sitting at picnic tables in front of food trucks at the Stormville Airport Flea Market

8. Stormville Airport Antique Show & Flea Market. October 12th & 13th. Stormville, NY. 

As seen on HGTV’s original show ‘Flea Market Flip’ the Stormville Airport Antique Show & Flea Market is a fun, family-friendly atmosphere that draws thousands of shoppers to each show. With acres and acres of merchandise this market offers a wide variety of bargains, treasures, and unique items for everyone. The Stormville Airport Antique Show & Flea Market is located in the historic and scenic Hudson Valley on a private airport located halfway between Manhattan and Albany, right off the beautiful Taconic State Parkway.

The Stormville Flea Market was started in 1970 with six tables and a handful of vendors’ on the front lawn. Today, they are one of New York’s largest and most popular outdoor flea markets with over 600 vendors, several of whom have been with them since the beginning! Their success is due to the quality of merchandise offered, the reliability of their vendors and a trust that has been built with their buyers. You will find a wide variety of bargains and treasures including: Apparel, Handbags, Jewelry and Tools…and the list goes on and on.

With over 600 hundred vendors from more than eight states there is always something new and exciting at the Stormville Flea Market. Shoppers go to the Stormville Flea Market and discover everything from antiques and collectibles; arts and crafts to new merchandise. Shoppers return year after year with some traveling over a hundred miles, often by the busload, to pursue the hunt for bargains. –
A table setting set out on a farm
7. Hudson Valley Bucket List Hosts Fall Foliage Wine Tour. October 12th. Various Hudson Valley Wineries. 
Experience this at least once in your lifetime, Fall Foliage in New York. You’ll be taken through the scenic Hudson Valley to visit small towns and sample wine of the region paired with local cheeses. Take in the fall foliage, the farm stands, and picturesque farms scattered between your visits to the wineries. Be sure to bring your camera on this unforgettable day in the heart of the Hudson Valley. Vineyard & Wine Tour visits 3 to 4 wine tasting locations. This is a 6-hour shuttled tour that includes tastings at three unique wineries of the region, paired with cheeses of the Hudson Valley, and a delicious picnic lunch with luring stories of the region. Depart with wine, farm stand goods, local treasures, and a new understanding of wine.

While driving to the second unique winery, Hudson Valley Bucket List will give you great insight on the region’s history, stories, and local lore. You’ll arrive to see an estate winery like one you would see in Napa Valley. Taste wine in its purest form while chatting with the winemaker. You’ll make your way outside for your catered pop-up picnic; a mix of gourmet sandwiches with the favorite being Humboldt Fog with fig spread, baby kale caesar salad with house-made dressing, and seasonal couscous salad, bottled water, and a sweet treat. They use as much of the local bounties for you to get a true sense of the Hudson Valley.

After lunch, you’ll have some time to relax, sit back, and enjoy the ride to the last winery, the oldest continuously operating winery or vineyard in America. Experience historic wine cellars that contain some of the oldest vintages. You’ll experience your last flight of wine. Leave with a greater understanding of the wine making process and the lore of the oldest wine making regions in the U.S.

You’ll have the opportunity to bring home your favorite vintage and shop in their quaint gift shop full of reminders of the region. Your day ends with many memories of a great experience and a new-found love for NY wine. The day ends where it began at your pick-up locations. –

An arch of carved pumpkins
6. The Great Jack O’Lantern Blaze. September 20-22; 26-29; October 3-31; November 1-3; 8-10; 15-17; 22-23; 29-30. Croton-on-Hudson.
The tri-state area’s biggest, most electrifying Fall event! Meander through an 18th-century landscape and discover a breathtaking display of more than 7,000 illuminated jack o’lanterns—all designed and hand-carved on site by their team of artisans! Tour the brand-new Museum of Pumpkin Art, where classic paintings get the gourd treatment, see who let the (pumpkin) dogs out, listen for the Headless Horseman—and watch out for swooping jack o’lantern bats! See the Pumpkin Carousel twirl and the Pumpkin Windmill whirl and step inside the Pumpkin Planetarium for a star show like you’ve never seen. You’ll certainly hold a torch for the 25-foot-tall jack o’lantern Statue of Liberty and get personal with Instagrammable signs of the zodiac. Complete with synchronized lighting and an original soundtrack, this one-of-a-kind event is not to be missed! More than 1,000 volunteers help scoop, carve, and light the pumpkins and every single jack o’lantern is hand-carved on site by their team of professional artists.

All proceeds from Blaze and our other Halloween events support the programs of Historic Hudson Valley, a non-profit education organization. –

graphic logo saying ' Oktoberfest'

5. Oktoberfest Handcrafted at Rhinebeck: A Family Harvest Celebration at Dutchess County Fairgrounds. October 5th & 6th. Rhinebeck, NY.

The Hudson Valley’s premier art and crafts festivals have been bringing makers, artists and art & craft-lovers together for nearly four decades. Since 1982, we’ve been supporting handmade by offering visitors one-on-one interactions with many of the country’s finest artists and craftspeople. You’ll experience an extensive assortment of art and craft demonstrations and live entertainment by regionally-based musicians, while enjoying the Hudson Valley’s best wines, spirits, craft beer and locally-produced gourmet specialties.

Quail Hollow Events hosts Rhinebeck’s first Oktoberfest at the fairgrounds. An artistic spin on a traditional Oktoberfest, this festival brings together the handcrafted, artisanal and agricultural — from wearable fine craft and laudable fine art to the Hudson River Valley’s best brew, wine, specialty foods and apothecary goods.

The young and young at heart will interact with farm animals and partake in an agri-venture center and creative free-play, while adults enjoy the season’s best beer, wine, spirits and gourmet specialties, while browsing handmade furniture, jewelry, ceramics, glass, fiber art, and much more.

  • October 5th – 10am – 6pm
  • October 6th – 10am – 5pm

Free Parking and the event is Rain or Shine –

three older men holding beer steins4. Bear Mountain Oktoberfest. September 27th – October 20th, Friday – Sunday. Tompkins Cove, NY.

The tradition continues! Oktoberfest 2019 will be hosted at Anthony Wayne Recreation Area, just a stone’s throw from Bear Mountain State Park – located at Exit 17 off the Palisades Parkway. Oktoberfest will be running every Friday, Saturday, and Sunday from September 27 through October 20. Festival hours are Fridays: 6 pm – 10 pm; Saturdays & Sundays: 12 pm to 6 pm; the bands play from 12:30 – 5:30 pm. –


Bear Mountain Oktoberfest is proud to present a host of improvements for this year’s festival!
Cash and credit accepted at all food and beverage stations
4 party wagons with 16 taps each
More bartenders at each wagon
Additional mobile food carts
Expanded buffet lines
VIP Experience Package

Band Schedule:

September 27 | Mountain Express
September 28 | Bavarski
September 29 | Alpine Squeeze
October 4 | Bratwurst Boys
October 5 | The Spitzbuam
October 6 | Alex Meixner Band (Grammy Winner)
October 11 | Fritz’s Polka Band
October 12 | The Alders
October 13 | DSB (die Schlauberger)
October 14 | Johnny Konig Band (12:30 pm – 5:30 pm)
October 18 | Royal Bavarians
October 19 | Jimmy Sturr Orchestra
October 20 | Heimatklange

Walkway Over the Hudson

3. Walktoberfest Weekend. October 5th and 6th. Highland, NY. (Accessible from the Poughkeepsie side of the walkway).

In celebration of their 10-year anniversary, Walkway Over The Hudson is bringing a curated selection of local distilleries, breweries, wineries, cideries, restaurants, artisans, and products to the Walkway Over the Hudson during Walktoberfest Weekend – Saturday, October 5 and Sunday, October 6.  Sample, taste, and purchase products right on site.

Walktoberfest takes place inside a beautiful clear-top tent located at the Ulster Welcome Center Plaza (87 Haviland Road, Highland, NY 12528), just steps away from the gates of the bridge.

Walkway Over the Hudson State Historic Park is fully open and accessible at no cost as usual throughout Walktoberfest. Tickets are solely for access to the Walktoberfest tent. –

Headshot of Gladys Knight

2. Gladys Knight Live at the Bardavon; 150th Anniversary Gala. October 6th. Poughkeepsie, NY. 

Bardavon 150th Anniversary GALA patrons will be treated to one of the most instantly recognizable and beloved voices in popular music as the seven-time Grammy Award winner and her band perform all of her R&B chart-toppers from, “Every Beat Of My Heart,” “I Heard It Through The Grapevine,” “I Don’t Want To Do Wrong,” her soul-pop smashes “If I Were Your Woman,” “Love Overboard,”  “You’re The Best Thing That Ever Happened To Me,” and of course what has become her unofficial anthem, “Midnight Train To Georgia.”

This year Gala guests will enjoy a PRE-SHOW dinner at the Grandview – Cocktail attire. 

A display of model buildings and cars on a table

1. 48th Annual Train and Hobby Show. November 10th. Poughkeepsie, NY.

Convenient to Amtrak/Metro North Trains and Bus Services

20,000 Square Feet of:

• Operating Layouts
• Railroadiana
• Model Exhibits
• Modular Layouts
• Railroad Clinics
• Dealer Tables
• Modeling Demonstrations
• Railroad Movies
• White Elephant Table
• Refreshments on Premises

This Event Sponsored By The Hudson Valley Railroad Society.  To visit or find out about the Hyde Park Train Station – click here

Facebook Event Page – Click Here


Front view of Bykenhulle House

Looking for more great things to do this season in our area? Check out our Events Calendar that is updated daily with new events. Whatever you decide to do, make sure you book your stay with us to be conveniently located to all of these great events!