An Insider’s Guide to October Events in the Hudson Valley

Hudson River tourism directors share their top picks for places to go, sights to see, and things to do throughout October.

We’ve said it before and we’ll say it again. There are a ton of things to do in the Hudson Valley each month. It seems to us that October is a particularly bustling month in the region, with live music, fall hikes, seasonal getaways, craft festivals, day trips, and more. Best of all, with the foliage in full swing, outdoor events are marked by the iconic beauty of our area.

To help scout out the best events in the Valley, we reached out to local tourism directors from Albany to Westchester for their top picks for things to do. Check out their selections, then get planning!

Albany County

Albany’s All-Hallow E’en Festival

Multiple locations in Albany
October 1–31

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In honor of Albany’s Halloween Festival from the early 1900s, the city transforms once again into an enchanted Halloween Dreamland over 100 years later. Come out to see illuminated streets, festive lighting and decorations, and revamped storefronts in the spirit of the spooky season. The revived Halloween festival celebrates the diversity of talent in Albany by featuring public art, community events, dramatic tours, historic exhibitions, and Albany’s first-ever Halloween House Ball.

The Great Cider Cycle

Nine Pin Ciderworks, Albany
October 15, 11 a.m.

 

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Nine Pin Ciderworks hosts this cider tasting event, complete with a bike ride. Head to Nine Pin in the morning to grab a token for the tasting room before hitting the Mohawk-Hudson Bike Trail to cycle your way through Troy. Once you reach the end, cool off with a delicious drink and dessert, and then head back to Nine Pin to enjoy a glass of cold cider.

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Autumn in the Arboretum

The Pine Hollow Arboretum, Slingerlands
October 21, 11 a.m. – 3 p.m.

Help raise funds to support the Pine Hollow Arboretum at this seasonal event where you can enjoy pumpkin painting, a photo station, nature inspired crafts, live music, cider and donuts, guided tours, a bird exhibit, and more. Bask in the great outdoors and pay homage to the fantastic foliage of the fall season.

Columbia County

Steepletop Open Days

Edna St. Vincent Millay’s Steepletop, Austerlitz
October 7 & 8, 10 a.m. – 5 p.m.

Visit Steepletop’s historic grounds this month as they’re open to the public for hour-long tours. Learn about the house and pick up some grounds and picnic passes to gain access to walk and explore the 200-acre property, which includes grounds, gardens, and trails. Purchase tickets in advance for a guaranteed spot at $10-$20.

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Cider Sunday

Samascott Orchards, Kinderhook
October 8, 11 a.m. – 5 p.m.

This annual event at Samascott Orchards will feature a pop-up cider bar by Nine Pin Cider in the middle of the orchard. Enjoy a long day of apple picking, cider drinking, food trucks, and live music with the whole family as you immerse yourselves in the beautiful orchard surroundings and indulge in Nine Pin’s most refreshing hard ciders made from the orchard’s apples. Whether you’re a cider connoisseur, apple lover, or just looking for a good time, Cider Sunday is the place to be.

Black Cat Bash

Catamount Mountain Resort, Hillsdale
October 28, 6:30–10:30 p.m.

Join Catamount Mountain as it hosts its first Black Cat Bash – a Halloween costume party for ages 21 and up. The theme of this year is “Carnival of Chaos,” featuring an old-time carnival setting with creepy carny vibes, sinister freak show acts, unsavory clowns, and other creatures of the shadows. Come in your best costume and enjoy treats, a photo booth, live music, dancing, and a special fire dancing performance. Be sure to get tickets in advance online before they sell out.

Dutchess County

Witch Perfect

Revel 32, Poughkeepsie
October 1, 7 p.m.

This award-winning spooktacular is only in town for one night, and you won’t want to miss it. Three Emmy-winning stars from RuPaul’s Drag Race star in this live-singing comedy parody on the cult-classic Disney film Hocus Pocus. The show features hits from pop icons Madonna, Britney Spears, and Cher, as well as music from other Disney classics and Broadway shows. The show is open to all ages, and tickets start at a great deal of $27.

New York State Sheep and Wool Festival

Dutchess County Fairgrounds, Rhinebeck
October 21 & 22

The Dutchess County Sheep and Wool Growers Association’s annual festival features a variety of competitions, along with workshops on weaving, knitting, and basket-making. Check out dozens of vendors selling artisanal goods, kids’ activities, an equipment auction, and more before catching the Black and White Sheep Show.

Harvest Hunt

Locust Grove Estate, Poughkeepsie
Weekends through October 31

All throughout October, you can embark on a scavenger hunt for decorated pumpkins hidden among the historic flowers and trees when you visit Locust Grove Estate. Celebrate the gardeners, tutors, maids, cooks, and everyone else who helped keep the estate alive over 120 years ago by finding a rooster, a bicycle, the man in the moon, and more made out of decorated pumpkins.

Greene County

Catskill Mountain Maker Camp

Blackthorne Resort, East Durham
October 6–9

Come together at Maker Camp with people of all ages to make, learn, and spectate. A combination of science, ingenuity, and creativity make Maker Camp a place for everyone, no matter their skill level or expertise. Demonstrators from all over the world will share their knowledge so that participants can leave the camp with new skills, friends, and appreciation for the power of making.

Hunter Mountain Oktoberfest

Hunter Mountain Resort, Hunter
Weekends through October 15

 

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Hunter Mountain’s Oktoberfest event is back for three weekends this October, bringing fun for the whole family. Enjoy German-themed live music, beer tents, food trucks, kids games, the doxie derby, hiking, scenic skyrides, and more. Vendors and the live performance schedule will be available on Hunter Mountain’s website in the coming weeks.

The Corn Maze

Hull-O Farms, Durham
Weekends through October 29

 

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Head to award-winning agritourism farm vacation destination Hull-O Farms for its legendary corn maze all October long. Navigate a labyrinth of corn that’s as high as an elephant’s eye and discover how getting lost can be so much fun. The corn maze is a challenge for all ages, and other attractions like hayrides, the critter corner, and panoramic views will keep you entertained all day.

Orange County

Warwick Applefest

Warwick
October 1, 9 a.m. – 5 p.m.

This huge festival welcomes over 30,000 apple lovers to Warwick for apple-inspired foods all day long. The fest features over 200 craft vendors, dozens of food vendors, music and entertainment, a children’s carnival, and an apple pie baking contest. This fun-for-the-whole-family event began in 1989, and proceeds benefit the Warwick Valley Chamber of Commerce, along with about 50 local nonprofit organizations.

Grape Stomping

Brotherhood Winery, Washingtonville
Weekends through October 15

The Grape Stomp returns to Brotherhood Winery this October with modified wooden barrels and a new competition format. Grab a teammate to stomp grapes for the chance to win a special prize, listen to music, and enjoy delicious food and drinks through mid-October. Whoever collects the most grape juice wins, so practice your smushing and stomping skills!

Sugar Loaf Halloween Festival

Sugar Loaf Performing Arts Center, Chester
October 28, 11 a.m. – 5 p.m.

Sugar Loaf Performing Arts Center is happy to present its first-ever Halloween Festival with a trunk or treat, witches meet and greet, and Halloween costume parade. Vendor Village will feature fall treats like cider, donuts, and more, a jack-o-lantern contest, music, games, and a dance performance by Warwick Center for the Performing Arts.

Putnam County

Robert Olnick Pavilion

Magazzino Italian Art, Cold Spring
All October

Magazzino Italian Art opens its new Robert Olnick Pavilion to the public this October, offering an additional 13,000 square feet of gallery and educational space, as well as a café and museum store. The Robert Olnick Pavilion is designed by Alberto Campo Baeza and Miguel Quismondo, the latter being the architect of Magazzino’s original building. The inaugural exhibitions are Mario Schifano: The Rise of the ‘60s, Ettore Spalletti: Parole di colore, and Carlo Scarpa: Timeless Masterpieces.

Open House on the Farm

Tilly Foster Farm, Brewster
October 21

Another October brings another open house at Tilly Foster Farm. This outdoor experience is packed with activities for the entire family to enjoy. From pumpkin and face painting to scavenger hunts and walks on nature trails, there will never be a dull moment at this open house. Admission is free but be sure to register ahead of time.

Hops on the Hudson Modern Makers Market

St. Mary’s Episcopal Church, Cold Spring
October 14 & 15, 11 a.m. – 5 p.m.

 

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Hops on the Hudson brings its Modern Makers Market to the Village of Cold Spring where you can shop local, listen to live music, and enjoy food at the venue. Over 40 artisans come together at this event to showcase their amazing handcrafted and small-batch goods. Browse woodwork, jewelry, potters, glass workers, clothing designers, and candle makers as you enjoy free admission – and feel free to bring your dog!

Rockland County

Bear Mountain Oktoberfest

Bear Mountain Inn, Tomkins Cove
Weekends through October 22

 

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Bear Mountain’s Oktoberfest is back with free admission for the largest Oktoberfest in New York. This year’s festival promises entertainment for the entire family, including food, live music, a play area with a bounce house, and, of course, plenty of beer. RSVP online for your chance to win a free t-shirt and invest in some VIP passes for unlimited food and drinks.

Nyack Halloween Parade

Downtown Nyack
October 28, 5:30 p.m.

Put on your favorite costume and head to Downtown Nyack for the largest Halloween event outside New York City. Drawing over 10,000 visitors each year, Nyack’s parade has been voted by the Travel Channel as one of the “Top 10 Halloween Parades in America.” Don your best look to win in categories like best couples costume, best group costume, best pet costume, or design a float to win a cash prize.

Pumpkin World

Clover Stadium, Pomona
Through October 31

 

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New York’s premier pumpkin extravaganza made its grand debut earlier this fall at the Clover Baseball Stadium. Immerse yourself in a captivating world of over 5,000 hand-carved pumpkins illuminating the night. Don’t miss the Pumpkin Village, featuring delicious food, refreshing drinks, thrilling competitions, and lively music.

Ulster County

Brews & Views

Belleayre Mountain, Highmount
October 7, 8, & 14

 

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Sample craft beers and cider from local breweries while taking in views of the Catskill Mountains at this free festival. Live music, craft vendors, and delicious food are the name of the game at Belleayre this fall, and visitors can enjoy the free Annual Fall Festival at the mountain, which is going on at the same time as Brews & Views and offers fun for the whole family with gondola rides and pumpkin painting.

Walktoberfest

Walkway Over the Hudson, Highland
October 21 & 22

This farmers and makers market takes place on the Highland side of the Walkway Over the Hudson and features over 190 vendors. Farms, distilleries, artisans, artists, and restaurants set up shop for the weekend so you can sample wine, beer, and other goods from the area. Children’s activities, farm animals, and live music keep the fun going all day.

Headless Horseman Hayrides and Haunted Attractions

Ulster Park
Through October 29

The “#1 Haunted Attraction in America” returns in a big way. This year, spectators will get closer to the horror than ever before. Visitors will walk the haunted woods where the Horseman lurks, without the safety of the typical hayride. Other attractions including spooky motels, monster-filled greenhouses, haunted corn mazes, and more bring the scares. Reservations are strongly encouraged. In addition, on October 7 and 21, the park tones down its scare level for Children’s Day.

Westchester County

“Myths and Mysteries” Guided Tour

Armour-Stiner Octagon House, Irvington
All October

The “Myths and Mysteries” Guided Tour takes participants on a captivating experience that’s offered all October long. Visitors will be immersed in the enchanting history and architectural secrets of the historic mansion, providing a fascinating glimpse into the past of the Armour-Stiner Octagon House.

Lyndhurst After Dark

Lyndhurst Mansion, Tarrytown
October 19, 22, 26, & 29, 6–10 p.m.

This exciting event hosted at Lyndhurst Mansion offers visitors a unique opportunity to explore the historic mansion and its beautiful grounds in an enchanting evening atmosphere. Immersive storytelling and entertainment make this experience the perfect way to see the historic Hudson Valley estate in a new light.

The Great Jack O’Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
Through November 19

The Blaze is back! The Hudson Valley’s electrifying Halloween event fills the grounds at Van Cortlandt Manor with more than 7,000 illuminated jack-o-lanterns in a variety of haunting shapes and sculptures. Advance reservations are required. The show burns through the fall season, kicking off Friday, September 15 and wrapping November 19. Keep your eyes peeled for glowing bees and the animated “Jack” Smith Shop.

Related: 9 Fall Food Festivals That Add Flavor to the Hudson Valley

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