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

Throughout Albany County
All October long

 

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Celebrating the tradition of the early 1900s, Albany transforms its city for the month of October into an enchanting Halloween dreamland. From public art installations to community events to dramatic tours, the month-long event immerses tourists and locals alike in the spirit of the spooky season.

Path Through History

Throughout Albany County
October 12, 11 a.m. – 4 p.m.

Explore the rich past of Albany County at the Path Through History event, presented by Ten Broeck Mansion. Start your journey at the Albany Rural Cemetery, Van Schaick Mansion, Irish American Heritage Museum, Huyck Preserve, Underground Railroad Education Center, or the American Italian Heritage Museum. Each site will feature special programming.

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Festival of Nations

Empire State Plaza Convention Center, Albany
October 27, 11:30 a.m. – 5 p.m.

Celebrate cultural diversity at Albany’s 53rd annual Festival of Nations this October. The event will feature representations of over 30 nations from around the world, along with the Parade of Nations, the crowning of Miss Festival of Nations, dances, music, food, arts, and other entertainment at the international level.

Columbia County

Corn Maze 2024

Samascott’s Garden Market, Kinderhook
All October long

Check out Samascott’s Garden Market this October for a visit to the onsite corn maze that’s themed after the orchard’s fall strawberry varieties. This year’s maze is the most challenging one so far, with eight hidden punch stations throughout the maze. Find all the stations and win a free, small soft serve ice cream! While on the farm, also sample apple cider donuts and other homegrown goodies.

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FilmColumbia

Crandell Theatre, Chatham
October 18–27

Columbia County’s premier annual cultural event, FilmColumbia screens the very best of upcoming American and international films. The 10-day event was launched in 1999 as the Crandell Theatre’s “little local festival that could” and is now an acclaimed, nationally recognized film event.

Black Cat Bash

Catamount Mountain Resort, Hillsdale
October 26, 6–10 p.m.

Catamount’s second annual Black Cat Bash, the late-October event is a 21-plus Halloween costume party at the mountain’s lodge. Themed “Monster Mash” this year, costumes are highly encouraged at the party, and tickets include several food stations, treats, a bar, photo booth, DJ music, dancing, and a costume contest.

Dutchess County

Time Warp: The Rocky Horror Live Experience

Barton Orchards, Poughquag
October 18-19, 8 p.m.

 

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Enjoy two unforgettable nights of music, madness, and mayhem at Barton Orchards’ live tribute to the cult classic Rocky Horror Picture Show. The event is set in Barton Orchards’ new event venue “The Monster,” and costumes are highly encouraged. As per Rocky Horror standards, audience participation is a must.

New York Sheep and Wool Festival

Dutchess County Fairgrounds, Rhinebeck
October 19-20

The annual New York Sheep and Wool Festival returns to the Dutchess County Fairgrounds for two full days of all things sheep and wool in Rhinebeck. From workshops devoted to skills like weaving, knitting, and basket-making to a used equipment auction and kids’ activities, there’s something for everyone at the festival. Don’t miss out on the sheep shows during the event!

A Very Fluffy Halloween

Lilymoore Farm, Millbrook
Throughout October

 

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Not just for the kids, A Very Fluffy Halloween is for all kinds of animal lovers in Dutchess County. The Lilymoore Farm event is a not-so-spooky farm tour that invites visitors to meet nearly 200 animals who are dressed in adorable costumes, including alpacas, llamas, and many more friendly creatures.

Greene County

Hunter Mountain Oktoberfest

Hunter Mountain, Hunter
October 5-6, 11-12

 

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Celebrate Oktoberfest at Hunter Mountain with stein-holding competitions, Bavarian food, craft vendors, and plenty of authentic German beer. There’s something for everyone at the festival, with activities and entertainment like live bands, kids’ arts and crafts, a climbing wall, and the legendary Doxie Derby. While at the mountain, take in the changing fall foliage on a scenic SkyRide.

Windham Autumn Affair

Throughout Windham
October 12-13

Head to Windham’s Main Street this October for the town’s 30th annual Autumn Affair. Tokened “the gem of the Catskills,” Windham’s fall beauty is on full display during the seasonal event. Browse more than 50 vendors, craft food and drink, and special sales from local businesses. Shop, listen to music, and enjoy fall among the mountainscapes in the background.

Catskills Comedy Festival

Catskill
October 18–20

The highly anticipated Catskills Comedy Festival attracts top talents in comedy from across the country for an unforgettable weekend of stand-up, improv, workshops, parties, and more. The inaugural festival promises to be laugh-packed with headlining comedians and talent.

Orange County

Pure Terror Scream Park

Monroe
October 4–31

One of the most frightening haunted attractions in Orange County, Pure Terror Scream Park is sure to scare even the bravest of souls. The spine-chilling event features multiple haunted houses and attractions that are guaranteed to give you a good fright this spooky season.

Warwick Apple Fest

Throughout Warwick
October 6, 9 a.m. – 5 p.m.

Warwick is known for its annual Apple Fest in the heart of the town. Explore over 200 craft vendors, enjoy delicious bites from food stands, and have fun in an environment of music and entertainment for the whole family. Of course, there are many apple-themed creations and events throughout the day, so get ready to indulge in the apple pie baking contest and other tasty happenings.

Sugar Loaf Fall Festival

Sugar Loaf, Chester
October 12-13, 10 a.m. – 5 p.m.

Chester’s charming hamlet of Sugar Loaf has a lot to offer come the fall season. In the town, take in the live music, delicious food and drinks, and one-of-a-kind shopping experiences as you stroll the vendor-lined streets that are teeming with handcrafted treasures.

Putnam County

Spellbound Festival

Putnam County Veterans Memorial Park, Carmel
October 25-26

 

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An immersive, witchy, punk festival, Spellbound is unlike any other fall festival in the Valley. The event focuses on the magical, with attractions like live music, fire dancers, immersive scare experiences, and a mystic market. You won’t find the typical wares at this festival, which spotlights more obscure offerings like enchanted jewelry, broom makers, and tarot card readings.

Salinger’s Orchard

Brewster
All October long, 9 a.m. – 6 p.m.

The farmland that constitutes Salinger’s Orchard has been in the family since 1901. Take a trip to the Brewster farm to explore a selection of fresh produce this season, along with home-baked goods like pies, donuts, jams, and more.

Cornish Estate

Hudson Highlands State Park, Cold Spring
All October long

 

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If you’re looking for an outdoor adventure this fall, head to Cold Spring’s Hudson Highlands State Park to explore the ruins of Cornish Estate. A short hike will bring you to the clearing in the woods where the estate’s former driveway leads right to the site. While in the state park, try to conquer Breakneck Ridge or any number of surrounding challenging hikes.

Rockland County

Bear Mountain Oktoberfest

Anthony Wayne Recreation Area, Bear Mountain
October 5-6, 12-13

New York’s largest annual Oktoberfest celebration, Bear Mountain Oktoberfest returns to Rockland County this October. The pet-friendly fest takes place at the Anthony Wayne Recreation Area and features authentic Bavarian fun with beer, live music, and traditional German fare. A stein-holding competition, bouncy castle, face painting, and more await at the event.

Barefoot in the Park

The Antrim Playhouse, Tappan
October 18-27

Written by Neil Simon, Barefoot in the Park is a beloved comedy about newlyweds Corie and Paul Bratter as they begin their life together in Manhattan. The show is directed by Melinda Pinto and runs through October.

Nyack Halloween Parade

Downtown Nyack
October 26, 5:30 p.m.

 

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Now in its 35th year, the annual Nyack Halloween Parade is a community-wide event that celebrates the October holiday. This year’s parade will include costumes, floats, live music, food, and more kicking off at 5:30 p.m. Dress to impress and get in the spooky spirit for the late-October festivity.

Ulster County

Headless Horseman Hayrides & Haunted Attractions

Ulster Park
October 4–27

Returning for the 2024 spooky season, Headless Horseman Hayrides and Haunted Attractions was voted one of America’s scariest haunted attractions. This year, 13 horrific attractions — from hayrides to walking trails to haunted houses — will haunt you throughout your visit

Stockade Faire 2024

Kingston’s Stockade District, Kingston
October 5

Phoenicia Flea will line the streets of Kingston’s Stockade District this October for the 2024 Stockade Faire. Enjoy an afternoon of makers, small brands, live music, and more in the scenic Ulster County city.

Field + Supply Fall Market

Hutton Brickyards, Kingston
October 11–13

Field + Supply is celebrating 10 years as a top-tier modern makers market. The fall market at Hutton Brickyards features over 275 vendors, delicious foods and beverages from local spots, and a full music lineup of local talent. Attend live demonstrations and enjoy family-friendly activities throughout the weekend as well.

Westchester County

Ghost Tours

Tarrytown Music Hall, Tarrytown
October 2–31

One of the most haunted destinations in the Hudson Valley, Tarrytown Music Hall invites thrill seekers to join a ghost tour of the building. Each tour is guided by experts and takes visitors on an immersive journey through the venue’s haunted history, uncovering eerie stories and spooky corridors along the way.

Lyndhurst After Dark

Lyndhurst Mansion, Tarrytown
October 17–27

Explore the darker side of Tarrytown’s historic Lyndhurst Mansion on an after-dark tour of the grounds. Learn about the mansion’s history and its past inhabitants as you enjoy the atmosphere of seasonal decorations and displays that further highlight the superstitions of the era.

Twilight Village

Philipsburg Manor, Sleepy Hollow
All October long

Get into the Halloween spirit at Philipsburg Manor this October in the Twilight Village. The evening event offers a whimsical world where charming and mysterious characters reveal fortunes, sing eerie melodies, and tell captivating tales. While in town, browse Sleepy Hollow souvenirs, savor cocktails, and enjoy tasty bites.

Related: 10 Fall Food Festivals That Add Flavor to the Hudson Valley

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