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

Soukup Farms. Photo courtesy of Dutchess Tourism, Inc.

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

By Julia Colombo, with additional reporting by Matt Moment

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

Hallowed Harvest

Altamont Fairgrounds, Altamont
September 23 – October 31


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What’s October without a spooky Halloween festival for the whole family? Hallowed Harvest returns this year with iconic landscapes and carved pumpkins, plus an all-new jack-o’-lantern tunnel. General admission and VIP tickets are available as well as a season pass option. The Harvest uses organic, intricately carved pumpkins, so you’ll want to get to them before the critters do.

New York State Capitol Hauntings Tour

New York State Capitol, Albany
October 3-31, Monday – Friday

Did you know two U.S. Presidents visited the Capitol after they died? Or that the watchman who died in the 1911 Capitol Fire might still make his rounds? From lost murals to a Capitol curse encased in stone, New York’s Capitol is the home of several eerie tales and strange sightings. Make your free reservation soon to explore the secrets and mysteries hidden within the Capitol walls.

Murder at Cherry Hill: A Harrowing Walk Through a Historic Evening

Historic Cherry Hill, Albany
October 19-29

History buffs and horror fans alike will not want to miss this reenactment of the murder at Cherry Hill. Ticket holders will have the opportunity to relive the 1827 night and follow in the footsteps of Jesse Strang. How ever did he become the last man publicly hung in Albany? Cherry Hill suggests patrons be at least 12 years old. Shows begin at 5:30 p.m. and 7 p.m.

Columbia County

Corn Maze

Samascott’s Garden Market, Kinderhook
October weekends and Columbus Day, 11 a.m. – 4 p.m.

Samascott’s seven-acre corn maze changes every season, with the current design honoring Korra, Freya, and Scotty three pets you may meet if you visit Samascott’s store. While the maze is one of the most impressive in the entire region, there is plenty more to offer at the orchard and market. (Apple cider donut, anyone?) Tickets are only $9 per person, though children four and younger may roam the maze free of charge.


October 8, 11:30 a.m. – 10 p.m.

What are the two main ingredients of a great Hudson Valley festival? Excellent grub and local talent, of course! OctoberFeast boasts both. All day long, attendees can enjoy live performances from musicians like Mike McMann, Guilty Pleasure, and The Rob Beaulieu Band. An impressive list of vendors will serve baked goods, cider, craft spirits, wood-fired pizza, and more.


Crandell Theatre, Chatham
October 30-31


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The Wall Street Journal calls the Crandell a “palatial setting for a thriving film festival,” and we couldn’t agree more. What began as a small celebration of cinema has evolved into an “acclaimed, nationally recognized” event in the Hudson Valley. This year, film buffs can catch flicks like One Fine Morning, Turn Every Page, and Crouching Tiger, Hidden Dragon.

Dutchess County

New York Cider Week

Various cideries in the Hudson Valley
September 29 – October 9


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The cider industry is one of the gems of New York. Cideries across the state participate in Cider Week, including a baker’s dozen in the Hudson Valley. These cideries host tastings, dinners, tours, and more throughout the 11-day festival. Go to the Cider Week website for the list of local participants, events, and to get your tickets to celebrate the Hudson Valley’s pride and joy: cider!

Kevin McCurdy’s Haunted Mansion

Bowdoin Park, Wappingers Falls
October 1 – 31, 7 p.m.

Kevin McCurdy’s Haunted Mansion has been delivering Halloween frights for 46 years, and they never disappoint. This year’s mansion will feature The Asylum, haunted by tortured souls, and The Wicked Woods, loaded with horrific attraction after horrific attraction. You must purchase tickets ahead of time, but don’t dawdle! Limited tickets are available for each night.

ArtEast Open Studio Tour

Dutchess County
October 15, 16, 22, 23, 11 a.m. – 5 p.m.


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On these select days throughout October, art appreciators can visit artists in their studios and learn about their work. Patrons can plan their own self-guided tour of the studios of Dutchess County’s finest artists, including painters, photographers, sculptors, and more. Visit the ArtEast website for information to plan your tour.

Orange County

Grape Stomp

Brotherhood Winery, Washingtonville
September 10 – October 16, 10 a.m. – 5 p.m.

Brotherhood Winery has amped up its Grape Stomp this year, with an all-new stomping stage, authentic wine barrels, and a competition! Partners enter their name in Brotherhood’s raffle drum when they arrive and wait to be called. When chosen, the “Stomper” will mush all the juice out of the grapes with their feet while the “Mucker” collects as much juice as possible. Entry is free, and food and drinks are available for spectators.

Pure Terror Scream Park

Museum Village, Monroe
Weekends through October 30, 7 p.m.

If you consider yourself a haunted house junkie, you will not want to pass up the Guinness World Record-holding 1.2-mile walk-through of one of New York’s scariest attractions. Ten haunted houses, live actors, professional sets, and special effects combine to deliver a truly frightening experience. Be sure to purchase your tickets online to have the horror experience of your nightmares.

Dogwood Acres Annual Fall Fest

Dogwood Acres Family Farm, Middletown
Weekends through October 30, 8 a.m. – 6 p.m.

Dogwood Acres’ Fall Fest returns once again with food, the corn cannon, hayrides, mazes, farm animals, inflatables, arts and crafts, pumpkin bowling, and countless more activities for the entire family. Admission is $15 at the gate for a day full of family fun.

Putnam County

Hearts of the Hollow

Whipple Feeley Chapel, Carmel
Weekends through October 31

Many of us know the story of Ichabod Crane and the Headless Horseman, but you’ll want to see the twists and turns added to the classic Halloween tale in this new musical. With 20 new songs and several new characters, the whole family will want tickets to see this enchanting show on stage. Enjoy the show Fridays and Saturdays at 8 p.m. or catch a 2 p.m. matinee on Sundays. 

Spellbound Festival

Veteran’s Memorial Park, Carmel
October 29-30, 3-10 p.m.


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Megara Inc. has ventured off the beaten path of ‘fall festivals.’ Its take on the autumnal experience brings punk-rock and witchy vibes to Halloween with the first-ever Spellbound Festival. Lovers of music and all things mystical will not want to miss the live bands, vendors, and haunted attractions that Spellbound has to offer. General admission is $15 online or $20 at the gate, with a weekend pass option and discounts for teens.

Open House on the Farm

Tilly Foster Farm, Brewster
October 22, 11 a.m. – 3 p.m.

Another October brings another open house at Tilly Foster Farm. This outdoor experience is packed with activities for the entire family to enjoy, with a rain date of October 23. 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.

Rockland County

Bear Mountain Oktoberfest

Anthony Wayne Recreation Area, Harriman State Park
Weekends, 12-5 p.m.


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Bear Mountain’s Oktoberfest is back for the first time since 2019. 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. When planning your trip, be sure to purchase your tickets and parking passes ahead of time online.

Apple Picking

Dr. Davies Farm, Congers
October, 10 a.m. – 4 p.m.


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It wouldn’t be fall in the Hudson Valley without apple picking. Dr. Davies is one of many farms in Rockland County opening its orchards to the public. The whole family can enjoy picking apples off the trees, bringing them home, and baking them into delicious pies and crisps. After picking, guests can munch their newly picked apples on a hayride through Dr. Davies grounds. The farm is open every day in October, but make sure you reserve your time slot on the website.

Annual Nyack Halloween Parade

Memorial Park, Nyack
October 29, 5 p.m.


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The time has come again for Nyack’s Annual Halloween Parade! Grab your creepiest (or cutest) costumes, build your most festive floats, and pre-register for the costume and float contests, or bring the family to watch the spooky procession down Main Street. Contestants check in with the judges in Memorial Park at 3 p.m., and the winners are announced at the Gazebo on Main Street. If Mother Nature decides to rain on the parade, it will take place on October 30.

Ulster County

Fifth Annual Kingston Design Showhouse

October 7-23, 12-5 p.m.

Each fall, the Kingston Design Connection brings together designers, artists, makers, contractors, and vendors for an annual Showhouse. The Showhouse gives creatives the opportunity to build community, network, and branch out. It brings attention to local businesses and allows them to show off their craftsmanship on a national platform. Purchase tickets online to support local artisans. All ticket fees benefit nonprofits in the region.

The Pumpkin Express

Catskill Mountain Railroad, Kingston
October 22-30, 10 a.m. – 4:45 p.m.


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Looking for a relaxing family activity? Love fall foliage and pumpkins? The Catskill Mountain Railroad’s Pumpkin Express offers all of these and more. Families can enjoy a panoramic train ride on the former Delaware Railroad with a unique view of the Catskills. Riders can even choose a pumpkin to bring home and decorate. Purchase your tickets online ahead of time to experience this unique fall family endeavor.

Westchester County

The Great Jack-O’-Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
September 16 – November 20

The Great Jack-O’-Lantern Blaze has returned to Westchester County! Van Cortlandt Manor is decked out with over 7,000 pumpkins, each one meticulously carved by artisans. New to the Blaze this season is the animated “Jack” Smith shop. Make sure to go online to purchase tickets when planning your visit.

Myths and Mysteries Tour

Armour-Stiner House, Irvington
September 29 – October 31, 10 a.m. – 4 p.m.

The Armour-Stiner House is located in the heart of Sleepy Hollow and has often been the subject of spooky speculation. This fall, patrons 12 and older are invited to the Myths and Mysteries Tour. The tour dives into the history and the mythology of the house, with first-person accounts of inexplicable events that have occurred onsite. The Octagon House is a privately owned residence, so tickets bought in advance are a must to appreciate this unique, magical, and architectural marvel.

Día de los Muertos

Caramoor, Katonah
October 16, 2-5 p.m.

Celebrate Día de los Muertos with the Caramoor Center for Music and the Arts. The whole family will enjoy live music, colorful crafts, passionate stories, and an exquisite performance by the Calpulli Mexican Dance Company. Be sure to RSVP ahead of time to this free event to secure your spot.

Related: The Best Events & Fests to Hit in the Hudson Valley This Fall