The October Events You Need to Check out in the Hudson Valley

Fall festivals, Halloween happenings galore, and more to-dos add color to the Hudson Valley in October.

Hudson Valley recommendations are objective, unbiased, and curated by the editorial team. If you buy something through our links, we may earn an affiliate commission at no cost to you.

Brick-or-Treat

Goshen

Throughout October

Beware! Monsters are taking over LEGOLAND this October for the ultimate Halloween celebration, featuring live entertainment, themed attractions, character meet and greets, and trick-or-treating. Kids are encouraged to wear costumes and stop by all 10 candy locations throughout the park.

Fall Foliage Walk

Voorheesville

October 5, 1–2 p.m.

Get back to nature and take in the sights of the season on this one-hour guided hike through Albany County’s Thacher State Park.

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Poughkeepsie Regatta

Poughkeepsie

October 5, 7:30–10:30 a.m.

Head to the Poughkeepsie Waterfront for this annual three-mile rowing race along the Hudson River. Crews from New York, New Jersey, and Connecticut will come together to compete in Junior, Collegiate, and Masters events including three types of boat racing. Spectators can view the races for free from various parks in Poughkeepsie; try the Walkway Over the Hudson for the best views.

Hunter Mountain’s Oktoberfest

Hunter

October 5–6 & 12–13

Oktoberfest at Hunter Mountain Resort is back for another year of fall festivities. Enjoy specialty food and beverages, live music from multiple bands, shopping from local vendors, scenic sky rides along the mountain, and more.

Warwick Valley Chamber of Commerce
Photo courtesy of Warwick Valley Chamber of Commerce

Warwick Applefest

Warwick

October 6, 9 a.m.–5 p.m.

Orange County’s largest festival has returned for another year. This free one-day event offers over 200 craft vendors, music and entertainment all day, an apple pie baking contest (with slices for sale), and much more.

Edward Scissorhands

Pleasantville

October 9, 2 p.m. & 7 p.m.

Head to the Jacob Burns Film Center to watch this classic film in a brand-new way. Matthew Bourne’s dance version of Tim Burton’s tale brings new life to this spooky story. Buy your tickets online.

Taste NY at Todd Hill Outdoor Maker’s Market

Poughkeepsie

October 11–12 & 14, 12–4 p.m.

Explore the flavors of New York at this three-day family-friendly gathering of vendors. Local farms, food businesses, and artisans come together with a wide array of all that New York has to offer, from handmade goods to artisanal drinks and seasonal produce.

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Night Market at Peace, Love & Pumpkins

Bethel

October 11–12, 18–19, 25, 6:30–9 p.m.

Grab a seat and a treat during this weekend market at Bethel Woods. This pop-up will include craft and specialty food vendors along with festive fun during the annual Peace, Love, and Pumpkins walk-through experience, full of hand-crafted jack-o’-lanterns and pumpkin-themed art.

Stormville Airport Antique Show and Flea Market

Stormville

October 12–13, 8 a.m.–4 p.m.

Hunt for the perfect find at this massive antique show and flea market at the Stormville Airport. Hundreds of vendors will offer antiques, furniture, new and vintage clothing, artwork, and more. Admission and parking are free, and food and drinks are available to purchase on-site.

Harvest Festival Weekend at Barton Orchards

Poughquag

October 12–14

Stop by the farm for the perfect way to spend a fall weekend. Enjoy hayrides, live music, children’s entertainment, a corn maze, pig races, and more to celebrate the harvest season.

Fall Foliage Half Marathon and 5K

Rhinebeck

October 13, 10 a.m.–1 p.m.

Whether you’re looking for one more training run before the New York City Marathon or want to explore the autumnal views of the Hudson Valley, this annual race has your name on it. Spots are limited, so register as soon as possible to secure your place.

Lyndhurst After Dark

Tarrytown

October 17–20 & 24–27, 6–10 p.m.

Roam the halls of this historic Victorian mansion by candlelight on select nights this fall. This spooky tour will guide guests through several rooms in the estate, shining a light on special on-site collections.

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Walkway at Night

Poughkeepsie

October 18, 8–9:30 p.m.

Experience the beautiful views of the Mid-Hudson Bridge under the moonlight on the Walkway. Enjoy the sights on your own or take a peek at the stars through a telescope provided by the Mid-Hudson Astronomical Association.

Boos and Brews Weekend at Barton Orchards

Poughquag

October 19–20, 10 a.m.–6 p.m.

Check out this spirited weekend of Halloween fun at Barton Orchards, set to include live music, drinks, a flashlight corn maze, and more.

Haunted Tales from the Crow’s Wood

Rensselaer

October 19, 6:30–8 p.m.

Pull up a lawn chair around this campfire for an evening of haunted tales of ghosts and specters at Crailo State Historic Site’s riverfront park. This program is for ages 12 and up, but younger siblings and scared adults are still welcome to attend and participate in a less spooky activity: pumpkin painting. Mulled cider and donuts will also be available. Check online for registration information.

Hounds of Halloween 2024

Albany

October 19, 11–3 p.m.

Unleash your hounds (and dress them in their best costume) for the annual Hounds of Halloween dog trick-or-treating event in downtown Albany. The best-dressed pups have a chance to win a prize in the Canine Costume Contest. “Yappy Hour” specials will also be available at participating bars and restaurants.

Sheep & Wool Festival
Photo by Benjamin Fractenberg

New York State Sheep & Wool Festival

Rhinebeck

October 19–20

This annual festival returns for another year of activities for animal lovers and fans of fiber arts. Eat, shop, craft, and enjoy all that this festival has to offer with various vendors, workshops, and animal shows. This festival also has children’s events and workshops, so the whole family can enjoy the wooly weekend. Purchase tickets and register for workshops online.

Beacon Sloop Club Pumpkin Festival

Beacon

October 20, 12–5 p.m.

Embrace the fall harvest this season at The Beacon Sloop Club’s annual Pumpkin Festival. Located on the shore of the Hudson River, this event provides guests with lots to do, see, and eat. There will be live music all day, children’s entertainment, free sails on The Beacon Sloop Club’s boat, and of course, lots of pumpkins. Admission to this event is free.

The Wassaic Project’s Annual Haunted Mill and Monster’s Ball

Wassaic

October 25–27, 4–7 p.m.

Beware of this chilling weekend at the Haunted Mill. All ages are welcome to participate in the scary surprises that are in store for this three-day event. Adults ages 21 and over are invited to continue the party at the Monster’s Ball on Saturday, featuring a costume contest and live music.

Candlelight: A Haunted Evening of Halloween Classics

Albany

October 25–26, 6–8:30 p.m.

For an elevated night of chilling entertainment, enjoy Halloween-inspired music by candlelight in The Kenmore Ballroom, where the magic of the music to life through this multi-sensory experience.

Walktoberfest
Photo by Valen Golden

Walktoberfest

Highland

October 26–27, 12–5 p.m.

The annual Walktoberfest returns with a full-on fall experience. The Farmers and Makers Market provides the best of what the region has to offer, from art to wine to fresh produce with over 190 vendors to choose from. Samples of wine, beer, and spirits from over 30 local businesses are included with admission.

MyKingstonKids Halloween Fest and Parade

Kingston

October 26, 2–7 p.m.

Get ready to “blast off” at this Halloween Fest and Parade where the theme is space. The day begins with a parade for kids to show off their out-of-this-world costumes, followed by the festival, where families can enjoy performances, interactive activities, and treats.

Nyack Halloween Parade

Nyack

October 26, 5:30 p.m.

The 35th annual Halloween Parade in Downtown Nyack has returned for another year. Check out why the Travel Channel voted this parade as one of the “Top 10 Halloween parades in the U.S.” Come dressed in your best costume and enjoy the attractions, including floats, live music, and food vendors.

Boo at the Zoo

Catskill

October 27, 1–6 p.m.

Head to the Bailiwick Animal Park for a day full of family-friendly Halloween entertainment and activities. Trick-or-treat around the zoo alongside costumed characters and provide treats for the animals at the petting and feeding areas throughout the zoo. The event will also include a maze, pumpkin patch, and a witch’s cauldron bonfire.

movie
Theater: Danr13 / Adobe Stock; On Screen: Surachet / Adobe Srock.

Make a Date on the Dark Side

It’s the spookiest time of the year and the Jacob Burns Film Center in Pleasantville is poised to extend the dark and shadowy season with a new film series entitled, Noirvember: Film Noir From Yesterday to Today. Beginning November 4, theatergoers will have the chance to catch classic film noir flicks on the big screen—Gilda, Mildred Pierce, Klute, Chinatown, and Bound—along with lectures and discussions with NYU Tisch professors, a murder-mystery party (period attire encouraged), and post-show “unhappy” hours in the on-site Take 3 Wine Bar & Café. For a family friendly foray into the spine-tingling genre, Who Framed Roger Rabbit will be shown on the first three Saturdays of the month. For more chilling details, visit burnsfilmcenter.org. – Michelle Gillan Larkin

Chinatown
Chinatown. Courtesy of Jacob Burns Film Center.
Gilda
Gilda. Courtesy of Jacob Burns Film Center.
Mildred Pierce
Mildred Pierce. Courtesy of Jacob Burns Film Center.
Bound
Bound. Courtesy of Jacob Burns Film Center.

Related: 8 Cool Fall Concerts to Catch in the Hudson Valley

 

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