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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.

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. Even in the face of the coronavirus, there exist dozens upon dozens of ways to experience the best of what the region has to offer. While they might not be traditional per se (haunted walking trails, anyone?), they are engaging, entertaining, and 100-percent #flattenthecurve-approved.

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

Discover Albany President and CEO Jill Delaney shares her top recommendations for the month.


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Chalk the Walk

Helderberg-Hudson Rail Trail, Delmar
October 2, 11 a.m.

Art on the Rail Trail (ART) hosts its annual chalk art competition to start the month. It all kicks off at the Albany County Helderberg-Hudson Rail Trail, and all proceeds benefit ART. Register by September 30 to chalk your own 3-ft by 3-ft design on the trail.


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Hollowed Harvest

Altamont Fairgrounds, Altamont

We blinked, and Halloween festivities arrived in the Hudson Valley. In the Capital District, Hollowed Harvest leans into spooktacular celebrations with more than 7,000 jack o’ lanterns shaped into stunning landscapes, dinosaurs, zombies, castles, and more. Tickets must be purchased online in advance to attend. This seasonal event features displays as tall as three stories and as long as 60 ft.  

Autumn in the Arboretum

The Pine Hollow Arboretum, Slingerlands
October 17, 11 a.m. – 2 p.m.

This October, the Capital Region escape opens its grounds for pumpkin painting, live music, and more. The Pine Hollow Arboretum celebrates its third Autumn in the Arboretum with live music. Register in advance to attend, and embark on several guided tours of the arboretum. The birds of prey exhibit shines a light on some of the incredible creatures that call the Hudson Valley home.

Murder at Cherry Hill

Historic Cherry Hill, Albany
October 20-30 

There’s been a murder in the Capital Region. This historic retelling immerses guests in the 1820s, on the night of a grisly murder that led to Albany’s last public hanging. An actor brings Jesse Strang to life, and showcases the sensational nature of the trials that had the talk of the town. Get tickets for a nighttime experience Wednesdays through Saturdays.

Columbia County

Read up on Columbia County Tourism’s highlights for things to do in the Hudson Valley this month.


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Samascott’s Garden Market

65 Chatham St, Kinderhook
Through October  

Beloved by Hudson Valleyites for U-pick fun during fall, Samascott’s also delivers with an abundant market that’s stocked with everything from gardening supplies to cider donuts. As for the corn maze, it’s a massive affair filled with twists and turns that will challenge even the most seasoned maze runners.

FilmColumbia 2021

The Crandell Theatre, Chatham
October 22-31

An impressive 22 years of cinema mark celebrations of this year’s FilmColumbia festival. The Crandell Theatre screens flicks from major studios and independent filmmakers alike. Plus, the fest shows documentaries, international films, animated features, and children’s shorts.

Dutchess County

Dutchess Tourism President and CEO Melaine Rottkamp shares her top recommendations for the month.

Soukup Farms

Soukup Farms | Photo courtesy of Dutchess Tourism, Inc.

Harvest Festival at Soukup Farms

Soukup Farms, Dover Plains
Weekends in October, 11 a.m. – 5 p.m.

Visit Hudson Valley farms for crisp, fall air and delicious homegrown treats. Soukup Farms hosts harvest festival weekends, taking guests on hayrides through the scenic Dutchess County property. Feast on desserts with Soukup Farms maple syrup before strolling through the expansive pumpkin patch. Wander through the corn maze, explore the “two by two zoo,” and more.

The Wicked Woods

Kevin McCurdy’s Haunted Mansion, Wappingers Falls
Weekends in October, 7:30 p.m.

Do you dare adventure your way through The Wicked Woods? Kevin McCurdy’s Haunted Mansion debuted its terrifying outdoor experience last year. This year’s theme is “Deadtime Stories” for the walking trail, and “The Procedure” for the indoor attraction. In the latter, an evil doctor seeks to carry out his diabolical plans on unsuspecting victims. Get ready for one mile of spooky surprises in a socially distant setting. Reservations must be made online and in advance.


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Sheep and Wool Festival

Dutchess County Fairgrounds, Rhinebeck
October 16 & 17

This October, the Sheep and Wool Festival camps out at the Dutchess County Fairgrounds for a fun-filled two days. Join the crafting community at large as it turns out for book signings, competitions, demonstrations, and shopping galore. Visitors will love browsing the stands of raw wool, yarn, rugs, and fibers. Vendors come from all over the country, so expect to see a wide variety of goods and materials. For kids, the sheep shearing and fiber arts demonstrations are bound to fascinate. The scaled-back hybrid event is spaced for social distancing, and features virtual tours, demonstrations, and sales.

Greene County

Look no further for the coolest attractions and activities in Greene County during the month.

Flyday Music Festival

Blackthorne Resort, East Durham
September 30—October 3

This Catskill Mountain music festival showcases acts in a variety of genres. Catch heart-pumping EDM shows, room-shaking rock acts, and funk bands that will get you dancing. You can also browse through vendors’ stands, sample microbrews, and munch on a meal — or try a tie-dye workshop or a calming session of yoga. Spend the weekend at Blackthorne Resort for the full Flyday Music Festival experience.


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Mountain Top Historical Society, Haines Falls
October 8 & 9

There’s nothing quite like fall hikes in the Hudson Valley. Gorgeous destinations like Kaaterskill Falls are just around the corner from Mountain Top Historical Society. The annual hikefest dives into the history of Hotel Kaaterskill and the area’s influence on Hudson River School Painters. Guest can choose between two trails, one leading up to the site of the former Catskill Mountain hotel and the other climbing the Kaaterskill escarpment trail.

Windham’s Annual Autumn Affair

Windham New York Farmer’s Market, Windham
October 9 & 10

Explore the sights, sounds, and flavors of the Catskills at Windham’s Annual Autumn Affair. The two-day event unites more than 50 vendors, including restaurants, beverage producers, and artisans. Plus, guests will enjoy live music from Guilty Pleasure, a six-piece band that plays pop songs from throughout the decades. Additional activities for kids include the spooky hay maze, a circus workshop, pony rides, and a reptile show. Adults will love wine tastings, mountain biking, and so much more.

Scribner’s Fall Fest

Scribner’s Catskill Lodge, Hunter
October 9 & 10, 16 & 17, 23 & 24

Hunter draws travelers every autumn on their quest to find the most incredible foliage around. Scribner’s Catskill Lodge celebrates the season with three weekends of food, beer, and live music. The Bluestone Patio offers sweeping views of the upper Hudson Valley and the colorful Catskill Mountains. Each weekend brings new food pop-ups, keeping eats as eclectic as possible.

Orange County

Check out Orange County Tourism Director Amanda Dana’s selections for the best things to do this month.


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Hudson Valley Empanada and Latin Festival

Orange County Farmers Museum, Montgomery
October 9, 1-5 p.m.

No, you’re not dreaming. There really is a whole festival dedicated to the empanadas of the Hudson Valley. Head to Montgomery for perfect dough pockets filled with chicken, pork, steak, seafood, and vegan options galore. The region’s top Latin food trucks and restaurants will be onsite, so get tickets before they sell out.

Greenwood Lake Oktoberfest

Greenwood Lake Elks Lodge, Greenwood Lake
October 15-17 

Grammy Award-winning polka artist Jimmy Sturr performs at this annual Oktoberfest celebration in Greenwood Lake. Three days of food, music, and beer delight families throughout the region. Delight in the fun-filled carnival, and boogie down to German-themed bands all weekend long.

Halloween Craft Fair/Flea Market

Stewart Airport, New Windsor
October 17, 11 a.m. – 5 p.m.

This “spooktacular” craft fair showcases the work of Hudson Valley artisans. Shop everything from handmade jewelry and candles to curated gift baskets and decorative henna tattoos. Skincare products range from seasonal-themed bath bombs, bubble bars, and essential oils. Plus, dig into sweet treats like artisanal chocolate, candy apples, cupcakes, and more. Dress up the kiddies in their costumes and take them trick-or-treating from noon to 3 p.m.


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Murder Mystery Dinner

Meadowbrook Catering Hall, New Windsor
October 22, 6:30 p.m.

It’s time to solve a murder. The Meadowbrook Catering Hall hosts Murder Cafe, for an evening of twists and turns. Come in costume to enter a contest. Music, dancing, and dinner precede the whodunnit caper. Can you crack the case?

Harvest Fest at the Farm

Freedom Hill Farm, Otisville
October 30, 3-8 p.m.

Searching for the perfect family outing for Halloween? Head to Freedom Hill Farm for a scare-free harvest festival. Few things are cuter than the children’s costume contest, but the fall-themed petting zoo is a close second. County-gospel group Tenbrooks Molly performs live music. The Bus food truck serves Latin American comfort food, while Westtown Brew Work’s beer truck pours draughts.

Putnam County

Read up on Putnam County Tourism Director Tracey L. Walsh’s picks for things to do this month.

Oktoberfest 2021 at Putnam County Golf Course

Putnam County Golf Course, Mahopac
October 1, 6:30-10:30 p.m.

Play a round of golf and the celebrate with a stein at Putnam County Golf Course. This Oktoberfest celebration costs $29 per person and features a menu of seasonal staples like bangers, knockwurst, and kielbasa alongside Hudson Valley barbecue. The Amish Outlaws take the stage for a full evening of raucous music.


Photo courtesy of Putnam County Tourism

Collaborative Concepts Outdoor Art

Tilly Foster Farm, Brewster
Through October 31

Collaborative Concepts sets up almost 50 sculptures across Tilly Foster Farm’s landscape. Spread across 199 rolling acres, the large-scale show is a delight for sculpture fans who want to get out and stretch their legs in the scenic Hudson Valley. While onsite, enjoy farm-to-table dining, hiking trails, and adorable farm animals. Guests can visit this exhibit seven days a week.

Manitoga / Photo courtesy of Putnam County Tourism

Manitoga Sunset Tours

Manitoga: The Russel Wright Design Center, Garrison
Through October 31

Manitoga’s studio, house, and woodland garden are absolutely magical during golden hour. Bask in a majestic sunset with a glass of wine in hand during these special tours. An easy-going hike takes visitors up a stone staircase, and to Dragon Rock’s terraces that overlook the Quarry Pool. Later this year, a new gallery of Wright’s home designs opens its doors to the public.

Putnam History Hikes

Fahnestock State Park, Carmel
October 30, 10 a.m.

Curious about the history of Putnam County’s landscapes? Travel back in time to explore Fahnestock State Park on foot while learning about its history through the many artifacts that still exist in the park. This timeline takes visitors through early indigenous Native American history, the American Revolution, and the Civil War all the way through FDR’s involvement. This hike lasts seven hours and spans eight and a half miles of Sunk Mine Road, with several fun detours along the way.


Photo courtesy of Putnam County Tourism

Oktoberfest Weekend 2021 at Tilly Foster Farm

Tilly Foster Farm, Brewster
October 23 & 24, 6-10:30 p.m.
The best Hudson Valley festivals take place on scenic farms. Brewster’s Tilly Foster Farm holds a two-day celebration of all things beer and brats. Bring blankets and lawn chairs to enjoy the Fast Lane Eagles Tribute Band and The Nerds. At $10 per car, this event is perfect for friends and family.

Rockland County

Take a browse through the top picks of things to do in Rockland County this month.

Photo courtesy of Rockland County Tourism

Ride ‘Round Rockland

Rockland Lake State Park, Valley Cottage
October 9, 7 a.m.

Bike your way into October with this socially distant ride through Rockland County. With three routes ranging from 40 to 100 miles, the ride is open to groups and soloists alike. Plus, there will be a 3.2-mile loop around Rockland Lake for kids.


Photo courtesy of Rockland County Tourism

Beer and Food Truck Festival

Palisades Credit Union Park, Pomona
October 9, 12 p.m. – 7 p.m.

There’s always something exciting happening where the NY Boulders play. More than 20 food trucks will showcase their cuisines at the first annual beer and food truck festival. Beer fanatics can sample more than 100 varieties, all while serenaded by live music. Admission is just $5 per person.


Photo courtesy of Rockland County Tourism

God-Stock II

Rockland GAA, Orangeburg
October 10, 4-6 p.m.

Neil Berg and Johnny Markowski put together a collection of musicians and rock enthusiasts to honor the great performers that have passed. The second iteration of “God Stock” takes place outside at the Rockland GAA. Listen to your favorite songs covered respectfully by Hudson Valley artists.

Oktoberfest Piermont

Photo courtesy of Rockland County Tourism

Piermont Oktoberfest

478 Piermont Ave, Piermont
October 23, 12 p.m. – 8 p.m.

What’s better than a day of fresh German beers, giant pretzels, and brats? An Oktoberfest celebration along the Hudson River, of course. Piermont’s iteration of the seminal Bavarian holiday brings live music, a car show, and children’s games to the banks of the Hudson. Follow the Village of Piermont on Facebook for all the juicy details.

Fall Art Crawl

Garner Arts Center, Garnerville
October 30 & 31 

Garner Arts Center hosts a Halloween weekend of craft vendors, live music, and tons of art. Enjoy performances from Haitian ensemble Fanmi Asòtò and creative activities for kids led by Debbie Ameera Ali. At night, explore the gallery exhibition that showcases Jonathan Demme’s massive collection of art.

Ulster County

Read up on Ulster County Tourism’s event highlights for the month.

Woodstock Film Festival | Photo courtesy of Ulster County Tourism, october

Woodstock Film Festival | Photo courtesy of Ulster County Tourism

Woodstock Film Festival

Multiple locations
September 29 – October 3

A favorite fall happening in the Hudson Valley, the Woodstock Film Festival keeps local film aficionados happy with its programming. More than 150 films screen throughout the Hudson Valley. Special programming includes drive-in showings, Q&As with filmmakers, and panels with industry leaders. Head to the website to scout out the full lineup.

Hudson River Maritime Museum Boat Tour: Lantern Cruise

Hudson River Maritime Museum, Kingston
October 1, 2, 8, 9, 15, 16, 22, 29, 30, 11 a.m. – 11 p.m.

Have you always wanted to traverse the Hudson River after dark? Kingston’s Maritime Museum launches lantern-lit boat cruises along the river. Explore the Rondout Creek by searchlight as crew members tell spooky tall tales of local legends. From the fictional works of Washington Irving to newspaper headlines of the past, these nighttime tours will certainly get you in the Halloween spirit.

Courtesy of Headless Horseman Haunted Attractions and Ulser County Tourism

Photo courtesy of Headless Horseman Haunted Attractions and Ulster County Tourism

Headless Horseman Haunted Attractions

Headless Horseman Haunted Attractions, Ulster Park
Through October 31

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. Eight other attractions including spooky motels, monster-filled greenhouses, haunted corn mazes, and more bring the scares. Opening night features discounted tickets, and reservations are strongly encouraged.


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Stockade Faire

Stockade District, Kingston
October 2, 11 a.m. – 11 p.m.

This year’s Stockade Faire highlights the incredible restaurants, shopping destinations, creators, and musicians of Uptown Kingston. Phoenicia Flea curates a host of street vendors, from artisans to craft beverage producers. The autumnal street festival stretches from Wall Street between John and North Front street to North Front street between Wall and Crown streets. Plus, this year marks the first iteration of OMG ArtFaire. For more fall craft fairs, click here.

Walktoberfest on the Walkway

Walkway Over the Hudson, Highland and Poughkeepsie
October 2 & 3, 12-5 p.m.

Does food taste better above the Hudson River? We certainly think so. Walkway Over the Hudson brings together the best of local distillers, brewers, vintners, cidermakers, and restaurants. Keep an eye out for cooking demonstration announcements as the festival date approaches to learn from some of the most skilled chefs in the Hudson Valley. Ticket are $25 apiece, and include samples of many local delicacies.

Old-Dutch-Church-Kingston-photo-by-Steve-Aaron-courtesy-of-Ulster-County, october-Tourism

Photo courtesy of Ulster County Tourism

Old Dutch Church Cemetery Tours

Old Dutch Church, Kingston
October 2, 9, 16, 24 at 1 p.m.

A little spooky and a lot educational, Old Dutch Church’s cemetery tours take visitors back to the early days of the Hudson Valley to explore the chilling history of the region. Tickets cost $15 per person and must be purchased online in advance. This year’s focus brings visitors back to Kingston in the 1920s.

Westchester County

Discover the hottest happenings according to Westchester County Tourism this month.

October blaze

This is a view of the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson on October 12, 2015. (Photo by Tom Nycz) / Courtesy of Historic Hudson Valley

The Great Jack O’ Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
Through October

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. To ensure social distancing, advance reservations are required. The show burns through the fall season, kicking off Friday, September 17 and wrapping November 21. Check out pumpkin versions of dinosaurs, the Statue of Liberty, and even the Tappan Zee Bridge.

Sleepy Hollow 

Sleepy Hollow
Through October

Chills and thrills run rampant in Westchester County during the Halloween season, and nowhere is this more apparent than at Sleepy Hollow. Visit the hallowed grounds to reminisce upon Washington Irving’s tale of the same name. In the cemetery, spot the grave of the author himself, along with the headstones for Andrew Carnegie, William Rockefeller, and members of the Hamilton family. Events and activities such as The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow,” Evening Lantern Tour and The Good, the Bad and the Unusual are all taking place this month.

Octagon House, Myths & Mysteries Tour

The Armour-Stiner Octagon House, Irvington
Through October

Can you solve the mysteries surrounding Irvington’s Octagon House? The Myths and Mysteries tour shines a light on the most compelling elements of the property—from its unique dome shape resembling an ancient Roman temple to its octagonal floor plan rooted in 19th-century phrenology. For all the ghost hunters out there, there’s a rumor that a former resident haunts the grounds to this day. Get tickets online today.

Lyndhurst After Dark

Lyndhurst Mansion, Tarrytown
Through October

Lyndhurst Mansion lets guests tour the property after the sun goes down for the Halloween season. Special collections of items and artifacts highlight superstitions of the time, and spooky decorations add a certain edge to the atmosphere. Dig into festive snacks including cider donuts, orange-and-black cookies, and more.

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

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