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



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. In fact, when it comes to actually choosing between one event or another, there’s potentially too much to do. Food fest on Saturday? Great. But there’s also that play you wanted to see. Oh, and that workshop you RSVP’d for in the afternoon. And the…oh wait, that’s already two things too many!

To help scout out the best events in the Valley, we reached out to local tourism directors from Albany to Ulster 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.


Capitol Hauntings Tours

New York State Capitol, Albany
Through November 1

October thrills take a historic turn at Albany’s New York State Capitol this month. For its limited tour series, the edifice opens its hallways to inquisitive Hudson Valleyites – and maybe a few spirits, too. If you’ve ever wondered about secret demons in the Capitol or the night watchman lost to the Capitol fire of 1911, you’re not going to want to miss this. Visit the website for specific times and dates for the free tours.


Drink Albany

Photo courtesy of Discover Albany


Drink Albany

New York State Museum, Albany
October 4, 6-9 p.m.

Albany’s craft beverage scene is thriving, so it’s no surprise that the Capital Region goes all out for its fifth annual Drink Albany. A pop-up market and tasting event at the New York State Museum, the one-day hoopla invites locals to try new sips and treats from nearby artisans. To sweeten the deal, the Capital Craft Beverage Trail is partnering with Capital City Trolley to offer a free stop at the museum door on the big day. If it all sounds like a drinkable dream come true, be sure to act fast. Last year’s event sold out before the museum doors opened.


Murder at Cherry Hill

Historic Cherry Hill, Albany
October 16, 7-8 p.m.

Mayhem and murder are the name of the game at Historic Cherry Hill’s live-action mystery experience. The interactive happening throws participants down the rabbit hole to 1827, when a notorious murder leads to two trials and the last public hanging in Albany. As amateur detectives make their way through the evening, they’ll meet the historical players and maybe, just maybe, discover whodunit.

Dutchess County

Take a peek at President & CEO of Dutchess Tourism, Inc. Mary Kay Vrba’s top picks for things to do in Dutchess County this month.



The Bardavon / Photo courtesy of Dutchess Tourism


Gladys Knight Live at the Bardavon 150th Anniversary Gala

Bardavon, Poughkeepsie
October 6, 8 p.m.

The one and only Gladys Knight lights up the stage at the Bardavon for an unforgettable night of R&B and soul in October. As part of the opera house’s 150th anniversary gala, the seven-time Grammy Award winner belts out signature hits like “Every Beat of My Heart,” “I Heard It Through the Grapevine,” and, of course, “Midnight Train to Georgia.” Warning: this one will sell out.


Soukup Farm

Soukup Farms / Photo courtesy of Dutchess Tourism


Fifth Annual Harvest Festival

Soukup Farms, Dover Plains
October 12-13, 19-20, 11 a.m. – 4 p.m.

The harvest festival at Soukup is so popular that the farm has extended it to two weekends this year. Head over to Dover Plains for pick-your-own pumpkins and hayrides on the grounds, then adventure to the top of the hay pyramid or navigate the twists and turns of the hay maze. As for lunch, J.S.K. Cattle Co. serves up farm-to-table fare that pairs wonderfully with maple syrup, candy, and glazed nuts from the farm.


NYS Sheep and Wool Festival

New York State Sheep & Wool Festival / Photo courtesy of Dutchess Tourism


New York State Sheep & Wool Festival

Dutchess County Fairgrounds, Rhinebeck
October 19-20, 9 a.m.

It’s back! This year, the Hudson Valley’s signature sheep and wool festival weaves its way along every nook and cranny of the Rhinebeck fairgrounds. The annual to-do is fun for all ages, with petting zoos, artisan markets, herding dog demonstrations, and sheep shearing displays on the itinerary. While shopping is undoubtedly one of the highlights of the event, the curated workshops, which touch upon topics like “Design Your Own Raglan” and “The Art of Navajo Weaving,” are a delightful way to spend an October afternoon.

Greene County

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



Oktoberfest / Photo courtesy of Great Northern Catskills of Greene County



Hunter Mountain, Hunter
October 5-6, 12-13, 19-20

It’s Oktoberfest month in the Hudson Valley! Hunter Mountain kicks it into high gear with not one, but three epic weekends of German brews, food, and traditional entertainment. Each weekend features a distinct theme, hopping from a Motorcycle Rally with off-roading to Das Laufwerk Eurocar Rally to Wineries in the Catskills at the end of the month. Did we mention the views at Hunter are pretty incredible, too?


Bronck Museum Heritage Craft Fair

Bronck Museum, Coxsackie
October 6, 12-4 p.m.

Take a step back in time at Coxsackie’s Americana craft fair in October. Hosted at a 355-year-old Dutch farmstead, the fest features charming details like horse-drawn wagons, artisanal vendors, and American bluegrass tunes from Running the River. Admission is free for all.



25th Autumn Affair

October 12-13, 10 a.m. – 5 p.m.

The entire village of Windham unites to celebrate the spirit of fall in the Hudson Valley at its 25th annual autumn fest. With more than 50 vendors lined up along Main Street, the sidewalk shopping event enlivens the two days with music, a DJ, and an art show in the Centre Church. For kids, the winding hay maze at the Catskill Mountain Country Store, not to mention pony rides and pumpkin decorating, will get them more than a little excited for the changing seasons.


Hudson Valley Dance Festival

Historic Catskill Point, Catskill
October 12, 2 p.m. and 5 p.m.

A unique one-day event, Catskill’s dance festival invites established and emerging companies and choreographers to the town’s historic warehouse for two breathtaking performances. Featured dances range in style from contemporary to African and jazz, and companies include Dance Lab New York, Gallim Dance, and RIOULT Dance NY, to name a few.

Orange County

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



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OCNY West Fall Fest

Brown Barn Farms, New Hampton
October 5, 2-9 p.m.

As any local knows, Hudson Valley farms are the place to be come fall. After all, where else can you find autumn essentials like cider, donuts, and candy apples alongside craft brews, cocktails, and authentic farm-to-table eats? This time around, Soons Orchards brings the sweet treats, while Orchard Hill Cider Mill, Westtown Brew Works, and Orange County Distillery keep everyone sipping happy. On the foodie side of things, the Bear Eats Food Truck and Pierson’s Farm deliver addictive bites throughout the afternoon.


Warwick Applefest

October 6, 9 a.m. – 5 p.m.

Warning: Warwick’s Applefest is not for the faint of heart. An apple fest like no other, it draws thousands of apple lovers from the Hudson Valley and beyond to celebrate everyone’s favorite fruit of the season. Get there early if you plan on going, then spend the day shopping from more than 200 vendors, wandering the stands at the onsite farmers’ market, and letting the kids loose at the children’s carnival. If you’re up for it, test your pie prowess at the fest’s annual apple pie baking contest, which smells so heavenly you’ll walk away a winner either way.



The beauty seems endless from the top …

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Autumn at the Park Chairlift Rides

Mount Peter, Warwick
October 19-20

Make the most of leaf peeping season with Mount Peter’s seasonal chairlift rides. A one-of-a-kind fall experience, the sky-high jaunt takes visitors up the mountain to view the autumnal panoramas of the Hudson Valley in a whole new way. One the rainbow rides touches back down at the base, visitors can stick around for the mountain’s annual ski sale to take advantage of pre-season discounts.


Boo at the Zoo

Trailside Museums and Zoo, Bear Mountain State Park, Bear Mountain
October 26, 10:30 a.m. – 3 p.m.

Just in time for Halloween, Trailside Museums takes the scary out of the season in order to teach little ones about the creepy, crawly critters of the region. Beginning with a spooky snack workshop at the bear den, the educational day also gives children the chance to touch real animal skulls, examine stuffed specimens up close, and participate in hands-on crafts.



Who doesn’t love Cupcakes ? Get ready, because Cupcake-a-Palooza is 3 weeks away!

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Safe Harbors of the Hudson, Newburgh
October 26, 1-4 p.m.

Get your cupcake on at this sweet little shindig in Newburgh. An annual to-do, it features a delightful medley of professional and amateur bakers, who compete to see who can craft the fluffiest, most flavorful confection of the day. Admission runs $5 apiece and includes tasting, beverages, and the chance to vote for the public favorite.

Rockland County

Take a browse through Director of Economic Development and Tourism Jeremy Schulman’s picks the hottest things to do in Rockland County throughout the month.



#apple #pickyourown #drdaviesfarm

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Apple Picking

Orchards of Concklin, Pomona and Dr. Davies Farm, Congers

Find the apple(s) of your eye at the Orchards of Concklin in Pomona this month. On top of its pick-your-own programming on the weekend, the Rockland spot keeps the fall feels going with a corn maze and farm stand that’s ready to serve fresh pressed apple cider, homemade pies, and warm donuts.

On the hunt for even more apple fun? Dr. Davies Farm in Congers offers apple picking during the week as well as on the weekends. Of course, the farm’s grocery stand is always a worthy pitstop for fresh fruits and vegetables.


Fall Family Festival

131 Germonds Rd, West Nyack​
October 20, 12-4 p.m.

For a jam-packed afternoon of autumnal entertainment in the Hudson Valley, look no further than West Nyack’s seasonal shindig. With horse-drawn hayrides, pumpkin picking and decorating, and sheep shearing demonstrations, it’s a wonderful medley of crafting and education. Stick around for the colonial dance performance!


32nd Annual Nyack Halloween Parade

Downtown Nyack​
October 26, 2-8 p.m.

There are Halloween parades, and then there’s Nyack’s Halloween parade. A much-anticipated to-do, the event embraces the chills and thrills of the season with costume contests and a sweet trick or treat trail for kids. The grand parade kicks off from Memorial Park at 5:30 p.m. If you go, keep any eye out for dancing ghouls, marching bands, retro rides, and the most spooktacular getups around.

Ulster County

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


Woodstock Film Festival

Woodstock Film Festival / Photo courtesy of Ulster County Tourism


Woodstock Film Festival

Kingston, Rosendale, Saugerties, Woodstock
October 2-6

Roll tape! This October, the Woodstock Film Festival takes over Ulster County for its 20th annual celebration of the nation’s groundbreaking independent films. Throughout the course of the week, the festival hops through the region to showcase more than 150 films and concerts. For the full schedule of screenings and events, visit the festival’s website here.


O Positive Festival

O+ Festival / Photo courtesy of Ulster County Tourism


O+ Festival

October 11-13

For community, culture, and art galore, there’s no better place to be than Kingston’s 10th annual O+ Festival this month. If you’ve never experienced the creative to-do before, expect a citywide celebration that honors the multitude of makers in the region. As for events, they run the gamut from concerts and mural showcases to health expos and healing arts sessions. A true Hudson Valley gem, it has a little something for everyone.


Italian Festival

Ulster Italian Festival / Photo courtesy of Ulster County Tourism


Ulster Italian Festival

Rondout waterfront, Kingston
October 13, 11 a.m. – 7 p.m.

Thanks to Ulster’s Italian Festival, everyone can savor la vita bella in the Hudson Valley. For its 12th year in a row, the festa sets up shop on the scenic Kingston waterfront to showcase the sumptuous Italian flavors in the region. A true family to-do, it keeps locals of all ages entertained with traditional music, educational presentations, and, of course, meatballs and sauce galore.

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