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The Best Hudson Valley Fall Events Around: Don’t you Dare Miss Any!

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Plan the next perfect outing with this free list of Hudson Valley, NY outings for $10 or less.

When Autumn rolls around in the Hudson Valley, the whole region appears to dress up in its best colors. The wind gets cooler and the leaves begin to change all in preparation for the wonderful Hudson Valley Fall Events that the region will host.

[Post updated: 11/4/2019]

The Best Autumn Events only happen in the Hudson Valley. Check out this list to find your favorites!

This is my favorite time of the year and is a very special time in the Hudson Valley. I always fill my calendar and regret not having more time to see and do more things.

With so much to do and so much to see, it is hard to keep up with all that’s going on in the area. It is often difficult to narrow down the best places to visit in the Hudson Valley any time of the year.

Pumpkins are popular for the Fall and especially for Hudson Valley Fall Events

My advice: Take out a piece of paper and pen and start jotting down some of these Special Events. Make sure you take some time to experience all the great things the Hudson Valley has to offer this time of the year.


According to the website, IloveNY:

“Fall festivals and farm tours will deepen your greatest wanderlust. Whether you’re tasting the season’s harvest at craft cideries, checking out fall events… the autumn air is filled with adventure.”


This post may contain affiliate links.Affiliate links mean that I get a little money, to help run this blog, with each purchase you make on this post. This comes at no extra cost to you. Please read my disclosure for more information.


Hudson Valley Fall Events – Halloween Events


Sleepy Hollow and Tarrytown are some of the most famous places to visit during the Halloween Season.

A fall leaf lays on the ground in the Hudson Valley, NY

Situated along the Hudson River, Sleepy Hollow is the setting of Washington Irving’s, “The Legend of Sleepy Hollow”. That alone makes it the most popular Hudson Valley Destination in October.

Below are just some events that take place in the area in honor of Halloween.

Sleepy Hollow Cemetery Tours

October – November
Not sure if this is your sort of your thing, but this is something I would love to do someday! Any history-lover or admirer of statues will love this tour. They offer several different tours during the season. Check their website for this season’s schedule and current prices.

Horseman’s Hollow at Philipsburg Manor

October & First Weekend in November
During the month of October, Philipsburg Manor is transformed into an interactive and terrifying scene as it is immersed in the “Legend of Sleepy Hollow”. Check their website for this season’s schedule and current prices.

Irving’s Legend

October & First Weekend in November
If the Horsemen’s Hollow doesn’t scare you enough, why not try Irving’s Legend at the Old Dutch Church. Check their website for the season’s schedule and current prices.

Ghost Tours at Tarrytown Music Hall

Unexplained happenings and paranormal activity have been experienced at our 134-year-old historic theater.

The Great Jack 'o Lantern Blaze is the ultimate Halloween event in Westchester County.

The Great Jack O’ Lantern Blaze

Late September – End of November
Another popular event in Westchester County is the Great Jack O’ Lantern Blaze. This yearly event takes place in Croton-on-Hudson at Van Cortlandt Manor. This event is NOT to be missed! Check their website for the season’s schedule and current prices.

Brick or Treat @ Legoland Discovery Center

Select days in October until October 27, 2019
The Halloween party built for kids is bringing a whole NEWspooktacularway to play with LEGO bricks!

Haunting Stories from Fishkill’s Past

October 12, 2019
Music, Stories, Dance, and more at the Van Wyck Homestead.

Jay Ghoul’s House of Curiosities

October 17 – 31, 2019
Down the road from the center of Tarrytown is Lyndhurst Mansion. This spectacular location hosts Jay Ghoul’s House of Curiosities. This yearly event also offers a 40-minute performance. There are too many things to list here. You just have to go and see for yourself. Check their website for the season’s schedule and current prices.

Headless Horseman Hayrides and Haunted House in Ulster Park

September – November
Voted the ‘Scariest Haunted House in the Northeast’, the hayride and haunted house are not for the faint of heart. Make sure to check their website for the season’s schedule and current prices.

Annual Witchingtonville

October 19th, 2019
Food trucks, live music, a visit from the Headless Horseman and much more…

No Scare Halloween @ Museum Village

October 19 & 20, 2019
Wear your not-so-scary costumes and parade around on our grounds! We’ll have lots of fun activities for the children with crafts and games! 

Greenwood Lake Halloween Festival

October 19th, 2019
Get your scare on and get ready for a day of spooktacular Halloween fun!

Annual Haunted Firehouse in Salisbury Mills, NY

October 25th & 26th, 2019
Salisbury Mills Fire Company is hosting our annual Haunted Firehouse this year on Friday, October 25th & Saturday, October 26th from 7 pm-10:30 pm. The cost is $5 per person.

Rocky Horror Picture Show @ Tarrytown Music Hall

October 26, 2019: 8pm & 11:30 pm
Tickets and Tickets with Participation Kits may be purchased on the website. Don’t miss this cult classic and Halloween tradition.

Halloween Haunts & Happenings at Mohonk Mountain House

Enjoy Halloween weekend featuring frightening festivities, campfires, a costume ball, trick-or-treating, and more!

Hocus Pocus Parade in Beacon, NY

October 27th, 2019: 1- 3 pm
A beloved Beacon tradition! The parade will start on the West End of Main Street at 1 pm

Muscoot Farm Boo Walk

October 27th, 2019
Go on a Halloween-themed scavenger hunt around the farm, then claim a Halloween treat at the end as your prize. Children are encouraged to come in costume.

Pumpkins lit up in the Hudson Valley, Ny for Halloween

Annual Trunk or Treat!

October 27, 2019
The Social Kid Society is so excited to have partnered with Lowe’s of Yonkers, NY for our Trunk or Treat!!

Night of 1,000 Jack O’ Lanterns

Select dates in October
Night of 1,000 Jack O’Lanterns takes place in 2019 at FOUR locations across the US, including at the century-old, farmer-founded, Yorktown Grange Fairgrounds in Westchester County.

Philipse Manor Hall Haunted House

October 31, 2019
You are invited to Philipse Manor Hall’s “Haunted House” walk-thru from 4 – 7 PM on Halloween day (for ages 12 and under only).


Hudson Valley Fall Events – Autumn/Fall Festivals in October


If Harvest Festivals are more your speed, then make sure you visit several popular ones.

Fall Leaf on a bench in the park in the Hudson Valley, NY

Harvest Fest at Stone Barns in Pocantico Hills

October 5, 2019
This event offered wonderful activities all set on the grounds of Stone Barns. Advanced tickets are required.

Pumpkin Festival in Campbell Hall

October 5, 2019
Enjoy an afternoon of all things pumpkin at the Hill-Hold Museum.

Heart of the Hudson Bounty Festival in Milton

October 5, 2019
A fun-filled annual family event that showcases agriculture and businesses of the Hudson Valley.

Heritage AppleFest in Garrison

October 6, 2019
This ‘Pay as you wish’ Festival is hosted on the grounds of Historic Boscobel. And that fact alone should make you want to go to this event.  

TraubenFest / Oktoberfest in Tappan

October 6, 2019
This festival at the German Masonic Park is sure to be loads of fun.

AppleFest in Warwick

October 6, 2019
Said to be the “Orange County’s Largest Festival”, the festival hosts a Pie Baking Contest that gets visitors from near and far

Hudson Valley Hogtoberfest

October 12, 2019
This event will be filled with the most amazing bacon and German vendors with a beautiful backdrop of the Orange County Farmers Museum in Montgomery NY.  

Pearl River Day in Pearl River

October 12, 2019
This Annual Event is full of food, music, and a great sense of community. It’s a fun-filled event that highlights the restaurants, shops and other businesses in Real River.

Muscoot Farm Pumpkin Picking Weekend

October 12, 2019
Muscoot Farm will offer pumpkin picking, hayrides, and much more on Columbus Day weekend as part of its Pumpkin Picking Autumn Celebration. 

Adams Annual Harvest Fest, Newburgh

October 12, 2019
Celebrate fall at the Adams Annual Harvest Fest! There’s lots of free farm fun for the whole family!

Harvestfest @ Philipse Manor Hall

October 12, 2019
Come celebrate the fall harvest by participating in many fun-filled, family-oriented, fall crafts and activities!

Belleayre Fall Festival in Highmount

October 12 & 13, 2019
German food highlights this wonderful family-fun event.

Fall Festival at Hurds Family Farm in Modena

October 12 & 13, 2019
What better way to admire the Fall foliage but at Hurd’s Family Farm. And apple and pumpkin picking make the day complete.

Soukup Farms Harvest Festival in Dover Plains

October 12, 13, 19, & 20, 2019
In addition to pumpkin picking, at this event, you can climb a pyramid made of hay and you can get lost in the hay maze.

Dog enjoying the pumpkin patch at Stuart's Farm

Fall Fest @ Nostrano Vineyards

October 13, 2019
This Annual at the Vineyard hosts a variety of Estate Wines, Autumn Sangria, Local Craft Beer & a curated shopping experience of local Hudson Valley artisans.

PumpkinFest in Pine Island

October 14, 2019
A fun-filled afternoon for children and parents alike.

Adams Annual Harvest Fest, Kingston & Wappingers

October 14, 2019
Celebrate fall at the Adams Annual Harvest Fest! There’s lots of free farm fun for the whole family!

Harvestfest on the Hill in Yonkers

October 19, 2019
Trick-or-Treat, Pumpkin carving demos, music, food and so much more at Ridge Hill.

NYS Sheep & Wool Festival in Rhinebeck

October 19 – 20, 2019
Here is another great event that takes place at the Dutchess County Fairgrounds in Rhinebeck, NY.

Heritage of West Nyack Fall Festival in West Nyack

October 20, 2019
This great event also combines music, food, hayrides and pumpkin decorating in a wonderful community atmosphere.

Adams Annual Harvest Fest, Poughkeepsie

October 20, 2019
Celebrate fall at the Adams Annual Harvest Fest! There’s lots of free farm fun for the whole family!

Bear Mountain Oktoberfest

Weekends (Sept 27 – Oct 20, 2019)
Lots of fun will be had at the Annual OktoberFest Celebration at the Anthony Wayne Recreation Area. A $10 per vehicle fee applies for the festival.

Pumpkin Festival in Beacon

October 20, 2019
The Beacon Sloop Club is host to this wonderful family fun event.

Fall Harvest Festival Kickoff Weekend at Fishkill Farms

Weekends – September & October
Apple Picking, live music and fresh cider, Oh My!  


Hudson Valley Fall Events – Other Events in October


Hudson Beach Glass in Beacon is a Highlight during the Second Saturday Event

Second Saturday in Beacon

October 12, 2019
Second Saturday is a city-wide celebration of the arts held on the second Saturday of every month. Special events, art gallery openings, artist receptions, and culinary tastings. Many galleries and shops stay open until 9 pm.

Nyack’s Famous Street Fair

October 13, 2019
The name says it all! Go see what all the buzz is about!

Stormville Airport Antique Show & Flea Market

October 12 & 13, 2019
With more than 600 vendors coming from various states, this is the largest local Antique Show and Flea Market around!

Stony Point Battlefield State Historic Site Continental Soldiers Take Over

October 19, 2019
Join the 2nd New York as they demonstrate how an American unit in the first year of the American Revolution, 1775, would march, drill, charge bayonets, and fire in unison.

Hudson Valley VegFest

October 19 & 20, 2019
Coming to Kingston, NY, this event showcases food vendors, products, art and so much more!

Photowalk at Untermyer Gardens

October 20, 2019
Join the Untermyer Gardens Conservancy’s Jessica Norman for a Photowalk at 9 am Sunday, June 23 in the gardens.

Hiking Through the Hudson River History on the Croton Aqueduct

October 20, 2019
Learn about the history of the Hudson River while taking pictures of the colorful autumn foliage from the vantage of the Croton Aqueduct, a location that has figured into the history and lore of New York State and City.

Chocolate is everyone's favorite and is one of the Hudson Valley Fall Events
Photo by Acharaporn Kamornboonyarush from Pexels

Walkway at Night

October 26, 2019
Enjoy breathtaking twilight views from 212 feet above the Hudson River. 

The Chocolate Expo

October 27, 2019
The largest chocolate event in the United States comes to visit Museum Village in Monroe.

Lyndhurst Mansion Autumn Open House Weekends

September 26 – October 31, 2019
This classic tour gives you the best of the mansion tour with the added bonus of the beautiful Autumn decor.


A FEW THINGS TO CONSIDER BEFORE ATTENDING ANY OF THESE EVENTS:
> Many of these events and festivals require a ticket for admission.
> Popular events, like the Great Jack O’ Lantern Blaze, typically sell out quickly
> Many of these events are rain or shine, although some do offer rain dates.
> Check each site for updated information.


Hudson Valley Fall Events in November


Autumn is at its peak in the month of November. Fall Festivals and the famous Hudson Valley Restaurant Week all take place in November. And if you love Craft Fairs, then November is the best month of the year to get your fill.

Make sure to get a piece of paper, write down some or all of these activities and get out and enjoy November in the Hudson Valley.

The Culinary Institute of America is located along the Hudson River in Hyde Park, NY

The Red Hook & Chocolate Festival

November 2, 2019
Chocolate, Hayrides, and History all in Red Hook, NY.

Angry Orchard Farmers Market

November 2, 2019
Angry Orchard is the perfect place to host a variety of vendors, particularly before the holiday season.

Stormville Airport Antique Show & Flea Market

November 2 & 3, 2019
With more than 600 vendors coming from various states, this is the largest local Antique Show and Flea Market around!

Hudson Valley Restaurant Week

November 4 – 17, 2019
Some of the best meals I have had have been during Hudson Valley Restaurant Week. Some of our favorites have been:

  • Henry’s at the Farm in Milton, NY
  • The Bocuse Restuarant at the Culinary Institute of America in Hyde Park, NY
  • Cosimo’s on Union in Newburgh, NY

Make sure you book your reservations early because many of the restaurants sell out. Check The Valley Table Website for the list of participating restaurants, the current prices and to make reservations.

Second Saturday in Beacon

November 9, 2019
Second Saturday is a city-wide celebration of the arts held on the second Saturday of every month. Special events, art gallery openings, artist receptions, and culinary tastings. Many galleries and shops stay open until 9 pm.

Annual Train & Hobby Show at the Mid-Hudson Civic Center

November 10, 2019
A train hobbyist mega-event, all under one roof!

Lyndhurst Mansion Presents: Sherlock Holmes ‘The Adventure of the Dying Detective’

November 16 – December 8, 2019
When a wealthy man suddenly becomes ill and dies, his widow calls in Sherlock Holmes to unravel a mysterious tale of family rivalries.

A favorite Hudson Valley Fall Event is the Annual Train & Hobby show

Applewood Wine & Chocolate Pairing

November 16 & 17, 2019
Applewood Winery’s Wine and Chocolate pairing! November 16th and 17th 12-5! Tickets include 5 wine and chocolate pairings and souvenir glass.

Holiday Hudson Valley Hullabaloo

November 23 & 24, 2019
The Holiday Hudson Valley Hullabaloo is a local favorite and showcases local vendors in a party-like atmosphere.

Angry Orchard’s Friendsgiving

November 23, 2019
Celebrate the start of the holidays at the Angry Orchard Cider House for our Third Annual Friendsgiving! This gathering will feature small plate appetizers presented by Chef Shawn Hubbell of Amuzae Catering complete with small-batch New York cider styles available exclusively at the Cider House.

Holiday Extravaganza & Thanksgiving Farmers Market

November 23, 2019
Buy Local for the Holidays!

Rosendale International Pickle Festival

November 24, 2019
The Rosendale Pickle Festival hosts approximately 100 vendors and also features 20-25 pickle vendors. In addition, there is a pickle contest and the famous Pickle Triathlon: Pickle Eating Contest, Pickle Juice Drinking Contest, and the Pickle Tossing Contest.

Santa on the Walkway Over the Hudson

November 29, 2019
Santa will be available for pictures on the Poughkeepsie entrance of the Walkway. Come join in the fun!

Wine Tasting at Benmarl Winery

November 29, 2019
Come breathe in the fall, get a free tasting on us for our annual Black Friday Sale.

Holiday Opening Weekend @ Lyndhurst Mansion

November 29 – December 1, 2019
During Black Friday Weekend only, visitors can walk through the mansion without a guided tour, view the holiday decorations at their own pace, and take in the wonders of the historic mansion.

Annual Craft Fair at Dutchess Community College

November 30 & December 1, 2019
This craft fair is the highlight of Thanksgiving Weekend. In addition to showcasing local artists, it helps people get a jumpstart on holiday shopping.

The Craft Boutique at the Van Wyck Homestead Museum

November 30 & December 1, 2019
Join the vendors in the wonderful museum as they showcase their creations and have lunch by the fire in their 1732 kitchen.

Lyndhurst Mansion is host to many wonderful Hudson Valley Events all year long

No matter what you choose to do in Fall, make sure you go out and enjoy some of these wonderful events. You will see, firsthand, the incredible sense of community and Hudson Valley pride that is showcased through and through.


Sharing is Caring!
When visiting local attractions, be sure to tell them that you found them on Hudson Valley Exposed!


My Hudson Valley Events Facebook Group is updated daily featuring all the best events and activities throughout the Hudson Valley.
Bookmark it and don’t forget to visit often!


Until the Next Adventure…



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Candy corns adorn this photo signifying that the Hudson Valley Halloween season is upon us!
A photo of a pumpkin means that Hudson Valley Fall Events are underway!
50+ Fall Experiences you can only have in the Hudson Valley

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