Upcoming Hudson Valley Events
You will Love (2021)

Looking for Hudson Valley Events that are fun for the whole family? You’ve come to the right place!

I have done you the favor of combing through Facebook and have had my browser full of open tabs in order to provide you all with a comprehensive list of popular Hudson Valley Events taking place this year.

In addition to my Facebook Events Group (See Link Below to Join), which is FULL of Popular Hudson Valley Events that will be sure to fill every weekend of your personal calendar, this article will also be updated regularly.

This article contains affiliate links. I make a small commissions for purchases made through links at no extra cost to you.
Read my disclosure for more info.


Why are Hudson Valley Events So Special?


From Westchester County to Rockland County to Orange County, all the way up to Greene County and Albany, Hudson Valley Events bring together community and local businesses in the best way possible.

When the warmer weather arrives, not only do some animals awake from their winter slumber, but many locations in the Hudson Valley open for the Season. Outdoor events are abundant and are perfect for the entire family.

During the cooler months, Hudson Valley events include chances to get out, pick fruit and celebrate fall harvests. The Hudson Valley region is full of orchards and farms, so there are plenty to choose from.

Hudson Valley Events & Attractions are the best around and you should take full advantage of them. Since most Hudson Valley Events were cancelled last year, this year brings a heightened buzz and excitement.


Things to know before attending one or more Hudson Valley Events

  • These upcoming Hudson Valley events are subject to change or cancellation. Make sure to confirm the information before making your plans.
  • Holiday weekends (including Memorial Day weekend, Labor Day weekend, Columbus Day weekend) are popular times for Hudson Valley Events.
    • Make reservations or buy tickets early because they usually sell out fast
  • Many local artists and local businesses participate in fairs and farmers markets, so this is the perfect time to support local!


Essentials you need for any Hudson Valley Outing:


Hudson Valley Directory

Personalized Hudson Valley Directory

Personalized Hudson Valley T-shirts

Picture Perfect Adventures in the Hudson Valley Ebook and Planning System

101+ Things to do in the HV for $10 or less

Recommended Items for a Great Day at Hudson Valley Events:

Outdoor Waterproof Boonie Hat

Skechers Women’s Go Walk 2 Slip-On Walking Shoe

Plastic Water Bottle

Click below to see items I always have during my Hudson Valley Outings:

  • Because ‘you never know’ when an accident happens, you need this product in your life. This is a great buy for under $15
  • If you’re going to be out all day exploring, you never REALLY know what the weather will be like. Even if you think you do know, this is an essential item. This is another great buy for under $15.
  • My favorite walking shoes, by far, are these because they are soft and the memory foam feels great on my feet.

PRO TIP:
EVENT TITLES are linked directly to the organizer’s websites for your convenience. (where applicable)



Hudson Valley Events taking place this September


Hudson Valley Hot Rods Friday Night Car Cruise 2021

Every Friday Night from April – September: 5:30pm – 8pm
29 West Main Street, Washingtonville

We are a car club located in Washingtonville, NY. Join us Friday nights @ 29 W Main St Washingtonville, NY from 5:30PM – 8:30PM. We support the Blooming Grove Humane Society.

New York Renaissance Faire

Weekends throughout September
Tuxedo, NY

2021 marks the 44th Anniversary Celebration of the New York Renaissance Faire, located in Tuxedo, New York. The Faire is a rollicking romp through Elizabethan England, set within the Majestic Groves of Sterling Forest.

READ MORE:
Click here to read my article all about the NY Renaissance Faire

MCOC All American Saturday Night Car Cruise

Every Saturday until October 30th: 5pm – 9pm
Boston Market Parking Lot, Route 211, Middletown

50/50 Raffle, Music, Coffee & Donuts


Learn to Disc Golf

September 2nd: 9am
Wilcox Park, Route 199, Milan

On Thursday, September 2nd, we will be offering a Learn to Disc Golf workshop at Wilcox Park. Learn all about the sport of disc golf and the Dutchess Disc Golf course located at Wilcox. Dan Doyle, course designer and competitive Professional Disc Golf Association player and instructor, will be on hand to teach beginners the basics. Reserve: 845-486-2555

First Thursday Gallery Hop

September 2nd: 5:30pm – 7pm
Downtown Yonkers

Artists and art lovers can stop by all three downtown Yonkers Art Galleries to preview current exhibitions:▪️Blue Door▪️Riverfront Art Gallery▪️Urban Studio Unbound/Warburton Galerie In collaboration with this event many downtown restaurants will offer 10% discounts on food and beverages to Gallery Hop visitors via a photo of the Gallery Hop poster with date displayed in each location.

HV Hot Air Balloon Festival

September 3 – 5
Tymor Park, Union Vale

Bring your blankets and chairs to watch hot-air balloons ascend from the designated picnic area. Watch in awe as hot-air balloons fill the skies and as they light the night with an illumination moon glow with fireworks on full display. Reservations can be made on a per person basis for a donation of $14.00 for evenings and $7.00 for mornings.  A reservation must be made in advance as donations will not be accepted at the gate.  Donation is non-refundable and non-transferable.

Pine Bush UFO Fair

September 4th: 10am – 4pm
Main Street, Pine Bush

Come by to watch, or join-in with the fantastic Cosplay Characters and Extra-terrestrials of all shapes and sizes in attendance! FREE All Day Entertainment: The family-friendly celebration also includes live music, kid’s activities and games, food vendors and tons of unique art, and craft vendors!

Tractor Parade & Farm Day

September 4th: 12 noon
Village of Montgomery

Activities for kids, tractor displays, garden tractor pulls, hit and miss engines, food, square dancing at 7pm. Chicken BBQ at 5pm (tickets for food $15) Reservations: 845-457-3453

Movies in the Park

September 4th: 8pm
Freedom Lake, Pleasant Valley

Register for the much-anticipated Movies In the Park at Freedom Lake featuring Jumanji: Welcome To the Jungle (rated PG-13) on Saturday, September 4th starting at 8pm! The beach will open at 7pm for games such as volleyball, ping-pong, etc available to play until the movie begins. All activities will end when the movie begins at 8pm. Don’t forget your beach chairs or blankets! Our Concession Stand will be open and selling pre-packaged snacks and drinks. You may also bring your own snacks and drinks but remember no glass, no dogs, and no smoking of any kind allowed anywhere in the park. Bring your friends! Register at www.lagrangeparksandrec.com.

The Two Ladies Market

September 4th & 18th : 10am – 3pm
Greenville Drive-In, Greenville

Come join us for lots of fun, raffles, balloons, etc. We have a little bit of everything for everyone. Fresh Meats, Fresh Vegetables and so many Crafters.

Stormville Airport Flea Market

September 4th & 5th: 8am – 4pm
Stormville Airport

Shoppers come to the Flea Market and discover everything from antiques and collectibles; arts and crafts to new merchandise. Free parking & Free Admission.

Hudson Valley Events

Barbeque and Brews

September 4th – 6th
Barton Orchards, Poughquag

Each year, the farm hosts a wide variety of fun events full of live music, live entertainment, games, and delicious food. 2021 will be no different. Mark your calendars because it’s going to be a great year!

Family Adventure Tour: Walled Garden

September 5th, 12th, 19th, & 26th: 10am – 11am
Untermyer Gardens, Yonkers

Our kid-friendly Family Adventure Tours take place on Sundays at 10 AM from May 16-September 26. Our guides will engage your kids in a lively exchange about plants, mythology, architecture, sculpture and ruins. Choose from three tours offered in rotation: Walled Garden, Vista through the Ruin Garden, and Temple of Love through the Dell. These tours are intended for children between 7-12 who must be accompanied by at least one adult. Cost: $10 per child (10 maximum), adults (and children under two) are free so long as they accompany a child.

Fireworks in Newburgh

September 6th: 9pm
Consolidated Iron Site, Newburgh

The firework show will begin at approximately 9:00 p.m. at the Consolidated Iron Site, with great viewing from our waterfront area.Don’t forget today is the last day to enjoy the City’s festival at Delano Hitch Park!

JazzFest

September 9th – 12th
White Plains

Plan to jazz up your calendar with our upcoming JazzFest performances! For its tenth year, the festival remains true to its roots, presenting jazz from an outstanding roster of Westchester and NYC musicians.

Yorktown Grange Fair

September 10th – 12th
99 Moseman Road, Yorktown Heights

Enjoy a great time with friends and neighbors. Fairs are a sensory feast: the sights of the midway, the tastes and smells of the delicious food, the sounds of fun and great entertainment.

Screenings under the Stars

September 10th: 6:30pm
Croton Point Park

Tickets are on sale now for the WP Hospital’s Screenings Under the Stars viewing of Pixar’s SOUL at Croton Point Park, Friday, Sept. 10, 6:30 p.m. Buy now: https://bit.ly/3gSndT6!

Stargazing Program

September 10th: 9pm – 11pm
Rockefeller State Park Preserve

Join members of the Rockland Astronomy Club for an evening of stargazing at the Preserve. You’ll have the chance to view the night sky through a telescope and maybe even catch a glimpse of one of our planetary neighbors. Cost: $3 + Eventbrite fees. Maximum: 20 people.To register: www.rockefellerstateparkpreserve.org/events

Living History: Family Art, Health & History in the Ten Broeck Gardens

September 11th: 10am – 10:30; 11am – 11:30am; 12noon-12:30pm
Ten Broeck Mansion, Albany

Get creative & get healthy! Free summer family programs about art, health, and history with hands-on activities in 4 acres of gardens. Taste! Jamming in Arbor Hill. Discover the wonders of the tastes and textures of plants in the Ten Broeck Gardens. Enjoy healthy eating recipes and a tour of plants that are fuzzy, wuzzy, sweet and neat, sticky (and sometimes icky)! Learn about the history of Arbor Hill and our own grape arbor, and learn how grape jam is made.

Albany Riverfront Jazz Festival

September 11th: 12pm – 8pm
Albany Riverfront

A day of live music

Patriot Day BBQ

September 11th: 1pm – 6pm
50 Legion Road, Poughkeepsie

American Legion Post #1466 is hosting a BBQ. Tickets will be sold at the event.

Brews with Views: Beer and Cider Festival

September 11th: 2pm
Boscobel House and Gardens

40 plus brewers, over 100 taps, food trucks, live music, cornhole mania and a big raffle. If your coming by train there will be a free shuttle bus running all day long from Cold Spring station. Tickets and event information at Hopsonthehudson.com

20th Anniversary of Sept. 11
Unveiling of Memorial

September 11th: 3:30pm
Kensico Dam Plaza, Valhalla

Join us on Saturday, September 11th at 3:30 as we honor and remember the Westchester County residents we have lost. This year, we will be unveiling a memorial dedicated to those first responders who lost their lives from 9/11 related illnesses.

Family Fun Weekend

September 11th & 12th
Barton Orchards, Poughquag

Each year, the farm hosts a wide variety of fun events full of live music, live entertainment, games, and delicious food. 2021 will be no different. Mark your calendars because it’s going to be a great year!

HV Wine & Food Festival

September 11th & 12th: 11am – 6pm
Dutchess County Fairgrounds, Rhinebeck

The Hudson Valley Wine & Food Fest celebrates the bounty of wine, food and fun in the Hudson Valley all in one place. This annual event takes place the weekend following Labor Day, every September at the Dutchess County Fairgrounds.

Esopus Meadows Lighthouse Tour

September 12th: 9am – 12pm
Hudson River Maritime Museum, Kingston

Visit the Esopus Meadows Lighthouse aboard Solaris, the 100% solar powered boat built by the Hudson River Maritime Museum. This experience includes a guided tour. All tickets include boat ride and general admission to the Hudson River Maritime Museum, open 11 am to 5 pm.


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Writers Hike

September 12th: 9:30am – 11:30am
Quiet Cove Riverfront Park, Poughkeepsie

Feel free to register online at https://www.eventkeeper.com/code/ekform.cfm?curOrg=POKLIB… or contact Bradley Diuguid (845) 485-3445 x3325 bdiuguid@poklib.org.

Little Tree Huggers

September 14th, 21st & 28th: 10:30am
Teatown Lake Reservation, Ossining

For ages 3-5 with caregiver. Explore the dwindling days of summer and the start of fall in this program for the youngest nature lovers. Through hikes, play, experiments, and projects, we’ll find out what seasonal changes are taking place. Please dress for the weather and a full outdoor program.

Saugerties Food Truck Festival

September 16th: 4:30pm
Cantine memorial Field, Saugerties

It’s the final Saugerties Food Truck Festival of the season! Please join us at Cantine Field’s Large Pavilion on Thursday, September 16th for even more Food Trucks & Food Vendors, Beer & Wine, Local Products & Crafts, Raffles & Live Music!

Festival at the Falls

September 18th
Mesier Park, Wappingers Falls

This annual event has become the Village of Wappingers Falls’ community day, providing a great family atmosphere and attracting people from all areas of the Hudson Valley. It also gives us a great opportunity to showcase all of the local businesses that the Village of Wappingers Falls has to offer.

Science Saturday

September 18th: 11am
Westchester Children’s Museum, Rye

On September 18th, join Doc Harmon and get measured up! Find out how to measure some very interesting things! You’ll make a trundle wheel and use it to measure lengths of objects with very unusual shapes! Recommended ages 8-12

Hyde Park Community Day

September 18th: 12pm – 5pm
Hacket Hill Park, Hyde Park

We are continuing the celebration of Hyde Park’s Bicentennial with our annual Community Day!
Extended hours!
Extra performances!
More vendors!
Hyde Park History!
And more!!

Rockin’ on the River

September 18th: 12pm – 4pm
Rhinecliff Waterfront

Come enjoy the afternoon by the river and stay for the sunset. Featuring: Mad Props playing live music, Food Truck TBD, T-Spoon Dessert Food Truck, Tivoli Sailing Co, Hudson River Maritime Museum and their solar powered boat – the Solaris and members of the Clearwater Sloop.

Oktoberfest

September 18th & 19th
Barton Orchards, Poughquag

Each year, the farm hosts a wide variety of fun events full of live music, live entertainment, games, and delicious food. 2021 will be no different. Mark your calendars because it’s going to be a great year!

Suffern Street Fair

September 19th: 10am – 5pm
Suffern, NY

We have so many fun events planned for you and we will be adding more.. so stay tuned! We will, of course, have our Kids Zone (that was improved a few years ago). Entertainment, Karaoke and more…

Wildflower Walk

September 22nd: 9am – 11am
Rockefeller State Park Preserve, Pleasantville

Celebrate the change of seasons on the autumnal equinox with our wildflower expert, Patty Butter. Enjoy a leisurely walk through the Preserve and learn about the identification of autumn wildflowers and how you can contribute as a citizen scientist to increase our knowledge of the ecology of the Preserve.Dress for a moderate hike with sun protection and bring plenty of water.Bring a camera or cell phone to take pictures and add the iNaturalist app to your phone. Cost: $3 + Eventbrite fees. Maximum: 12 Participants.To register: www.rockefellerstateparkpreserve.org/events

Tree Identification Hike

September 23rd: 9am – 10:30am
Rockefeller State Park Preserve, Pleasantville

Come join Flora Steward, Devyani Mishra, on a walk through the Preserve to learn more about trees and other plants in the area and how to identify them. Meet at the Visitor’s Center courtyard. The hike will be short with frequent stops for discussion. In the event of heavy rain, the hike will be canceled and a full refund will be issued. You will be notified via email the day before. Cost: $3 + Eventbrite fees. Maximum: 15 people.

The Brewery Comedy Tour

September 24th: 8pm – 9:30pm
Bad Seed Cider Co, Highland

This stop is set to feature a lineup whose credits include top festivals, TV and major club appearances. This comedy tour takes top comedians who you’ve seen on TV and sends them out on the road to perform at breweries throughout the country.

Bird Walk

September 25th: 8:30am – 10am
Untermyer Gardens, Yonkers

Fall is the perfect time to go or to start birdwatching. Many birds are migrating south, passing along the Hudson River, which is a part of the Atlantic Flyway. Untermyer Gardens, with its views of the Hudson and the Palisades, can be a good place to spot bald eagles, among other raptors, and songbirds going south for warm winter weather.

Modern Makers Market at Cold Spring

September 25th: 10am – 6pm
St. Mary’s Episcopal Church, Cold Spring

Families and friendly dogs welcome. Food, music, several taps of NY craft beer and cider, and a big fundraising raffle for St. Mary’s in the Highlands. Woodworkers, glass makers, potters, artists, jewelers, leather maker, food makers, and much more. No reselling at this event.

Drawing in the Gardens

September 25th: 10am – 12 noon
Untermyer Gardens, Yonkers

This class is great for beginner or experienced artists. Please arrive on time and bring your own drawing supplies, preferably 18 x 24 sketch paper so you can freely draw large. At a minimum you’ll need drawing paper, a board to lean on, and soft pencils, black marker, charcoal sticks or ink — whatever you are comfortable using. Donna’s favorite Graphite sticks will be shared for use during the class.

History Hike

September 25th: 11am – 12:30pm
Lake Oscawana

Learn about the late 19th and early 20th century resort industry at Lake Oscawana in Putnam Valley.

Collage Montage

September 25th: 11am
Westchester Children’s Museum, Rye

In this workshop children will be shown a fun way to create art and express themselves using paint, found objects, interesting paper, magazines cut outs and fabric etc. Children will create a collage that can be just a free flowing exercise or something powerful and meaningful. Students will learn about color, composition and perspective through this process

Catskill Food Festival

September 25th: 12noon – 6pm
Dutchmen’s Landing Park, Catskill
Saturday, September 25th we are back in Catskill with Food Trucks, Food Vendors, & Live Music.

Fall Festival

September 25th: 12noon – 7pm
Palaia Winery and Meadery, Highland Mills

$10 at the gate/person (kids under 12 free) – amazing bands- Hurley Mountain Highway 12-3 and Mighty Spectrum Band 3:30-6:30 – horns, vocals, talent – they fill the stage
bring a chair. Celebrate Fall with pumpkins, vendors, wine, beer, cider games and more.

Hard Cider Fest

September 25th: 1:30pm – 5:00pm
Cortlandt Waterfront Park

Hard cider sampling 🍔 food trucks 🎶 music 🥧 apple pie eating contest & more…

Paint & Sip and After Party

September 25th: 6:30pm – 9pm: 9pm – 12am
Imagine Studios, Yorktown Heights

Back by popular demand is our PAINT-N-SIP event on Saturday, September 25, 2021 from 6:30pm to 9pm. If you missed out on our last Paint-N-Sip fun, check out the highlights here: https://www.youtube.com/watch?v=YbfOv3_TB8c
Paint-N-Sip tickets are just $45 and include painting instructor, all paint and painting materials, appetizers, and FREE admission to our “After Dark” adult social party that commences after Paint-N-Sip from 9pm to 12 midnight! A night to remember!ADVANCED TICKETS ONLY. Buy tickets here: https://www.imaginevrs.com/paint-sip

Fall Festival

September 25th & 26th: 10am – 8pm
Barton Orchards, Poughquag

This change means that our Apple Orchard is open for picking, with a fantastic crop! After you pick, head into our midway for some live music, family-friendly entertainment, and excellent food. However, make sure you save room for our famous Apple Cider Donuts!

Rhinebeck New York Cider Festival

September 25th & 26th
Dutchess County Fairgrounds, Rhinebeck

New York Cider Tasting glass, and unlimited cider tastings included with admission price. The Original Rhinebeck New York Cider Festival – Taste More than 100 craft ciders from New York State’s finest Cider Regions

Alpacas Days

September 25th & 26th
Lilymoore Farm, Pleasant Valley

Each person (age 9 and up) walks with an alpaca in a group trek, then onto a guided farm tour, next we stop for tea, coffee and pastries, finally a fabulous class. More info & tickets in their website.

Rombout Colonial Days Weekend & Encampment

September 25th & 26th
Brinckerhoff House Historic Site

$5 suggested donation per person. This event is a part of this years Hudson River Valley Ramble.

Hudson Valley Free Day

September 26th: 10am – 6pm
DIA:Beacon

Hudson Valley residents receive free admission to DIA Beacon on the last Sunday of each month.

Woodstock Film Festival

September 29th – October 3rd
13 Rock City Road, Woodstock

The Woodstock Film Festival is coming back in full force this fall at indoor venues across the Hudson Valley locales of Woodstock, Kingston and Saugerties! Enjoy a diverse lineup of in-person screenings, talks and other special events from today’s hottest indie talents.

Oktoberfest at the Factory

September 29th – October 3rd
Sloop Brewing Company, Hopewell Junction

We’ll have insane beer specials, limited edition glassware, traditional live music, a special menu & more.This event will be FREE admission to the public & all beer selections/menu items will be ala carte. 🥨

OMG Art Faire

September 30th – October 3rd
Wall Street Music Hall, KIngston

A four-day art fair in historic uptown Kingston.

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Hudson Valley Events taking place this October


OMG Art Faire

September 30th – October 3rd
Wall Street Music Hall, KIngston

A four-day art fair in historic uptown Kingston.

Fall Festival

Fri, Sat, Sun & Columbus Day throughout October
Dogwood Acres Family Farm, Middletown

Family Fun during October

Lantern Cruises

Select days: October 1st – 30th
Hudson River Maritime Museum, Kingston

Explore the Hudson River and Rondout Creek by searchlight and listen to legends and lore of the Hudson River from the pages of Washington Irving or straight from newspaper headlines of centuries past. Guides will share stories including the tale of the serpent of the Hudson River, the terrible crime of William Salisbury, and Rondout’s barge graveyard.

Starry Starry Night

October 1st: 6pm – 10pm
Upper Landing Park, Poughkeepsie

Sip craft cocktails, savor local delectables from renowned Hudson Valley chefs, and stroll through an enchanting Upper Landing Park on the Hudson River waterfront in Poughkeepsie (just beneath the Walkway!) before riding the 21-story glass-enclosed elevator skyward to enjoy special entertainment and one-of-a-kind twilight views from the world’s longest elevated pedestrian bridge. Tickets: https://app.mobilecause.com/e/pWj6_A?vid=lqvj0

Poughkeepsie Regatta

October 2nd: 7am – 10:30am
Walkway over the Hudson

The Hudson River Rowing Association and Mid Hudson Rowing Association will be co-sponsoring a 3 mile rowing race on the Hudson River in Poughkeepsie on Saturday, October 2, 2021. Races are scheduled to run from 7:15 AM to 10:30 AM. The start is at the Culinary Institute of America’s main campus in Hyde Park and the finish is under the Mid-Hudson Bridge in Poughkeepsie. The entire race can be viewed from the Walkway Over the Hudson (2.5 miles from the start).

Bird Walk

October 2nd: 8:30am – 10am
Untermyer Gardens, Yonkers

Fall is the perfect time to go or to start birdwatching. Many birds are migrating south, passing along the Hudson River, which is a part of the Atlantic Flyway. Untermyer Gardens, with its views of the Hudson and the Palisades, can be a good place to spot bald eagles, among other raptors, and songbirds going south for warm winter weather.

Twin Forts Day

October 2nd: 10am – 4pm
Fort Montgomery State Historic Site

Join us at Fort Montgomery State Historic Site on Saturday, October 2nd as we commemorate the 244th anniversary of this bloody battle. Reenactors from the 5th New York and 6th Connecticut Regiments and Mott’s Artillery will be here! There will be cannon firings, military drill, dramatic performances, children’s games and living history demonstrations throughout the day. Please note there will be NO BATTLE REENACTMENT.

Touch a Truck

October 2nd: 10am – 4pm
Forsyth Park, Kingston

Explore vehicles from fire engines, tractors, construction trucks and much more. $5 per person.

Boots by the Bandshell

October 2nd: 3:30pm – 8:30pm
Bowdoin Park, Wappingers Falls

The Wolf (WCZX, 97.7FM), the Wakin’ Up with CJ and Jess Show and Townsquare Media Group, will host a free, family-friendly country music and line dancing event, “Boots by the Bandshell,” on Saturday, October 2nd at the bandshell at Bowdoin Park starting at 3 p.m. featuring Thunder Ridge Band and CJ McIntyre as well as activities such as a Fall Scavenger Hunt, a bonfire with s’mores, and a family game area and a fireworks display at 7:45 pm.

Harvest Festival

October 2nd & 3rd: 11am – 5pm
Soukup Farms, Dover Plains

The days are starting to get shorter and that can only mean one thing, fall is approaching! Save the dates for our seventh annual Harvest Festival. We look forward to seeing everyone back at our farm again soon!

Walktoberfest Farmers and Makers Market

October 2nd & 3rd: 12 noon – 5pm
Walkway over the Hudson Highland Entrance

The Walktoberfest Farmers and Makers Market brings a curated selection of the Hudson Valley’s finest producers – farms, distilleries, breweries, wineries, restaurants, artists, artisans, and more – to the Hudson Valley Rail Trail and west approach to Walkway Over the Hudson State Historic Park on Saturday, October 2 and Sunday, October 3 from 12-5 p.m. Vendors will exhibit their wares for tasting or purchase, allowing participants to support several local agribusinesses in one location. Over 100 vendors. $25 Tasting Tickets: https://app.mobilecause.com/e/sfzACQ?vid=lqvo2

Handcrafted Octoberfest at Rhinebeck

October 2nd & 3rd
Dutchess County Fairgrounds, Rhinebeck

This festival brings together the handcrafted, artisanal, and agricultural — from wearable fine craft and laudable fine art to the Hudson River Valley’s best brew, wine, specialty foods, and apothecary goods.

HV Garlic Festival

October 2nd & 3rd
Cantine Field, Saugerties

Tickets will be available soon at all four Adams Fairacre Farm Stores (Kingston, Wappinger, Poughkeepsie and Newburgh), Smith Hardware in Saugerties and M&T and Sawyer Savings Bank in Saugerties. Pre-event prices are $7.00 for adults, $5.00 for seniors. Price at the gate: $10.00. Children under 12 are free.

Country Music Jamboree

October 2nd & 3rd
Barton Orchards, Poughquag

Bring a family and enjoy the day at Barton Orchards.

Home Cider Making & Tasting

October 3rd: 4pm
Tarrytown, NY

Fall is cider season….and it’s a great time to learn how to make your own! This outdoor workshop hosted by Into Leaf: A Workshop Series includes a flight of hard ciders, the chance to hand-press and grind apples, a half-gallon of fresh juice to take home, and all the instructions and resources you need to continue your cider journey on your own.

Wine Glass Painting

October 6th: 6pm
The Barking Goose, Newburgh

Autumn is fast approaching and we couldn’t be more excited about it! 🍂 On Wednesday, October 6th at 6:00 pm, we’ll be at The Barking Goose to guide you step by step through this new Fall-themed wine glass painting. 🍷 Everyone will receive two stemmed glasses and all painting materials at the start of the class.

First Thursday Gallery Hop

October 7th: 5:30pm – 7pm
Downtown Yonkers

Artists and art lovers can stop by all three downtown Yonkers Art Galleries to preview current exhibitions:▪️Blue Door▪️Riverfront Art Gallery▪️Urban Studio Unbound/Warburton Galerie In collaboration with this event many downtown restaurants will offer 10% discounts on food and beverages to Gallery Hop visitors via a photo of the Gallery Hop poster with date displayed in each location.

The Brewery Comedy Tour

October 8th: 8pm – 9:30pm
Bad Seed Cider Co, Highland

This stop is set to feature a lineup whose credits include top festivals, TV and major club appearances. This comedy tour takes top comedians who you’ve seen on TV and sends them out on the road to perform at breweries throughout the country.

Revel in the Laughter

October 8th: 7pm – 11pm
Revel 32, Poughkeepsie

Join us for a night of laughs, music, and fun at Stand Up Comedy Night with headliners Drew Fraser and Ashley Morris! The show will be hosted by Eddy A Sloshower. Guest comics are Bobby Underwood and Jody Carroll. A complimentary glass of wine, beer, or your choice of signature cocktail included in your ticket! Light bites will be available for purchase. $30

Hudson Valley Farm & Flea

October 9th: 10am – 4pm
Museum Village, Monroe

the premiere regional event to spotlight Hudson Valley’s finest makers, artisans, designers, and vintage collectors. Added to this unique mix are locally crafted food, and our Riverside Theatre Arts Academy performers, all in one location at the Museum Village in Monroe. This event will create a place where people can come to enjoy local products and be immersed in a total Hudson Valley lifestyle experience.

Harvest Festival

October 9th, 10th & 11th: 11am – 5pm
Soukup Farms, Dover Plains

The days are starting to get shorter and that can only mean one thing, fall is approaching! Save the dates for our seventh annual Harvest Festival. We look forward to seeing everyone back at our farm again soon!

Barn Star’s Fall Antiques at Rhinebeck

October 9th & 10th
Dutchess County Fairgrounds, Rhinebeck

Barn Star Productions presents the annual fall show on Columbus Day weekend. You’ll find many of your favorite dealers and new exhibitors as well.

Esopus Meadows Lighthouse Tour

October 10th: 9am – 12pm
Hudson River Maritime Museum, Kingston

Visit the Esopus Meadows Lighthouse aboard Solaris, the 100% solar powered boat built by the Hudson River Maritime Museum. This experience includes a guided tour. All tickets include boat ride and general admission to the Hudson River Maritime Museum, open 11 am to 5 pm.

Pinot Noir Release Party

October 10th: 11am – 6pm
Nostrano Vineyards, Milton

Farm-to-Table Food Specials Smokeycrane BBQ Pinot Pairings
Black Canvas Live Music
Locally Curated Pop-Up ShopsThis is a ticketed event and reservations must be made online in advance through Tock!Tickets are $12/person include a logo wine glass with your first glass of wine.
*Children are free to attend*
*We welcome leashed well behaved pups whose owners clean up after them!*

Ulster County Italian Festival

October 10th: 11am – 8pm
Kingston Waterfront

Join us this year for our Ulster County Italian Festival we will be having on Sunday, October 10 at the Kingston Waterfront. Shuttle buses to the festival will be available at Kingston Point (handicap accessible); Kingston Plaza and the Cornell Street municipal parking lot. The festival is free.

Poets’ Corner Open Mic

October 10th: 3pm
729 Peekskill Hollow Road, Putnam Valley

Live on our outdoor stage, join our monthly Open Mic for writers and readers of spoken word of all types. D. Adam Boaz will be this month’s featured poet. Immediately following will be our open mic for those who have signed up to read. All writers are welcome on our *outdoor stage in the bucolic setting of Putnam Valley.

Boos & Booze Halloween Drag Show

October 15th: 5pm – 10pm
Barton Orchards, Poughquag

Join us at Barton Orchards on Friday, October 15th for an adult friendly Boos and Booze Drag Show, hosted by Summer Orlando and Barbra Joan Streetsand! Tickets include a live singing drag show and access to our Jack O’ Lantern trail. Superior Sounds DJ will be there to kick off the event! Costume contest with a cash prize for the winner!

Dutchess County Irish Festival

October 16th: 10am – 8pm
Tymor Park, Union Vale

Join the Dutchess County Gaelic Athletic Association in celebrating all things Irish. The day includes Gaelic Football games, food, dance and music. Children under 18 are FREE, with PAID General Admission. No ticket sales day of.

Annual Cider Tasting

October 16th: 11am – 3pm
140 Cedar Ave, Poughkeepsie

This marks our 9th annual “Old Fashioned Cider Tasting” event at the Mill! All proceeds benefit the restoration of the Kimlin Cider Mill. Tickets:
-Free entry
-$15 – hard & sweet ciders, with souvenir tasting glass
-$5 – sweet ciders only
-$0 – sweet cider for ages 12 and under
-Tasting tickets are available at the door, but if you purchase online through eventbrite (link included in this event), you will be entered into an exclusive raffle of a jug of Kimlim Cider! Our small-batch cider is made especially for this event only and is not sold or otherwise available except for tasting.
-Lunch, apple fritters, apple butter, and merchandise available for purchase at the event

New York State Sheep & Wool Festival

October 16th & 17th: 10am – 5pm
Dutchess County Fairgrounds, Rhinebeck

The Northeast’s thriving sheep industry is showcased and celebrated each year in this famous festival that draws 30,000 visitors from across the country to the lovely village of Rhinebeck.

Harvest Festival

October 16th & 17th: 11am – 5pm
Soukup Farms, Dover Plains

The days are starting to get shorter and that can only mean one thing, fall is approaching! Save the dates for our seventh annual Harvest Festival. We look forward to seeing everyone back at our farm again soon!

Bring the Kids Outside

October 23rd
Boscobel House and Gardens, Garrison

This hour-long, family-focused walking tour, given by our Museum Educator Lisa DiMarzo (aka Miss Lisa), will give highlights of Boscobel’s 68 acres of gardens and grounds. A new theme each month! Children’s craft included.

Bird Walk

October 23rd: 8:30am – 10am
Untermyer Gardens, Yonkers

Fall is the perfect time to go or to start birdwatching. Many birds are migrating south, passing along the Hudson River, which is a part of the Atlantic Flyway. Untermyer Gardens, with its views of the Hudson and the Palisades, can be a good place to spot bald eagles, among other raptors, and songbirds going south for warm winter weather.

Harvest Festival

October 23rd & 24th: 11am – 5pm
Soukup Farms, Dover Plains

The days are starting to get shorter and that can only mean one thing, fall is approaching! Save the dates for our seventh annual Harvest Festival. We look forward to seeing everyone back at our farm again soon!

Lagrange Bicentennial Weekend

October 23rd & 24th: 12 noon – 5pm
Freedom Park, Lagrange

Hulda’s Night

October 27th, 28th, 29th, 30th: 6pm & 7pm
Rockefeller State Park Preserve, Pleasantville

Hulda’s Night is like nothing else you’ve ever experienced. Join us for a night in our woods and let us take you back in time. Tickets: $28 Tickets go on sale Friday, Sept 3, 2021 10:00amwww.rockefellerstateparkpreserve.org/events

History Hike

October 30th: 10am – 5pm
Fahnestock Park
Learn about Native American history, the American Revolution, the discovery of iron within the park, the role the mines played during the Civil War, Odelltown and Dennytown, the last ditch effort to revive iron mining at Fahnestock in the 1890s by Thomas Edison, and the purchase and acquisition of the land as part of the Fahnestock Estate, and lastly the bequeathing of the land by Ernest Fahnestock to Governor Franklin Roosevelt and New York State, to be made into a park memorializing his brother Clarence in perpetuity.

I SPY Halloween Scavenger Hunt

October 30th: 11am – 3pm
Hudson Highlands Nature Museum

Not-yet-Member Registration opens online: Monday, October 4 at 10am. Join us for a Monster Mash this Halloween at Kenridege Farm! Ghosts and Ghouls are invited to celebrate Halloween at HHNM along the I Spy Halloween Trail! Find all of the items hidden along the I SPY trail and a treat will be waiting upon your return! This self-guided activity is a great way for families to celebrate Halloween with COVID-19 precautions in place. Costumes are encouraged! $10 p/p

A Very Fluffy Halloween

October 30th & 31st: 10:30am – 2:30pm
Lilymoore Farm, Pleasant Valley

If you are looking for Halloween events – don’t miss this one! It’s our version of a Halloween fest – only way cuter. This year has more alpacas in Halloween costumes, goats too – who knows maybe Ducky the llama will join in the fun this year. Come dressed up for the event or just let our alpaca Lady Valentina Von Sparkles shine. Either way you will have a ton of fun. Event is 1.5 hours long. Limited space. Buy tickets in advance.

Hudson Valley Free Day

October 31st: 10am – 6pm
DIA:Beacon

Hudson Valley residents receive free admission to DIA Beacon on the last Sunday of each month.


Hudson Valley Events taking place this November

First Thursday Gallery Hop

November 4th: 5:30pm – 7pm
Downtown Yonkers

Artists and art lovers can stop by all three downtown Yonkers Art Galleries to preview current exhibitions:▪️Blue Door▪️Riverfront Art Gallery▪️Urban Studio Unbound/Warburton Galerie In collaboration with this event many downtown restaurants will offer 10% discounts on food and beverages to Gallery Hop visitors via a photo of the Gallery Hop poster with date displayed in each location.

History Hike

November 13th: 12noon – 3pm
Revolutionary War North & South Redoubts in Garrison
Learn about the role the Hudson Highland’s played in the American Revolution, discussing the history of chaining the Hudson, and how the redoubts helped defend the chain and West Point.

Bring the Kids Outside

November 13th
Boscobel House and Gardens, Garrison

This hour-long, family-focused walking tour, given by our Museum Educator Lisa DiMarzo (aka Miss Lisa), will give highlights of Boscobel’s 68 acres of gardens and grounds. A new theme each month! Children’s craft included.

The Brewery Comedy Tour

November 19th: 8pm – 9:30pm
Bad Seed Cider Co, Highland

This stop is set to feature a lineup whose credits include top festivals, TV and major club appearances. This comedy tour takes top comedians who you’ve seen on TV and sends them out on the road to perform at breweries throughout the country.

The Wonderland of Lights

November 25th – December 26
Dutchess County Fairgrounds, Rhinebeck

The Wonderland of Lights has been a part of thousands of families’ holiday tradition across the country for over two decades. Now Rhinebeck and surrounding communities will have a chance to start a new tradition November 25 through December 26, 2021!

Hudson Valley Free Day

November 28th: 10am – 6pm
DIA:Beacon

Hudson Valley residents receive free admission to DIA Beacon on the last Sunday of each month.


Hudson Valley Events taking place this December

First Thursday Gallery Hop

December 2nd: 5:30pm – 7pm
Downtown Yonkers

Artists and art lovers can stop by all three downtown Yonkers Art Galleries to preview current exhibitions:▪️Blue Door▪️Riverfront Art Gallery▪️Urban Studio Unbound/Warburton Galerie In collaboration with this event many downtown restaurants will offer 10% discounts on food and beverages to Gallery Hop visitors via a photo of the Gallery Hop poster with date displayed in each location.

Bring the Kids Outside

December 4th
Boscobel House and Gardens, Garrison

This hour-long, family-focused walking tour, given by our Museum Educator Lisa DiMarzo (aka Miss Lisa), will give highlights of Boscobel’s 68 acres of gardens and grounds. A new theme each month! Children’s craft included.

The Brewery Comedy Tour

December 10th: 8pm – 9:30pm
Bad Seed Cider Co, Highland

This stop is set to feature a lineup whose credits include top festivals, TV and major club appearances. This comedy tour takes top comedians who you’ve seen on TV and sends them out on the road to perform at breweries throughout the country.

The Wonderland of Lights

November 25th – December 26
Dutchess County Fairgrounds, Rhinebeck

The Wonderland of Lights has been a part of thousands of families’ holiday tradition across the country for over two decades. Now Rhinebeck and surrounding communities will have a chance to start a new tradition November 25 through December 26, 2021!


In addition to these Hudson Valley events taking place all over the region, do you know that many farmers markets also open for their season.


The Ultimate Guide to Hudson Valley Farmers Markets

Make sure to reference my article all about Hudson Valley Farmers Markets. It’s the Ultimate List of all the Hudson Valley Farmers Markets that you can visit any time of the year.


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Until the Next Adventure…

Signature for Jackie at Hudson Valley Explored


Jacqueline Ramirez

Jackie is one of the top bloggers in the Hudson Valley. She has been featured (along with some of her photos) in several local and national publications. Read Jackie’s crazy story, “From a Naive NYC Girl to Popular Hudson Valley Blogger & Author“. Feel free to send Jackie a message here.