An Insider’s Guide to September Events in the Hudson Valley

Hudson River tourism directors share their top picks for places to go, sights to see, and things to do throughout September.

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. September is an especially exciting month in the area, as fall festivities begin in the way of apple picking, outdoor festivals, leaf peeper day trips, Halloween-themed attractions (a little early, but we’re not complaining), and so much more.

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

Albany Riverfront Jazz Festival

Jennings Landing, Albany
September 9, 12-8 p.m.

 

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The City of Albany Jazz Festival has featured a wealth of great jazz artists for over 18 years. The festival includes both critically acclaimed and up-and-coming artists performing in front of the city’s most spectacular views. Stay all day for world-class music, vendors, and great food and beverages at this free event for all ages.

Capital Apple and Wine Festival

Altamont Fairgrounds, Altamont
September 16-17

 

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Head to the Capital Region in mid-September for this food and wine festival that’s packed with family fun. Specialty food, music, car shows, and crafts are the main attractions, with kids’ activities like a bounce house, pumpkin painting, archery, and pony rides to keep everyone entertained. The start of the show, of course, are the apples which you can find in all forms, especially cider and donuts!

Columbia County

Festival of Books

Spencertown Academy Arts Center, Spencertown
September 2-4


This September, Spencertown celebrates its 18th annual Festival of Books, which will feature a giant book sale, children’s programs, authors presentations, and more. Stop by on Saturday, Sunday, or Monday morning to pick from an affordable selection of gently used books, CDs, DVDs, and audio books (teachers can show ID for 20 percent off). Bring the kids out on Saturday to meet Lyle the Crocodile, stick around for presentations from authors Eleanor Henderson, Tamar Adler, and Wesley Brown, and come back on Sunday to hear the winners of the annual Young Writers Contest read their entries.

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Fall Fest

Catamount Mountain Resort, Hillsdale
September 23, 10 a.m. – 5 p.m.


This year, Catamount hosts its second annual Fall Fest, complete with craft beers and ciders, fall foods, kids’ activities, and live music. The free, family-friendly event invites everyone to reconnect with Catamount’s mountain community and share in the excitement of the upcoming ski season as the venue unofficially kicks off its winter countdown. Kids can enjoy pumpkin painting, sugar cookie decorating, and tie dye before they line up for the pie-eating contest, which will also have an adult division. Attendees can book scenic chairlift rides that offer stunning aerial views from the surrounding area, purchase tasting packages to try a dozen fall beers and ciders from the tap, and enjoy a rocking show from The Tom Prettys, an all-female Tom Petty tribute band.

OctoberFeast

Main Street, Chatham
September 30, 11 a.m. – 4 p.m.

Chatham gears up for its food-focused fall festival right on Main Street. Take a stroll through town to taste-test fall foods and delicious dishes from local restaurants before heading to the street for food trucks and other vendors. Aside from edible attractions, there will also be plenty of live entertainment, free activities, drinks, and more.

Dutchess County

Hudson Valley Hot-Air Balloon Festival

Tymor Park, Union Vale
September 1-3

 

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Take to the skies in a hot-air balloon this September at this three-day festival of family fun. Come out to see dozens of hot-air balloons dot the clouds and take a ride in a tethered or free one yourself if you’re feeling adventurous. Helicopter rides will also be offered along with fireworks each night of the festival. New attractions this year include amusement park rides and games as a bonus for the festival’s 32nd year.

Sunflower Festival

Barton Orchards, Poughquag
September 1-4

 

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Celebrate the end of summer with beautiful fields of over 100,000 sunflowers at Barton Orchards. The fifth annual festival runs for four days and includes hayrides, live music, and cutting your own sunflowers to take home. Fill up on craft beer and wine from the taproom and food truck cuisine like lobster rolls before checking out the craft vendors and farm market. Dogs are welcome!

Hudson Valley Wine and Food Fest

Dutchess County Fairgrounds, Rhinebeck
September 9-10

This year marks the 23rd anniversary of Hudson Valley’s beloved Wine and Food Fest. Enjoy all the finest products from the area and sample products from regional wineries, craft breweries, and distilleries. Local restaurants will serve up gourmet foods, various vendors will have their goods on display, and live music and educational seminars, like cooking demonstrations, throughout the weekend will provide the perfect entertainment for the event.

Orange County

Stampede Bull Riding Rodeo

Summer Stage at The Barn, Middletown
September 3, 12 p.m.

Ever wondered what a rodeo is like? Attend the Stampede Bull Riding Rodeo to find out! This jam-packed event is all about the excitement of bull riding and living like it’s the Wild West. Feel free to bring chairs and blankets for seating on the lawn and grab a bite from the onsite vendors. Adults attend for $39.15 while children five and under get in for free.

“Original Flea” Outdoor Market

Newburgh Vintage Emporium, Newburgh
September 9, 9 a.m. – 6 p.m.


Some say that the first ever flea/outdoor market was held right in the Hudson Valley in Newburgh in 1752, and the Newburgh Vintage Emporium carries on the tradition each year. Outside the shop on September 9, you’ll find more than 30 vendors of vintage, antiques, collectibles, local makers, food trucks, and anything else you can think up. Plenty of onsite parking makes it possible for you to come out and enjoy the traditional market.

The Moon Festival

New Century Film, Port Jervis
September 16-17  

Orange County’s Moon Festival is the largest multi-cultural event of its kind in the region celebrating one of Asia’s most revered holidays. Community members of all ages will connect through music from traditional Chinese instruments like the erhu pipa while enjoying moon cakes and other authentic dishes from different regions in China, the Philippines, Thailand, Vietnam, and Taiwan. Kids can participate in fun activities like crafting lanterns and lucky moon rabbits before hopping in the moon bounce.

Putnam County

Boscobel Chamber Music Festival

Boscobel House and Gardens, Garrison
September 1-10


Boscobel House and Gardens is known for its visually stunning architecture and grounds, but this September it showcases a more auditory event with its second-ever Chamber Music Festival. The nine-day event will take audiences on a classical music journey led by Artistic Director and violinist Arnaud Sussmann. The festival’s musical roster includes internationally acclaimed violinists, violists, pianists, and cellists and other engaging and educational offerings for audiences of all ages.

Blues and BBQ Festival

The Patterson Firehouse, Patterson
September 9-10

Calling all barbecue fans to the Blue and BBQ Festival in Patterson this September! Sink your teeth into delicious, mouthwatering barbecue as you listen to live music from a number of bands including Not Tuna, Alternate Universe, and TNT Dyn-O-Mite Band. This celebration of community is fun for everyone with a bouncy house for the kids and drinks for the adults.

Collaborative Concepts Outdoor Art

Tilly Foster Farm, Brewster
September – October


Collaborative Concepts is back at Tilly Foster Farm this year, displaying its must-see sculpture exhibit. Twenty-five artworks engage with the 199-acre farmland using media ranging from metal to fabric and repurposed materials. The farm provides the perfect pastoral background for the sculptures to be enjoyed, offering vista views, hiking trails, charming animals, and a farm-to-table dining experience for when the sun sets.

Rockland County

Brick Alley Block Party

Garner Arts Center, Garnerville
September 23, 8 p.m. – midnight


This longtime nightlife favorite returns for 2023 with art, pop-ups, craft beverages, food trucks, and more. Starlit DJ sets by DJ Wawa and Morgana headline this event, so get on your dancing shoes, and check out the immersive art in 19th-century industrial spaces to travel to a different time. Grab a drink from Industrial Arts Brewing and made-to-order pizza from Brick Oven Pizza Events to cap off the night.

The Flavors of Haverstraw Food Crawl

Downtown Haverstraw
September 24, 1-5 p.m.


To celebrate its diverse culinary community, Haverstraw Riverwide Arts and the Village of Haverstraw have teamed up to present this restaurant crawl to the foodies of the Hudson Valley and beyond. Beginning at the Webster Bank parking lot on New Main Street, participants can sample small plates from over 20 restaurants for $5-$10 per plate. Grab a seat outside if the weather is nice; tents, tables, and chairs will be set up on New Main and Main Street.

Phoenix Festival

Nyack
September 28 – October 21

The Phoenix Theatre Ensemble presents this festival of world-class professional live theater, music, dance, and more. This celebration of arts and culture takes place in the beautiful riverside village of Nyack and features both indoor and outdoor performances from Wind in the Willows, Children’s Shakespeare Theatre, Honduras, and other talented groups.

Ulster County

Woodstock-New Paltz Arts and Crafts Fair

Ulster County Fairgrounds, New Paltz
September 2-4


DIY interior designers and craft lovers in the Hudson Valley should plan a visit to this fair over Labor Day weekend. The fair packs over 200 juried artists and craftspeople onto the Ulster County Fairgrounds to celebrate the region’s foremost craftspeople. With shopping, children’s activities, and massage therapy as only a few of the onsite attractions, this event is one for the books.

Woodsist Festival

Arrowood Farms, Accord
September 23-24

Ulster County’s premier music festival, Woodsist, is back this season with a great lineup and good eats. Two stages provide the entertainment space for almost 20 artists and performances, including Kevin Morby, Aquarium Drunkard DJs, Daniel Higgs, Cass McCombs, and more. The culinary lineup is just as good with vendors Bjorn Qorn, Taste of Santorini, and Oyster Party, along with a number of other food choices and craft beers.

Hudson Valley Garlic Festival

Cantine Memorial Complex, Saugerties
September 30 – October 1


The 35th installment of the ever-popular Garlic Festival marks the welcoming of autumn to the Hudson Valley. Referred to as the Stinking Rose by garlic afficionados, garlic is the Hudson Valley crop that truly tastes good in anything – even ice cream. If you’re looking for interesting eats that are uncommonly flavored with garlic, this place is for you. In addition to grabbing a bite, local vendors will be set up for browsing or buying, and live entertainment tops it all off.

Westchester County

The Great Jack O’Lantern Blaze

Van Cortlandt Manor, Croton-on-Hudson
September 15 – November 19


Van Cortlandt’s historic grounds will be filled to the brim with carved pumpkins at the annual Great Jack O’Lantern Blaze. Magnificent displays of over 7,000 illuminated jack o’lanterns that have been hand-carved onsite by a team of artisans will light up the night sky. This year’s show will include a new twirling pumpkin Ferris wheel and gourd-eous circus side show.

Lyndhurst Landscape Ramble

Lyndhurst Mansion, Tarrytown
Sundays in September

In honor of the Hudson River Valley Ramble, Lyndhurst Mansion offers walking tours of its property this September. The Ramble is a celebration of history, culture, and natural resources that make the Hudson Valley great, and Lyndhurst showcases its Gothic Revival masterpiece estate along with its award-winning rose garden, fern garden, rock garden, specimen trees, and aged Lindens for which the property is named.

Harvest Moon Orchards Apple Picking

Harvest Moon Farm & Orchard, North Salem
September 9 – October 29


Enjoy a perfect fall day at Westchester’s Harvest Moon Orchards, where you can pick apples by the bushel and visit the farm store for fresh baked goods and meats. Explore stunning hillside orchards, adorable farm animals, and a glass of Hardscrabble Cider or the Apple Cider Smash – a fresh apple cider slushie that’s topped with soft serve vanilla ice cream and an apple cider donut.

Related: Your Official Hudson Valley Apple Picking Farm Guide

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