20 September Events in New York That’ll Have You Dropping Everything
- Hudson Valley Happenings
- Aug 26
- 11 min read
Updated: Aug 28
September in New York isn’t just a season — it’s a full-throttle vibe that takes over the entire state. The mornings snap crisp, the afternoons glow golden, and the trees start showing off flashes of fire before bursting into full color. Every weekend feels like a festival waiting to happen — food that makes you forget your diet, music spilling into the streets, craft fairs that double as treasure hunts, and block parties that feel like the whole town showed up. From Hudson Valley harvest bashes and city-wide balloon festivals, to Finger Lakes grape stomps and Adirondack adventures that look ripped from a postcard, this is your ultimate HVH roadmap to the fall weekends you’ll be talking about all year.
Hudson Valley + Westchester
When it comes to fall kickoffs, the Hudson Valley doesn’t mess around. Between world-class music, massive craft shows, riverside circuses, and the first glow of pumpkins, you’ll find yourself spoiled for choice every weekend. Westchester adds its own mix of fairs and festivals that keep the vibe lively and close-to-home.
Fridays and Saturdays
📅 September Thru October 5, 2025
📍 Tuxedo Park, NY
Hear ye, hear ye—fall weekends just got legendary. The New York Renaissance Faire transforms Sterling Forest into a 16th-century village where knights joust, jesters banter, and fairies and pirates roam like it’s the most natural thing in the world. Artisan shoppes brim with leather, steel, jewelry, and hand-crafted treasures, while turkey legs, tankards of ale, and festival eats fuel the adventure.
This isn’t just an event—it’s an escape. One minute you’re cheering sword fights, the next you’re caught in improv, fire-whip stunts, or Celtic tunes that make you dance in the dust. Come in costume and join the fantasy, or roll up in jeans and let the magic do the rest—you’ll fit right in. Each weekend brings fresh stage schedules, new performances, and new reasons to return. September and October are peak season, and the forest backdrop makes it feel like stepping straight into a storybook. Grab your crew, raise your goblet, and don’t just watch history—live it.
📅 August 30 – September 1, 2025
📍 Ulster County Fairgrounds,
New Paltz, NY
Fall doesn’t officially start until you’ve strolled the aisles of the Woodstock–New Paltz Art & Crafts Fair. Nestled at the Ulster County Fairgrounds beneath the Shawangunk Ridge, this Labor Day tradition brings together over 200 juried makers offering ceramics, fiber art, jewelry, woodworking, fine art, and more. Live music drifts through the festival grounds, while small-batch food, craft beverages, and sweet treats keep energy high. It’s the rare mix of artisan excellence and community spirit that has drawn thousands back year after year.
Beyond the shopping, the fair thrives on connection. Watch master potters, jewelers, and woodworkers demo their craft in real time, or drop the kids at the supervised craft tent where creativity runs wild. Add in live bands, food trucks, and a crowd that celebrates art made by real hands, and you’ve got more than a fair — you’ve got a fall pilgrimage for anyone who loves creativity and local soul in the Hudson Valley.
📅 Sept 1–7, 2025
📍 Hudson River towns
(Beacon, Poughkeepsie, Kingston & more)
This isn’t your average circus — it floats. The Flotsam River Circus drifts into towns on a handmade raft, bringing high-energy performances straight to the waterfront. Expect jugglers, acrobats, puppeteers, and musicians all putting on a free, all-ages show with the Hudson River as their backdrop.
The beauty of this event is the spontaneity. One night you’re catching a tightrope walker under the stars, the next you’re laughing at slapstick comedy with neighbors crowded on the riverbank. It’s quirky, unexpected, and pure joy — the kind of event that feels like stumbling into a secret you’ll never forget.
📅 Sept 5–14, 2025
Boscobel House & Gardens
Garrison, NY
Set on the sweeping lawns of Boscobel, this chamber music festival feels like a scene out of a movie. As dusk settles over the Hudson River, ensembles perform in a tented space where music meets breathtaking views. It’s elegant, intimate, and absolutely transportive.
What makes this festival special is the variety. Over ten days, you’ll catch everything from timeless classical pieces to bold new works, plus lectures and family-friendly concerts. If you’re looking for a culture fix that still feels rooted in the Hudson Valley’s natural beauty, this is your ticket.
📅 September 6–7, 2025
📍Dutchess County Fairgrounds
Rhinebeck, NY
This isn’t just another wine fest—it’s the Hudson Valley’s main stage for sipping, savoring, and celebrating all things delicious. For two glorious days, Rhinebeck transforms into a tasting paradise where top New York wineries pour by the glass, local breweries and distilleries keep things buzzing, and the food scene hits hard with everything from gourmet bites to indulgent festival favorites. Add in live chef demos from Food Network pros like Ric Orlando and J. Jackson, plus cocktail and pairing classes that make you feel like a pro, and you’ve got a foodie playground that’s as fun as it is flavorful.
The energy? Electric. You’ll drift through rows of tastings with music from the Carrie Zazz Band in the background, a plate stacked high from food trucks in one hand, and your next favorite vintage in the other. Between shopping handmade crafts, learning from top chefs, and discovering why USA Today named this one of America’s top wine festivals, you’ll quickly realize this isn’t just an event—it’s the September weekend to beat. Tickets start at $35, but the bragging rights you’ll leave with? Priceless.
Use Promo code WINE5 for an additional $5 off Tasting Tickets.
September 6, 2025
The Oasis at Fence Road Farm
Warwick, NY
Warwick’s biggest fall party is back and louder than ever. Chowtober Fest VI brings the heat with live sets from crowd favorites like Sonic Crusaders, The Nerds, and Kasim Sulton — bands built to keep you moving from the first chord to the last encore. Pair that with local craft beer and wine, food vendors dishing out everything from smoky BBQ to sweet festival indulgences, and the unbeatable vibe of a Hudson Valley September night, and you’ve got a recipe for pure magic.
But Chowtober Fest isn’t just about the music and food — it’s about giving back. The festival was created as a tribute to local legend David Ciaudelli, and it doubles as a fundraiser that pours heart and soul into the community. Families will find pony rides, a petting zoo, and face painting for the kids, while the evening ends with a laser and hologram show that lights up the fields. It’s one unforgettable day where every ticket means more than just a good time — it means supporting a cause and celebrating together. Grab your crew, raise a glass, and don’t miss the Hudson Valley’s end-of-summer festival that hits all the right notes.
📅 Sept 5th - 7th 2025
📍Yorktown Heights, NY
The Yorktown Grange Fair is Westchester’s true country fair — the kind where tractors parade down the main road and kids show off prize pumpkins they grew themselves. It’s a charming, small-town celebration that blends nostalgia with good old-fashioned fun.
Expect rides, carnival games, livestock competitions, and plenty of fried fair food to keep you fueled. Between the craft vendors, pie contests, and live entertainment, this fair delivers a full-day escape without ever leaving Westchester.
📅 Sept 12–14, 2025
📍 Lyndhurst Mansion
Tarrytown, NY
Every September, the sweeping grounds of Tarrytown’s historic Lyndhurst Mansion transform into one of the most celebrated craft fairs in the Northeast. The Artrider Crafts Fair brings together over 200 juried artists, makers, and designers offering handmade goods you won’t find anywhere else. Think vibrant ceramics, fine jewelry, textiles, furniture, photography, and wearable art — all sold directly by the artists themselves. Add in gourmet specialty foods, small-batch spirits, and live entertainment, and you’ve got a full-on feast for the senses.
But what sets this event apart is the setting. With the Gothic towers of Lyndhurst as a backdrop and the Hudson River shimmering in the distance, shopping here feels like an escape into another world. Stroll tree-lined paths between tents brimming with creativity, stop for a snack or local brew, then sprawl out on the lawn to catch some live music. It’s more than just a market — it’s an autumn tradition that blends world-class craftsmanship with the kind of atmosphere that makes you want to linger all day.
📅 Sept 12 – Nov 16, 2025
📍 Van Cortlandt Manor
Croton-on-Hudson, NY
The Blaze is a rite of passage in the Hudson Valley. More than 7,000 hand-carved pumpkins are arranged into glowing sculptures — think pumpkin carousels, towering arches, and entire scenes brought to life in light. It’s part art installation, part Halloween wonderland.
Timed tickets make it easy to stroll at your own pace. The soundtrack, lighting effects, and riverside setting give it an almost magical quality, making it one of the most Instagrammed events in the region. Pro tip: snag tickets early — they sell out fast every year.
📅 Sept 20–21, 2025
📍 Multiple venues
Kingston, NY
Kingston’s creative spirit shines during this weekend-long art crawl. Dozens of galleries, studios, and pop-up spaces throw open their doors, inviting you to see, touch, and talk about art with the makers themselves.
The best part is the variety — one stop might feature modern sculpture, the next, live painting, and another, handmade crafts. Whether you’re an art collector or just love a good wander, this is a chance to experience Kingston as a living, breathing canvas.
📅 Sept 20–21, 2025
📍 New Century
Port Jervis, NY
The Moon Festival is a radiant two-day celebration of Asian heritage, tradition, and community spirit. Lanterns glow along the walkways, stages burst with music, dance, and martial arts, and the aroma of sizzling street food fills the air. For one unforgettable weekend, Port Jervis transforms into a cultural crossroads where you can taste, see, and experience the vibrancy of the Asian diaspora right here in the Hudson Valley.
Beyond the incredible performances and food, the festival is about connection. Families can join interactive activities, kids dive into crafts and games, and everyone walks away with a deeper appreciation for the meaning of the Mid-Autumn Festival. From lion dances and drumming to storytelling and community art, every moment feels joyful and rooted in tradition.
Now in its 10th year, the Moon Festival has grown into one of Port Jervis’s most anticipated events — a true celebration of diversity that shines brightly in this river town. Whether you come for the flavors, the family fun, or the cultural immersion, you’ll leave feeling part of something bigger.
📅 Sept 27–28, 2025
📍 Cantine Field
Saugerties, NY
This festival is garlic everything. Picture rows of food stands serving garlic knots, garlic ice cream, roasted bulbs, and even craft beer brewed with the good stuff. Add in live music and rows of artisan vendors, and you’ve got one flavorful weekend.
It’s not just about eating either — cooking demos, farm talks, and quirky garlic merchandise make this festival as educational as it is indulgent. Bring breath mints, but don’t miss it.
📅 Sept 27–28, 2025
📍 Croton Point Park
Croton-on-Hudson, NY
History gets loud at REV FEST 250. This festival honors Revolutionary War heritage with reenactments, cannon fire, and costumed characters. But it’s not all history — live music, craft beverages, and food vendors keep it fresh.
The setting at Croton Point Park makes it even better. With sweeping river views and plenty of open space, it’s the kind of festival where you can balance learning something new with dancing to a band and grabbing a bite.
Capital Region + Adirondacks
The Capital Region comes alive in September with harvest flavors on every menu, city-wide block parties buzzing with energy, and one of the most spectacular hot air balloon festivals in the entire country. Head a little farther north and the Adirondacks transform into a bucket-list backdrop, where crisp mountain air and fiery fall colors make every hike, paddle, and scenic drive feel like pure magic.
Keller 📅 Sept 10, 2025
📍 Empire State Plaza
Albany, NY
Albany’s Empire State Plaza comes alive with the taste of fall. Local breweries, cideries, and food vendors pour and plate their best, while live bands soundtrack the evening.
It’s the perfect after-work event or night out with friends — casual, scenic, and delicious.
With the Capitol building lit up in the
background, it’s an Albany moment you don’t
want to miss.
📅 Sept 10–14, 2025
📍 Downtown White Plains, NY
This multi-day jazz festival combines free outdoor performances with intimate ticketed shows from world-class talent. Downtown White Plains buzzes with energy as music fills plazas, parks, and local venues.
It’s a great way to experience the city on foot, hopping between acts and soaking in the diverse sounds of modern and classic jazz. For music lovers, it’s a September highlight.
📅 Sept 13, 2025
📍 Grafton State Park
Grafton, NY
Part dog festival, part live concert, part picnic in the park — Bark n’ Brew is all about fun for you and your four-legged bestie. Expect agility courses, a guide-dog walk, live bands, and craft beer flowing.
It’s family-friendly, dog-friendly, and loaded with vendors offering everything from treats to pet gear. If your pup’s been waiting for their moment in the spotlight, this is it.
📅 Sept 13–14, 2025
📍 Columbia County Fairgrounds
Chatham, NY
The Capital Apple & Wine Festival is a two-day celebration of everything we love about fall in New York. Picture rows of wineries and cideries pouring their best vintages, food trucks sending up the aroma of BBQ and sweet treats, and artisan vendors filling the fairgrounds with crafts, gifts, and local goods. It’s the ultimate taste of the harvest season, all in one place.
Live music keeps the energy buzzing throughout the weekend, while families can enjoy hayrides, kids’ games, and plenty of hands-on fun. One of the festival’s biggest draws is the annual classic car show — a lineup of polished vintage beauties gleaming in the autumn sun. Whether you’re there to sip and sample or just soak in the atmosphere, this event has that perfect mix of small-town charm and big fall flavor.
📅 Sept 18–21, 2025
📍 Queensbury & Glens Falls, NY
Few things feel as magical as watching hot air balloons rise against the Adirondack peaks at sunrise. The festival also features night glows, craft vendors, and family activities that fill the fairgrounds.
Best of all? It’s free. Pack a picnic, grab a blanket, and settle in for one of the state’s most photogenic traditions.
📅 Sept 20, 2025
📍 Lark Street
Albany, NY
This 21+ music festival is Albany’s ultimate block party. Multiple stages line Lark Street with bands covering everything from throwback hits to local originals, plus beer gardens and food vendors.
The vibe is unpretentious and fun, with the entire neighborhood turning into one big street party. It’s the kind of event that keeps you dancing long after sundown.
Finger Lakes + Central NY
The Finger Lakes light up September with serious flair—downtowns glow with dazzling light shows, orchards burst with apple harvest celebrations, and the region’s grape festival serves up sweetness you’ll never forget. It’s art, food, wine, and small-town magic rolled into one unforgettable fall escape.
📅 Sept 5–6, 2025
📍 Downtown Binghamton, NY
Imagine entire buildings transformed into massive art pieces, glowing with projection mapping and immersive storytelling. That’s LUMA — a futuristic celebration of light and creativity.
The festival is walkable and family-friendly, with installations scattered across downtown. Whether you’re into tech or just want to feel transported, it’s one of the most unique festivals in the state.
📅 Sept 26–28, 2025
📍 Downtown Ithaca Commons
Ithaca, NY
The Commons turn into a bustling street fair with cider donuts, apple pie, and every apple
treat you can imagine. Add street performers, live music, and local artisans, and you’ve got an event that feels like fall distilled into one weekend.
Kids love the games and rides, while adults can browse craft stalls or sample Finger Lakes
cider. It’s wholesome, fun, and very Ithaca.
📅 Sept 27–28, 2025
📍 Naples, NY
This festival is all about the grape. From fresh grape pies to wine tastings, it’s a Finger Lakes celebration of harvest season that draws tens of thousands.
Beyond the food, live music and artisan vendors keep the energy buzzing all weekend. If you’ve never had grape pie, this is the place to do it.
Your September Playbook
There you have it — twenty ways to turn September into a highlight reel you’ll be talking about all winter. The only real danger? Sitting home and watching the month slip by while everyone else is sipping wine in Chatham, dancing in Albany, or eating garlic ice cream in Saugerties (yes, it’s delicious, don’t @ us).
So clear your weekends, rally your crew, and start plotting your route. Because September in New York isn’t meant to be scrolled past — it’s meant to be lived, tasted, and experienced one pumpkin glow, grape pie, and balloon launch at a time. Miss it and, well…let’s just say you’ll be stuck scrolling everyone else’s photos wondering where it all went wrong. Don’t do that to yourself. We’ll see you out there.
NEVER STOP EXPLORING!
Follow us
