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

Hudson River tourism directors share their top picks for things to do throughout the month.


Taste of New Paltz

Photo by CC Photo Media


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.


Apple Wine Festival

Apple & Wine Festival / Photo courtesy of Discover Albany


The Capital Region Apple & Wine Festival

Altamont Fairgrounds, Altamont​
September 14-15, 10 a.m.

If anything represents September in the Hudson Valley, it has to be apples…or maybe wine…or, is both a possibility? The Capital Region thinks so, which is why it shines a light on the dreamy duo during its mid-month festival at the Altamont Fairgrounds. With a juried arts and crafts show, Pride of NY food vendors, and tons of wine tastings from New York wineries, the food-filled fest is one for the books. For the kids, a haunted house, face and pumpkin painting, and pony rides make for great seasonal entertainment, too.


Albany Book Festival

UAlbany Uptown Campus, Albany
September 14, 10:30 a.m. – 4:15 p.m.

Presented by the New York State Writers Institute, the Albany Book Festival returns to UAlbany for the second year in a row, bring a slew of award-winning authors with it. More than 100 writers, including Jamaica Kincaid, Joyce Carol Oates, and Ricardo Cortés, flock to the campus on September 14 for a full day of author talks, signings, and workshops. Visit the website for more information on the day’s programming, then get ready for lessons on “How to Haiku” and “Writing Short Stories.”



N. Pearl St between Pine St and Sheridan Ave, Albany
September 14, 11 a.m.

The biggest music festival to hit downtown Albany, PearlPalooza takes over Pearl Street for its 10th year. It’s an all-day, outdoor music marathon spread across two stages and featuring musicians like Wild Belle, Victory Soul Orchestra, and In The Valley Below, to name only a few. In addition to a jampacked lineup of performers, attendees can look forward to YogaPalooza, a mass yoga gathering, at 11 a.m., followed by a cornhole tournament at noon.



LarkFest / Photo courtesy of Discover Albany



Lark Street Business Improvement District, Albany
September 21, 10:30 a.m. – 5:30 p.m.

An incredible outdoor festival in the heart of Albany’s thriving Lark Street district, LarkFest features an abundance of local, regional, and national bands, along with dozens of artisans and food stands. The family-approved event, which is now in its 39th year, anticipates a turnout of 80,000 people, so don’t mind the crowds if you go. Stay tuned to the Facebook event page as the event date draws nearer for the full lineup of bands and vendors.

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.


Hudson Valley Wine & Food Fest

Dutchess County Fairgrounds, Rhinebeck​
September 7-8, 11 a.m.

As anyone who’s been to the Hudson Valley Wine & Food Fest can attest, the annual September shindig is one for the books. Presented by, it brings together hundreds of New York breweries, cideries, distilleries, and wineries, along with food trucks and gourmet brands. In addition to an endless amount of sipping and sampling, visitors to the fairgrounds can stop by demonstrations from Food Network Chopped champion Roshni Gurnani, Aroma Thyme Bistro owner Chef Marcus Giuliano, and Hudson Valley recipe developer Arlyn Osborne.


Dutchess County Classic

Dutchess County Classic / Photo courtesy of Dutchess Tourism, Inc.


41st Annual Dutchess County Classic

Dutchess Community College, Poughkeepsie
September 15, 8 a.m.

Fitness takes center stage at the Dutchess County Classic in September. Designed for all ages, the day features races ranging from a one-mile for kids to a 5k and half and full marathons for runners and wheeled competitors. The course celebrates the beauty of Dutchess County, extending along the rail trail and above the Hudson River via the Walkway Over the Hudson. A portion of proceeds from the race go to United Way of the Dutchess and Orange Region, with which the Mid-Hudson Road Runners Club, the event organizer, has collaborated for more than a decade.


Orvis Game Fair

Orvis Game Fair / Photo courtesy of Dutchess County Tourism, Inc.


Orvis Game Fair & Sporting Weekend

Orvis Sandanona Shooting Grounds, Millbrook
September 21-22, 9 a.m. – 5 p.m.

Anyone who loves Orvis for outdoor adventures will be all over the recreation brand’s Game Fair and Sporting Weekend. Held on the Sandanona Shooting Grounds in Millbrook, it honors the traditions of field and hunt with two full days of fly-fishing demonstrations, dog-training seminars, birds of prey exhibitions, and more. On September 21, a sporting clays competition adds to the festive out-of-doors experience as well.

Greene County

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


Catskill Mountain Thunder Motorcycle Festival

Blackthorne Resort, East Durham
September 11-15

This September, head to Blackthorne Resort for what promises to be the largest motorcycle festival in upstate New York. An adrenaline-filled event, it brings all the excitement with stunt shows and rodeo games, plus live music and a vendor expo. On September 11, the festival kicks the party off with a pub crawl in town, followed by a pre-festival party the next day. For visitors who want to stick around throughout the weekend, on-site lodging and RV and camping options are available.


Greenville Day

Vanderbilt Park, Greenville
September 28

A full day of fun for Greene County, Greenville Day returns for its 10th year of carnival rides, craft vendors, and petting zoo fun. Attendees can shop for pre-loved goods at the townwide yard sale, then hit the farmers’ market for seasonal produce and unwind with live music throughout the course of the day.




Hunter Mountain, Hunter
September 28-29, October 5-6, 12-13, 19-20

There’s no Oktoberfest quite like the one at Hunter Mountain! This year, the slopeside spot hosts not one, but four free-to-attend seasonal weekends to showcase the best of German and German-American entertainment in the Hudson Valley. The mountain starts the party at the end of September with “Ciders in the Catskills,” a tasting event with New York cideries. Going into October, stay tuned for themes like “Colors in the Catskills” with off-roading, “Das Laufwerk Eurocar Rally,” and “Wineries in the Catskills.”

Orange County

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



General Montgomery Day

Village Hall, Montgomery
September 7, 10 a.m. – 9 p.m.

As far as community fests in the Hudson Valley go, it’s hard to beat the Village of Montgomery’s yearly hoopla A delightful family occasion, it keeps all ages entertained with amusement rides, a parade through town, an 8k race, a soapbox derby, and more.


5th Annual Orange County Sweet Corn Festival

366 Cty Rte 12, New Hampton
September 8

Celebrate the bounty of the Black Dirt region at Orange County’s Sweet Corn Festival this month. Tickets cost $10 per car, and admission includes access to local craft and food vendors, along with music, games, and contests galore. For attendees of all ages, the twisty, turning corn mazes are a worthwhile adventure.



Happy #moonfestival

A post shared by Jim Leach (@jim_leach8) on


4th Annual Moon Festival

New Century, Port Jervis
September 13-15

New Century’s 40-acre property in Port Jervis plays host to the fourth annual Moon Festival in September. Designed to honor Asian tradition, the event bridges the gap between eastern and western cultures with traditional performances and presentations designed to educate and entertain. With a medley of local vendors and a solid community turnout, it’s an easy, festive way to spend a weekend in the Hudson Valley.



Warwick Food Truck Festival

St Stephen – St. Edward School, Warwick
September 19-20, 4-9 p.m.

Who doesn’t love a good food truck? The best of the best head to Warwick this September for the town’s foodie get-together. Tickets are $10 per person, with eats and drinks available for purchase from vendors like The Brownie Bar, Empanada Master, Potenza Old World Pizza, Glenmere Brewing Co. and Parked Prosecco. Come hungry!


46th Annual Fall Festival

Main St, Cornwall
September 22

When it comes to fall festivals in the Hudson Valley, Cornwall doesn’t cut corners. Instead, it pulls out all the stops with two live entertainment stages, pony and train rides, a hay maze, and dozens of vendors. The fun-for-all event is in its 46th year, which means it’s a must-do for the season.

Rockland County

Take a browse through the hottest things to do in Rockland County throughout the month.


SeptemberFest Street Fair

Main St and Broadway, Nyack​
September 8, 10 a.m. – 5 p.m.

Nyack is on top of the local street fair game, and its SeptemberFest is no exception. Presented by the Nyack Chamber of Commerce in partnership with Montefiore Nyack Hospital, the fair features a special fashion show at 2 p.m. to raise awareness for breast cancer. All models are dressed by village boutiques, with local salons set to style everyone before they hit the catwalk. On top of that, more than 300 vendors fill the streets with jewelry antiques, crafts, and collectibles galore.


10th Annual Highlands Bluegrass Festival

Harmony Hall, Sloatsburg​
September 8, 1-6 p.m.

The sweet sounds of bluegrass serenade the Hudson Valley at Rockland’s music festival this month. The laid-back occasion features three bands: Blue Plate Special, Eugene Tyler Band, and Moonshine Falls. Bring lawn chairs and blankets to listen to the music, then take breaks to browse the craft and food vendors on the great lawn. As for Fido, feel free to bring him too! The bluegrass festival is pup-approved (as long as they’re on leashes).



Dance, Eat, Drink & Crafts shopping at the Haverstraw Riverwide Arts & Music Festival - 9/14 - 11-5pm in Emeline Park, #Haverstraw, NY. Live music by @Tronanddvd @kirametcalf, #FodaySuso, #LaFamiliaSextet & #DJGinnyNorfleet. Live Art Event with professional artists creating parklets alongside the #HudsonRiver, kids’ activities, #Annieandthenaturalwonderband, #Craftvendors, #ArtVendors, outdoor wining & dining at waterfront restaurant Don Coqui. Rain or shine. Free admission. 30 miles north of #nyc <<INFO in our Bio link.>> #musicfestivals #artfestival2019 #artfestival #craftshow #kidsactivities #hudsonvalleyevents #escapebrooklyn #upstater #hudsonvalleyart #hudsonvalleyartists #hudsonvalleygetaway #waterfrontfestival #nyart #nyartists @musicfestivalcentral #rocklandcounty #inthestrawny #foodtrucks #hudsonriverpark #hudsonvalley #freeadmission #rocklandcounty #freeconcert

A post shared by Non Profit Arts Organization (@haverstrawriverwidearts) on


Haverstraw Riverwide Arts & Music Festival

Emeline Park, Haverstraw​
September 14, 11 a.m. – 5 p.m.

A rain or shine event, Haverstraw’s festival kicks off just before lunch with DJ sets and music, live professional art making, and paper lantern painting for kids. Local artisans showcase their wares onsite, while food and drink vendors keep everyone fortified with snacks and sips.


National Hunting and Fishing Day

Congers Lake Memorial Park, Congers
September 28, 9 a.m. – 3 p.m.

Cast a line, break out the bow and arrow, and stock up on worms for National Hunting and Fishing Day festivities in Congers. Locals can savor the sunshine as they test out archery and fly fishing or catch demonstrations on trapping, foraging, and hunting in the region. Anyone who wants to do a little fishing can even craft a bamboo pole and fish for free at the lake – no license required!

Ulster County

Read up on Ulster County Tourism's event highlights for September.


Taste of New Paltz

Ulster County Fairgrounds, New Paltz​
September 15, 11 a.m. – 5 p.m.

If ever there was a day to visit New Paltz, September 15 would be it. After all, when else do the village’s food, drink, and entertainment vendors flock together for an incredible day of fall fun in the Hudson Valley? Main stage entertainment begins at 11 a.m., with the Best of Taste award results slated for the end of the day. Skim the full list of vendors online in advance, then plan to spend the day wandering from booth to booth and savoring the last few days of summer.


Catskill Conquest

Catskill Conquest / Photo courtesy of Ulster County Tourism


Catskill Conquest Rally

Catskill Visitor Center, Mount Tremper​
September 21

Hudson Valley auto enthusiasts, this one’s for you! On September 21, vintage rides from across the region and beyond assemble in Mount Tremper for a noncompetitive 65-mile tour through the Catskill Mountains Scenic Byway. Arrive early to watch the classic cruisers depart at 9 a.m. or register online in advance to cruise with the retro group.


Headless Horseman Hayrides

Headless Horseman Hayrides / Photo courtesy of Ulster County Tourism


Headless Horseman Hayrides and Haunted Houses

778 Broadway, Ulster Park
September 21 – November 2

Get ready for chills, thrills, and more than a few bloodcurdling screams at the Headless Horseman in Ulster Park. Named the top haunted attraction in America, the nightmarish (in the best way) venue celebrates 25 years of fear with a tingling one-mile hayride and corn maze, plus a terrifying assortment of spooktacular themed destinations. A serious fear spot, Headless Horseman is recommended for ages 13 and up, with reservations required.


Hudson Valley Garlic Festival

Hudson Valley Garlic Festival / Photo courtesy of Ulster County Tourism


Hudson Valley Garlic Festival

Cantine Field, Saugerties​
September 28-29, 10 a.m.

Vampires, beware! The Hudson Valley Garlic Festival is back, better, and more pungent than ever this September. The annual to-do honors everyone’s favorite allium with local chefs and lecturers, vendors, and performances throughout the course of the two days. While garlicky goodness in the form of garlic knots and rice balls are par for the course, garlic-filled chocolate bars and ice cream test the devotion of even the most adamant garlic lovers.

Related: Discover Fun and Fantasy at the New York Renaissance Faire

Edit Module
Edit ModuleShow Tags
Edit Module
Edit Module