September arrives with a full calendar—harvest festivals, outdoor theater, live music, and a few unexpected finds worth clearing your weekend for.
Cider Excursion
Thursday, September 3
Fishkill Farms, Hopewell Junction
A behind-the-scenes look at hard cider from orchard to glass—walking tour, wagon ride through the orchard, and five pours of Treasury Cider.
fishkillfarms.com
8th Annual Sunflower Festival
September 4–7
Barton Orchards, Poughquag
One of the area’s most beloved summer traditions—sunflowers, live music, craft vendors, and family fun.
bartonorchards.com
35th Annual Hot Air Balloon Festival
September 4–6
Tymor Park, Lagrangeville
Five mass balloon ascensions, evening moon glows, nightly fireworks, live entertainment, food trucks, and family activities all weekend. dcrcoc.org
Churchtown Chamber Music Festival
September 4–6
Round Barn at Churchtown Dairy, Hudson
World-class soloists and chamber musicians in the stunning Round Barn at Churchtown Dairy, an acoustical wonder.
chambermusicchurchtown.org
Labor Day Weekend BBQ
Saturday, September 5
Troutbeck, Amenia
Chef Vinny cooks a whole pig on a fire truck, with vegetarian and pescatarian options. Peach hand pies, cookies, and watermelon for dessert.
troutbeck.com
Troutbeck Field Day
Saturday, September 5
Troutbeck, Amenia
Field Day returns after a century-plus break—egg-on-spoon, wheelbarrow, and tug of war on the lawn. Free, all ages, no sign-up. troutbeck.com
New Re Institute Exhibition
Saturday, September 5
The Re Institute, Millerton
Opening night, 4–6 pm, of knee deep in this body of water—a show exploring containment, shared resources, and distant connection. thereinstitute.com
All-Vinyl DJ Set
Saturday, September 5
Lasting Joy Brewery, Tivoli
DJ Pete Pop spins vinyl favorites at Lasting Joy Brewery, 1–7 pm.
lastingjoybrewery.com
Stormville Airport Flea Market
September 5–6
Stormville Airport, Stormville
Antiques, collectibles, arts and crafts, and new merchandise. Free admission and parking.
stormvilleairportfleamarkets.com
Garlic Jam Festival
September 5–6
MJN Convention Center, Poughkeepsie
Garlic goodies, pickled treats, beer, music, and artisan vendors at the annual Garlic Jam Festival.
mjncenter.org
Art Studio Views 2026: A Weekend of Creativity
September 5–6
Studios throughout Northern Dutchess and Columbia Counties
An annual exhibit introducing participating artists’ work and helping you plan your studio visits.
artstudioviews.com
Oyster Party
September 5–6
Fishkill Farms, Hopewell Junction
Freshly shucked oysters and lobster rolls at the Treasury Cider Bar at Fishkill Farms.
fishkillfarms.com
The Tano Jones Revelry plus Lauren Mian
Sunday, September 6
Daryl’s House, Pawling
More than live music—through their Soup & Seeds initiative, the band partners with The Pawling Resource Center to support local food insecurity efforts.
darylshouse.com
The Trial, by Franz Kafka at Savage Wonder
September 5, 12, 19, 26
Savage Wonder, Beacon
Five actors play 25 parts in Kafka’s mysterious tale, done in Savage Wonder’s classic flash-to-bang style. Tickets include curated food and cocktails by The Grape Rebellion.
savagewonder.org
Oldtone Roots Music Festival
September 10–13
Cool Whisper Farm, Hillsdale
Food, dancing, camping, and music for all ages. Pack your gear and dancing shoes.
oldtone.org
Hudson Valley Wine and Food Festival
September 12–13
Dutchess County Fairgrounds, Rhinebeck
Celebrating 25 years with wine, cider, beer, gourmet bites, artisan shopping, and live entertainment.
hudsonvalleywinefest.com
Poughkeepsie Art Mile
September 12–13
Gallery 40, Poughkeepsie
A free celebration of local art, music, and culture—U-Haul trucks transformed into immersive pop-up galleries by local artists and curators.
gallery40pok.com
Fall Harvest Festival Weekends
September 12–13, 19–20, 26–27
Fishkill Farms, Hopewell Junction
Apple picking, wagon rides, live music, corn mazes, and cider at Fishkill Farms every weekend through October.
fishkillfarms.com
Plein Air Art Day
Saturday, September 12
Maitri Farm, Amenia
Paint a scenic landscape with local artist Mahala Miller at Maitri Farm. Free for all.
maitriny.com
Seeing with Intent: An Early Morning Walk of Discovery
Saturday, September 12
Innisfree Garden, Millbrook
A nature walk before the garden opens to the public, learning to notice the details most visitors walk right past.
innisfreegarden.org
Closing Reception at the Wassaic Project
Sunday, September 13
Maxon Mills, Wassaic
Closing reception of Wassaic Project’s 2026 Summer Exhibition, Because now, it is the time of monsters—artists’ talks, studio tours, and a live performance of Barbershop: The Art of Queer Failure.
wassaicproject.org
Golf Tournament and Gala Dinner
Monday, September 14
Millbrook Golf and Tennis Club, Millbrook
Grace Church of Millbrook’s annual fundraiser benefits Food of Life, The Lunch Box meal program, the Millbrook Community School, and more.
gracemillbrook.org
Dracula: The Journal of Jonathan Harker
September 16–20
Bannerman Castle, Pollepel Island, Beacon
Dracula performed live at Bannerman Castle, with a round-trip cruise to the island and a full-service concession stand.
bannermancastle.org
Guided Landscape Walk of Staatsburgh’s Grounds
Friday, September 18
Staatsburgh State Historic Site, Staatsburg
A guided tour of Staatsburgh’s historic grounds, revealing the landscape built for the estate’s gilded-age owners.
staatsburgh.com
The Importance of Being Earnest
September 18–20
Wilderstein Historic Site, Rhinebeck
Outdoor theater at Wilderstein in partnership with New Deal Creative Arts Center. Arrive early for a mansion tour.
wilderstein.org
Natural Dye Workshop
Saturday, September 19
Maitri Farm, Amenia
Bundle dyeing with fresh flowers, leaves, and botanicals harvested from the farm. Learn to create one-of-a-kind patterns using natural plant dyes.
maitriny.com
The Wappingers Dahlia Show
Saturday, September 19
Mesier Homestead, Wappingers Falls
The Wappingers Historical Society marks the 125th anniversary of the first dahlia show in America—held right in Wappingers.
wappingershistoricalsociety.org
Rhinebeck Porchfest
Saturday, September 19–20
Historic Porches, Rhinebeck Village
Live music on 20 historic porches throughout Rhinebeck village, rain or shine.
rbkporchfest.com
Micro Film Festival
Sunday, September 20
The Yard, Beacon
Free outdoor screening of Beacon filmmakers’ short films, plus 1922’s Nosferatu. Beer and food available.
theyardbeacon.com
Catoberfest 2026
Sunday, September 20
Hudson Valley Brewery, Beacon
Craft beer, food, live music, and family fun benefiting Mid Hudson Animal Aid, a no-kill, free-range cat sanctuary in Beacon. catoberfest.cat
Hike Through Time
Saturday, September 26
Wilderstein Historic Site, Rhinebeck
Science writer Robert Titus leads a geo-journey across Wilderstein’s landscape, tracing the region’s layered geologic past and Ice Age legacy.
wilderstein.org
15th Annual Fall Foliage Half Marathon & 5K
Saturday, September 26
Rhinebeck
Run through the fall foliage of Rhinebeck. Registration is open.
fallfoliagehalf.com
Kesicke Fall Festival
September 26–27
Kesicke Farm, Rhinebeck
Corn mazes, wagon rides, a petting zoo, pumpkin picking, and apple cider donuts every weekend, September 26 through November 1. kesickefarms.com
Spirit of Beacon Day
Sunday, September 27
Main Street, Beacon
A parade, craft vendors, food, and activities celebrating community in the heart of Beacon.
spiritofbeacon.org