Welcome to October in Dutchess County, when the maples blush and every farm stand smells like cider donuts. Spend your days picking apples and pumpkins, riding hayrides, and wandering harvest festivals, then stay out late for costume parades, trick-or-treat activities, and haunted parties. Discover the best October events in Dutchess County.
Pilates & Pours at Fishkill Farms
Thursday, October 1
Treasury Cider Porch, Fishkill Farms, Hopewell Junction
Enjoy Pilates and a nine-ounce cider pour set on Treasury Cider’s covered wraparound cider porch overlooking the orchards and surrounding mountains.
treasurycider.com
Grand Opening of Kevin McCurdy’s Haunted Mansion
Friday, October 2
McCurdy’s Haunted Mansion, Wappingers Falls
Celebrate the 50th season of Kevin McCurdy’s Haunted Mansion with more immersive elements, special effects, and family fun. Enjoy spooky nights and kid-friendly days alike.
thehauntedmansion.com
Starry Starry Night
Friday, October 2
Walkway Over the Hudson, Upper Landing Park, Poughkeepsie
At twilight, ascend the Walkway’s glass elevator for after-hours access to the bridge and spectacular views above the Hudson River. A brilliant fireworks display caps off the evening.
walkway.org
Discovery Land Company Masters Horse Show
October 2–4
Keane Stud, Amenia
The Discovery Land Company Masters brings together top-tier riders, exceptional horses, and passionate spectators for one of the Northeast’s premier equestrian competitions.
highlandshudsonvalley.com
Tivoli Street Painting Festival
Saturday, October 3
Broadway, Tivoli Village, Tivoli
Be part of the legendary day of creativity and family fun all along Tivoli’s Broadway thoroughfare. Free registration and materials.
tivolinow.com
Cider Excursion: Orchard & Cidery Tour
Saturday, October 3
Fishkill Farms, Hopewell Junction
Get a behind-the-scenes look at how Fishkill Farms’ hard cider goes from orchard to glass. Get a walking tour of the cider production facility, followed by a wagon ride while enjoying five three-ounce tasting pours.
treasurycider.com
Pumpkin Patch Dance Party
Saturday, October 3
Stissing Center for Arts & Culture, Pine Plains
A lively night with beloved dance band Jungle Love, back by popular demand. Promising great music and great vibes, spend an autumn evening boogy-ing on the dance floor.
thestissingcenter.org
Dassai Blue’s 3rd Anniversary Celebration
October 3–4
Dassai Blue Sake Brewery, Hyde Park
Three years ago, Dassai Blue began its journey in Hyde Park, bringing the spirit and craftsmanship of Dassai to America. Enjoy a two-day anniversary celebration filled with sake, food, Japanese culture, and craft.
dassai-blue.com
Apple Festival at Barton Orchards
October 3–4
Barton Orchards, Poughquag
Celebrate apple-picking season at Barton Orchards with unlimited hayrides, a petting zoo, a haunted house and corn maze, mini golf, food, and fun.
bartonorchards.com
12th Annual Harvest Festival at Soukup Farms
October 3–4, 10–12, 17–18, 24–25
Soukup Farms, Dover Plains
Head to Soukup Farms during the first four weekends in October for harvest festival celebrations. Enjoy hayrides, a pick-your-own pumpkin patch, a corn maze, and fun family activities.
soukupfarms.com
Troutbeck Symposium Kickoff Event
Sunday, October 4
Troutbeck, Amenia
An autumn afternoon of conversation and exploration ahead of the next Troutbeck Symposium, bringing together students, educators, historical societies, artists, and community partners from across the region.
troutbeck.com
Beacon Flea Market
October 4, 11, 18, 25
Henry St. and South Chestnut St., Beacon
Enjoy an outdoor flea market while you can––the Beacon Flea Market is open every fine-weather Sunday until November. Shop for antique furniture, vintage clothing, unique crafts, and more.
beaconfleamarket.com
Tarot “Curds” Class
Tuesday, October 6
Beacon Cheese Shop, Beacon
Be guided through a personal tarot reading, pairing each card’s meaning with a cheese that reflects your energy and intuition.
thecheeseshops.com
9th Annual Bartender Wars
Thursday, October 8
Terrapin Restaurant Pavilion, Rhinebeck
Enjoy the 9th Annual Bartender Wars at Terrapin Restaurant for an evening of friendly competition, creative cocktails, and great food.
rhinebeckchamber.com
Skye Consort and Emma Björling
Saturday, October 10
Stissing Center for Arts & Culture, Pine Plains
Skye Consort and Emma Björling offer a textured musical experience that draws from the traditions of Scandinavia, Ireland, Britain, and French Canada. Combining voice with instrumentals.
thestissingcenter.org
Spooky Season Crafty Kids Story Hour
Saturday, October 10
Clermont State Historic Site, Germantown
Join Clermont for a Halloween-themed story hour. Librarian Jane Miller reads a curated selection of storybooks about the changing of the seasons, followed by crafting Halloween decorations.
friendsofclermont.org
October Curator’s Tour
Saturday, October 10
Innisfree Garden, Millbrook
Join landscape curator Kate Kerin for a lively tour exploring Innisfree, a powerful icon of mid-20th-century design now recognized as one of the world’s ten best gardens.
innisfreegarden.org
Barton Orchards Harvest Festival
October 10–12
Barton Orchards, Poughquag
It’s festival season––make the most of it at Barton Orchards. Enjoy live music, kids’ entertainment, delicious food, farm fun, and of course, hard cider and beers.
bartonorchards.com
Columbus Day/Indigenous Peoples’ Day | Innisfree Open for Holiday
Monday, October 12
Innisfree Garden, Millbrook
Spend the day in reflection on the layered histories of the land, honoring the Indigenous peoples who first stewarded it and the many generations who have shaped the American landscape since.
innisfreegarden.org
Sushi Dinner at Mill House Brewing Company
Thursday, October 15
Mill House Brewing Company, Poughkeepsie
Join Mill House for its first sushi dinner special. Start with a welcome cocktail featuring Dassai Blue Sake Brewery, then enjoy a three-course meal featuring different Asian cuisine dishes.
millhousebrewing.com
St. James’ Historic Graveyard Tours
October 16–17, 23–24
St. James’ Church, Hyde Park
Enjoy a family-friendly living history tour, with guides and actors dressed in period costume. These are not haunted tours and are meant to be informative, not frightening.
stjameshydepark.org
Yoga in the Orchard
Saturday, October 17
Rose Hill Farm, Red Hook
Enjoy a relaxing yoga class in the middle of the scenic orchard of Rose Hill Farm. Treat yourself afterward with a donut by Mighty Donuts.
rosehillfarm.com
Wicked Wappingers Halloween Festival & Parade
Saturday, October 17
Main St. and Mesier Park, Wappingers Falls
A day of spooky celebration in the Village of Wappingers Falls, featuring aTrunk-or-Treat, a live DJ, food, vendors, pumpkin patch, contests, and games.
wickedwappingers.com
Kesicke Farm Fall Festival
October 17–18
Kesicke Farm, Rhinebeck
One of the best fall festivals in our area––hay wagon rides, pumpkin picking, a corn maze, live animals to feed and pet, and delicious apple cider donuts.
kesickefarms.com
New York State Sheep & Wool Festival
October 17–18
Dutchess County Fairgrounds, Rhinebeck
The Sheep & Wool Festival brings together fiber enthusiasts, shepherds, artisans, and educators for a weekend featuring hundreds of vendors, hands-on workshops, livestock exhibits, and fleece competitions and demonstrations.
sheepandwool.com
Haunted Mill & Monster’s Ball
October 23–25
Luther Barn, Wassaic Project, Wassaic
Join the Wassaic Project’s Haunted Mill, with a monster candy feast, fairy tale forest, shadow puppet show, dancing clown installation, and so much more. Make sure to show up in costume.
wassaicproject.org
Walkway Market: A Taste NY Experience
Saturday, October 24
Walkway Over the Hudson, Poughkeepsie
This open-air farmers market brings together a handpicked lineup of New York State makers, growers, and artisans in a setting you can’t find anywhere else. Taste, shop, and discover.
walkway.org
Tract-or-Treat at Barton Orchards
Saturday, October 24
Barton Orchards, Poughquag
Looking to get lost? Visit Barton Orchards for a flashlight corn maze experience, with delicious food, ciders and beers, and other concessions waiting for you at the end of the maze.
bartonorchards.com
Heritage Harvest Festival
Saturday, October 24
Primrose Hill Farm, Staatsburg
The perfect harvest family day–enjoy a variety of educational and entertaining activities planned for the entire day. Educational demonstrations, workshops, hayrides, lawn games, and more.
primrosehillfarm.com
ArtEast October Open Studio Tour
Sunday, October 25
Participating Art Studios Across the County
Artists in Dutchess County welcome you to their studios to share their artwork and studios. Visit artists in Holmes, LaGrangeville, Hopewell Junction, Pawling, Poughquag, and Wingdale.
arteastdutchess.com
Halloween Gade-O-Ween at Heritage Financial Park
Sunday, October 25
Heritage Financial Park, Wappingers Falls
Hayrides, games, spooky inflatables, and more. Enjoy trunk-or-treating in the afternoon, and stick around for a classic showing of Halloweentown.
heritagefinancialpark.com
Halloween Candy & Cheese Class
Thursday, October 29
Beacon Cheese Shop, Beacon
Explore the surprisingly delicious world of candy and cheese combinations, learn why sweet and salty pairings work, and discover which Halloween favorites hold their own against artisan cheese. Go in costume, and arrive hungry.
thecheeseshops.com
Pasture Kitchen Wine Tasting
Thursday, October 29
Pasture Kitchen, Millerton
Small-producer wines, clean food, a mesquite wood fire, benefiting a worthy cause. Broaden your palate with a carefully curated selection of biodynamic wines from @millertonwineandspirits paired with your favorite dishes @pasturekitchen. 10% of sales will support Crew Slater’s medical expenses.
More info
Halloween Snacks with Chef Emma at Troutbeck
Saturday, October 31
Troutbeck, Amenia
Throw on your Halloween costume and join pastry chef Emma Isakoff to create delicious—and only slightly terrifying—Halloween treats. Open to all ages.
troutbeck.com
Trick-or-Treat at Clermont
Saturday, October 31
Clermont State Historic Site, Germantown
Swing by the Clermont visitor center between 10:30 am and 4 pm to trick-or-treat. Come for the candy, stay for the photo ops at spooky-cute Halloween photo stations.
friendsofclermont.org
Trunk-or-Treat at Four Brothers Drive-In
Saturday, October 31
Four Brothers Drive-In, Amenia
In partnership with the Amenia Town Hall, the drive-in hosts its annual trunk-or-treat event, with spookily decorated cars and candy galore. Come in costume, and grab lunch at the Four Brothers Restaurant.
playeatdrink.com
Jessica Lynn’s Halloween Bash
Saturday, October 31
Daryl’s House, Pawling
Jessica Lynn covers favorite hits from every genre for this Halloween bash. Costumes, games, dancing, and a costume contest with Daryl’s House Club prizes.
darylshouse.com