October in the Hudson Valley = nonstop magic. ✨🍂
From world-class show jumping and Downton Abbey on the big screen to harvest festivals, floral film nights, ghost tours, and sheep & wool traditions—this month is overflowing with experiences you won’t want to miss. Here’s your guide to the very best of fall in Dutchess County! Be sure to check out our curated Halloween Events list to see what fun, bewitching activities are going on in October to get you into the spooky spirit!
Silo Ridge Masters
October 1 – 5
Keane Stud, 217 Depot Hill Road, Amenia
Experience five days of elite show-jumping at the Silo Ridge Masters, October 1–5, featuring the $125,000 CSI3 Grand Prix, thrilling competitions, live entertainment, luxury hospitality, and unforgettable Hudson Valley scenery.
siloridgemasters.com
The Millerton Moviehouse – Downton Abbey: The Grand Finale
October 2nd
The Moviehouse: 48 Main St., Millerton
Catch the third and final film of the Downton Abbey franchise at the Moviehouse. Grab popcorn and drinks from the bar/lounge area before you watch the Crawley family enter the 1930s at Millerton’s independent, 3-screen cinema.
themoviehouse.net
The Five O’Clock at Bullis Hall
Friday, October 3rd
88 Hunns Lake Road, Bangall
Bangallworks presents: The Five O’Clock, at Bullis Hall, a professional and neighborhood mixer! View one of the most historic sites in Bangall, NY and enjoy live music, beverages, and catered bites. RSVP with steve.bruman@corcorancl.com.
bangallworks.com
The Female Gaze: Women in Photography
October 4th (Opening Night Soiree) – November 16th
Mad Rose Gallery’s Mercantile, 5 Main St., Millerton
Eight contemporary female photographers — Barbara Bosworth, Han Feng, Kerry Madigan, Jan Meissner, Beatrice Pediconi, Ava Pellor, Pamela Takiff, and Barbara Woike — showcase technical mastery and expressive insight, offering powerful, fresh perspectives through photography.
madrosegallery.com
Soukup Farms’ 11th Annual Harvest Festival
October 4 – 5
Soukup Farms, 271 Halls Corners Road, Dover Plains
Experience Soukup Farm’s annual harvest festival! Enjoy hayrides, a corn maze, and a pick-your-own pumpkin patch! Their kitchen will be serving up delicious fall-inspired foods such as chili, bratwurst, harvest bowls, and pulled pork sandwiches – with products sourced from local farms.
soukupfarms.com
Harvest Full Moon Hike & Music
Tuesday, October 7
Winnakee Land Trust, Rhinebeck
Enjoy an enchanting evening at Drayton Grant Park with live music, breathtaking Hudson Valley views, sunsets, and moonrise. Family-friendly with light snacks provided; bring your own drinks or enjoy a picnic.
winnakee.org
Highlands Cup
October 8 – 12
Keane Stud 217 Depot Hill Road, Amenia
The Highlands Cup brings five thrilling days of world-class show-jumping, October 8–12, featuring Major League Show Jumping, the $340,000 CSI5 Grand Prix, live music, luxury hospitality, and rare cars. Don’t miss the live concerts – Third Eye Blind featuring Dinosaur Jr. on October 10th, or Brothers Osborne featuring LeAnn Rimes on October 11th!
siloridgemasters.com
Vaudeville Night at Savage Wonder!
October 10
Savage Wonder, 139 Main St., Beacon
savagewonder.org
Step right up for Savage Wonder’s Vaudeville Nights in Beacon! Hosted by Bradford Scobie, this variety show bursts with comedy, theater, improv, circus tricks, live music, magic, and unforgettable surprises.
Fishkill Farms Fall Harvest Festivals
October 11-12, 18-19, 25-26
Fishkill Farms, Hopewell Junction
fishkillfarms.com
Every weekend in October, including 10/13 Columbus Day, visit Fishkill Farms for their autumn fun packed Harvest Festival Weekends! Pick apples straight from the orchard, get lost in their corn maze, enjoy wagon rides, hard cider, live music, food, and more!
Floral Film Night
Saturday, October 11
Foxtrot Farms & Flowers, Stanfordville
Join Foxtrot for an evening blending art and agriculture with a picnic hour, short film screenings on flowers and farming, and a panel discussion with local creatives.
foxtrotfarmflowers.com
Oldtone Music Festival & Fall Benefit Bash
October 11
Chaseholm Farm, 115 Chase Rd., Pine Plains
Support Oldtone’s community of artists and musicians by joining their unique music festival and fundraiser farm party! Participation is preservation, as they say. Get ready for a night full of music and dancing, with over 20 different artists performing live at Chaseholm Farm!
oldtone.org
Pick-Your-Own Dahlias Experience
Saturday, October 11
Bear Creek Farm, Stanfordville
Join Bear Creek Farm for a serene autumn afternoon, gathering vibrant dahlias from their fields, exploring the farm’s beauty, and enjoying a hands-on floral experience that lingers long after your harvest.
bearcreekfarm.com
Fall Foliage Half Marathon & 5k
Sunday, October 12
Dutchess County Fairgrounds, Rhinebeck
Celebrate fall in Dutchess County with a Half Marathon or 5K! Enjoy stunning foliage, and receive a custom shirt and finisher medal. Savor post-race food, fun, and community—perfect NYC Marathon prep.
fallfoliagehalf.com
Pumpkin Bombing
October 11-12 & 18-19
Old Rhinebeck Aerodrome, Red Hook
Take flight at Old Rhinebeck Aerodrome’s Pumpkin Bombing season finale! Experience historic aircraft, thrilling air shows, open-cockpit biplane rides, festive food, and family fun to close out an unforgettable season.
oldrhinebeck.org
Haunted History Ghost Tours
Friday, October 17
Old Rhinebeck Aerodome, Red Hook
Visit the Old Rhinebeck Aerodrome this October for a 70 minute walking tour of the property, filled with lost pilot tales, tragic adventure stories, and anecdotes of the haunted history of Rhinebeck.
oldrhinebeck.org
Rocky Horror 50th Anniversary Live Experience
October 17 & 18
Barton Orchards, 63 Apple Tree Ln., Poughquag
Celebrate Rocky Horror’s 50th Anniversary at Barton Orchards with RuPaul’s Drag Race star Loosey LaDuca, outrageous costumes, cult-classic chaos, live performance, and a thrilling costume contest. Make a day of it and get to the orchard early for the corn maze and haunted house!
bartonorchards.com
Molly Gochman’s Monuments to Motherhood and inseparable
Saturday, October 18
Maxon Mills, 37 Furnace Bank Road, Wassaic
Experience the unveiling of Molly Gochman’s Monuments to Motherhood and inseparable, featuring interactive outdoor artworks that honor caregiving, community, and connection through monumental bronze sculpture and tactile, Braille-inspired land art.
wassaicproject.org
New York State Sheep & Wool Festival
October 18 – 19
Dutchess County Fairgrounds, 6550 Spring Brook Ave., Rhinebeck
Celebrate two days of sheep and wool with workshops, kids’ activities, sheep shows, herding demos, fiber arts shopping, gourmet foods, and over 300 vendors showcasing weaving, knitting, basket-making, and more creative traditions.
sheepandwool.com
Kesicke Fall Festival
October 18-19 & 25-26
Kesicke Farm, Rhinebeck
Spend a crisp autumn day (or weekend) at the Kesicke Farm, exploring corn mazes, enjoying wagon and hay rides, meeting animals, and savoring cider donuts. Purchase pumpkins, fall decorations, and Kesicke natural meat-products at their farm stand.
kesickefarms.com
Poughkeepsie Farm Project Harvest Fest 2025
Saturday, October 25
Poughkeepsie Farm Project, 51 Vassar Farm Ln., Poughkeepsie
Celebrate fall at Poughkeepsie Farm Project’s Harvest Fest, a family-friendly day with live music, food trucks, farm tours, and kids’ activities. Enjoy craft drinks, a maker market, and support local farming, all while supporting Poughkeepsie families.
farmproject.org
Morning Light: Sunrise at Innisfree
Sunday, October 26
Innisfree Garden, 362 Tyrrel Rd., Millbrook
Experience the Hudson Valley’s fall beauty at Innisfree, opening before sunrise. Capture golden light, lake reflections, and vibrant foliage, while enjoying picnics, birding, art, and a full day immersed in nature.
innisfreegarden.org
Hocus Pocus Screening at Heritage Financial Park
October 30
Heritage Financial Park, 1500 NY-9D, Wappingers Falls
Join Gade-O-Ween at Heritage Financial Park for a spooktacular evening of Trunk-or-Treat, hayrides, games, and a big-screen Hocus Pocus. Enjoy concessions, costumes, and family-friendly Halloween fun for all!
heritagefinancialpark.com
