UPDATING FOR 2026... STAY TUNED!
There is nothing quite like autumn in New York’s Hudson Valley, and a visit to Dutchess County this October promises to make your heart sing!
See the fall foliage in all its colorful beauty as the Hudson Highlands blaze forth in unparalleled magnificence.
Feel the crisp, refreshing breeze and hear the soft rustling of fallen leaves as you hike along one of our many scenic trails.
Taste the goodness and purity of our local farmland in our world-renowned farm-to-table cuisine.
Smell the unmistakable aroma of fresh-baked pies and apple cider donuts as you venture into one of our orchards to pick your own apples.
Located in the heart of the Hudson Valley — only a 90-minute train ride north out of New York City and less than four hours from Boston and Philadelphia — getting to Dutchess is easy-peasy. Once you arrive, there is so much to see and do. The foliage is the star of the show — click here to see weekly foliage reports — but Dutchess also features fascinating historic sites, a vibrant arts and culture scene and all the outdoor adventure the Hudson River has to offer.
I Love N.Y.’s Path Through History Weekend is set for Oct. 10–12, 2026, and features fun and informative events at historic landmarks throughout the state, including several right here in Dutchess. Stay tuned for details on all sorts of fun Halloween events and attractions for kids and adults alike.
Here is a list of 10 more can’t-miss events (okay, this one goes to 11) here in Dutchess County in October 2026. Keep that camera handy! Feel free to share your pictures here and tag @DestinationDutchess on social media.
Happy travels!
Throughout October at multiple locations
• Barton Orchards, Poughquag: Head to Barton Orchards each weekend in October and enjoy a full day of fun for the whole family. There will be live music and entertainment, pig races, the fun park, the corn maze, the haunted house, a petting zoo, and the dog park. There will be apples and pumpkins for picking (call ahead for availability). Stop by the taproom for local craft beer and hard cider, and don't forget to grab your fresh cider donuts. Each weekend will have its own theme: there will be Country Music Weekend (Sept. 26–27), the Hudson Valley Apple Festival (Oct. 3–4), Harvest Festival Weekend (Oct. 10, 11 and 12); Boos & Brews (Oct. 17–18); Tract-or-Treat Weekend (Oct. 24–25); and the Beer, Whickey and Wine Festival (Nov. 7).
• Fishkill Farms, Hopewell Junction: Fishkill Farms hosts its annual harvest festival featuring live music each weekend from mid-September through October, as well as Columbus Day/Indigenous Peoples Day, Oct. 12. Sit back, relax and enjoy a wagon ride in the orchard or venture into the corn maze. Taste apple cider donuts and delicious food straight from the grill, wash it all down with some hard cider from the Treasury Cider Bar (Fun fact: They named it Treasury Cider in honor of the farm’s founder, Henry Morgenthau Jr., who, after a career in farming and conservation, served as the Secretary of the Treasury under President Franklin D. Roosevelt). Make sure to book an appointment to pick your own apples, pears, pumpkins and more!
• Kesicke Farm, Rhinebeck: Harvest festivals are scheduled every Saturday and Sunday through Nov. 1, as well as Columbus Day/Indigenous Peoples Day, Oct. 12. Enjoy a stroll in the corn maze, wagon rides and hayrides. Feed and pet farm animals and enjoy delicious apple cider donuts. While you're there, pick up some of Kesicke Farm's own farm-raised, natural beef, pork, lamb, and chicken. You can also enjoy their farm-fresh eggs all year round. The farm is cash-only; there is an ATM on site.
• Kimlin Cider Mill, Poughkeepsie: The Cider Mill Friends host their 14th-annual Old Fashioned Cider Tasting on Saturday, Oct. 3, at the historic mill. Taste authentic Kimlin Cider, which is only available at this event, as well as other local sweet and hard ciders. There will be live music by John Mueller, and the From the Ground Up food truck will be serving up tasty treats. Enjoy apple fritters (a historic Dutch treat) by the Fishkill Historical Society, and lots of kid-friendly fun, including farm animals by the John Jay High School Future Farmers of America, children's crafts by Crazy Over ART, a meadow maze, and a scavenger hunt. Take a behind-the-scenes Mill tour and enjoy a demonstration of cider pressing with an antique press, live music and more. The Mill, with its mid-19th century barn, was part of a larger farm originally owned and operated by the Kimlin family since the early 1850s. It was a popular local attraction for decades, but it closed in 1990. The property was sold to a developer whose plan was to demolish the mill and build something different in its place. However, The Cider Mill Friends of Open Space & Historic Preservation purchased the property in 2008 and saved the mill from the wrecking ball. Preservation and restoration efforts have been ongoing ever since.
• Poughkeepsie Farm Project: The Poughkeepsie Farm Project's third-annual Harvest Fest on Saturday, Oct. 3, at the Vassar Preserves will celebrate the connections between food, farm and community. Enjoy a family-friendly, music-festival atmosphere with several live performances, headlined by Pulso de Barro, along with local food and drink vendors, a makers market, kids activities and more. Plus, you can pick your own flowers!
• Soukup Farms, Dover Plains: Soukup Farms' 12th annual harvest festival will be held every Saturday and Sunday from Oct. 3–25, as well as on Columbus Day/Indigenous Peoples Day, Oct. 12. Enjoy a scenic hayride out to the pick-your-own pumpkin patch and corn maze, as well as lots of fun family activities! Be sure to pick up some delicious Soukup Farms maple syrup and maple products.
• Stony Kill Farm, Wappingers Falls: Head to Stony Kill Farm on Oct. 3 and enjoy fall fun for visitors of all ages, including live music, visits with farm animals, barn and livestock tours, and craft vendors and demonstrations. Food will be available to purchase, including food truck fare, homemade soups from the Verplanck Garden Club, and a variety of baked goods and beverages.
Related: Pick-Your-Own Apples, Pumpkins and More at These Dutchess Farms
.jpg)
Oct. 2–4 and Oct. 9–11, 2026 at Keane Stud, Amenia
Get ready for two world-class equestrian show-jumping competitions held back-to-back, making Amenia the place to be for a two-week celebration of sport and culture! The Discovery Land Company Masters Horse Show features three action-packed days (Oct. 2–4) of elite show-jumping, including the $116,500 Discovery Land Company CSI3 Grand Prix. The Highlands Cup Horse Show features three more thrilling days (Oct. 9–11) of elite competition, including the fan-favorite Major League Show Jumping team competition and the $340,000 Highlands Cup CSI5 Grand Prix. Along with the horse shows, you'll enjoy the Bridlemont Concours at Highlands, a world-class showcasing of more than 30 rare and iconic cars and motorcycles on Oct. 11. Click here for complete details.
Sunday, Oct. 4, 2026, 10:30 a.m.–5:30 p.m., at multiple locations
This self-guided tour highlights historic barns and working farms in Rhinebeck, Red Hook and Tivoli and includes some fun and educational activities along the way! If you like, pack a picnic, as there are sure to be some prime spots to sit and enjoy a relaxing lunch. Before you embark on your tour, pick up guidebooks, coffee and donuts between 10:30 a.m. and 12:30 p.m. at Wilderstein's Historic Carriage House in Rhinebeck. Guides will be stationed at each participating site to provide information and answer questions. Afterward, head to the after-party featuring live music from The Decoys, seasonal farm-fresh fare from Chef Meri Puccio, local wines, and more. To purchase tickets, click here.
Saturday and Sunday, Oct. 10 and 11, 2026, 10 a.m.–5 p.m., at the Dutchess County Fairgrounds, Rhinebeck
Now in its seventh year, this unique Octoberfest offers something for everyone, combining the best of Oktoberfest traditions with a handcrafted twist. You'll find over 120 juried exhibitors showcasing their work in a wide variety of media. As you shop, you can also taste seasonal food delights, sip a pint of craft beer and enjoy live music and themed performers. Stick around for ongoing demonstrations from woodworkers, fiber spinners, metal forgers and jewelers. Take a relaxing horse-drawn carriage ride around the fairgrounds, and catch the weigh-in of giant pumpkins! Click here for complete details and to purchase advance tickets at a discounted rate.
Related: Top 10 Places to View Fall Foliage in Dutchess County
• ClayWay Annual Studio Tour (Oct. 17 and 18, 2026, 10 a.m.–5 p.m., at multiple locations): Visit nine clay studios, including several here in Dutchess County, during this self-guided, two-day event and meet 25 ceramists working in a wide variety of styles and techniques. For details and a printable map of locations, click here.
• ArtEast Open Studio Tour (Oct. 17, 18, 24 and 25, 2026, at multiple locations): This annual event is a highlight of the fall art season in the Hudson Valley! More than 25 artists in eastern Dutchess once again open their studios for this free, self-guided driving tour through Wingdale, Poughquag, Hopewell Junction, Patterson, Pawling, and Holmes. There will be plenty to see, with artists of many disciplines opening their studios. It’s the perfect chance to meet and greet talented local artists and get a behind-the-scenes look at where they create their masterpieces. Click here for details.
Related: Connect with your creativity with the Destination Dutchess Inspiration Finder Arts & Culture Trail
...
Saturday and Sunday, Oct. 18 and 19, at the Dutchess County Fairgrounds, Rhinebeck
A Dutchess autumn tradition continues with the annual Sheep and Wool Festival, two days filled with all things sheep and wool! There will be plenty of vendors and workshops devoted to all sorts of weaving, knitting and basket-making topics and techniques, as well as with kids’ activities. Don't miss the book signing, presented in partnership with Merritt Bookstore in Millbrook, and be sure to stick around for the sheep shows and the used equipment auction. Click here to learn more.
Oct. 9–14, New York City to Saratoga Springs
Enjoy autumn foliage, beautiful Hudson Valley scenery and fine dining at the Culinary Institute of America in Hyde Park on this six-day bike ride that begins in Manhattan, makes stops in Brewster, Poughkeepsie, Hudson and Albany before finishing in Saratoga Springs and includes a trip across the Walkway Over the Hudson during peak foliage season. Most of this roughly 250-mile ride is on bike paths which are relatively flat and easy to navigate. This tour is customizable, meaning participants can select any combination of days and the cost of the tour is prorated. Click here for complete details, including a day-by-day itinerary.
