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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.
Only a 90-minute train ride north out of New York City, 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. 12–14 and features fun and informative events at historic landmarks throughout the state, including several right here in Dutchess.
Be sure to check out the New York State Sheep and Wool Festival at the Dutchess County Fairgrounds in Rhinebeck Oct. 19–20, and there are 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 this October. Keep that camera handy! Feel free to share your pictures here and tag @DutchessTourism 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 featuring the mega slide, the newly refurbished haunted house, a corn maze, hayrides, a petting zoo, the wooden ship playground, and a dog park. There will be apples and pumpkins for picking. Stop by the taproom for local craft beer and hard cider. Don't forget to grab your fresh cider donuts. Each weekend will have its own theme: there will be Country Music Weekend (Sept. 28–29), BBQ and Brews (Oct. 5–6), Harvest Festival Weekend (Oct. 12–14); Boos & Brews (Oct. 19–20), and Tract-or-Treat Weekend (Oct. 26–27).
• Fishkill Farms, Hopewell Junction: Fishkill Farms hosts its annual harvest festival featuring live music each weekend in October. 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 Oct. 27, as well as Columbus Day/Indigenous Peoples Day, Oct. 14. 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.
• Kimlin Cider Mill, Poughkeepsie: The Cider Mill Friends host their 12th annual Old Fashioned Cider Tasting on Oct. 5 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 lots of kid-friendly fun, including Pygora Goat petting by Clover Brooke Farm, children's crafts 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 had been such 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.
• Locust Grove Estate, Poughkeepsie: Locust Grove presents two days of kid-friendly fun at its Harvest Fest on Oct. 26 and 27. The little ones will love the costume parade, the Harvest Hunt scavenger hunt, treats, games, performances and more!
• Poughkeepsie Farm Project: The Poughkeepsie Farm Project's second-annual Harvest Fest on Oct. 5 at the Vassar Preserves will celebrate the connections between food, farm and community. Enjoy a family-friendly, music festival atmosphere with several live performances, food trucks, local beer, wine, and cider vendors, a maker market, lawn games and more.
• Soukup Farms, Dover Plains: The 10th annual harvest festival will be held every Saturday (11–5 p.m.) and Sunday (11–4 p.m.) from Oct. 5–27, as well as on Columbus Day/Indigenous Peoples Day, Oct. 14 (11 a.m.–4 p.m.). 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. 5 and enjoy fall fun for visitors of all ages, including visits with farm animals, hayrides, craft vendors and live music. There will be plenty to eat, with homemade soup and baked goods from the Verplanck Garden Club, as well as food truck fare.
Related: Pick-Your-Own Apples, Pumpkins and More at These Dutchess Farms
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Thursday through Sunday, Oct. 3–6 at the Silo Ridge Field Club, Amenia
Silo Ridge Field Club hosts this elite competition featuring Olympic-level equestrian athletes and national classes for the top junior and amateur riders. Enjoy food truck fare, kids activities, a farmers market and live entertainment at the four-day event, which culminates with the $125,000 Silo Ridge Masters Grand Prix on Sunday. Click here to see the daily schedule and to purchase tickets. Tickets will not be sold at the gate.
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Saturday, Oct. 5, 7:30 a.m. on the Poughkeepsie Waterfront
Presented by the Mid-Hudson Rowing Association and the Hudson River Rowing Association, the Poughkeepsie Regatta is a three-mile rowing race on the Hudson River that offers a glimpse into the proud history of rowing on the Hudson. Crews from New York, New Jersey, and Connecticut will compete in Junior, Collegiate, and Masters events. Races run between the Culinary Institute of America campus in Hyde Park and the Mid-Hudson Bridge in Poughkeepsie, following the same course as the one used for the historic Intercollegiate Rowing Association (IRA) Regatta from 1895 to 1949. In fact, the best-selling book "The Boys in the Boat" — and the George Clooney film based on that book — tells the story of the University of Washington rowing team that prepared for the 1936 Olympics in Berlin by competing in the Poughkeepsie Regatta, which was an Olympic qualifying event. That same team won the gold medal for the United States in Berlin in true rags-to-riches fashion. In those days, Poughkeepsie was known as the "Rowing Capital of the World," and thousands of spectators — Gilded Age dignitaries and Franklin and Eleanor Roosevelt among them — lined the shores on both sides of the Hudson to see the action. These days, fans can watch the from places like Quiet Cove Park, Waryas Park, and Kaal Rock Park in Poughkeepsie. Of course, for the best view of all, walk out onto the The Walkway Over the Hudson, from which the starting line will be visible to the north and the finish line to the south.
Saturday and Sunday, Oct. 5 and 6, 10 a.m. at the Dutchess County Fairgrounds, Rhinebeck
Now in its fifth year, this unique Octoberfest offers something for everyone, combining the best of Oktoberfest traditions with a handcrafted twist. Taste seasonal food delights, sip a pint in the beer garden and enjoy live music and themed performers. Stick around for ongoing demonstrations from woodworkers, fiber spinners, metal forgers, jewelers — even an expert pumpkin carver! Take a relaxing horse-drawn carriage ride around the fairgrounds, and catch the weigh-in of giant pumpkins — one of which will likely top 1,200 pounds! Click here for complete details and to purchase advance tickets at a discounted rate.
Oct. 5–13 at multiple locations
Presented by the New York Cider Association, this festival celebrates all the best of the booming craft cider industry in the Hudson Valley and beyond. Here is a look at some upcoming cider-themed events right here in Dutchess. For details and updates, be sure to use the N.Y. Cider Trail app.
• Hard Core Grand Cider Tasting Celebration (Sept. 28, 12–5 p.m. at Boutique Wines, Spirits & Ciders, Fishkill): Taste over 40 hard ciders, from sweet to dry, traditional heritage to funky new trends. Meet cider makers and industry pros who can guide you through their range of products. All products being sampled will be available for purchase.
• Pottery Class and Cider Sipping (Thursday, Oct. 10, 4 p.m. at Fishkill Farms, Hopewell Junction): Enjoy a flight of Treasury Cider, Fishkill Farms’ own tree-to-bottle cider, as you craft a fall-themed plate with instruction and materials provided by Nature's Impact. Non-alcoholic cider alternatives will be available.
• Treasury Cider Pairing with Essie's Restaurant (Friday, Oct. 11, 6–9 p.m. at Essie's Restaurant, Poughkeepsie): Chef Brandon Walker of Essie’s Restaurant hosts an evening of meticulously crafted meals expertly paired with Treasury Cider.
Related: Top 10 Places to View Fall Foliage in Dutchess County
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Saturday, Oct. 5, 11 a.m.–4 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. A map of the participating locations will be provided, and guides will be stationed at each site to provide information and answer questions. Afterward, head to Old Adriance Farm in Staatsburg for the after-party from 4–6 p.m. featuring live music, locally produced, farm-fresh food and drinks. To purchase tickets, click here.
Sunday, Oct. 13, 8:30 a.m. at the Dutchess County Fairgrounds, Rhinebeck
Admire the beautiful fall colors as you test your skill and endurance in either the half-marathon or five-kilometer race. It's a perfect warm-up for the famous New York City Marathon, which will be held three weeks later on Nov. 3. Run for the fun of it or take a shot at one of the course records. Either way, it's sure to be a fun time! Every participant in both races will receive an official race shirt and a finisher medal. Stick around for post-race food and fun. Click here to register.
Oct. 19, 20, 26 and 27 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 Amenia, Dover Plains, Wingdale, Poughquag, Hopewell Junction, LaGrangeville, 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 Dutchess Tourism's Inspiration Finder Arts & Culture Trail
Sunday, Oct. 20, 3 p.m. at Edgewater, Barrytown
The Fall Concert at Edgewater will feature the Hudson River Consort performing a selection of French Baroque music for strings in Edgewater’s intimate parlor. A light reception will accompany the performance. Click here to reserve tickets. A riverfront estate built in 1824 for Rawlins Lowndes Brown and his wife, Margaretta Livingston Brown, Edgewater was once owned by writer Gore Vidal. The estate is open to for public tours every third Saturday, May through October.
Friday, Oct. 25, 6:30 p.m. at Staatsburgh State Historic Site, Staatsburg
Join author Debra Bruno as she discusses her new book, "A Hudson Valley Reckoning: Discovering the Forgotten History of Slaveholding in My Dutch American Family." The book tells the story of Debra's deep dive into the lives of her ancestors in the Hudson Valley, some of whom were enslavers. Through her research, Debra came in contact with Eleanor Mire and learned that they both descended from families from Greene County. They also discovered that Debra’s Dutch ancestors had enslaved one of Eleanor’s African American ancestors, a revelation about which Debra wrote in a 2020 Washington Post Magazine article called “History Lessons.” Eleanor provided a moving epilogue in Debra's book. At this event at the Mills family's Gilded Age estate, Debra will give a presentation on her research, followed by a book signing and light refreshments. Click here to complete the required registration.
Oct. 10–15, 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.
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