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Top 10 Dutchess Events in October

Date Published: September 26, 2023

There is nothing quite like autumn in New York’s Hudson Valley, and a visit to Dutchess County this October promises to be a treat for all five senses. 

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. 7–9 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. 21–22, 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! 

Soukup Farms, Dover Plains
Soukup Farms, Dover Plains

Weekend Harvest Festivals 

Throughout October at multiple locations 

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! Click here to buy festival tickets. 

• 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 new mega slide, a rock n’ roll 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. 30-Oct. 1), Harvest Festival Weekend (Oct. 7-9); the Jack O’Lantern Jubilee (Oct. 14-15), Boos & Brews (Oct. 21-22) and Tract-or-Treat Weekend (Oct. 28-29). Click here for updates. 

• Soukup Farms, Dover Plains: The ninth annual harvest festival will be held every Saturday (11-5 p.m.) and Sunday (11-4 p.m.) from Sept. 30 through Oct. 22, as well as on Columbus Day/Indigenous Peoples Day Oct. 9 (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. Click here to learn more. 

Related: Pick-Your-Own Apples, Pumpkins and More at These Dutchess Farms 

Treasury Cider, Fishkill Farms, Hopewell Junction
Treasury Cider, Fishkill Farms, Hopewell Junction

New York Cider Week 

Oct. 6–15 at multiple locations 

Presented by the New York Cider Association, this 10-day festival celebrates all the best of the booming craft cider industry in the Hudson Valley and beyond. Dutchess participants include Treasury Cider at Fishkill Farms in Hopewell Junction and Boutique Wines, Spirits and Cider in Fishkill. Stay tuned for details on tastings, tours and more. For updates, click here. Treasury Cider is one of the participating establishments on the Dutchess Tourism Taste Finder, a mobile passport program that serves up perks at the various craft beverage tasting rooms and tap houses on the trail. Show your Taste Finder pass at participating locations to unlock each producer’s special offer, including free flights, pints, or custom glassware. Click here to obtain the pass that fills your glass! 

Related: Top 10 Places to View Fall Foliage in Dutchess County

1895 Stanford White Barn, Kaatsbaan Cultural Park, Tivoli
1895 Stanford White Barn, Kaatsbaan Cultural Park, Tivoli

Winnakee Land Trust Historic Barns Tour 

Saturday, Oct. 7, 11 a.m.–4 p.m. at multiple locations 

Now in its 15th year, 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. Light refreshments will be provided before the tour. Afterward, head to the 1895 Stanford White Barn at Kaatsbaan Cultural Park for the after-party from 4–6 p.m. featuring live music, farm-fresh food and locally produced beer, wine and cider, along with a raffle. To purchase tickets, click here.

Livingston Mansion, Clermont State Historic Site, Germantown
Livingston Mansion, Clermont State Historic Site, Germantown

“A Conversation About Slavery in the Hudson Valley” 

Saturday, Oct. 7, 1:30–3:30 p.m. at Clermont State Historic Site, Germantown 

Through a Facebook group called “I’ve Traced My Enslaved Ancestors and Their Owners,” Debra Bruno and Eleanor Mire learned that they both descended from families from Greene County, on the western bank of the Hudson River. They also discovered that Debra’s Dutch ancestors had enslaved Eleanor’s African American ancestors, a revelation about which Debra wrote in a 2020 Washington Post Magazine article called “History Lessons.” At this event on the South West Lawn at the Livingston Mansion, Debra and Eleanor will recount this story in a speech that alternates between them. They will share and discuss pictures of their ancestors, including the “Van Bergen Overmantel,” which was painted in about 1733 and is now housed at the Fenimore Art Museum in Cooperstown. The iconic painting by John Heaten is a visual representation of Dutch life in America. It depicts the Marten Van Bergen farm in Greene County and features African, Indigenous and European people — including, most likely, both Debra’s and Eleanor’s ancestors. Click here to reserve tickets for this event, which is presented by the Maurice D. Hinchey Hudson River Valley National Heritage Area.

Barn Star’s Fall Antiques Show 

Sunday, Oct. 8, 11 a.m.–4 p.m. at the Dutchess County Fairgrounds, Rhinebeck 

Browse through exceptional items from about 150 vendors at this annual event, which will be held in three buildings at the Dutchess County Fairgrounds. You’ll find all sorts of antiques, including fine art, folk art, decorative art, textiles, vintage clothing, samplers, weathervanes, furniture, quilts, jewelry, pottery, silver, Oriental rugs and more! Grab a bite to eat at the food truck. Enjoy a free trolley ride from the front gate to the show. Tickets are available online or at the gate and are good for the entire weekend. Click here to purchase tickets online; buy before Sept. 30 to lock in the discounted rate. 

Four Brothers Drive In Theatre, Amenia
Four Brothers Drive-In Theatre, Amenia

Fall Craft Fair and Movie Double Feature 

Sunday, Oct. 8, 11 a.m.–4 p.m. at Four Brothers Drive-In Theatre, Amenia 

What could be better than a fall craft fair featuring approximately 30 vendors offering everything from handmade jewelry and candles to toys and books? How about a craft fair followed by a double-feature movie event at one of Dutchess County’s most unique destinations? That’s what the folks at Four Brothers Drive-In Theatre were thinking when they planned this annual event. Grab a bite to eat at Four Brothers Pizza Inn next door or at the Grand Shack at the drive-in. Click here for details. 

Rhinebeck Porchfest 

Saturday, Oct. 14, 11 a.m.–6 p.m. in Rhinebeck 

Take a walk down Livingston and Chestnut streets and catch performances by local musicians on front porches everywhere you turn. The big finale will be on the corner of Platt and Mulberry streets. Grab a bite to eat from a variety of food trucks as you enjoy all types of music. Name a musical style, and you’ll likely see it represented at Rhinebeck Porchfest. Folk, bluegrass, rock, blues, swing, jazz, alternative, punk, reggae, country – there's even a washboard band on the schedule! It’s a family-friendly music event you don’t want to miss. For updates, click here.

Kimlin Cider Mill, Poughkeepsie
Kimlin Cider Mill, Poughkeepsie

Cider Mill Friends' Cider Tasting 

Saturday, Oct. 14, 11 a.m.–3 p.m. at Kimlin Cider Mill, Poughkeepsie 

The Cider Mill Friends present their 11th Annual Old Fashioned Cider Tasting event at the historic Kimlin Cider Mill. Taste samples of local sweet and hard ciders, including Kimlin Cider, which will only be available at this event. There will be plenty of attractions and activities for the kiddos at this family-friendly event, too, like Pygora Goat petting by Clover Brooke Farm, arts and crafts projects, and the Poughkeepsie Public Library District's Rover Roaming Library van. Grab a bite to eat from the Reconnect Foods food truck, and make sure to pick up some delicious apple fritters — a traditional Dutch dessert — served up by the Fishkill Historical Society. There will also be behind-the-scenes Mill tours, a demonstration of cider pressing with an antique press, live music from the Roundabout Ramblers, and more! Click here for more information and to reserve tickets. The Kimlin Cider 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. The cider mill, which had been such a popular local attraction for decades, 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.    

ArtEast Open Studio Tour 

Oct. 14, 15, 21 and 22 at multiple locations 

This 17th annual event is the must-see event 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. You can request a brochure by emailing info@arteastdutchess.com.   

Related: Unlock discounts at some of Dutchess County’s best art galleries and performance venues with the Dutchess Tourism Inspiration Finder.

Hudson River Sloop Clearwater
Hudson River Sloop "Clearwater"

Walktober Fest Sails Aboard the Hudson River Sloop "Clearwater" 

Saturday, Oct. 21, 1 and 4:30 p.m. at Waryas Park, Poughkeepsie 

Step aboard the Hudson River Sloop "Clearwater" for a sail out of the historic City of Poughkeepsie for two sails during Walkway Over the Hudson's "Walktober Fest," one at 1 p.m. and one at 4:30 p.m. "Clearwater" will be docked in Waryas Park as a part of the Pumpkin Sail community event series, and there will be deck tours and dockside programs for the community that will include pumpkin-themed activities, music and refreshments available free of charge, but with a suggested donation. Click here to purchase tickets. Launched in 1969, “Clearwater” is a replica of the Dutch boats that sailed up and down the Hudson River in the 18th and 19th centuries. Nicknamed “America’s Environmental Flagship,” “Clearwater” was the brainchild of folk singer, activist and New York native Pete Seeger, who was distraught over the condition of the Hudson River after decades and decades of industrial pollution. Seeger decided to “build a boat to save the river,” and with the help and support of his wife, Toshi, and a group of fellow musicians and activists, he did just that. They believed the boat would allow people to experience the beauty of the mighty river and be inspired to preserve it. In 2004, “Clearwater” was named to the National Register of Historic Places for its groundbreaking role in the environmental movement. 

Bonus Event 

“Silver Linings: Celebrating the Spelman Art Collection” 

Sept. 30 through Jan. 28 at the The Frances Lehman Loeb Art Center, Vassar College, Poughkeepsie 

Vassar College’s Frances Lehman Loeb Art Center presents the exhibition “Silver Linings: Celebrating the Spelman Art Collection,” which, through the work of about 40 artists, was created to uplift the legacy of artists of African descent, many of whom have been overlooked by mainstream art museums. Spelman College is a historically Black liberal arts college for women in Atlanta which began collecting art in 1899. Vassar, which has been co-ed since 1969 but was founded by Matthew Vassar as a college for women in 1861, was the first college or university to include an art collection as part of its original plan. “Silver Linings” highlights the parallels between the two colleges’ commitment to art, as Vassar will celebrate 160 years of collecting art this academic year and the 30th anniversary of "The Loeb.” Spelman has a similar history, which includes the creation of the Spelman College Museum of Fine Arts 27 years ago. This exhibition at "The Loeb” is the first show in a five-stop, nationwide tour for “Silver Linings.” The permanent collection at “The Loeb” features more than 22,000 works, including paintings, sculptures, drawings, photographs, textiles, and glass and ceramic pieces. Admission is free and open to all. Click here for details. 

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