Fall is on the horizon here in the heart of New York’s Hudson Valley, and September is a wonderful time to visit Dutchess County.
Our acres and acres of rolling farmland are offering up their bountiful harvests and supplying our many world-class restaurants with plenty of fresh farm-to-table produce. Views of the Hudson River and the surrounding highlands will soon be set ablaze by autumn's colorful splendor. It's prime picking season for apples and/or pumpkins at our local farms — including Barton Orchards in Poughquag; Cedar Heights Orchard in Rhinebeck; Dykeman Farm in Pawling; Fishkill Farms in Hopewell Junction; Greig Farm in Red Hook; Mead Orchards in Tivoli; Meadowbrook Farm in Wappingers Falls; and Rose Hill Farm in Red Hook — and a hayride with the family and some cider donuts on a crisp autumn afternoon is a memory that will last a lifetime.
Here is a list of 10 (okay, 11) guaranteed-to-please events in Dutchess County this September. Always keep that camera handy, and feel free to share your photos here and tag @DestinationDutchess on social media.
Plus, check out our Labor Day Spotlight for tips on making this holiday weekend a memorable one here in Dutchess, and use our guide to Fall Food, Craft Beverage and Harvest Festivals when planning your autumn getaways.
Happy travels!
Throughout September 2026 at various locations
The annual Hudson River Valley Ramble is a popular event series that highlights the fascinating history, diverse culture, plentiful natural resources and awe-inspiring landscape of the Maurice D. Hinchey Hudson River Valley National Heritage Area and the Hudson River Valley Greenway. Hinchey, a native New Yorker, served for 20 years in the U.S. House of Representatives from 1993–2013 and was a vocal proponent of environmental protection and conservation. The “Ramble” events are generally outdoor events that celebrate the splendor of the Hudson Valley and Hinchey’s efforts to preserve it. There are quite a few “Ramble” events scheduled in Dutchess County, including nature hikes, farm tours, historic site visits, music festivals, art exhibitions, canoe excursions, and so much more. Click here for details. Several “Ramble” locations are also participants on the Destination Dutchess Zen Finder Outdoor Experience Trail, a curated itinerary of one-of-a-kind outdoor experiences. Click here to obtain your free pass.
Related: Top 10 Hidden Gem Hikes in Dutchess County
• Art Studio Views Open Studio Tour (Sept. 5–7, 2026): Labor Day weekend is the perfect opportunity to enjoy this free, self-guided tour featuring roughly 30 artists — including painters, sculptors, photographers, ceramic artists, textile artists and mixed media artists — in Northern Dutchess and Southern Columbia counties.
• Wassaic Project Open Studios (Sept. 13, 2026): Explore the studios of the Wassaic Project’s September residents in Luther Barn.
• Poughkeepsie Open Studios Art Tour (Sept. 12 and 13, 2026): Enjoy a free, self-guided art tour in Poughkeepsie and meet local artists in their studios! Partake in family-friendly art-making activities, artist demonstrations, interactive experiences and more. You’ll meet dozens of artists working in a wide range of mediums in various studios.
• Rhinebeck Arts Walk (Sept. 19. 2026): On the third Saturday of the month from June through October, galleries, studios and businesses with exhibition spaces in Rhinebeck open their doors and allow visitors to learn about a variety of artistic styles and mediums and explore the creative process.
• Public Art in Poughkeepsie Tour (By appointment, April through October, 2026): Led by award-winning muralist Franc Palaia, this tour includes 35 indoor and outdoor murals, sculptures, historical monuments and works of stained glass in downtown Poughkeepsie. Highlights include the New Deal-era murals commissioned by Franklin D. Roosevelt, large-scale contemporary murals, the Civil War and Vietnam War monuments and more. Call (845) 505-3123 to make reservations.
Friday, Saturday and Sunday, Sept. 4, 5 and 6, 2026, at Tymor Park, LaGrangeville
Dozens upon dozens of hot-air balloons will take to the skies over the Hudson Valley during Labor Day weekend at one of Dutchess County's most popular festivals. Among the festival favorites are the tethered hot-air balloon rides, full hot-air balloon flights, morning yoga, fireworks, live music and entertainment, food trucks, a beer and wine tent, local vendors, a whole bunch of family activities and more. Bring a picnic blanket and chairs and watch the action from the designated picnic area. Click here to purchase tickets (no tickets will be available at the gate).
Sept. 2, 16 and 30, 2026, 1 p.m., at Mount Gulian Historic Site, Beacon
History is, quite literally, at your fingertips this September at one of the Hudson Valley's most fascinating historical sites. At Mount Gulian's exclusive White Glove Tours, you will have the opportunity to examine artifacts representing 300 years of history at Mount Gulian dating back to the time when Indigenous people inhabited the banks of the Hudson River. Put on a pair of white, cotton curatorial gloves, and you can hold items from the museum collection, including precious family letters; documents and artifacts from the 18th and 19th centuries; English and Dutch family bibles; women’s and men’s Victorian Era clothing; military artifacts and more! The White Glove Tour includes a tour of the Verplanck family homestead, the circa 1730 Dutch Barn, and the Heritage Garden. Call (845) 831-8172 or email info@mountgulian.org to book your White Glove Tour.
Friday, Saturday and Sunday, Sept. 11, 12 and 13, 2026, at Germania of Poughkeepsie
Put on your favorite lederhosen and head to Germania of Poughkeepsie for an authentic, three-day Bavarian fall festival experience complete with live music and dancing, games and activities for the kiddos, and, of course, plenty of tasty German food and beer! Musical acts will include the Dave Betz Band, The Bratwurst Boys, Alpine Squeeze and Bernie's Orchestra. Be sure to catch a traditional German dance performance by Germania Almrausch Schuhplattler Verein. It's sure to fill your heart with the spirit of "Gemütlichkeit" (a feeling of warmth, friendliness, and good cheer)! Click here for details.
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Select dates throughout September 2026 at Bannerman Castle, Pollepel Island, Beacon
Relax and enjoy a scenic cruise out to Pollepel Island and enjoy a one-of-a-kind theater experience, as Bannerman Castle provides the perfect setting for performances of "Dracula: The Journal of Jonathan Harker." Duane Boutté portrays Jonathan Harker, along with nine other characters in this tour de force thriller. The show is performed in front of the Bannerman Residence (the smaller castle). Click here to purchase tickets, which include the boat ride to and from the dock in Beacon — which is within walking distance of the Beacon train station on the Metro-North Hudson Line.
Saturday, Sept. 19, 2026, 11 a.m.–6 p.m., Village of Rhinebeck
What a great way to spend a late-summer Saturday! Stroll down Livingston and Chestnut streets in the Village of Rhinebeck and enjoy performances by local musicians playing on front porches everywhere you turn. Grab a bite to eat and a beverage from a variety of food vendors. Click here for a list of participating musicians.
Saturday, Sept. 19, 2026, 10 a.m.–10 p.m., in the Village of Red Hook
The streets of Red Hook will be filled with music all day and into the night during this popular annual festival. Stay tuned for details on this year's lineup of performers and activities. There will be plenty of delicious food available from local food trucks, and lots of Hudson Valley cider products available in the cider tent. Click here for updates.
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Saturday and Sunday, Sept. 19 and 20, 2026, at Orvis Sandanona Shooting Grounds, Millbrook
There is fun for the whole family at the annual Orvis Game Fair, which features two solid days of clay-shooting competitions, fly-casting and shooting lessons, falconry and hunting-dog exhibitions, and game-cooking demonstrations, along with a variety of hands-on activities for the kids. Plus, you’ll find dozens of exhibitors and vendors, food concession and more! It’s a weekend-long celebration of the fun, excitement and camaraderie of the sporting life and the great outdoors. For more details, click here.
Related: Top Fishing Spots in Dutchess County
Saturday, Sept. 26, 2026, 2 p.m. at the Poughkeepsie Family Partnership Center
Get ready to dance and sing along and let your spirit soar! Arts Mid-Hudson presents the seventh-annual Hudson Valley Gospel Festival, a wonderful afternoon of gospel singers, choirs and praise dancers. Experience the Hudson Valley Gospel Festival Choir, led by Dinesa Hansen Johnson, and the Hudson Lily of the Valley Praise Dancers, led by Linda Molina, along with invited regional gospel artists as they take the stage with dynamic vocals, uplifting movement, and high-energy performances. To reserve tickets, click here.
Sunday, Sept. 27, 2026, 11 a.m.–5 p.m., Main Street, Beacon
Held annually since 1977 on the last Sunday of September, Spirit of Beacon Day is a celebration of all the best of what the city has to offer. This year's theme will be “Unity in the Community.” Head to Main Street for live music, local vendors, and the parade, which will be held from 1–2 p.m. Click here to learn more.
