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Top 10 Dutchess Events in September

Date Published: August 21, 2023

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.

Views of the Hudson River and the surrounding highlands are especially beautiful when set ablaze by autumn’s colorful splendor. 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.

From scenic hikes and bike rides to fascinating historic sites and a vibrant arts and culture scene, there is so much to see and do here in Dutchess all year long. Be sure to check out the 32nd annual Hudson Valley Hot-Air Balloon Festival at Tymor Park in LaGrangeville Sept. 1–3, as well as the 23rd annual Hudson Valley Wine & Food Festival at the Dutchess County Fairgrounds in Rhinebeck Sept. 9 and 10 — these events are always crowd-pleasers and seem to get bigger and better every year! 

And harvest festivals — complete with hayrides, apple-picking and fresh cider donuts — are huge hits at places like Fishkill Farms in Hopewell Junction and Barton Orchards in Poughquag.

Plus, for the first time since 2019, postseason baseball will return to Heritage Financial Park (formerly Dutchess Stadium) this September, as the Hudson Valley Renegades, the New York Yankees Class-A affiliates, have qualified for the South Atlantic League playoffs.

Here is a list of 10 more (okay, 11) can’t-miss events in Dutchess County this September. There is something here for everyone. Always keep that camera handy, and feel free to share your photos here or tag @dutchesstourism.com. 

Check out our Labor Day Spotlight for tips on making this holiday weekend a memorable one here in Dutchess.

Tivoli Bays
Tivoli Bays

Hudson River Valley Ramble

Throughout September at various locations

The annual Hudson 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, pollinator seminars, canoe excursions and so much more. Click here for details. Several “Ramble” locations are also participants on the Dutchess Tourism 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

Mural being painted in Poughkeepsie
Mural being painted in Poughkeepsie

Public Art Tours and Open Studios

ChaNorth Open Studios (Sept. 2): Explore the artists' private studios and connect with the community at ChaNorth in Pine Plains, which is the international artist residency of Chashama. To learn more, click here.

Art Studio Views Open Studio Tour (Sept. 2 and 3): Labor Day weekend is the perfect opportunity to enjoy this free, self-guided tour featuring 30 artists — including painters, sculptors, photographers, ceramic artists, textile artists and mixed media artists — in Northern Dutchess and Southern Columbia counties. Click here for details.

Poughkeepsie Open Studios Art Tour (Sept. 9 and 10): 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. For a list of participants and locations, click here.

Rhinebeck Arts Walk (Sept. 16): 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. Click here for a list of participants and their hours of availability.

Wassaic Project Open Studios (Sept. 17): Explore the studios of the Wassaic Project’s September residents in Luther Barn. Click here for information.

Public Art in Poughkeepsie Tour (By appointment, April through October): 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.

Kaatsbaan Cultural Park, Tivoli
American Ballet Theatre Performers Joo Won Ahn and Christine Shevchenko at Kaatsbaan Cultural Park, Tivoli (Photo by Quinn Wharton)

Kaatsbaan Fall Festival

Sept. 9–Oct. 1 at Kaatsbaan Cultural Park, Tivoli

The picturesque 153-acre campus at Kaatsbaan Cultural Park provides the wonderfully serene backdrop for the annual Fall Festival. Spread over three weekends, the festival features a series of enchanting dance and musical productions, both indoors at the Black Box Theater and outdoors on the Mountain Stage. They include performances of works by Kenneth MacMillan, Gemma Bond and Herman Cornejo on Sept. 9–10; the world premiere of "The Missing Fruit" by Roderick George, the founder and artistic director of kNoname Artist, on Sept. 22–23; performances by New York Theatre Ballet on Sept. 24; a performance by the baroque music band Ruckus featuring acclaimed line dance caller Sargent Seedoo on Sept. 29; and performances of Tan Dun's "Ghost Opera" featuring pipa virtuoso Wu Man and the Attacca Quartet on Sept. 30 and Oct. 1. For show times and ticket information, click here.

Hudson Valley Craft Beer Festival

Saturday, Sept. 16, 12:30–5:30 p.m. at Pete and Toshi Seeger Riverfront Park, Beacon

Local craft beer, live music and scenic views of the Hudson River — it’s the perfect combination for a fun late-summer Saturday afternoon! Sample more than 100 different beers, including products from right here in the Hudson Valley and across the country. Tunes by Art Thief, SSJB, Blue Museum and Folkano keep the party hopping all day. Grab a bite to eat from a food truck, shop from local vendors and stick around for games, giveaways and more. Click here for more details and to purchase tickets, including designated driver, general admission and VIP ticket options. 

Related: Dutchess Tourism Taste Finder Craft Beverage Trail

Vanderbilt Mansion National Historic Site, Hyde Park
Vanderbilt Mansion National Historic Site, Hyde Park

Guided Tour of the Vanderbilt Gardens

Sunday, Sept. 17 at the Vanderbilt Mansion National Historic Site, Hyde Park

On select dates throughout the spring and summer, the F.W. Vanderbilt Garden Association offers free guided tours of the formal gardens on the grounds of the Vanderbilt Mansion National Historic Site. Your trained tour interpreter will walk you through each garden and highlight its unique features and history. You’ll see thousands of blooms of all shapes, sizes and colors. This is the final scheduled tour for this season. Click here for more details and to register for a tour. The Vanderbilt Estate, with its “Millionaire’s View” of the Hudson River, was the lavish country home of Frederick and Louise Vanderbilt from 1896-1938.

Orvis Game Fair and Sporting Weekend

Sept 16 and 17, 9 a.m.-5 p.m. 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, hunting dog, and game cooking demonstrations; and a variety of hands-on activities for the kids. Plus, you’ll find dozens of exhibitors and vendors, food concession and a farmers market on both days! 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

Hardscrabble Music Festival

Saturday, Sept. 23, 10 a.m.–9 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. The day’s festivities start with some music and entertainment for the kiddos on the main stage, followed by teen bands from Community Music Space and the School of Rock in the afternoon. In the evening, performances begin at 6 p.m. 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.

Walkway Over the Hudson, Poughkeepsie
Walkway Over the Hudson, Poughkeepsie

Poughkeepsie Regatta

Saturday, Sept. 30, 7:30 a.m. at the Poughkeepsie Waterfront

The Hudson River Rowing Association and the Mid-Hudson Rowing Association team up to host this three-mile, head-style race following the historic course used by the Intercollegiate Rowing Association for the national collegiate championship races from 1895–1949. Crews will race downstream from the Culinary Institute of America's main campus in Hyde Park to the Mid-Hudson Bridge in Poughkeepsie, passing under the Walkway Over the Hudson State Park and rowing past several other Poughkeepsie Waterfront landmarks. There are great places to watch the races along the course. The Walkway Over the Hudson offers unencumbered views of the entire racecourse – along with breathtaking views of the Hudson River and surrounding highlands. Quiet Cove Riverfront Park, Waryas Park and Kaal Rock Park also offer prime viewing locations and parking. Click here for more information, including a schedule of the day’s events.

Hudson Valley Gospel Festival
Hudson Valley Gospel Festival

Hudson Valley Gospel Festival

Saturday, Sept. 30, 7-9 p.m. at the First Congregational Church, Poughkeepsie

Get ready to dance and sing along and let your spirit soar! Arts Mid-Hudson presents the annual Hudson Valley Gospel Festival, a wonderful evening of gospel singers, choirs and praise dancers. Featured performers include the Hudson Valley Gospel Festival Choir, the Praise Dance Team, and Miss Rene Bailey and the Rainbow Singers. To reserve tickets, click here. Remarkably, the First Congregational Church was founded in 1837 by a group of anti-slavery activists in Poughkeepsie who were reportedly dissatisfied with their own churches’ unwillingness to oppose “the buying and selling human beings or holding them in involuntary servitude.” That is certainly praiseworthy!

What’s Out There Weekend: Rhinebeck and the Mid-Hudson Valley

Sept. 30 and Oct. 1 at various locations

Presented by The Cultural Landscape Foundation, What’s Out There Weekend events are held across the country and showcase each location’s unique attractions and history. This particular event features an action-packed weekend of free, expert-led tours of parks, gardens and open spaces throughout Dutchess County. Participating locations include Wilderstein Historic Site and 'T' Space Reserve in Rhinebeck; Staatsburgh State Historic Site in Staatsburg; Locust Grove Estate, the Springside National Historic Landmark, College Hill Park, Vassar College, the Walkway Over the Hudson State Historic Park and the Poughkeepsie Rural Cemetery in Poughkeepsie; Edgewater in Barrytown; Hackett Hill Park, the New Guinea Community, Bellefield, the Home of Franklin D. Roosevelt National Historic Site, the Eleanor Roosevelt National Historic Site and the Vanderbilt Mansion National Historic Site in Hyde Park; Mount Gulian Historic Site, Denning's Point and Long Dock Park in Beacon; Innisfree Garden in Millbrook; Wethersfield Estate and Garden in Amenia; and Blithewood Garden and Montgomery Place in Annandale-on-Hudson. Click here for additional information and to register for these fantastic events.

Bannerman Castle, Pollepel Island
Bannerman Castle, Pollepel Island

Bonus Event

“The Anastasia File” at Bannerman Castle

Sept. 8 and 9 at Bannerman Castle, Pollepel Island, Beacon

Relax and enjoy a scenic cruise out to Pollepel Island, home of historic Bannerman Castle, for a stage reading of “The Anastasia File” featuring the actors Brian Petti, Ron Morehead, Emily Clare Zempel and Audrey Rapoport. A brilliantly executed drama, “The Anastasia File” seeks to answer the unsolved mystery of the daughter of Nicholas II, the last emperor of Russia. Was Anastasia executed with the rest of the Imperial Family in 1918, or was she the girl discovered in an asylum in 1920? Click here to purchase tickets, which include the boat ride from the dock in Beacon — which is within walking distance of the Beacon train station on the Metro-North Hudson Line — to the island and back again.

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