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woman drinking wine at a festival with the "Upstate Weekend Plans" text written across the Hudson Valley, NY photo.

What to Do in the Hudson Valley This Weekend Sep 6 – Sep 8

By inside + out | September 4, 2024

Wine + Food Fest, Comedy Stand-up, Oldtone Music Festival, RC Jamboree, Kayaking Tour, Toga Party, and more! There is something for everyone. Choose your event below…

🛶 Chatham, Fri Sep 6th, 9am – 12pm. Floating Friday at Hand Hollow.
Borrow or bring a kayak to float around Meizinger Lake while helping remove invasive water chestnuts. All are welcome at this fun, friendly volunteer event. Info HERE.

✈️ Red Hook, Fri Sep 6th – Sun Sep 8th, 2:30pm. The 54th Annual Radio-Controlled (RC) Airplane Jamboree at Old Rhinebeck Aerodrome.
Continuing 54 years of tradition with the RC Model Airplane competitions between airshows. Info HERE.

🎨 Athens, Fri Sep 6th, 5pm – 7pm. First Fridays at Athens Cultural Center.
New exhibitions, art lovers, and drinks await! Join us at the Athens Cultural Center to immerse yourself in art, share ideas, and feel the welcoming vibe. See you soon! Info HERE.

🖼️ Kingston, Fri Sep 6th, 5:30pm – 7:30pm. Opening soirée “In Repose: The Paintings of Kristin Osterberg” at Kingston Social.
Fall 2024 brings a new exhibition where we’ll explore a genre we haven’t shown before, a type of expressionistic realism made magical by the talents of painter Kristin Osterberg. Info HERE.

🤡 Catskill, Fri Sep 6th, 8pm. Catskills Comedy Festival Sneak Peek: Hudson Valley Improv.
Hudson Valley Improv hits the stage with their fast and furious improv games and a sneak peek of their original Law & Order spoof, CRIME DRAMA @theavalonlounge. Info HERE.

🎶 New Paltz, Fri Sep 6th – Sun Sep 8th, Music on the Mountain at Mohonk Mountain House.
Music abounds as the mountaintop summer ends with compelling + powerful artists. A weeklong festival highlights an ocean of musical expressions including Natalie Merchant, Scott Chasolen, Scott Robinson + more. Info HERE.

🎻 Hillsdale, Fri – Sep 6th – Sun Sep 8th. Oldtone Music Festival at Cool Whisper Farm.
A packed weekend of music, dancin’, camping, food, crafts + hands-on instrument workshops. Info HERE.

🍷 Rhinebeck, Sat Sep 7th + Sun Sep 8th, 11am – 6pm. Hudson Valley Wine + Food Fest.
Experience the Hudson Valley Wine & Food Festival with 300+ vendors, gourmet delights, fine arts, live music + chef demos in a perfect summer setting. Info HERE.

🍻 New Paltz, Sat Sep 7th, 12pm – 5pm. Hudson Valley Craft Beverage Festival at Twin Star Orchards.
Tasting of 25+ producers of delicious craft cider, wine, beer, spirits, mead, hard seltzer, kombucha, and cocktails. Enjoy + support small businesses. Info HERE.

💛 Kingston, Sat Sep 7th, 12pm – 8pm. 2nd Annual Street Festival The Heart of Midtown: Go All In for Mental Health.
A street festival combining a day of music, art workshops, information, and resources dedicated to helping people cope with mental health issues, especially teens and young adults. Info HERE.

📜 Woodstock, Sat Sep 7th, 3pm – 4pm. In Defiance – Runaways From Slavery in the Hudson Valley.
The Historical Society of Woodstock will present a talk by Susan Stessin-Cohn on her newest research and the second edition of her publication, “In Defiance: Runaways from Slavery in New York’s Hudson River Valley 1735-1831.” Info HERE.

🏛️ Kingston, Sat Sep 7th, 4pm – 8pm. Keegan Ales 21st Birthday TOGA Party.
Celebrate 21 years with an “Animal House” style Toga party! Info HERE.

💃 Woodstock, Sat Sep 7th, 6pm – 9pm. Reggae Woodstock Junior Toots at Woodstock Playhouse.
Junior Toots, son of reggae legend Toots Hibbert of Toots & The Maytals, was born in St Mary, Jamaica, and has captivated international audiences with his high-energy ska and reggae performances, soul-filled vocals, and socially relevant lyrics, continuing his father’s legacy on the world stage. Info HERE.

🎸 Kingston, Sat Sep 7th, 8pm. Cat Power Sings Dylan: the 1066 Royal Albert Hall Concert at UPAC.
Cat Power recreates Bob Dylan’s iconic 1966 “Royal Albert Hall Concert,” where he famously went electric + changed rock history. Info HERE.

🍎 Marlboro, Sun Sep 8th, 10am – 6pm. Weed Orchards & Winery Honeycrisp Festival.
It’s time for all things Fall! Live music, delectable apple-themed food and drinks, apple picking, hayrides, and so much more! Info HERE.

👨‍🌾 Explore Hudson Valley’s vibrant Spring to Fall Farmers Markets + CSA, which support small local farms, foster a sense of community, and promote healthy living. From live entertainment to family-friendly activities, they offer a fun and diverse experience for all! Info HERE.

👉 Know of more cool events happening in the Hudson Valley/Catskills area?
Leave them in the comments below.

Have a wonderful weekend from Inside+Out Upstate NY!

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