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deli with the "Upstate Weekend Plans" text written across the photo for the Hudson Valley, NY

What to Do in The Hudson Valley This Weekend Sep 8 – Sep 10

By inside + out | September 7, 2023

Music festivals, Wine & Food 🍷 + more! Upstate NY has events for all ages this weekend 🌞 Take your pick below…

🎸 Stone Ridge, Fri Sep 8th – Sun Sep 10th. Meadowlark Fest.
Enjoy some of the most storied names in Americana, indie rock, and experimental music with a roster of local and emerging artists at Stone Ridge Orchard! Info HERE.

⚾️ Wappingers Falls, Fri Sep 8th, 7:05 PM. Snooki Night.
The Jersey Shore star herself will be in the building for a one-of-a-kind event with a post-game fireworks show! Info HERE.

🎷 Kingston, Fri Sep 8th, 7:30 PM. Jazz at Senate Garage.
A jazz show featuring John Menegon at Senate Garage with wine, beer + snack. Info HERE.

🪩 Woodstock, Fri Sep 8th, 10:00 PM. The Nightcap Cabaret.
Stop by for a nightcap at Colony. Enjoy a show filled with the glitz and glamour of vintage acts, and also the campy side of burlesque that will have you laughing your head off! Info HERE.

🧚 Hudson, Sat Sep 9th. Second Saturday Sessions.
A faerie-tale fusion of dark cabaret, gothic polka and post-punk music with Dustbowl Faeries at Park Theater Hudson. Info HERE.

👩🏽‍🌾 Marlboro, Sat Sep 9th + Sun Sep 10th, 10:00 AM – 3:00 PM. RootsNCulture X Liberated Lands Festival.
A celebration of nature, community, and liberation. Music, art, and vegan food made with ingredients harvested locally. Join us to connect and celebrate the power of the Earth and the power of the people. Info HERE.

🍷 Rhinebeck, Sat Sep 9th – Sun Sep 10th, 11:00 AM – 5:00 PM. HV Wine & Food Fest.
Celebrate the bounty of the Hudson Valley with wine, cider, spirits, craft beers, + gourmet foods at Dutchess County Fairgrounds! Info HERE.

🛍️ Beacon, Sat Sep 9th, 11:00 AM – 9:00 PM. Beacon Second Saturdays.
Second Saturday is a lively day into night celebration of Beacon’s galleries, restaurants and other businesses on the second Saturday of each month. Learn More HERE.

🌭 Catskill, Sat Sep 9th, 12:00 PM. Catskill Food Festival.
Food Trucks, Food Vendors, & Live Music by Wyld Blu at the Catskill at Dutchman’s Landing Park. Info HERE.

🪇 Shady, Sat Sep 9th, 4:30 PM – 6:30 PM. Cacao Kirtan Consciousness.
Beginning with a heartfelt Cacao ritual followed by a guided meditation to further open the heart and elevate the senses. Then, drop into the enchanting rhythms of Kirtan, a meditative mantra journey of ancient origins. Info HERE.

🎭 Woodstock, Sat Sep 9th + Sun Sep 10th, 7:00 PM + 5:00 PM. Mystery at the Art Colony.
The Historical Society of Woodstock presents a Victorian Era Whodunit set in 1902. At the Mescal Hornbeck Community Center. Info HERE.

🪕 Mount Tremper, Sat Sep 9th, 5:00 PM. A Night of Mountain Music with Two Dark Birds.
An end-of-summer fete celebrating live music, food, friends and the outdoors. All the stuff that’s best about our community. Info HERE.

🚜 Cold Spring, Sat Sep 9th, 5:00 PM – 8:00 PM. Bids & Bites: Annual Auction & Summer Soirée.
Bid on unique items in support of the next generation of farmers. Info HERE.

🏞️ Millbrook, Sun Sep 10th, 10:00 AM – 12:00 PM. Hudson River Valley Ramble – Forest Ecology Walk.
Dr. Charles Canham will lead an interpretive walk along the Wappinger Creek Trail sharing the history of Dutchess County’s forests from the first settlers in 1750 to the current day—over 250 years of land use patterns that have transformed Hudson Valley landscapes. Info HERE.

🕵️‍♂️ Woodstock, Sun Sep 10th. 11:00 AM – 1:00 PM. A Wonderful Woodstock Scavenger Hunt.
Enjoy a wide variety of carefully curated checkpoints as you interpret creative tasks, accept wacky challenges, and get outside your comfort zone! Info HERE.

🌽 Hudson Valley Area, Check out the Hudson Valley Farmer’s Markets near YOU!
From year-round to seasonal markets, here’s your insider’s go-to Hudson Valley Farmer’s Markets. 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!


  • Final four performances of Bridge Street Theatre’s I AM BARBIE Sept 7-10. Thursday thru Saturday at 7:30pm, Sunday at 2:00 (sorry, Sunday’s matinee is already sold out). Tickets at

    September 7, 2023

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