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Upstate Weekend Plans with fall foliage leaves

What To Do In The Hudson Valley This Weekend Oct 14-16

By inside + out | October 14, 2022

Harvest festivals, 🍂 foliage train rides, theater and more! Stop by the Hudson Valley + Catskills this weekend for events for all ages ☀️

🎭 Tivoli, Fri – Sun Oct 14th – 16th, Village Kind at Tivoli Town Hall.

A documentary theater piece based on conversations with residents of Tivoli, NY, and historical documents presented by a cast of star-studded names in the industry! Read more about it from Inside+Out’s blog HERE. Benefit for the Tivoli firehouse capital campaign. Info & Tickets: Storyhorse Documentary Theater

🎃 Kingston, Fri – Sun, Oct 14th – 16th, 10:00 AM – 3:15 PM, Catskill Fall Foliage Adventure & Pumpkin Express.

Take a train ride on a Fall foliage adventure, with pumpkin picking. Info & Tickets: Catskill Mountain Railroad

🐑 Rhinebeck, Fri + Sat, Oct 15th + 16th, NYS Sheep & Wool Festival.

Peruse fiber and finished crafts, workshops, specialty food + drink, and petting zoo. Info: Dutchess County Tourism

🌾 Woodstock, Sat Oct 15th, 1:00 PM – 5:00 PM, Scarecrow Fest.

Scarecrow Fest will be a celebration for all ages. The event will feature fun opportunities to engage with the unique environment and culture of Woodstock. We have a super fun line up of activities, exhibitors, and vendors. Info: Woodstock Land Conservancy

🧺 Woodstock, Sat Oct 15th, 2:00 PM – 6:00 PM, Harvest Picnic Gala.

Woodstock Animal Sanctuary will feature a vegan picnic with open bar, exclusive vegan product gift bags, a silent auction, and more! Tickets + Donations: Woodstock Animal Sanctuary

🍺 Peekskill, Sat Oct 15th 2:00 PM – 8:00 PM, 14th Anniversary Block Party.

Peekskill Brewery’s 14th Anniversary Block Party will feature live music, food trucks, beer tents, local artisans, and family-friendly activities! Info: Peekskill Brewery

👻 Saugerties, Sat Oct 15th, 4:00 PM – 8:00 PM, Outdoor Halloween Nite Market.

Costume Contest for Adults, Children & PETS💀(LINEUP STARTS AT 5pm. Spooky vendor tents, Halloween music, food, baked goods + fun! Info: Stoned Homemade

🖼 Catskill, Sat Oct 15th, 5:30 PM – 7:30 PM, Fall Exhibitions Opening Reception + Afterparty.

Foreland Catskill features the opening reception of three exhibitions followed by an after-party. Info: Foreland Catskill

🏡 Kingston, Sat + Sun Oct 15th + 16th, 12:00 PM – 5:00 PM, 2022 Kingston Design Showhouse & Benefit.

Kingston Design Connection brings together designers, artists, makers, contractors and vendors to produce something truly unique in the region. All proceeds go to Ulster County Habitat for Humanity. Read more about it from Inside+Out’s blog HERE. Info + Tickets: Kingston Design Showhouse events

🍁 Hunter, Sat + Sun Oct 15th + 16th, Colors in the Catskills Fall Festival at Hunter Mountain.

Hunter’s Fall Festival features vendors, a DJ, drinks, live bands, and scenic skyride tix. Info: Hunter Mountain

🏃🏻‍♂️ Red Hook, Sun Oct 16th, Cider Donut Trail Race.

Hosted on Greig Farm, runners can participate in a 5k or a 1/2 mile race for kids. Enjoy the koi pond, friendly goats, cider donuts, + market. Info: Greig Farm

🥒 Rosendale, Sun Oct 16th, 10:00 AM – 5:00 PM, Rosendale International Pickle Festival.

Meet up to 100 vendors who sell pickles, groceries, hot food, baked goods, crafts and much more. Info: Rosendale International Pickle Festival


👉 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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