Upstate Fall Diary

Upstate Fall Diary

New month, new season, new opportunities. It’s hard to say goodbye to summer, but the Hudson Valley really shines in autumn. We’re embracing this season of warm sweaters and bonfires with open arms. Here are several upstate spots and festivals we plan to enjoy as the leaves change. Hope to see you out there! 


Starting in September, locals, tourists, and weekenders alike descend on farms to pick things. Usually it’s apples, but there are also grapes and berries and pumpkins. We especially love organic orchards; their practices protect the earth, farm workers, and us all. For raspberries, which can continue to grow late into the fall, we adore Westwind Orchard, which also has apples. There are so many other choices, too, most of them generational family businesses. For not-entirely-organic but still less-harsh growing practices, keep an eye out for IPM (integrated pest management) orchards. There’s Love Apple Farm in Ghent, Fishkill Farms in Hopewell Junction, Prospect Hill Farms in Milton, Rhinebeck Apples in Rhinebeck, and Stone Ridge Orchards in Stone Ridge, among many others. If you’re curious about the growing practices of any orchard, just ask. Most farmers are proud of their trees and happy to talk.

Woodsist Festival

The lineup of bands at this music festival, featuring Woodsist label family past and present, is not to be missed: Real Estate, Waxahatchee, Kevin Morby, Hand Habits, Whitney, and more. In the past, Woodsist has been held in California. This year, it’s at Arrowood Farms in Accord on 9/28. Book a room at the new Hotel Kinsley  for that night and you might just score a pair of festival tickets. Want more music in October? Graham Nash is performing songs and telling stories at Bethel Woods on 10/15.

Field + Supply

We never miss this modern makers craft fair, now in its sixth year. This fall, it takes place 10/11 to 10/13 at the Hutton Brickyards in Kingston. Expect a wide range of exhibitors, crafts, and goods (old and new) – all against the gorgeous backdrop of the Hudson River. The fair represents many aspects of why we call the Hudson Valley home: artisans, nature, culture, expansion, plus a lot of good friends. Stop by our table and say hello. When you head back into town, make sure to grab a beer at Kingston Standard.

Sheep and Wool

You don’t have to have a sheep to enjoy this yearly fiber-arts festival in Rhinebeck the weekend of 10/19. There are kids activities, demonstrations, and, yes, plenty of sheep. If you’re there to shop, there’s something for everyone: art, fiber, used sheep equipment, and even animals if you’re in the market. Workshops cover everything from felting to basketry to rug making.

Tivoli Street Painting Festival

Tivoli’s fun on any weekend, but on 9/28 it comes alive with its street painting festival. If you’re game, register early for a square and painting supplies. Or, go as an observer, and enjoy the live music and colorful community.


If you find yourself in Livingston Manor or Narrowsburg, head to either location of this lifestyle store founded by former Vogue design director Anna Bern. Her curatorial eye is unpatrolled. Browse furniture, clothing, and art. Pick up something to cozy to get you through the winter.

The Great Jack O’ Lantern Blaze

This wild display of over 7,000 illuminated jack o’ lanterns is just the thing for Halloween lovers young and old. They’re designed and hand-carved by a team of artisans, plus there’s a Museum of Pumpkin Art to visit with gourds done up as classic paintings and more. It’s open from mid-September to early November, and all proceeds go to Historic Hudson Valley, a non-profit.

Woodstock Film Festival 

This is a film lover’s festival. Now in its 20th year, it’s known to have retained its fiercely independent leanings. The average Netflix binger might recognize some but not all of the directors’ names (there’s is Noah Baumbach’s latest, Marriage Story), but chances are they’ll be captured by the narrative and documentary features plus shorts being shown 10/2 to 10/6. There are also panels and awards to attend. This year also marks the 50th anniversary of the Woodstock music festival, as well as the 100th anniversary of Woodstock as America’s oldest colony of the arts. A big year for all things Woodstock art.