Visit These 5 Funky Fall Fests in the Hudson Valley

A grape stomping party, a redheaded get-together, and more from this week’s top picks for things to do in and around the Valley.

The League of Extraordinary Red Heads meets in Troy on Wednesday. / Photo courtesy of Duncan Crary Communications
The League of Extraordinary Red Heads meets in Troy on Wednesday. / Photo courtesy of Duncan Crary Communications

Night of the Walking Red VI

Ryan’s Wake, Troy
October 3, 5-8:30 p.m.

This Wednesday, The League of Extraordinary Red Heads reunites for its sixth annual meeting in the Hudson Valley. The fall fest brings together redheads from in and around the region to sip seasonal pumpkin ales and bond over their shared hair color. Admission is free and “un-red heads” are welcome to attend (although wigs are encouraged). The sunset group photo shoot takes place at 6:15 p.m., so plan to get there ahead of time if you want to join in on the picture party.

O+ Festival

October 5-7

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Celebrate the arrival of October at Kingston’s O+ Festival this weekend. The artistic event represents the exchange of medicine and art within the community in the hopes of promoting a collective wellbeing. The jampacked schedule begins on Friday and continues through Sunday evening. Whether you go to the kickoff parade and party on Friday, participate in a bikram yoga session or a collage workshop on Saturday, or taken in the live music and art exhibits on Sunday, you’ll walk away with a newfound appreciation for the Valley’s talented artists.

Field + Supply returns to Kingston this weekend. Photo by Scott Rudd / @scottruddevents
Field + Supply returns to Kingston this weekend. Photo by Scott Rudd / @scottruddevents

Field + Supply

Hutton Brickyards, Kingston
October 5-7; Friday 2-6 p.m, Saturday 11 a.m. – 6 p.m., Sunday 11 a.m. – 5 p.m.

If you’re itching to get a head start on holiday shopping, make the trek over to Kingston’s Hutton Brickyards. Now in its fifth year, Field + Supply brings together dozens of artisanal craftspeople and vendors from the Hudson Valley and beyond. If you’re feeling inspired, try your hand at one of the walk-up activity stations to learn how to screenprint, make botanical watercolor cards, or even design your own earrings.


Hudson Valley Brewery, Beacon
October 5, 6-10 p.m.

Now in its seventh year, the annual Catoberfest kicks off at Hudson Valley Brewery on Friday. Stop by the Beacon hotspot to snack on fall-friendly eats like beef stew, beer-poached kielbasa, and apple strudel. As you munch, tap your feet to the live tunes and sip on a local beer. Barb’s Butchery supplies the foodie treats, while Quinn’s donates the apple-packed dessert. A portion of all the funds raised will help support Mid Hudson Animal Aid (MHAA), a no-kill, free-range cat sanctuary in town.

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Hudson Valley October Grape Stomping Festival

Benmarl Winery, Marlboro
October 6-7; Saturday 11 a.m. – 7 p.m., Sunday 12-6 p.m.

If you’re looking for something unique to do this weekend, join Benmarl Winery for its seasonal grape stomp festival. Attendees can smash some grapes, which is a novel experience in itself, then kick back with a glass of wine and live music. Hayrides and vineyard tours are also available throughout the day. Children 12 and under are free.

Related: An Insider Guide to the Catskills Wine and Food Festival

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