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Here’s What to Do in the Hudson Valley This Week


A drive-thru fair food festival, an event for hot-air balloon lovers, and more from this week’s picks for Hudson Valley events.

Drive-Thru Fair Food Festival

Orange County Fair Speedway, Middletown
September 24-27

Fairs might not have been a thing in the Hudson Valley this summer, but fair food is! This weekend, the Orange County Fair rounds up its favorite vendors for a foodie celebration in Orange County. The free-to-attend event features treats like funnel cakes, fried Twinkies, sausages and peppers, and more, so head to the website to browse the drive-thru food route in advance.

Olana After Hours

September 24, 6-7 p.m.

Did you know that Olana State Historic Site in Hudson once had a working orchard? Learn more about the apple scene in the Hudson Valley during a chat with Alejandro del Peral of Nine Pin Cider and Jake Samascott of Samascott Orchards. Registration is $10, with Zoom links sent out before the event.

Hudson Valley Hot-Air Balloon Festival

Tymor Park, Union Vale
September 25-27

Yes, the Hudson Valley’s hot-air balloon festival is happening this year. For its 29th annual celebration, the fest heads to Tymor Park for a drive-in event to keep everyone safe. Attendees can watch the balloons take flight from the comfort of their cars and are welcome to bring their own food, beverages, blankets, and chairs while social distancing. Reservations are required, so book a spot online now.

Livestream Concert: Amy Helm

September 25, 8 p.m.

In collaboration with City Winery, Caramoor presents a special livestream concert with singer-songwriter Amy Helm. The ticketed event costs $10 and is the opening night of the Westchester art center’s vibrant fall season in the Hudson Valley.

Record Store Day: Drop II

Darkside Records, Poughkeepsie
September 26, 9 a.m. – 9 p.m.

Continuing with its three-part Record Store Day shindig, Darkside Records invites locals for socially distant shopping and entertainment in Poughkeepsie. Record lovers will have a blast browsing the exclusive records at the store, which will host sales and giveaways throughout the day. Plus, did we mention The Poughkeepsie Grind will be serving up free coffee, too?

EscapeMaker’s Sixth Annual Applepalooza

Stone Ridge Orchard, Stone Ridge
September 26, 12-6 p.m.

The more apples, the better is the motto to follow at EscapeMaker’s apple-centric event. Held at Stone Ridge Orchard, the event loops in pick-your-own apples, cider and kombucha tastings, activities for kids, and donut-eating contests. All to-dos will have social distancing measures in place to ensure good, healthy fun for all.

Looking for more Hudson Valley happenings this week? Our apple picking guide is a must for family fun, while our drive-in movie theater guide has the top places to catch an al fresco flick. Plus, take a peek at our monthly insider guide for book festivals, craft fairs, and pre-Halloween happenings.

If you’re craving a jaunt outdoors, our sculpture park, stargazing, and waterfall guides are must-reads. On the adventure front, local explorers won’t want to pass up a scroll through our camping, kayaking, and rail trail guides. For foodies, our recipe index has everything from beautiful breakfasts and lunches to divine desserts straight from Hudson Valley chefs. You won’t want to miss any of it!

Want even more? Check out our Hudson Valley event calendar guide.

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