The fall may even be the best time of the year in the Hudson Valley. Picturesque mountains shine with shades of yellows, reds, and browns with peak fall foliage. Local farms open their gates to apple picking and fresh cider donuts. Pumpkins line the roads. The air is crisp.
It’s also a time when the Hudson Valley boasts some of its very best fairs and festivals that attract locals and tourists alike.
We compiled a list of our top ten fall fests in the area. Several of them have already happened by the time of this publication, so remember them for next year. Don’t miss the rest!
Here’s what you need to know.
1. Hudson Valley Garlic Festival
9/28-9/29; Cantine Memorial Complex, Saugerties
This is the biggest garlic feasible in the Northeast, and possibly in the entire U.S. That’s why it’s topping our list.
“The festival has been a Saugerties tradition since 1989 when Pat Reppert started it at Shale Hill Farm,” said organizer Patricia Praetorius.
In 1990, over 425 garlic lovers attended the event in Reppert’s herb gardens, quadrupling the previous year’s attendance and stretching the facilities at the farm to their limits. In 1991, tickets were pre-sold to control the crowds, and Reppert had over 1500 phone calls. Ever since then,
The event has only continued to grow in success.
There will be over 200 booths of garlic farmers, food vendors, packaged food vendors, and crafters. Special for this year will be a beer garden featuring NYS craft beers. There will also be live entertainment each day, all day.
“If you love garlic the place to be on the last weekend in September is the Hudson Valley Garlic Festival,” said Praetorius.
2. Barton Orchard’s Harvest Festival Weekend
10/12-10/14; Barton Orchards, Poughquag
Apple picking season is officially here. Everything is opening with a bang during the fall festival weekend at one of the area’s favorite farms.
For the little ones, there is a corn maze, a fun park, hayrides, a wooden ship playground, farm games and activities, a petting zoo, and more.
Adults can enjoy the tap room that boasts a wide variety of beer and more. Food on site can be enjoyed at one of the many picnic tables.
The star of the show is the pick-your-own apples and pumpkins. A ticket to this fall festival gets you access to each of the activities.
If you can’t make it Barton Orchards hosts many events during peak season, including BBQs and Brews on October 5 and 6.
3. The NYS Sheep & Wool Festival
10/19-10/20; Dutchess County Fairgrounds, Rhinebeck
Over two days of fiber-filled fun, visitors can find 300 vendors, 90 workshops, fiber competitions,sheep and goat shows, and a lot more.
This year in particular, they are expanding their educational offerings.“You’ll see a few more slots added to our Shepherd’s Talks, which are geared toward aspiring shepherds and casual enthusiasts alike, and the Northeast Regional Fibershed will be back to share all the ways that wool producers and textile manufacturers interact in our area,” said Nena Johnson, festival manager.
When you’re there, expect to also find a fleece sale, book signings, barns full of fiber animals to meet close up: leaping llamas, a used equipment auction, demonstrations, and a daily livestock parade.
“The NYS Sheep & Wool Festival is the perfect Hudson Valley outing to celebrate fall,” said Johnson. “It really kicks off one of our most beautiful and recognizable seasons up here.”
4. Apples and Wine Fest at Weed Orchards & Winery
9/28-9/29, 10/5-10/6; Marlboro
Heading into the fall, Weed Orchards & Winery is likely to be packed on most weekends. Special programming includes an Apples and Wine Fest, where visitors can enjoy face painting, hayrides, live music, apple cider donuts, ice cream, and apple picking. It’s family- and dog-friendly, so bring everyone along.
Come back later in the fall on October 12 and 13 for the fall festival that offers all that and more, including fall-themed food and drinks, seasonal beers and sangria, pumpkin picking and painting, and caramel apples.
5. Windham’s 30th Anniversary of the Annual Autumn Affair
10/12-10/13; Main Street, Windham
This free outdoor street festival showcases this quintessential Hudson Valley’s downtown.
“It is centered around our beautiful downtown, promoting our unique shops and restaurants, and highlighting abundant recreational opportunities that help make Windham so special,” said Lisa Jaeger, Windham Chamber of Commerce board president.
For two days, Main Street is filled with live music, entertainment, food trucks, wildlife demonstrations, and haywagon and pony rides. Visitors can find over 65 arts and crafts vendors, baked goods, special tastings, and more.
New this year, they will have axe throwing and a baking contest. The Winham Mt. Club Sky Ride, a fan favorite for the best views, will be open. There is free parking when using the town shuttle.
“Come visit Windham during the prettiest time of year,” said Jaeger.
6. Handcrafted Octoberfest at Rhinebeck
10/5-10/6; Dutchess County Fairgrounds, Rhinebeck
An artfully reimagined Octoberfest will return to Rhinebeck for its fifth anniversary. Produced by Quail Hollow Events, the festival is centered around the concept of handmade. It’s infused with harvest energy and Oktoberfest staples like beer drinking and polka dancing.
You can find everything from one-of-a-kind goods by the finest makers and artisans to the Hudson Valley’s best wine and spirits. There will be seasonal grub, a beer garden, live musical performances, horse-drawn carriage rides, and even master pumpkin carving.
Kids will enjoy a family arts and crafts area with creative free play and a petting zoo.
“Handcrafted Octoberfest champions the craft, training and story behind each object and attraction,” said Ola Rubinstein, director of Quail Hollow Events, in a press release. “Featuring works of art and craft, but also gourmet specialty foods, local wine and spirits, and agricultural marvels, this celebration highlights the idea of small-batch and hand-spun, with lots of harvest fun for all ages on the side.”
7. Warwick Applefest
10/6; Warwick
With over 150 craft vendors, over 75 food vendors, four stages of live music, and apple pie baking and eating contests, this is a fall festival you don’t want to miss.
It’s been running since 1989, when it started out as just a simple harvest celebration. Today, it brings in over 30,000 visitors to the one-day event, traveling from neighboring states to experience the variety of Warwick’s apples, culture, and entertainment.
It’s produced by the Warwick Valley Chamber of Commerce, with festival proceeds benefiting them and some 50 local non-profits, for whom the event is their biggest annual fundraiser.
Admission is free. Inside there are farmers’ markets, a children’s carnival, nearby shops, restaurants, and more.
8. Walktoberfest Farmers’ and Makers’ Market
10/26-27; Poughkeepsie
The Walkway Over the Hudson hosts some of the most grand events in the region throughout the year. In October, its Walktoberfest Farmers’ and Makers’ Market brings a curated selection of Hudson Valley’s producers to the Hudson Valley Rail-Trail and west approach to Walkway Over the Hudson State Historic Park.
Visitors can find more than 150 vendors, including farms, distilleries, breweries, wineries, restaurants, artists, artisans, and more. Walktoberfest features not only farm-fresh products, food from local restaurants, and beer, wine, and spirits samples in a designated tasting area, but also art installations, locally made goods, a special area for children’s activities, and more.
All proceeds from Walktoberfest benefit the Friends of the Walkway and Hudson Valley Rail-Trail, who have partnered to present this farmers’ market.
9. Food Truck and Craft Beer Festival
9/21; Craryville
The sixth annual Food Truck and Craft Beer Festival at Copake Country Club invites guests on the first fairway of its 18-hole lakeside golf course for a day filled with food and craft beers.
The vendor lineup is made up of some of the best in the region, including Cousins Maine Lobster, Aloha Tacos, Supreme Soft Serve, Roe Jan Brewing Co., Copper’s Daughter Spirits, and more. There will be live music by Beer Stained Fiddle, games, and a bounce house,
Come hungry and expect free tastings throughout the day amongst beautiful views.
10. Cauliflower Festival
9/21; Margaretville
It’s the 20th annual Cauliflower Festival in the Catskill Mountains. The festival celebrates farming, cooking, and culture of the past, present, and future. There is cauliflower for sale, live music, a unique selection of vendors, community organizations and activities, and a large selection of foods.
Kicking off the day will be a tractor parade. Later on, enjoy a 1903 auto rally of antique and restored vehicles. While you’re there, you can also explore Main Street Margaretville by shopping locally.
Join the family! 
