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Prost! 12 Oktoberfest Events in the Hudson Valley

Adobe Stock / Karepa

Oktoberfest is happening now in the Hudson Valley, and everyone’s breaking it down Bavarian-style with brats, pretzels, and brews galore.

By Raphael Beretta, Zarah Kavarana, Alexandra Rivera, Sabrina Sucato, and Kait Waterman

It’s time to bust out your lederhosen and welcome Oktoberfest, a traditional German fall festival that’s perhaps better known to most Americans as the biggest beer fest of the year. The celebration dates back to the early 19th century and was intended to celebrate the marriage of Prince Ludwig of Bavaria and Princess Therese von Sachsen-Hildburghausen in 1810. Though the original Oktoberfest lasted less than a week (October 12–17), today the festival is more readily celebrated between mid-September and early October in the U.S. to accommodate weather concerns.

Whether this is your first Oktoberfest or you’re a seasoned sauerkraut fiend, join us in raising a brew-filled Bavarian bierstein mug to these Oktoberfest events in our region. Cheers! Or, as the Germans say, “Prost!”

5th Annual Oktoberfest

Sugar Loaf Engine Company, Chester
September 17, 3-8 p.m.

Mark your calendars, Hudson Valley! Oktoberfest is happening in Chester. Throughout the day, attendees can dig into hot dogs, bratwurst, soft pretzels, and more while sipping on German brews. Cornhole, giant Jenga, and other games are available for playing.

Oktoberfest at Peekskill Brewery

Peekskill Brewery, Peekskill
September 18, 12-5 p.m.


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Do you have what it takes to out-yodel all the other yodelers in the Hudson Valley? This brewery in Westchester will host a day of Oktoberfest fun with a yodeling contest, vendors, German food, a stein holding competition, and live music from The Brass Rascals. Contest winners will receive a prize package filled with Peekskill Brewery goodies, making this a hot attraction for beer lovers in the region.

Oktoberfest Weekend 2022 at Tilly Foster Farm

Tilly Foster Farm, Brewster
September 23, 6:30 p.m.


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The best Hudson Valley festivals take place on scenic farms. Brewster’s Tilly Foster Farm holds a celebration of all things beer and brats. Bring blankets and lawn chairs to enjoy a performance by David Clark titled Song Attic, his tribute to Billy Joel. At $30 a person, this event is perfect for a friends and family evening!

The Hudson Valley Oktoberfest

Ice Time Sports Complex, Newburgh
September 24-25, 11-5 p.m.; October 1-2, 11-5 p.m.

Whether you’d prefer to jam out to the tunes of Alpine Squeeze or try your hand at the Oktoberfest Olympics, this event packs German-inspired fun into two autumn weekends. If axe throwing and a cornhole championship aren’t quite your speed, sit back and enjoy potato pancakes, bratwurst, and enough homemade desserts to make you burst at the Hudson Valley Oktoberfest. This stellar festival sold out last year, so snag your tickets while you still can!

Oktoberfest Weekend at Long Lot Brewery

Long Lot Farm Brewery, Chester
September 24, 12-9 p.m.

Let the Oktoberfest games begin at Long Lot Brewery! Do you have what it takes to be the ultimate champion? Compete in a keg squat, a stein lift, a keg toss, and, of course, a cornhole tournament. Plus, music from TJ Santiago and Dusty, Dave and The Boys keep things festive. Be sure to check out the newly reopened beer garden, pick up a unique Long Lot Oktoberfest stein, and don your best attire.

Sleepy Hollow’s Annual Oktoberfest!

Kingsland Point Park, Sleepy Hollow
September 24, 1-5 p.m.

If you’ve never paid a visit to the legendary village of Sleepy Hollow, consider attending this Oktoberfest event. With cider and hot chocolates for the kids, local food and beer for friends, and live Bavarian music for everyone, the Sleepy Hollow Annual Oktoberfest is the perfect occasion to ring in autumn.

Riedlbauer’s Resort Presents Nussy’s Oktoberfest

Riedlbauer’s Resort, Round Top
September 24, 3 p.m.

It’s not too late to enjoy authentic Germain cuisine at Riedlbauer’s Resort in Round Top. This second Oktoberfest weekend at Nussy’s Bier Garten features live music, dancing, and a bit of Hudson Valley history. The mountaintop resort offers breathtaking views and a stunning biergarten. With live music by Mountain Xpress starting at 6 p.m., it’s the complete family-friendly festival.

Oktoberfest Weekend

Mountain Brauhaus, Round Top
September 24, 6-10 p.m.


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The Hudson Valley’s mainstay German restaurant hosts its own version of Oktoberfest at the end of September. The celebration loops in music from traditional bands, authentic Schuhplatter dancing, and German food and drink.

Oktoberfest 2022 at Putnam County Golf Course

Putnam County Golf Course, Mahopac
September 30, 6:30-11 p.m.

Play a round of golf and then celebrate with a stein at Putnam County Golf Course. This Oktoberfest celebration costs $37 per person (children 12 and under are half off at the door) and features a menu of seasonal staples like bangers, knockwurst, and kielbasa alongside Hudson Valley barbecue. The Amish Outlaws will take the stage for a full evening of raucous music.

Walktoberfest on the Walkway

Walkway Over the Hudson, Highland & Poughkeepsie
October 1-2, 12-5 p.m.


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Now this is how to do festival fun in the Hudson Valley. On the first weekend in October, the Walkway Over the Hudson State Historic Park partners with the Hudson Valley Rail Trail to host a Walktoberfest Essential Farmers Market. All proceeds from the $25 tickets benefit Friends of the Walkway and Hudson Valley Rail Trail and give guests access to samples from local distilleries, restaurants, and wineries.

Handcrafted Octoberfest: A Family Harvest Celebration 

Dutchess County Fairgrounds, Rhinebeck
October 1-2, 10 a.m. – 5 p.m.

Quail Hollow Events, the team behind the fall-favorite Woodstock-New Paltz Arts & Craft Fair, hosts a reimagined Oktoberfest celebration. This open-air event pays homage to German traditions with a distinct focus on local artisans and makers. Peruse art, hand-spun crafts, pumpkin carving, woodworking, and much more. Dance to live music and check out a wild animals demonstration.


Bangallworks, Stanfordville
October 22, 1-4 p.m.


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This Dutchess County community space goes all out for Oktoberfest as a fundraiser for the Stanford Recreation Campaign.  Be sure to wear your very best holiday attire—lederhosen and all—as there will be awards for best dressed individual, couple, and family. But the competition doesn’t end there; attendees can also go head-to-head in Oktoberfest’s test of strength: stein holding. For those who’d rather chef it up, enter the slaw-off with your most creative slaw-based concoction. Of course, there will also be live traditional music, bites, and brews galore. If you plan to attend the event, be sure to RSVP here.

Related: The Best Events & Fests to Hit in the Hudson Valley This Fall