Tilly’s Foster Farm Oktoberfest | September 20
Tilly’s Farm in Brewster brings a whole new spin on Oktoberfest with “Piano Men.” The performance is a face-off between David Clark as Billy Joel and Bill Connors as Elton John. The tribute concert will feature classics like “I'm Still Standing” and “Piano Man.” A bar and beer truck will serve seasonal beers and cocktails. The show starts at 8:00 and the doors open at 6:30. Tickets can be purchased online for $30.
Mountaintop Oktoberfest | September 20-22
The Mohonk Mountain house has a packed schedule for its three- day Oktoberfest. From Friday to Sunday the Mountain House will have all sorts of boozy events from the Tapping Ceremony to the Cannon Commencement. The festival starts on Friday with a parade of local breweries, wineries, cideries and spirits. They'll serve traditional German food like Beef Rouladen with Potato Pancakes, Veal and Pork Dumplings, and Pork Schnitzel and Spätzle. The events are open to any Mountain House guests as well as anyone with ticket reservations.
Bear Mountain Oktoberfest | September 21-22, 28-29, October 5-6, October 12-13
Bear Mountain hosts New York's largest free Oktoberfest, bringing a slice of the Bavarian tradition to the Hudson Valley. The festival is much more than just drinking. Eight different musical groups will entertain the crowds including Jimmy Sturr Orchestra, an 18-time Grammy Award winner on October 21, and Fritz’s Polka Band will tie off the festival on the last day. Festival goers can find European dishes like pierogies, waffles, and pretzels. The festival runs from 11am to 1pm.
Oktoberfest at Rough Cut Brewing Co. | September 28-29
Get ready for two days of live music, delicious German fare, and family-friendly fun in Kerhonkson—all paired with your favorite Rough Cut beers. The festival now has expanded to the outdoor area for even more festivities, including a stein-holding contest, games for all ages, and exciting raffle giveaways! Pre-purchase a limited-edition commemorative stein for just $20.! Your stein includes: The first pour of our traditional Marzen-style Oktoberfest beer, a raffle ticket for a chance to win fantastic prizes plus, all refills during the event will be a generous 20-ounce pour for the price of a standard pint! You can stop by Rough Cut from 12- 9pm.
Long Lot Farm Brewery Oktoberfest | September 28-29
Long Lot’s free Oktoberfest has all the staples of the German Festival: music, games, food and of course- beer. This family-owned farm in Chester brews with all locally sourced ingredients. On Saturday, you can catch Brotherhood & Sons of Hudson and on Sunday Bill L Quintet will hit the Oktoberfest stage. You can grab a bite to eat at 2 Hacks in a Shack food truck and enjoy discounted stein refills all weekend.
Kingston Maennerchor and Damenchor Oktoberfest | September 28
This will be Kingston Maennerchor’s 4th Annual Oktoberfest event. All meals include a potato pancake with applesauce, pretzel with mustard, sauerkraut, and a dessert of plum cake. You choose chicken or two bratwursts ($24) orcChicken and two brats ($30), with additional brats for sale for $3.. While you enjoy a delicious dinner, Joe Unger will be the event’s musical guest. You can stop by the Maennerchor from noon to 5 p.m.
Hunter Mountain Oktoberfest | September 28-October 13
Hunter Mountain has all the Oktoberfest works with traditional food and beer while also showcasing live bands and local vendors. They also hold a steinholding contest for guests over 21. Steinholding is the Bavarian game of strength in which participants hold one liter of beer out in front of them with a straight arm. The festival is free to enter and park and is open to all 11am to 5pm.
Crystal Brook Resort Mountain Brauhaus Oktoberfest | October 4-5
The Mountain Brauhaus is known for its classic Bavarian beerhouse experiences and with its location near Blackhead Mountain trailhead, hikers and tourists turn to the restaurant for a classic pint, or liter, of German beer. The festival is full of live music from German bands, and authentic schuhplattler dancing.
Chatham October Feast | October 5
The October Feast is full of local food and beverages like newly opened Fork & Whisk and Stony Kill Coffee. The family-friendly event offers pumpkin decorating, a magic show, hay rides, and a Ratatouille screening. You can listen to live music from Insolent Willies, Love Button, and Whiskey Highway. Celebrate the harvest season in the Village of Chatham from 11am till -10pm.
Hudson Oktoberfest Upper Depot Brewing Company | October 5
For this year’s block party, Upper Depot is bringing together more breweries, more food vendors, more live music, more hours, and less cost thanks to a sponsorship from Columbia County. Some of the local breweries include Hudson Brewing Company, Return Brewing, and Subserving Malting and Brewing. Pre-sale tickets are $20 until September 29 and include your first pour of beer, admittance into contests, and the first 250 attendees will receive a commemorative stein. Tickets are available in the Upper Depot taproom or online. You don’t want to miss this great community event! October 5, 12:00-6:00 pm.
Handcrafted Octoberfest at Rhinebeck: A Family Harvest Celebration | October 5-6
Get ready for an unforgettable experience as Handcrafted Octoberfest returns to the Dutchess County Fairgrounds.! Celebrating its fifth anniversary, this festival combines the best of Oktoberfest traditions with a vibrant, handcrafted twist, promising an event perfect for all ages. Produced by Quail Hollow Events, Handcrafted Oktoberfest offers much more than beer—though you'll find plenty of that. This festival has earned a spot in Sunshine Artist Magazine's 200 Best of 2024, showcasing the nation's top contemporary craft fairs. It’s a celebration that has something for everyone! The festival runs October 5, 10am-6pm, and October 6, 10am-5pm.
Hudson Valley Oktoberfest | October 12-13
At this year’s Hudson Valley Oktoberfest, located at the scenic Craigville Park In Goshen, guests can enjoy craft beer, traditional German food and other delicious snacks from the 20+ food trucks, and over 100 craft vendors. You can drink beer in a traditional Bavarian dining hall while listening to German music artists. On Saturday you can catch Melina & The Oompahs and Black Dirt Bandits. On Sunday Glen Miller, Bratwurst Boys, Die Schlauberger and Garret Gardner will perform. The festival goes on all day from 11am-11:00pm.
Walktoberfest Farmers & Makers Market | October 26-27
The fourth annual Walktoberfest Farmers & Makers Market brings over 190 vendors to the Walkway Over the Hudson. This market will feature items from farms, distilleries, breweries, wineries, restaurants, artists, and artisans from around the Hudson Valley. The event’s live entertainment will include a team trivia game from Trivia Break, as well as music from groups like the rap, rock, and pop band 7he 7eam. A children’s activity area by the Highland gate will feature a dance performance from Madeline's Dance Center and a building table from Brickhouse Resellers. Walktoberfest will take place near the west side entrance of Walkway Over the Hudson, located at Haviland Road in Highland—there are no vendors located on the Poughkeepsie side of the Walkway. The market runs October 26-27 from 12pm to 5pm, and $5 daily general admission tickets can be purchased online.
