Lucky for us, October has five weekends this year which means an extra weekend of live music, German food, and fun for Oktoberfest in Hermann. We’ve rounded up some of the must-do events and activities to make the most of this once-a-year celebration of Hermann’s deep German legacy. Find the full list of activities and events for October 20-24 and October 27-31.

Iconic Oktoberfest

In case you missed it, everything you need to know about Oktoberfest including where to find amazing German food and music, can be found in this guide. Below we’ll cover some of the under-the-radar things to do and where to eat. 

Brandy & Chocolate Pairing

On Wednesday, October 20, HogsHead Lounge is hosting a Brandy & Chocolate Pairing. Stop in for this special after-hours event featuring a brandy, cognac, and armagnac tasting paired with a variety of chocolates.

Downtown Hermann Horse-Drawn Carriage Rides

Enjoy a relaxing and scenic ride through downtown Hermann with Wine Country Wagon Rides. Hear stories of Hermann’s past along with the soft clip-clop of the horses’ hooves, making it easy to imagine life long ago in Hermann. Check the weekend schedule for October 20-24 and October 27-31 for days and times.

Wine and Witches

Don’t miss the ultimate ladies night out on Thursday, October 21 at Wine & Witches. This event checks all the boxes for a good time: shop local vendors, dancing, wine, food, costume contest and more. 

Tour the White House Hotel

Built in 1868, the 36-room White House Hotel is part boutique hotel and part living history museum. Take a tour for a glimpse of life in the 1800s before relaxing with a glass of wine or beer in the outdoor courtyard. The White House Hotel is considered one of the “last remaining examples of a post-civil war Victorian hotel” and is a must-see for the grandeur of 19th century design.

The Wine Experience 

Sip award-winning California wine from three wineries at the Dierberg – Star Lane – Three Saints Tasting Room at The Wine Experience on Friday, October 22 and Friday, October 29. This premium wine tasting includes samples of red, white, and sparkling wines paired with a tasty dish for a full sensory experience. As you sip and snack, you’ll expand your wine vocabulary with details on wine descriptors, flavor profiles, and wine terminology that you can use to impress at your next social gathering.

The Muskrat Society

Don’t miss the unique display of a Muskrat Keelboat along with education sessions and historic artifacts. Oh, and of course, the infamous “Boatman’s Chili,” all happening at Riverfront Park Pavilion from 10am – 6:30pm on October 23-24.

Food Trucks on First

New this year! Take advantage of bites and snacks in between your main meals just for special occasions in Hermann. The parking lot at 219 East First Street transforms into a food truck paradise with a variety of cuisine on the weekends from a variety of vendors including: Mr. Murphy’s, Quench by Marley, Moving Munchies, Daddy O’s Cheesesteaks, Billy Hinson’s Old School BBQ, Smoked Artisan Barbecue, 2 Odd Dawgs. Check the Facebook page for the latest updates on who will be open when you walk through.

Live Music Day and Night

You can’t throw a rock without hitting a stage with live music during October weekends in Hermann. We don’t condone rock throwing, but we do highly recommend using the Oktoberfest weekend guides for the 20-24 and 27-31 to plan your fun. Music starts as early as 10 am and ends as late at 1am with a range of moods and genres, from rock to country and jazz. No matter where you end up, it will be a good time.  

Take a look at the event calendar for everything going on. Prost!