Fall brings many pleasures in its wake and one of the most enjoyable is celebrating Oktoberfest in a small river town setting amid colorful foliage and an Old World ambiance.

I bet you can’t guess where we were last weekend!

Main street view of Hermann with two story connect shop buildings built in brick

Held every weekend in October, the Hermann Oktoberfest has become a beloved tradition for thousands throughout the Midwest. The main shopping streets are alive with unique shops, antique stores, eateries, beer halls, and well-preserved architecture.


Vintage sign of blond wood with a stuffed fish with a red border

We love antique shopping, and Hermann delivered. Vintage shops and antique malls are to be found around the shopping district and each has its own character and specialty—some catering to rustic tastes, others to midcentury modern, farmhouse, or cottage looks, some to particular collecting tastes. But each is worth a visit no matter what your personal style.


Hermann Concert hall next door to the columned bank

Perhaps the coolest building in Hermann is the Concert Hall. Built in 1878, the Concert Hall was the hub of social life in early Hermann. On the first floor, a fine saloon was a favorite gathering place for locals and a destination for fun-loving St. Louisans. The spacious upstairs hall hosted plays, lectures, dances and concerts. Today, it’s the oldest continually operating tavern west of the Mississippi.



Architecture details of some downtown Hermann buildings

Examining the architectural details downtown is a study in commercial building styles of the 19th and early 20th century. Bracketed entablatures, fish scale ornamentation, arched windows, and more mix on the brick facades. Every building has it’s own character.


Hermann trolley of dark green and red next to hay bales and pumpkins

Once you’ve parked (sometimes a challenge on an Oktoberfest weekend), you can leave your vehicle and still get around most downtown attractions on foot or by other, more colorful means, like trolley rides. And who here doesn’t like trolley rides??


Horse pulling wagon loaded with people down a main street

If a more measured pace is your preference, opt for the horse wagon rides. We couldn’t choose between a trolley ride or a horse drawn wagon, so we walked. The decision was too difficult. Maybe we should have just done both?


Women on horseback

Or take a page from these ladies’ books and mount up for a ride around the sometimes-steep hills of the town. We went horseback riding once with no warm up. Couldn’t move the next day. That was on our honeymoon.  It was supposed to be romantic. Note to readers: Don’t do random horse riding unless you’re used to it! At least, if you plan to move the next day.


Missouuri Valley Ice cream sign with red lettering, blue banner that says Home of thSuper Malts with an image of an ice cream sunday

We also saw some really cool old advertisements in Hermann. The sides of several old buildings sport appealing painted signage that reinforces the vintage flavor of the town.


Georgian style Guest house

The Inn at Hermannhof , which was originally built in the mid 1800’s, is conveniently located downtown at the corner of First and Gutenberg, with the Missouri River, visible from many of the guest rooms, to the north. It’s such a pretty spot. You can’t help but feel like a fancy person there.



Hermann Wurst Haus building with tables and chairs and umbrellas out front

After walking around First Street, stop off for a quintessential German meal at the Hermann Wurst Haus. I repeat the same warning: don’t overdo if you want to move later.


Master wurst maker - he has a beard

Wurstmeister Mike Sloan, who handcrafts all the unique brat recipes, provides information about and samples of some of the featured wurst flavors on special. So good.


Huge cast of Wurst Deli meats with 4 shoppers in front of a large brick wall and chalk board menu

Now that you’ve tempted your taste buds, stop off at the Best of the Wurst Deli for a filling lunch of bratwurst, sides, and cold house-made beer or craft sodas.


Cooler filled with bratwurst flavors

After sampling and dining on brats, it’s time to pick some to take home. With over 47 flavors to choose from (we sampled LOADS and they’re all good!) you may be staring at this cooler for a while as you try to make up your mind. No worries if you can’t—they ship nationwide. Our favorites? We loved the Caramelized Pear & Gorgonzola Bratwurst, the Best of Show, and the Jalapeño & Peach brat. Oh, my gosh. I’m salivating just thinking about them. Nom Nom.



Tin Mill restaurant with a red caboose out front

If your taste leans toward traditional comfort food, grab a filling lunch at the Tin Mill Restaurant, housed in a beautifully restored venue that once serviced a traditional Ice House in the 1800’s. Located in the recently restored Hermann Mill Plaza (the tallest building in downtown Hermann), Tin Mill Restaurant offers beers from Tin Mill Brewing Company and wines from Hermannhof Winery.


Sheltered pramenade along a street bedected with American flags and fall trees in Hermann with shoppers walking past people in chairs

Schiller Street connects the main shopping thoroughfares with stores on one side and picturesque B&Bs on the other. It’s one of those streets you imagine when someone says ‘idyllic small town where everyone says “hello!” and people are always smiling’.


Brick Type Styles antique shop with vintage stuff out front

Type Styles is always a fun shop to visit and chat about the contents with the owner and assistants. Lots of fun typography-related vintage and gift items to be found here.


Antiques display n TYpe Styles shop

Vintage signs, lead type, menu boards, advertising, and more fill the walls and shelves. Thank goodness my mom, sisters, and ever patient husband were with me, otherwise I would have loaded so much stuff into my car…so much stuff.


Front of Gift shop with green benches and flowers and a flag that reads Open

Back Home Again is a great place to pick up accent or serving pieces and hostess gifts for the coming holiday season. And if you’ve got a not-so-keen companion or spouse (not naming names here), there’s a phalanx of benches just outside.


Shop sign listing Jam, water, salsa, pumpin [sic] butter, bulk tea, and cold rootbeer

When you visit small towns and events like this, you’ve got to try the local produce and concoctions. Otherwise, what’s the point?


Pocket garden with green foliage and bistro set

Take a peek between and behind some of the shops, pubs, and restaurants and you may find an inviting pocket garden where you can sit and enjoy either a bit of solitude or a quick sip. Just make sure you’re not trespassing. People don’t like it when you do that.


Shops on 4th street Hermann with cars going both directions up the hilly street

Shops continue down Fourth street. Don’t miss Topiaries, specializing in home, garden, gifts and art inspired by nature, on the corner of Schiller and 4th (across from the German School Museum) and make a special trip around back to see their garden.


Tin Mill Brewery with a big Brewery sign in gold and black hanging on an old brick building

Every self-respecting Oktoberfest has a crowd-pleasing bier garten and you can find Hermann’s at Sesquicentennial Park on Third and Gutenberg. Or for a more traditional pub atmosphere, stop in at the Tin Mill Brewery to sample what’s on tap. Set in a 100-year-old building, the Brewery is packed with authentic equipment shipped directly from Germany. They have 6 different brews for your tasting enjoyment.



Winery entrance with a fountain which a dozen people are standing and sitting on and around

Hermann, known as the “birthplace of Missouri wine country” boasts a number of wineries, and what started in the mid 1800s as a matter of economic survival—the German settlers who purchased the land found what they had bought was unsuitable for farming—has made this community the heart and soul of Missouri wine production. This imposing entrance to the Hermannhof winery Hofgarten with its French limestone fountain (a favorite gathering spot during the festival) features in a lot of selfies.


People enjoying a sit-down at the Winery

By the turn of the century, Hermann was one of the largest wine producing regions in the world until anti-German sentiment after World War 1 and Prohibition, followed by the Great Depression, took their toll. Now, prize-winning local wines fill the glasses at the Hofgarten. Two “German-stable”-inspired pavilions define the interior courtyard. Tour the stone wine cellars and building (both are on the National Register of Historic Places) up at the top of the hill where all the fermenting action takes place.



Stone Hill Winery sign with black text on white sign

As the afternoon wanes, you might find time for one more winery tour at the Stone Hill Winery, which boasts a hilltop vantage point over the vineyard. Stone Hill is the oldest winery in the area. They produce a whopping 350,000 gallons of wine per year. The wine cellar, underneath the winery grounds, is about 3 football fields long and wraps around the whole hillside. Inside the main building is the tasting area where you can sample several dozen different kinds of locally made wine.



Vintage 1847 restaurant sign with flowering mums and pumpkin

Finish your tour with dinner at the on-property Vintage Restaurant housed in a beautifully restored carriage house and horse barn, just steps from the winery.


Blanc de blancs wine with a filled wine glass on glossy wooden table

While the menu features delicious German fare, their wine list is varied. We sampled the crisp Brut-style Blanc de Blancs before dinner and ordered a medium-bodied Chambourcin that complemented our meal nicely.


Overview of Hermann Missouri from the winery with fall colors

The trip up to Stone Hill rewards you with a beautiful view of the town from the summit of the hill.


Detail of fall foliage with flowing grasses swaying in the breeze

The view is made even more spectacular by the vivid fall foliage.


White B&B House with large yellow tree

A full day demands a relaxing place to rest after all the activity. Charming bed & breakfasts add to the town’s character and to the options for a very pleasant overnight stay that will start off the next day’s schedule in style.

For more information about Hermann and about the Oktoberfest celebration, check out www.visithermann.com.



© Caruth Studio

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