Running parallel to the Missouri River, East First Street in Hermann, Missouri, is lined with 19th-century brick buildings that beckon people into the restaurants, coffee shops, bars and tasting rooms within. Seasonal flavors abound at these establishments, which also pay homage to the city’s rich history and German roots.
Black Shire Distillery

Named to honor the Black Shire horses raised at Hermann Farm, Black Shire Distillery produces vodka, gin and whiskey. The distillery, which offers tours and tastings, is located on the farm, but there’s also a tasting room in downtown Hermann. When the first frost hits, there’s nothing better than a Hot Toddy. Try one with cinnamon-infused rye whiskey or cinnamon-infused blackberry whiskey here. (Photo by Tony Carosella)
Black Shire Distillery, 111 Gutenberg St., Hermann, Missouri, 573.486.9911, blackshiredistillery.com
Downtown Deli & Custard Shoppe

Downtown Deli & Custard Shoppe knows how to keep its customers happy. Warm up with from-scratch soups, snag the signature roasted chicken salad or satisfy your burger craving with a hand-pressed quarter-pound patty made with meat from Bunkline Beef in Swiss, Missouri. It’s never too cold for the shop’s hand-dipped ice cream or frozen custard, so make sure you save room. (Photo by Tony Carosella)
Downtown Deli & Custard Shoppe, 216 E. First St., Hermann, Missouri, 573.486.5002, downtowndelihermann.com
Espresso Laine

This time of year, strolling through downtown is a little less chilly with a specialty coffee drink from Espresso Laine in hand. Try the Mrs. Claus (a salted caramel latte with brown sugar and cinnamon) or the Winter Wonderland (a white chocolate-peppermint latte). The Caramel Delight, another fan favorite, combines Ghirardelli caramel, espresso and steamed milk. If you want to stick around, the shop also has toys and games for all ages. (Photo by Tony Carosella)
Espresso Laine, 100 Schiller St., Hermann, Missouri, 573.486.2010, espressolaine.com
Fernweh Distilling Co.

Taking its name from the German word for wanderlust, Fernweh Distilling Co. makes four distinctive products: Stardust Vodka, Straight Bourbon Whiskey, Straight Rye Whiskey and Wildflower (a sherry cask-aged spirit infused with chamomile and rose). Stop by for a tasting or enjoy the spirits in craft cocktails during a meal. Seasonal specials include the Gingerbread Dude White Russian and the hand-breaded pork tenderloin served with housemade mashed potatoes, white pepper gravy and sautéed green beans. (Photo courtesy of Fernweh Distilling Co.)
Fernweh Distilling Co., 4 Schiller St., Hermann, Missouri, 573.486.2970, fernwehdistilling.com
Hermann Wurst Haus

Hermann Wurst Haus is dedicated to producing world-class bratwursts and sausages. Grab some to cook at home or enjoy them on site in deli items such as the caramelized pear and Gorgonzola bratwurst served with sauerkraut and housemade German mustard on a bun. The menu also features smoked meats in dishes such as the Cattleman’s Brisket with pit-smoked beef brisket smothered in a sweet and smoky barbecue sauce, topped with melted Swiss cheese and served on a potato bun. (Photo by Tony Carosella)
Hermann Wurst Haus, 234 E. First St., Hermann, Missouri, 573486,2266, hermannwursthaus.com
Hermannhof Winery

Established in 1852, Hermannhof Winery remains a small winery dedicated to quality rather than quantity. Its principal goal is to preserve each grape’s natural character, and so the winery utilizes the most advanced equipment and methods. Try Missouri varietals such as Chambourcin, Norton and Vignoles at the tasting room on East First Street. (Photo by Tony Carosella)
Hermannhof Winery, 330 E. First St., Hermann, Missouri, 573.486.5959, hermannhof.com
Tin Mill Brewing Co.

Located in a historic grain processing plant, Tin Mill Brewing Co. focuses on the art of authentic German brewing. Order a flight and explore its range of beers, from the Midnight Whistle (a classic dark Doppelbock with notes of coffee, chocolate and vanilla) to the Skyscraper (a premium German-style Pilsner with a mild malt flavor and a clean, crisp finish). The brewery offers pub food such as Bavarian-style pretzels with beer cheese, while the Tin Mill Restaurant (less than a block away on East First Street) has heartier entrées such as the grilled bone-in pork chop paired with charred Brussels sprouts and a spiced apple chutney. (Photo by Tony Carosella)
Tin Mill Brewing Co., 114 Gutenberg St., Hermann, Missouri, 573.486.2275, tinmillbrewery.com