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Verdant vineyards, charming B&Bs, and a lively piano bar…what more could you ask for!?

When it comes to planning a great small town getaway with your best girlfriends, Hermann, Missouri, should be high on the list. Originally established in 1837 by German immigrants who first landed in Philadelphia, the river town bears charming resemblance to the German Rhineland. In and around town, visitors are welcomed with wineries, wurst hauses, and dozens of other delightful ways to enjoy the deep pockets of German heritage.

The country fun of Hermann begins before you even set foot into town. If you’re traveling in from St. Louis or Kansas City, book a seat on Amtrak’s Missouri River Runner and you’ll rumble into town right along the water. From there, fun things to do in Hermann, Missouri including exploring the historic downtown (there are over 100 buildings listed on a historic registry!), antique shopping, sampling local libations, and immersing yourself in the ways of life of a 19th-century homestead via the immersive experience of Hermann Farm. Come nightfall, you can cap off a hearty dinner by belting out favorite tunes at a raucous piano bar, then tuck into a cozy room at a historic B&B.

So if you’re looking for something new and exciting to add to your fall bucket list, a trip to Hermann, Missouri will absolutely fill the bill. If you hit the right season, not only will there be leaf-peeping opportunities aplenty, you can also fill your social feeds with fun fall photoshoot ideas. Read on for our complete travel guide to Hermann, Missouri, including the best restaurants, shops, hotels, and things to do.

Start your morning with a pour-over coffee brewed from Missouri roasted beans at Stomp'n Grounds Espresso Bar.

Grocery magnate Jim Dierberg and wife Mary have invested heavily in Hermann's revitalization. Their 200-acre living history museum Hermann Farm offers a taste of life on an 1800s homestead, with soulfully—and beautifully—preserved barns and living quarters, plus a stable of white-hooved Shire horses.

Roam the aisles of Antiques Unlimited 2, then walk around the corner to Antiques Unlimited, where the finds include vintage firefighting memorabilia.

Hermann's rich German heritage makes its Oktoberfest a major draw. Savor the celebration year-round at Hermann Wurst Haus, which serves up award-winning bratwurst and sauerkraut.

In town, get in your steps with a self-guided mural walking tour. Across the river in McKittrick, cyclists can pick up Missouri's famed 240-mile Katy Trail (pictured), the country's longest continuous recreational rail trail.

175-year-old Stone Hill Winery draws in oenophiles with its signature Norton reds, while OakGlenn specializes in sweeter whites—and scenic river views. Family-owned Endless Summer crafts sweet fruit wines (the pineapple is especially popular), and distilleries such as Lionheart Whiskey Co. also abound.

Tourists and locals alike pop into Hannah and Miles James’s modern general store The Fancy Pheasant for apple butters, bath soaks, and other Missouri-made finds, while German beer steins and other collectibles beckon at Back Home Again.

Sing along to dueling piano players—or just kick back and enjoy the live music—at The Piano Bar, which donates half of their door cover charge to a local charity.

Cozy up in sleeping quarters outfitted in antiques at the Inn at Hermannhof. Known as a "bed & beverage," The Schiller House greets guests with drinks and keeps suites stocked with board games.

Find even more fall weekend fun in these favorite destinations: • 20 Ways to Have a Fun-Filled Day in Lambertville, New Jersey • 16 Ways to Spend the Perfect Fall Day in Sperryville, Virginia • 35 American Towns That Look Straight Out of Europe