Ages 21+ • Saturday 2/28/26 & Sunday 3/01/26 • A Valentine’s tradition for chocolate & wine lovers!
Discover the Chocolate Wine Trail in Missouri—an unforgettable February weekend event where six scenic wineries along the Hermann Wine Trail offer exquisite chocolate and wine pairings. Experience rich flavors, stunning river valley views, and warm local hospitality.
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Difficulty
easy
Duration
5–7 hours
Fitness Level
No special fitness level required; mostly casual walking within winery grounds.
Wildlife
History
Hermann was founded by German immigrants in 1837 and remains a center of Missouri’s winemaking heritage.
Conservation
Wineries along the trail follow sustainable vineyard practices to preserve soil and local ecosystems.
Hermann Wine Trail
Ages 21+ • Saturday 2/28/26 & Sunday 3/01/26 • A Valentine’s tradition for chocolate & wine lovers!
The Hermann Wine Trail brings together a collection of scenic wineries under a coordinated series of seasonal tasting events. The Trail organizes themed experiences that pair local wines with complementary foods and festival-style activities. Say Cheese Wine Trail, Holiday Fare Wine Trail, and Chocolate Wine Trail are the three highlighted events offered on the Hermann Wine Trail calendar.
Each featured trail visits six participating wineries, offering a planned route that suits day visitors, couples, and small groups. Events include curated pairings — such as wine-and-cheese pairings on Say Cheese and chocolate-and-wine pairings on the Chocolate Wine Trail — plus opportunities to purchase bottles at tasting rooms and to learn about tasting notes and food pairings from knowledgeable staff.
The Say Cheese Wine Trail includes award-winning selections and a souvenir tasting glass, and it aligns with seasonal festivities such as the Kristkindl Markt on select dates. The Holiday Fare Wine Trail focuses on seasonal food-and-wine pairings across multiple winery stops and runs on weekend dates. The Chocolate Wine Trail takes place over a dedicated weekend, emphasizing dessert wines and chocolate pairings.
Tickets typically cover tastings at six wineries and the special pairing items advertised for each trail. The Hermann Wine Trail provides an accessible way to experience multiple wineries in one planned itinerary, offering curated tastings, seasonal events, and local hospitality for visitors looking for a focused wine trail experience.
Trail Area
Hermann Wine Trail
Scenic wineries and tasting events
Event Dates
Nov 15-16, 2025; Dec 13, 2025; Last weekend Feb 2026
Scheduled seasonal trail dates
Wineries per Trail
6
Tastings and pairings at six wineries
Seasonal Trails
3 events
Say Cheese, Holiday Fare, Chocolate
Select tickets for Say Cheese, Holiday Fare, or Chocolate — each includes tastings at six scenic wineries and curated pairings.
Start Early
Begin your trail adventure early to fully enjoy tastings at all six wineries within the event hours.
Bring Valid ID
You must bring a government-issued photo ID and your email ticket with QR code to participate.
Plan Your Transportation
Transportation between wineries is not provided, so arrange a designated driver, shuttle, or rideshare beforehand.
Dress for Comfort
Wear comfortable shoes for walking between tasting rooms and dress in layers to accommodate variable February weather.
Commemorative Wine Glass
Included with your ticket; use it to enjoy tastings throughout the trail.
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Photo ID
Necessary for age verification at winery tastings.
Comfortable Walking Shoes
Ideal for strolling between winery tasting rooms over varied terrain.
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Layered Clothing
February weather can be changeable, so layers keep you comfortable indoors and out.
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