HERMANN WINE FIELD GUIDE
Chocolate and Wine Where the Missouri River Bends: Hermann’s Weekend Pairing Trail
A seasonal tasting event on the Hermann Wine Trail: visit six wineries for curated chocolate-and-wine pairings on the last weekend of February 2026, with tickets that include six featured pairings and a souvenir wine glass.
Chocolate and Wine Where the Missouri River Bends: Hermann’s Weekend Pairing Trail.
The Chocolate Wine Trail threads six scenic wineries along the Hermann Wine Trail, which hugs the Missouri River for about 20 miles between Hermann and New Haven. On the last weekend of February 2026, visitors can move between tasting rooms, sampling curated chocolate-and-wine pairings while taking in river views, award-winning wines and small‑town hospitality.
Highlights
Outing Highlights
Six Scenic Wineries Along the Missouri River
The trail comprises six stops on the Hermann Wine Trail, a roughly 20‑mile stretch of wineries between Hermann and New Haven—each stop framed by vineyard views and small‑town hospitality.
Chocolate‑and‑Wine Pairings at Every Stop
A single ticket covers the featured chocolate-and-wine pairing at each of the six participating wineries and comes with a souvenir wine glass; the curated tasting menu will be posted in November 2025.
A Valentine’s‑Era Tradition
Held on the fourth weekend of February, this event runs across a Saturday and Sunday and is a seasonal draw for chocolate and wine lovers during the Valentine’s period; participants must be 21 or older.
What the day feels like
What the Weekend Feels Like
The Chocolate Wine Trail is a paced tasting circuit: over five to seven hours you move between tasting rooms, pause for paired chocolate bites alongside a featured pour at each stop, and collect a souvenir glass along the way. Expect relaxed cellar‑door service, vineyard views and the steady rhythm of a small wine region in winter.
Suitability
Who it's for
Who this weekend works for—and who should sit this one out.
Practical planner
Details to review before reserving
The event takes place on the last weekend of February 2026: Saturday 2/28/26 and Sunday 3/01/26; plan on a five‑to‑seven‑hour outing while moving among six wineries.
Bring a valid photo ID and the email ticket confirmation with the QR code—your confirmation is your ticket.
Tickets are $35 and include the featured wine-and-chocolate pairing at six wineries and a souvenir wine glass; online ticket sales begin at the end of September 2025 and the tasting menu will be posted in November 2025.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
When is the Chocolate Wine Trail scheduled?
The event runs the last weekend of February 2026: Saturday, February 28 and Sunday, March 1, 2026.
How long does the trail take?
Expect to spend approximately five to seven hours moving among the six participating wineries.
How many wineries participate and where is the trail?
The trail includes six stops along the Hermann Wine Trail, which spans roughly 20 scenic miles between Hermann and New Haven.
What does my ticket include and when do tickets go on sale?
A $35 ticket includes the featured chocolate-and-wine pairing at six wineries and a souvenir wine glass; online ticket sales begin at the end of September 2025 and the tasting menu will be posted in November 2025.
Are there age restrictions or ID requirements?
Yes—attendance is restricted to ages 21 and older; bring a valid photo ID and your email ticket confirmation with the QR code as your ticket.
Where do I start the trail?
Begin the wine trail at any one of the six participating wineries—guests may choose their starting point.