Two Days, Six Wineries: Holiday Fare Along the Hermann Wine Trail

HERMANN WINE FIELD GUIDE

Two Days, Six Wineries: Holiday Fare Along the Hermann Wine Trail

A concise guide to the Holiday Fare progressive tasting—small holiday bites paired with wine at six wineries along a scenic 20-mile stretch of the Missouri River.

Two Days, Six Wineries: Holiday Fare Along the Hermann Wine Trail.

Duration
Five to Seven Hours
Location
Hermann
Operator
Hermann Wine Trail
Category
Wine
Robert Eric Crews
Founder & Editor, The Adventure Collective
Published Verified

The Holiday Fare Wine Trail stages a festive, progressive tasting across six wineries on the Hermann Wine Trail, featuring small holiday bites paired with wine as the trail winds along a 20-mile stretch of the Missouri River between Hermann and New Haven; the annual event takes place over a November weekend (the 2025 dates are November 15–16, 2025).

Highlights

Outing Highlights

THE ROUTE

A 20-mile riverside sweep

The Hermann Wine Trail hugs the Missouri River for 20 scenic miles between Hermann and New Haven, with six wineries arranged to create a progressive tasting route that emphasizes views and small-town hospitality.

THE TASTING

Six wineries, paired holiday bites

Holiday Fare is a progressive-style tasting: each of six participating wineries offers a featured wine paired with a small holiday-inspired bite, creating a curated string of pairings for the day.

THE TIMING

A compact weekend celebration

The festival runs across a weekend in mid-November; the 2025 event falls on November 15–16, and the 2026 dates are scheduled for November 21–22, providing a concentrated two-day wine-and-food experience.

What the day feels like

What the day feels like

The Holiday Fare experience is deliberately easygoing and social: begin at any participating winery, move between tasting stations at six properties, sample small seasonal bites paired with wines, and enjoy the river-facing scenery and friendly hospitality that define Hermann’s wine country.

Suitability

Who it's for

Who this event suits—and who should reconsider.

1
Wine EnthusiastsIdeal for people who want to sample multiple wines and curated pairings across several stops; attendees must meet the event's age requirements.
2
Groups & FriendsWell suited to small groups looking for a weekend tasting escape; note that the event is restricted to those meeting the stated age policy.
3
Families with childrenNot recommended for families traveling with minors due to the event’s age restriction for attendees.
4
Solo Travelers & CouplesA good match for solo visitors or couples seeking a paced, social tasting day—participants must comply with the event's age policy.

Practical planner

Details to review before reserving

What to Bring

Bring a valid photo ID and the email ticket confirmation with the QR code; that email confirmation/QR code is your ticket.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

When is the Holiday Fare Wine Trail scheduled?

The 2025 Holiday Fare takes place Saturday, November 15 and Sunday, November 16, 2025; the 2026 dates are scheduled for Saturday, November 21 and Sunday, November 22, 2026.

Who is allowed to attend?

The event is for adults meeting the stated age requirement; attendees must be 21 or older.

What does the ticket include?

The $35 ticket includes the featured wine and food pairing at six wineries and a souvenir wine glass.

How long should I expect to be on the trail?

Plan for a five- to seven-hour outing to move between wineries and enjoy the progressive tastings.

When do online ticket sales for 2026 begin?

Online ticket sales for the 2026 event will begin on November 19, 2025.

When will the tasting menu be announced?

The tasting menu for the event will be posted in July 2026.

What are the 2026 event hours?

For 2026 the hours are: Saturday 11/21/26 from 10:00 AM to 5:00 PM, and Sunday 11/22/26 from 10:00 AM to 4:00 PM.