Wine Festivals in Massachusetts 2026

3 wine festivals across Massachusetts — from harvest celebrations to destination food-and-wine events.

Worth the Trip

Festivals worth travelling to Massachusetts for.

Boston Wine & Food Festival

The nation's longest-running food and wine festival, held over 10+ weeks at the Boston Harbor Hotel from January through March, featuring 43+ events including winemaker dinners, cooking demonstrations, master classes, and themed vertical tastings. Its unprecedented longevity and depth — from casual tastings to Michelin-caliber dinners — make it the most comprehensive wine and food program in America. The waterfront setting at Rowes Wharf is spectacular in winter.

View festival details

2026 Calendar — All Massachusetts Wine Festivals

Every wine festival in Massachusetts, organised by month.

January(1)

Boston Wine & Food Festival

Boston, United States

February(1)

South Shore Food & Wine Expo

Plymouth, United States

March(1)

Boston Wine Expo

Boston, United States

Insider Tips

Boston Wine & Food Festival

The Opening Night Press Celebration is the most exclusive event, but the Regional Wine Dinners offer the best value — prix-fixe menus with winemaker access for under $200.

Boston Wine Expo

Register for a tasting class when you buy your Grand Tasting ticket — the 72-wine educator-led sessions fill fast and offer far more depth than the open floor.

South Shore Food & Wine Expo

The Vintner's Lounge is worth the upgrade ticket — smaller crowd, better pours, and direct access to the wine educators running the event.

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