October 28, 2026 · Boston, MA
Wine and Cheese Tasting: Pairing Award-Winning American Artisanal Cheeses
Free
View details
United States · Wine Travel
Massachusetts wine festivals & events
251 listings / 17 festivals / 234 events / peak april–july
Showing 193–216 of 232 events
Upcoming onlyFilters
October 31, 2026 · New Bedford, MA
11th New Bedford Food Truck & Craft Beverage Festival
$5–$59
View details
November 19, 2026 · Wakefield, MA
Get Thanksgiving Ready! Grazing Board Arranging Workshop
$85
View details
December 4, 2026 · Cambridge, MA
Classic Series: A Few of Our Favorite Things: Cheese, Charcuterie, Wine $75
$75
View details
December 10, 2026 · Shrewsbury, MA
Wine and Christmas Cookie Pairing Experience at Broken Creek Vineyard
$58
View details
December 10, 2026 · Chatham, MA
Chatham Bars Inn Holiday Wine Tastings - California Wines
$90
View details
December 12, 2026 · Foxboro, MA
Fortified Wines of the World: A Global Exploration.
$100
View details
December 12, 2026 · Fairhaven, MA
Pouring Over Pages: A Holiday Book and Wine Pairing Event
$50–$70
View details
December 12, 2026 · Cambridge, MA
Kendall Seasonal Wine Preview: Tasting Extravaganza! $50
$50
View details
Newsletter
Join The Pour
Get the best upcoming wine festivals, seasonal picks, and planning guides in your inbox each week.
No spam. Unsubscribe anytime.