Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near Middlebury, Connecticut

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Featured Local Events

Portland, Connecticut

Yoga Night At Arrigoni Winery

Wed, September 9, 2026

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Carmel, NY

15th Annual Putnam County Wine & Music Fest

Sat, August 22, 2026

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Portland, CT

Live Music At Arrigoni Winery!

Fri, August 21, 2026 to Sun, August 23, 2026

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All Upcoming Local Events

41 Events listed within 30 miles.

60 miles 30 miles 15 miles
  • Aug 21-23, 2026 (Fri-Sun)
Live Music At Arrigoni Winery!
Arrigoni Winery | Portland, CT
  • Aug 22, 2026 (Sat)
  • Aug 23, 2026 (Sun)
15th Annual Putnam County Wine & Music Fest
Putnam County Veterans Memorial Park (Upper) | Carmel, NY
  • Aug 22, 2026 (Sat)
Finger Lakes Wine Tasting
Spiritus Wines | Hartford, CT
  • Aug 22, 2026 (Sat)
Spirits With A Twist - A Flavored Spirits Exploration
Total Wine & More | Multiple Locations, Nearby
  • Aug 23, 2026 (Sun)
Live Music With Sweeter Than Wine
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Aug 23, 2026 (Sun)
Redwood Empire Tasting
The Gilded Curtain | Wallingford, CT
  • Aug 23, 2026 (Sun)
Fine Cigars Night
Aquila's Nest Vineyards | Newtown, CT
  • Aug 27, 2026 (Thu)
Paint & Sip At Paradise Hills Vineyard | Wine Glasses
Paradise Hills Vineyard & Winery | Wallingford, CT
  • Aug 28, 2026 (Fri)
Cheese & Charcuterie Workshop
Bon Appetit | Hamden, CT
  • Aug 28, 2026 (Fri)
Live Music With The Emily Mager Duo
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Aug 28, 2026 (Fri)
August Summer Cocktail Class With Nicole
68 Pratt St | Hartford, CT
  • Aug 29, 2026 (Sat)
Slow Tea: A Rare Tea Tasting Experience
33 Brook Rd | Cornwall, CT
  • Aug 29, 2026 (Sat)
Bartending Class With Tina
213 Saw Mill Rd | West Haven, CT
  • Aug 29, 2026 (Sat)
Heirloom Tomato Festival
White Silo Farm & Winery | Sherman, CT
  • Aug 30, 2026 (Sun)
Girl Scout Cookies & Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Aug 30, 2026 (Sun)
Live Music With Jon Condie
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 2, 2026 (Wed)
Summer Wine Trail - Fruit Punch-Glass Painting
Aquila's Nest Vineyards | Newtown, CT
  • Sep 4, 2026 (Fri)
  • Sep 5, 2026 (Sat)
  • Sep 6, 2026 (Sun)
  • Sep 7, 2026 (Mon)
Odyssey '26: A Greek Festival
Saint Barbara Greek Orthodox Church | Orange, CT
  • Sep 5, 2026 (Sat)
Slow Tea: A Rare Tea Tasting Experience
33 Brook Rd | Cornwall, CT
  • Sep 5, 2026 (Sat)
Cheesecakes & Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Sep 5, 2026 (Sat)
Bartending Class With Tina
213 Saw Mill Rd | West Haven, CT
  • Sep 6, 2026 (Sun)
Fine Pastries And Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Sep 8, 2026 (Tue)
New York Baking Class
617 Main St N | Southbury, CT
  • Sep 8, 2026 (Tue)
Teen Cuisine! Cooking For Teens
Wakeman Town Farm | Westport, CT
  • Sep 9, 2026 (Wed)
Yoga Night At Arrigoni Winery
Arrigoni Winery | Portland, Connecticut
  • Sep 10, 2026 (Thu)
Wine Trail - Garden Glass Painting
Tranquillity Vineyard & Winery | Middlebury, CT
  • Sep 10, 2026 (Thu)
California Uncorked - Napa Valley & Beyond!
Total Wine & More | Multiple Locations, Nearby
  • Sep 11, 2026 (Fri)
Deep Dive Into Argentina’s Top Terroirs (by Mascota Vineyards, El Esteco, And More!)
Total Wine & More | Multiple Locations, Nearby
  • Sep 12, 2026 (Sat)
California Uncorked - Napa Valley & Beyond!
Total Wine & More | Multiple Locations, Nearby
  • Sep 26, 2026 (Sat)
Singular Sensations - Getting To Know Single Malt
Total Wine & More | Multiple Locations, Nearby
  • Oct 7, 2026 (Wed)
Explore The Flavors Of California: Wine Class With Needle & Thread, Mother's Choice & More
Total Wine & More | Multiple Locations, Nearby
  • Oct 8, 2026 (Thu)
Sip N' Snack Pairings
Total Wine & More | Multiple Locations, Nearby
  • Oct 10, 2026 (Sat)
Sip N' Snack Pairings
Total Wine & More | Multiple Locations, Nearby
  • Oct 24, 2026 (Sat)
Icons Of Spirits
Total Wine & More | Multiple Locations, Nearby
  • Nov 5, 2026 (Thu)
Pop Open A Party - Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Nov 6, 2026 (Fri)
Special Guest Pablo De Simón Pours His Rioja Wines
Total Wine & More | Multiple Locations, Nearby
  • Nov 7, 2026 (Sat)
Pop Open A Party - Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Nov 12, 2026 (Thu)
Sips Of The Season: A Guide To Holiday Entertaining
Total Wine & More | Multiple Locations, Nearby
  • Nov 14, 2026 (Sat)
Around The World With Alexander Murray
Total Wine & More | Multiple Locations, Nearby
  • Dec 3, 2026 (Thu)
Distinguished Reds: A Global Tasting Journey
Total Wine & More | Multiple Locations, Nearby
  • Dec 5, 2026 (Sat)
Distinguished Reds: A Global Tasting Journey
Total Wine & More | Multiple Locations, Nearby

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Wine, Food & Drink in Middlebury: Frequently Asked Questions

What is the best source for wine and food events in Middlebury?

For over 25 years, LocalWineEvents.com has been the definitive go-to source for discovering the best wine, food, and drink events in Middlebury. From local wine tastings and boutique dinners to large-scale food festivals, we provide the most comprehensive, expert-curated calendar for Middlebury enthusiasts and professionals.

How can I find upcoming beer and spirits festivals near Middlebury?

LocalWineEvents.com features a dedicated discovery engine for Middlebury that includes craft beer festivals, spirits tastings, and distillery tours. As a leading industry resource since 2000, we ensure our Middlebury listings are updated hourly to help you find the perfect drink experience.