Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near Middlebury, Connecticut

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Premium Event

Nantucket Wine & Food Festival
  • Wed, May 27, 2026 to Sun, May 31, 2026
Nantucket, MA
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Featured Local Events

White Plains, NY

The Westchester Wine Warehouse Grand Portfolio Tasting (FREE EVENT)

Sat, April 25, 2026

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Nantucket, MA

Nantucket Wine & Food Festival

Wed, May 27, 2026 to Sun, May 31, 2026

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Carmel, NY

15th Annual Putnam County Wine & Music Fest

Sat, August 22, 2026

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Montgomery, New York

Earth Day At The Wineries | Hudson Valley Wine Trail Tasting Experience

Sat, April 18, 2026

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All Upcoming Local Events

85 Events listed within 60 miles.

60 miles 30 miles 15 miles
  • Mar 30, 2026 (Mon)
A Culinary Uprising, The Story Of Bloodroot/ Documentary & Vegan Dinner
Joylark Kitchen | Fairfield, CT
  • Mar 31, 2026 (Tue)
Pasta Making Class At Spuntino, Westbury!
Spuntino Wine Bar & Italian Tapas | Garden City, NY
  • Apr 1, 2026 (Wed)
Winter Wine Trail - Daisies - Wine Glass Class Painting
Aquila's Nest Vineyards | Newtown, CT
  • Apr 1, 2026 (Wed)
Spain And Portugal Cuisine Dinner By International Foods
Culinary Arts Center Dining Room L294 | Manchester, CT
  • Apr 2, 2026 (Thu)
Easter Charcuterie Workshop
Crystal Ridge Winery, Belltown Road, South Glastonbury, CT, USA | Glastonbury, CT
  • Apr 2, 2026 (Thu)
Sip & Pour Candle Making Class At Paradise Hill Vineyard
Paradise Hills Vineyard & Winery | Wallingford, CT
  • Apr 2, 2026 (Thu)
Zachys Cellar School: Spain 101
Zachys Wine & Liquor | Port Chester, NY
  • Apr 3, 2026 (Fri)
Live Music With Gemsong Productions
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 3, 2026 (Fri)
Spring Mixology At The Grey Goat: SECOND DATE ADDED!
Grey Goat Farmtique | Branford, CT
  • Apr 4, 2026 (Sat)
Easter Egg Hunt
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 4, 2026 (Sat)
Local Cheese & Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Apr 4, 2026 (Sat)
Distillery Tour & Tasting
Connecticut Distilling Tasting Lounge | Waterbury, CT
  • Apr 4, 2026 (Sat)
1st Annual Robibero Egg Toss
Robibero Winery | New Paltz, New York
  • Apr 7, 2026 (Tue)
Master Of The Green Lunch Buffet By Catering Management
Culinary Arts Center Dining Room L294 | Manchester, CT
  • Apr 7, 2026 (Tue)
In-person Class: Make Your Own Sushi (Long Island)
Holiday Inn Express Hauppauge-Long Island | Hauppauge, NY
  • Apr 8, 2026 (Wed)
Make Matzo
Troutbeck | Amenia, NY
  • Apr 8, 2026 (Wed)
Paint & Sip Night At The Twisted Vine Restaurant
Twisted Vine Restaurant | Derby, CT
  • Apr 8, 2026 (Wed)
South West & Rocky Mountains Dinner By Advanced Food Preparation
Culinary Arts Center Dining Room L294 | Manchester, CT
  • Apr 9, 2026 (Thu)
Legends Of Wine
Total Wine & More | Multiple Locations, Nearby
  • Apr 10, 2026 (Fri)
Live Music With Chris Marolda
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 10, 2026 (Fri)
Silver Oak Uncorked: Estate & Single-Vineyard Wines Of California
Westchester Wine Warehouse | White Plains, NY
  • Apr 10, 2026 (Fri)
Portuguese Cheese And Wine Tasting
Dom's Cheese Shop | Avon, CT
  • Apr 10, 2026 (Fri)
In-person Class: Cavatelli, Orecchiette And Foglie(Long Island)
SpringHill Suites by Marriott Long Island Brookhaven | Bellport, NY
  • Apr 11, 2026 (Sat)
  • Apr 12, 2026 (Sun)
Barrel Tasting Weekend
Robibero Winery | New Paltz, New York
  • Apr 11, 2026 (Sat)
Distillery Tour & Tasting
Connecticut Distilling Tasting Lounge | Waterbury, CT
  • Apr 11, 2026 (Sat)
Legends Of Wine
Total Wine & More | Multiple Locations, Nearby
  • Apr 11, 2026 (Sat)
18th Annual Taste Of Wethersfield Benefit
Keeney Memorial Cultural Center | Wethersfield, CT
  • Apr 11, 2026 (Sat)
SIP & STYLE - A Charcuterie Experience - *purchase Through Square*
R Dee Winery | Enfield, CT
  • Apr 12, 2026 (Sun)
Blanc & Franc Brunch Series
The Watershed Kitchen and Bar | Jamesport, NY
  • Apr 12, 2026 (Sun)
Live Music With DizzyFish
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 12, 2026 (Sun)
Caramoor & Stone Barns Center Present: Dinner With Ella & Louis
Blue Hill at Stone Barns | Tarrytown, NY
  • Apr 14, 2026 (Tue)
Hawaiian Cuisine Lunch By Advanced Food Preparation
Culinary Arts Center Dining Room L294 | Manchester, CT
  • Apr 14, 2026 (Tue)
Pizza Making Class - Spuntino, Westbury!
Spuntino Wine Bar & Italian Tapas | Garden City, NY
  • Apr 16, 2026 (Thu)
Zachys Cellar School: Bordeaux 101
Zachys Wine & Liquor | Port Chester, NY
  • Apr 17, 2026 (Fri)
Live Music With Eran Troy Danner
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 17, 2026 (Fri)
The Left Bank: Bordeaux’s Most Iconic Cabernet Wines
Westchester Wine Warehouse | White Plains, NY
  • Apr 17, 2026 (Fri)
Rose Wine Seminar With Jay In Monroe
574 Monroe Turnpike | Monroe, CT
  • Apr 17, 2026 (Fri)
Michter's Whiskey Masterclass
Total Wine & More | Multiple Locations, Nearby
  • Apr 17, 2026 (Fri)
Wine Dinner With Teal Walker Of Audeant Wines
Blue Hill at Stone Barns | Tarrytown, NY
  • Apr 17, 2026 (Fri)
In-person Class: Handmade Pasta 101 (Long Island)
SpringHill Suites by Marriott Long Island Brookhaven | Bellport, NY
  • Apr 18, 2026 (Sat)
Easy & Casual French - A Cooking Class With Tess Kelly
HGS Home Chef | Hillsdale, NY
  • Apr 18, 2026 (Sat)
  • Apr 19, 2026 (Sun)
Earth Day At The Wineries | Hudson Valley Wine Trail Tasting Experience
Shawangunk Wine Trail (Multiple Locations in Ulster and Orange Counties) | Montgomery, New York
  • Apr 18, 2026 (Sat)
Chocolate Fondue Dip & Sip
Aquila's Nest Vineyards | Newtown, CT
  • Apr 18, 2026 (Sat)
2026 Appetizer & Dessert Crawl Series At The Shops At Yale - 1 Of 4
The Shops at Yale (check-in is located at The Yale Bookstore) | New Haven, CT
  • Apr 18, 2026 (Sat)
Zachys Spring Grand Tasting
Zachys Wine & Liquor | Port Chester, NY
  • Apr 18, 2026 (Sat)
Brew U 2026
The Egg on the CIA Campus | Hyde Park, NY
  • Apr 18, 2026 (Sat)
Sourdough Focaccia Bread Art Workshop | Beacon, NY
Blooming Hearts Studio,The Lofts at Beacon | Beacon, NY
  • Apr 18, 2026 (Sat)
Estate & Elegance: An Alexander Valley Vineyards Epicurean Dinner
Madison Beach Hotel, Curio Collection by Hilton | Madison, CT
  • Apr 19, 2026 (Sun)
Coffee Tasting Experience By Ovelle Coffee X New England Coffee Guy
New England Coffee Guy (Cafe/Mobile Espresso Cart) | West Hartford, CT
  • Apr 19, 2026 (Sun)
Buen Provecho: An Introduction To Oaxacan Cuisine With Leah Guadagnoli
HGS Home Chef | Hillsdale, NY
  • Apr 19, 2026 (Sun)
8th Annual Cask Ales FUNdraiser
Sand City Brewing | Lindenhurst, NY
  • Apr 19, 2026 (Sun)
Island Spirit & Cocktail Convention
The Experience | Hauppauge, NY
  • Apr 19, 2026 (Sun)
Learn How To Judge Wine Like A Pro!
Tranquillity Vineyard & Winery | Middlebury, CT
  • Apr 19, 2026 (Sun)
Live Music With Tony Di & Carla Zipay
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 23, 2026 (Thu)
Pop Open A Party—Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Apr 23, 2026 (Thu)
Salud! An Introduction To Tequila & Mezcal
Total Wine & More | Multiple Locations, Nearby
  • Apr 24, 2026 (Fri)
Live Music With Carrie Ashton
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 25, 2026 (Sat)
The Westchester Wine Warehouse Grand Portfolio Tasting (FREE EVENT)
Westchester Wine Warehouse | White Plains, NY
Register
  • Apr 25, 2026 (Sat)
Grand Spring Hard Cider Tasting Event At Boutique
Boutique Wines, Spirits and Cider | Fishkill, NY
  • Apr 25, 2026 (Sat)
Salud! An Introduction To Tequila & Mezcal
Total Wine & More | Multiple Locations, Nearby
  • Apr 26, 2026 (Sun)
Live Music With Airborne Jazz
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Apr 30, 2026 (Thu)
Deep Dive Into Argentina’s Top Terroirs (by Mascota Vineyards, El Esteco, And More!)
Total Wine & More | Multiple Locations, Nearby
  • May 1, 2026 (Fri)
Deep Dive Into Argentina’s Top Terroirs (by Mascota Vineyards, El Esteco, And More!)
Total Wine & More | Multiple Locations, Nearby
  • May 2, 2026 (Sat)
Unlocking The Secrets Of Burgundy With The Boisset Family
Total Wine & More | Multiple Locations, Nearby
  • May 14, 2026 (Thu)
Vive La France
Total Wine & More | Multiple Locations, Nearby
  • May 15, 2026 (Fri)
Michter's Whiskey Masterclass
Total Wine & More | Multiple Locations, Nearby
  • May 16, 2026 (Sat)
Vive La France
Total Wine & More | Multiple Locations, Nearby
  • May 27-31, 2026 (Wed-Sun)
Nantucket Wine & Food Festival
Multiple Venues Across Nantucket | Nantucket, MA
  • May 28, 2026 (Thu)
Gin, Vodka & Tequila— A Battle Of The Clear Spirits
Total Wine & More | Multiple Locations, Nearby
  • May 30, 2026 (Sat)
Gin, Vodka & Tequila— A Battle Of The Clear Spirits
Total Wine & More | Multiple Locations, Nearby
  • Jun 4, 2026 (Thu)
Amici Cellars Wine Experience
Total Wine & More | Multiple Locations, Nearby
  • Jun 5, 2026 (Fri)
The State Of Single Estate Cognac With ABK6
Total Wine & More | Multiple Locations, Nearby
  • Jun 6, 2026 (Sat)
The State Of Single Estate Cognac With ABK6
Total Wine & More | Multiple Locations, Nearby
  • Jun 11, 2026 (Thu)
Under The Tuscan Sun
Total Wine & More | Multiple Locations, Nearby
  • Jun 13, 2026 (Sat)
Under The Tuscan Sun
Total Wine & More | Multiple Locations, Nearby
  • Jun 18, 2026 (Thu)
The Secret To Tequila & Cocktail Making With Código 1530
Total Wine & More | Multiple Locations, Nearby
  • Jun 19, 2026 (Fri)
The Secret To Tequila & Cocktail Making With Código 1530
Total Wine & More | Multiple Locations, Nearby
  • Jun 25, 2026 (Thu)
Bourbon - America's Native Spirit
Total Wine & More | Multiple Locations, Nearby
  • Jun 27, 2026 (Sat)
Bourbon - America's Native Spirit
Total Wine & More | Multiple Locations, Nearby
  • Jul 9, 2026 (Thu)
Cool Climate Craft: Pacific Northwest Wines
Total Wine & More | Multiple Locations, Nearby
  • Jul 11, 2026 (Sat)
Cool Climate Craft: Pacific Northwest Wines
Total Wine & More | Multiple Locations, Nearby
  • Jul 15, 2026 (Wed)
Cocktails That Are Fighting Hunger
Total Wine & More | Multiple Locations, Nearby
  • Jul 23, 2026 (Thu)
Rum For All And All For Rum!
Total Wine & More | Multiple Locations, Nearby
  • Jul 25, 2026 (Sat)
Rum For All And All For Rum!
Total Wine & More | Multiple Locations, Nearby
  • Aug 22, 2026 (Sat)
  • Aug 23, 2026 (Sun)
15th Annual Putnam County Wine & Music Fest
Putnam County Veterans Memorial Park (Upper) | Carmel, NY
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Wine, Food & Drink in Middlebury: Frequently Asked Questions

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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.

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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.