Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near Middlebury, Connecticut

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Featured Local Events

Riverhead, New York

Fish & Sips

Fri, November 13, 2026

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New York, NY

Taste Of Oakville: Live At Carnegie Hall

Tue, November 10, 2026

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All Upcoming Local Events

81 Events listed within 60 miles.

60 miles 30 miles 15 miles
  • Oct 25, 2026 (Sun)
Live Music With Jon Condie
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 25, 2026 (Sun)
Wine And Live Music: NOIZE
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 25, 2026 (Sun)
Chef & Winemaker Dinner Series: Sweet Notes: A Dessert And Wine Pairing
City Winery Hudson Valley | Montgomery, New York
  • Oct 25, 2026 (Sun)
Autumn Harvest Dinner By Artisan West Hartford
1 Memorial Rd | West Hartford, CT
  • Oct 26, 2026 (Mon)
A Decade Of Excellence — BNapoli Turns 10
bNapoli Italian | West Springfield, MA
  • Oct 28, 2026 (Wed)
Amazing Grace Soup Supper 2026
Cross Street AME Zion Church | Middletown, CT
  • Oct 29, 2026 (Thu)
Mollydooker Wine Tasting @ Glastonbury Wine & Spirits
Glastonbury Wine & Spirits | Glastonbury, CT
  • Oct 29, 2026 (Thu)
Wine And Chocolate Tasting Experience
Moksha Café | Northport, NY
  • Oct 29, 2026 (Thu)
Zachys Cellar School: Production 101
Zachys Wine & Liquor | Port Chester, NY
  • Oct 29, 2026 (Thu)
Beyond The Glass: A Bardstown Bourbon Sensory Masterclass
Westchester Wine Warehouse | White Plains, NY
  • Oct 29, 2026 (Thu)
Beyond Riesling: Discovering German Wine
Dare Bottleshop & Provisions | Lenox, MA
  • Oct 29, 2026 (Thu)
Spuntino, Westbury - Italian Accents Wine Walk Around
Spuntino Wine Bar & Italian Tapas | Garden City, NY
  • Oct 29, 2026 (Thu)
Spuntino Wine Walk Around: Italian Accents
Spuntino Wine Bar & Italian Tapas | Garden City, NY
  • Oct 29, 2026 (Thu)
Holiday Entertaining With Chef Steve
Rockland Community College Hospitality & Culinary Arts Center | Nyack, NY
  • Oct 30, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 30, 2026 (Fri)
Halloween Charcuterie Workshop At Crystal Ridge Winery
Crystal Ridge Winery, Belltown Road, South Glastonbury, CT, USA | Glastonbury, CT
  • Oct 30, 2026 (Fri)
The House Remembers An Immersive Halloween Dinner At The Inn At Stockbridge
The Inn at Stockbridge | Stockbridge, MA
  • Oct 30, 2026 (Fri)
Grand Tasting: Italy
Spiritus Wines | Hartford, CT
  • Oct 30, 2026 (Fri)
In-person Class: Italian Cheesemaking: Mozzarella & Burrata (Long Island)
FIV Fire Island Vines | Bay Shore, NY
  • Oct 30, 2026 (Fri)
10/30 Spooky Mixology Cocktails Workshop
Grey Goat Farmtique | Branford, CT
  • Oct 31, 2026 (Sat)
Halloween Snacks With Chef Emma
Troutbeck | Amenia, NY
  • Oct 31, 2026 (Sat)
Vines & Vinyl Peconic Bay Vineyards Presents DJ Henry
Peconic Bay Vineyards | Cutchogue, NY
  • Nov 1, 2026 (Sun)
Milk Kefir Workshop
Hemato Institute | Katonah, NY
  • Nov 1, 2026 (Sun)
Cold Weather Cocktails & Nibbles With Leah Guadagnoli
HGS Home Chef | Hillsdale, NY
  • Nov 1, 2026 (Sun)
Girl Scout Cookies & Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Nov 1, 2026 (Sun)
Sourdough Bread Making Class
16 Robinson Ave | Bedford Hills, NY
  • Nov 2, 2026 (Mon)
Perfect Pairings: How To Pair Cheese And Wine
Fairfield Cheese Company | Fairfield, CT
  • Nov 4, 2026 (Wed)
Breads And Spreads: A Berry Good Biscuit Workshop
Aquila's Nest Vineyards | Newtown, CT
  • Nov 4, 2026 (Wed)
Wine Dinner With Wine Maker Greg Brewer
Quattro's Italian Restaurant | Guilford, CT
  • Nov 5, 2026 (Thu)
Thursday Night Mini Cooking Class - Ghee Three Ways With Kogetsu
HGS Home Chef | Hillsdale, NY
  • Nov 5, 2026 (Thu)
Thanksgiving Charcuterie Class
Aquila's Nest Vineyards | Newtown, CT
  • Nov 5, 2026 (Thu)
Wine Tasting
The Woodwinds | Branford, Connecticut
  • Nov 5, 2026 (Thu)
Pop Open A Party - Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Nov 6, 2026 (Fri)
A Taste Of Possibility
The Culinary Institute of America | Hyde Park, NY
  • Nov 6, 2026 (Fri)
Cheese & Charcuterie Board Building @ Walker Road Vineyards
Walker Road Vineyards LLC | Woodbury, CT
  • Nov 6, 2026 (Fri)
Pouring Over Pages: A Book And Wine Pairing Event
Aquila's Nest Vineyards | Newtown, CT
  • Nov 6, 2026 (Fri)
Special Guest Pablo De Simón Pours His Rioja Wines
Total Wine & More | Multiple Locations, Nearby
  • Nov 6, 2026 (Fri)
Wagyu, Whiskey, And Wine - Morton's Great Neck
Morton's The Steakhouse | Great Neck, NY
  • Nov 7, 2026 (Sat)
It’s The Season! Holiday Baking With Miriam Rubin
HGS Home Chef | Hillsdale, NY
  • Nov 7, 2026 (Sat)
Fall Desserts & Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Nov 21, 2026 (Sat)
  • Dec 5, 2026 (Sat)
  • Dec 19, 2026 (Sat)
  • Nov 7, 2026 (Sat)
Behind The Scenes At Stoutridge Distillery & Winery - Tour & Tasting
Stoutridge Distillery and Winery | Marlboro, NY
  • Nov 7, 2026 (Sat)
Pour And Explore: Wines Of Tuscany
Two Hounds Public House | Newtown, CT
  • Nov 7, 2026 (Sat)
22nd Annual Cask Ales Festival
Blue Point Brewing Company | Patchogue, NY
  • Nov 7, 2026 (Sat)
Pop Open A Party - Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Nov 7, 2026 (Sat)
Tequila Tasting & Mixing Experience
Martie’s | West Springfield, MA
  • Nov 7, 2026 (Sat)
Autum Wine Experience
Moksha Cafe | Northport, NY
  • Nov 7, 2026 (Sat)
Wagyu, Whiskey, And Wine - Morton's White Plains
Morton's The Steakhouse | White Plains, NY
  • Nov 7, 2026 (Sat)
Sip And Taste
104 N Washington Ave | Hartsdale, NY
  • Nov 8, 2026 (Sun)
European Soups To Nourish Your Soul - Cooking Class With Kogetsu
HGS Home Chef | Hillsdale, NY
  • Nov 8, 2026 (Sun)
Ember & Vine: A Candle Making + Wine Experience At Bedell Vineyards
Bedell Cellars | Cutchogue, NY
  • Nov 8, 2026 (Sun)
Smoke On The Water - Whiskey & Cigar Pairing Event
40 Bridgeport Avenue, Milford, CT, USA | Milford, CT
  • Nov 9, 2026 (Mon)
Zachys X G.D. Vajra: Masterclass With Giuseppe Vaira
Zachys Wine & Liquor | Port Chester, NY
  • Nov 10, 2026 (Tue)
California Cuisine Lunch By Advanced Food Preparation -
Culinary Arts Center Dining Room L294 | Manchester, CT
  • Nov 10, 2026 (Tue)
Hands-On Cavatelli Pasta & Homemade Pumpkin Sauce Workshop!
Nest on Main | Northport, NY
  • Nov 10, 2026 (Tue)
Taste Of Oakville: Live At Carnegie Hall
Carnegie Hall | New York, NY
Buy Tickets
  • Nov 11, 2026 (Wed)
Create Your Own Tea And Spice Blend Gifts
The Spice & Tea Exchange of New Canaan | New Canaan, CT
  • Nov 11, 2026 (Wed)
Bordeaux Wine Dinner At The Roger Sherman Inn
Roger Sherman Inn | New Canaan, CT
  • Nov 11, 2026 (Wed)
Perfect Pairings: How To Pair Cheese And Wine
Greenwich Cheese Company | Cos Cob, CT
  • Nov 11, 2026 (Wed)
Apple Tart Tatin & Vanilla Bean Mascarpone Cream
Rockland Community College Hospitality and Culinary Arts Center | Nyack, NY
  • Nov 12, 2026 (Thu)
Wine Tasting To Benefit The Sunshine Kids
20 Wilton Rd | Westport, CT
  • Nov 12, 2026 (Thu)
Orin Swift Wine Dinner
The Waters Edge at Giovanni's | Darien, CT
  • Nov 12, 2026 (Thu)
Zachys Cellar School: Advanced – The Intercontinental Family Connection
Zachys Wine & Liquor | Port Chester, NY
  • Nov 12, 2026 (Thu)
DateNight Downtown Wine & Cheese Tasting At Manchester Historical Society
Manchester Historical Society | Manchester, CT
  • Nov 12, 2026 (Thu)
Sips Of The Season: A Guide To Holiday Entertaining
Total Wine & More | Multiple Locations, Nearby
  • Nov 12, 2026 (Thu)
Celebrate The Release Of "In Good Taste" With Kit Keenan At Athena Books!
Athena Books | Greenwich, CT
  • Nov 13, 2026 (Fri)
Chell's Charcuterie Holiday Wreath Class At Tranquillity Vineyard
Tranquillity Vineyard & Winery | Middlebury, CT
  • Nov 13, 2026 (Fri)
The Wines Of Spain: A Celebration Of Terroir, Tradition & Taste
Westchester Wine Warehouse | White Plains, NY
  • Nov 13, 2026 (Fri)
Around The World With Alexander Murray
Total Wine & More | Multiple Locations, Nearby
  • Nov 13, 2026 (Fri)
11/13 Mixology Class & Holiday Cocktail Preview
Grey Goat Farmtique | Branford, CT
  • Nov 13, 2026 (Fri)
Fish & Sips
Long Island Aquarium | Riverhead, New York
  • Nov 14, 2026 (Sat)
Around The World With Alexander Murray
Total Wine & More | Multiple Locations, Nearby
  • Nov 20, 2026 (Fri)
Chef & Winemaker Dinner Series: From Masa To Mole
City Winery Hudson Valley | Montgomery, New York
  • Nov 21, 2026 (Sat)
  • Nov 22, 2026 (Sun)
  • Dec 5, 2026 (Sat)
  • Dec 6, 2026 (Sun)
Uncork The Holidays On The Shawangunk Wine Trail
Multiple Locations Along the Shawangunk Wine Trail | Washingtonville, NY
  • 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
  • Jan 14, 2027 (Thu)
The King Of Grapes - Discover Cabernet Sauvignon
Total Wine & More | Multiple Locations, Nearby
  • Jan 16, 2027 (Sat)
The King Of Grapes - Discover Cabernet Sauvignon
Total Wine & More | Multiple Locations, Nearby
  • Jan 21, 2027 (Thu)
Barrel Aged Spirits: Whiskey, Tequila & More
Total Wine & More | Multiple Locations, Nearby
  • Feb 4, 2027 (Thu)
Wine And Chocolate - A Perfect Pair
Total Wine & More | Multiple Locations, Nearby
  • Feb 6, 2027 (Sat)
Wine And Chocolate - A Perfect Pair
Total Wine & More | Multiple Locations, Nearby
  • Feb 18, 2027 (Thu)
Smoke & Spice: The Bold Side Of Whiskey
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.

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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.