Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near Middlebury, Connecticut

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Premium Event

Hudson Valley Wine & Food Festival
  • Sat, September 12, 2026
Rhinebeck, NY
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Featured Local Events

Portland, Connecticut

Yoga Night At Arrigoni Winery

Wed, September 9, 2026

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Westborough, MA

Sake Day East 2026

Sat, October 3, 2026

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Portland, CT

Live Music At Arrigoni Winery!

Fri, September 4, 2026 to Sun, September 6, 2026

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Rhinebeck, NY

Hudson Valley Wine & Food Festival

Sat, September 12, 2026

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All Upcoming Local Events

105 Events listed within 60 miles.

60 miles 30 miles 15 miles
  • Sep 4-6, 2026 (Fri-Sun)
Month Of September @ Home Range Winery
Home Range Winery | Canaan, NY
  • Sep 4-6, 2026 (Fri-Sun)
  • Sep 11-13, 2026 (Fri-Sun)
  • Sep 18-20, 2026 (Fri-Sun)
Live Music At Arrigoni Winery!
Arrigoni Winery | Portland, 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 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)
Bartending Class With Tina
213 Saw Mill Rd | West Haven, CT
  • Sep 5, 2026 (Sat)
2026 Honey Harvest And Luncheon
5412 Sound Avenue, Riverhead, NY, USA | Riverhead, NY
  • Sep 6, 2026 (Sun)
Fine Pastries And Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Sep 6, 2026 (Sun)
Live Music With Gemsong Productions
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 6, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 7, 2026 (Mon)
Peconic Bay Vineyards Celebrates Labor Day With Live Music Event
Peconic Bay Vineyards | Cutchogue, NY
  • 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 9, 2026 (Wed)
Deep Dive Into Argentina’s Top Terroirs (by Mascota Vineyards, El Esteco, And More!)
Total Wine & More | Multiple Locations, Nearby
  • 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 10, 2026 (Thu)
Wood-Fired Pizza Suppers At Stonegate Farm 2026
Stonegate Farm | Newburgh, NY
  • Sep 11, 2026 (Fri)
Live Music With Bernie Gagliardi
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 11, 2026 (Fri)
Breads And Spreads: A Focaccia Workshop Experience
Aquila's Nest Vineyards | Newtown, CT
  • 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 11, 2026 (Fri)
Pouring Over Pages: A Book And Wine Pairing Event
Stappa Vineyard | Orange, CT
  • Sep 11, 2026 (Fri)
9/11 Mixology Class & Fall Cocktail Preview
Grey Goat Farmtique | Branford, CT
  • Sep 11, 2026 (Fri)
The Prestige Dinner
141 Main St | Beacon, NY
  • Sep 12, 2026 (Sat)
Fall Soups, Stews, & Comfort Foods
617 Main St N | Southbury, CT
  • Sep 12-13, 2026 (Sat-Sun)
2026 Hudson Valley Wine & Food Festival
Dutchess County Fairgrounds, U.S. 9, Rhinebeck, NY, USA | Rhinebeck, NY
  • Sep 12, 2026 (Sat)
  • Sep 13, 2026 (Sun)
Hudson Valley Wine & Food Festival
Dutchess County Fairgrounds | Rhinebeck, NY
  • Sep 12, 2026 (Sat)
  • Sep 26, 2026 (Sat)
  • Oct 10, 2026 (Sat)
  • Nov 7, 2026 (Sat)
Stoutridge Tour & Tasting With The Distiller/Winemaker
Stoutridge Distillery and Winery | Marlboro, NY
  • Sep 12, 2026 (Sat)
Old World Elegance: A Burgundy Tasting
Zachys Wine & Liquor | Port Chester, NY
  • Sep 12, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 12, 2026 (Sat)
NFA Wine Tasting Sunset Fundraiser
Holcombe Hill Wildlife Preserve | Newtown, CT
  • Sep 12, 2026 (Sat)
California Uncorked - Napa Valley & Beyond!
Total Wine & More | Multiple Locations, Nearby
  • Sep 12, 2026 (Sat)
Little Lion's Fall Wine Club
New England Spirits & Wine Purveyors | Hamden, CT
  • Sep 13, 2026 (Sun)
Western Mass Vegan Food Fest: September Edition
Abandoned Building Brewery | Easthampton, MA
  • Sep 13, 2026 (Sun)
Live Music With Airborne Jazz
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 13, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 13, 2026 (Sun)
Cooking Demo Dinner - Crew Restaurant & Bar
Crew Restaurant & Bar | Poughkeepsie, NY
  • Sep 13, 2026 (Sun)
Oktoberfest Bratwurst Chef Competition Fundraiser In Croton On Hudson
The Grand | Croton-on-Hudson, NY
  • Sep 13, 2026 (Sun)
Chefs For Sub-Edge
100 Tillotson Rd | Avon, CT
  • Sep 14-20, 2026 (Mon-Sun)
  • Sep 21-27, 2026 (Mon-Sun)
  • Sep 28-30, 2026 (Mon-Wed)
Harvest The Hudson On The Shawangunk Wine Trail
Shawangunk Wine Trail | Hudson Valley, NY
  • Sep 15, 2026 (Tue)
Gluten Free Baking Part 2
617 Main St N | Southbury, CT
  • Sep 16, 2026 (Wed)
Oktoberfest Beer Dinner
Tin Bridge Brewing Co. | Westfield, MA
  • Sep 17, 2026 (Thu)
Cigar & Whiskey Dinner At Haven Beer Company
Haven Beer Company | Hamden, CT
  • Sep 17, 2026 (Thu)
RoseHill Kitchen X Sport Hill Farm Dinner
Sport Hill Farm | Easton, CT
  • Sep 17, 2026 (Thu)
Fall In Tuscany - Adult Cooking Class With Laura Weinman
Wakeman Town Farm | Westport, CT
  • Sep 17, 2026 (Thu)
Napa Valley Wine Dinner At The Waters Edge At Giovanni's
The Waters Edge at Giovanni's | Darien, CT
  • Sep 17, 2026 (Thu)
Zachys Cellar School: Drinking Australia
Zachys Wine & Liquor | Port Chester, NY
  • Sep 17, 2026 (Thu)
Beyond Agave: A Mezcal, Sotol & Artisan Cheese Experience
Westchester Wine Warehouse | White Plains, NY
  • Sep 17, 2026 (Thu)
Great Lawn Supper Series At Canyon Ranch With Chef David Standridge
Canyon Ranch, Lenox, MA, USA | Lenox, MA
  • Sep 17, 2026 (Thu)
Wood-Fired Pizza Suppers At Stonegate Farm 2026
Stonegate Farm | Newburgh, NY
  • Sep 18, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 18, 2026 (Fri)
Live Music With Dave Crispino
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 18, 2026 (Fri)
Edible Art Dessert Workshop By Indulgences By Dee -Aquila’s Nest Vineyards
Aquila's Nest Vineyards | Sandy Hook, CT
  • Sep 19, 2026 (Sat)
Wine Trail -Tote Bags Painting
Aquila's Nest Vineyards | Newtown, CT
  • Sep 19, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 19, 2026 (Sat)
11th Annual BEER FEST!
2 Sarah Sanford Rd E | Bridgewater, CT
  • Sep 19, 2026 (Sat)
The Long Island Wine And Food Classic
Farmingdale State College | Farmingdale, NY
  • Sep 20, 2026 (Sun)
Green Tea: Leaf To Cup Workshop
Hemato Institute | Katonah, NY
  • Sep 20, 2026 (Sun)
Chocolate And Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Sep 20, 2026 (Sun)
Live Music With Tony Di & Carla Zipay
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 20, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 23, 2026 (Wed)
"A" Is For Apple Culinary Class For Kids
Stew Leonard's of Newington | Newington, CT
  • Sep 24, 2026 (Thu)
Blue Back Burger Bash
Blue Back Square | West Hartford, CT
  • Sep 24, 2026 (Thu)
Thursday Night Mini Cooking Class – Miracle Mayo & More With Lee Davenport
HGS Home Chef | Hillsdale, NY
  • Sep 24, 2026 (Thu)
Fall Wreath Making Workshop
Aquila's Nest Vineyards | Newtown, CT
  • Sep 24, 2026 (Thu)
Bergen Wine & Food Experience
Edgewood Country Club | River Vale, NJ
  • Sep 24, 2026 (Thu)
Spuntino, Westbury - World Tour Reds
Spuntino Wine Bar & Italian Tapas | Garden City, NY
  • Sep 24, 2026 (Thu)
Cheese 101
Fairfield Cheese Company | Fairfield, CT
  • Sep 24, 2026 (Thu)
Singular Sensations - Getting To Know Single Malt
Total Wine & More | Multiple Locations, Nearby
  • Sep 24, 2026 (Thu)
Ocean's Annual Luau On The Beach, Thursday, Sept 24
The Crescent Beach Club | Bayville, NY
  • Sep 24, 2026 (Thu)
Table 4 Tonight: New Haven | BEST FRIENDS EDITION
Restaurant of the Week | New Haven, CT
  • Sep 24, 2026 (Thu)
Singles Mixer In West Hartford CT!
Barcelona Wine Bar | West Hartford, CT
  • Sep 24, 2026 (Thu)
Wood-Fired Pizza Suppers At Stonegate Farm 2026
Stonegate Farm | Newburgh, NY
  • Sep 25, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 25, 2026 (Fri)
Live Music With Nick Fradiani Sr
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 26, 2026 (Sat)
Grand Fall Cider Tasting At Boutique 2026
Boutique Wines, Spirits, & Ciders | Fishkill, NY
  • Sep 26, 2026 (Sat)
Singular Sensations - Getting To Know Single Malt
Total Wine & More | Multiple Locations, Nearby
  • Sep 27, 2026 (Sun)
Live Music With DizzyFish
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 3, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 3, 2026 (Sat)
Sake Day East 2026
Julio's Liquors | Westborough, MA
  • 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 9, 2026 (Fri)
  • Oct 10, 2026 (Sat)
  • Oct 11, 2026 (Sun)
  • Oct 12, 2026 (Mon)
Famous Food Festival 2026 - Columbus Day Weekend
Tanger Outlets Deer Park | Long Island, New York
  • Oct 9, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 9, 2026 (Fri)
Explore The Flavors Of California: Wine Class With Needle & Thread, Mother's Choice & More
Total Wine & More | Multiple Locations, Nearby
  • Oct 10, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 10, 2026 (Sat)
Sip N' Snack Pairings
Total Wine & More | Multiple Locations, Nearby
  • Oct 11, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 15, 2026 (Thu)
Deep Dive Into Argentina’s Top Terroirs (by Mascota Vineyards, El Esteco, And More!)
Total Wine & More | Multiple Locations, Nearby
  • Oct 16, 2026 (Fri)
Deep Dive Into Argentina’s Top Terroirs (by Mascota Vineyards, El Esteco, And More!)
Total Wine & More | Multiple Locations, Nearby
  • Oct 17, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 18, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 22, 2026 (Thu)
Icons Of Spirits
Total Wine & More | Multiple Locations, Nearby
  • Oct 23, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 24, 2026 (Sat)
Icons Of Spirits
Total Wine & More | Multiple Locations, Nearby
  • Oct 30, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Oct 31, 2026 (Sat)
Vines & Vinyl Peconic Bay Vineyards Presents DJ Henry
Peconic Bay Vineyards | Cutchogue, NY
  • 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 13, 2026 (Fri)
Around The World With Alexander Murray
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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