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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Portland, CT

Live Music At Arrigoni Winery!

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

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Carmel, NY

15th Annual Putnam County Wine & Music Fest

Sat, August 22, 2026

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Rhinebeck, NY

Hudson Valley Wine & Food Festival

Sat, September 12, 2026

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All Upcoming Local Events

94 Events listed within 60 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)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Aug 22, 2026 (Sat)
Spirits With A Twist - A Flavored Spirits Exploration
Total Wine & More | Multiple Locations, Nearby
  • Aug 23, 2026 (Sun)
Tomato Tomahto: A Harvest Celebration With Leah Guadagnoli
HGS Home Chef | Hillsdale, NY
  • Aug 23, 2026 (Sun)
Live Music With Sweeter Than Wine
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Aug 23, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • 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 23, 2026 (Sun)
Sunset Supper
Blue Duck Brewing Company | Kingston, NY
  • Aug 25, 2026 (Tue)
2026 Seaport Association Sheffield Island Clambake
90 Water St | Norwalk, CT
  • Aug 25, 2026 (Tue)
Taste The Story
Gingerbites Haitian Bistro | Huntington Station, NY
  • Aug 26, 2026 (Wed)
NEW! Hands-On Focaccia Sourdough Bread-Making Workshop With Reanna
Nest on Main | Northport, NY
  • Aug 27, 2026 (Thu)
Paint & Sip At Paradise Hills Vineyard | Wine Glasses
Paradise Hills Vineyard & Winery | Wallingford, CT
  • Aug 27, 2026 (Thu)
Great Lawn Supper Series At Canyon Ranch With Chef Joe Cash
Canyon Ranch, Lenox, MA, USA | Lenox, MA
  • Aug 27, 2026 (Thu)
Spuntino, Westbury - Tour Of France
Spuntino Wine Bar & Italian Tapas | Garden City, NY
  • Aug 27, 2026 (Thu)
Spuntino Westbury - Tour Of France Wine Walk Around
Spuntino Wine Bar | Garden City, New York
  • Aug 27, 2026 (Thu)
Wood-Fired Pizza Suppers At Stonegate Farm 2026
Stonegate Farm | Newburgh, NY
  • Aug 28, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • 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)
Hands-on Korean Gimbap, A Cooking Class With Chef Sylvia Becker
HGS Home Chef | Hillsdale, NY
  • Aug 29, 2026 (Sat)
Bartending Class With Tina
213 Saw Mill Rd | West Haven, CT
  • Aug 29, 2026 (Sat)
Honey Luncheon "Making Of A Lady Beekeeper"
5412 Sound Avenue, Riverhead, NY, USA | Riverhead, NY
  • Aug 29, 2026 (Sat)
Heirloom Tomato Festival
White Silo Farm & Winery | Sherman, CT
  • Aug 29, 2026 (Sat)
Summer Forage Tea Party
Hilltop Hanover Farm, Yorktown Heights, NY, USA | Yorktown Heights, NY
  • Aug 29, 2026 (Sat)
Live Music At Peconic Bay Vineyards For Reggae Rasta Day
Peconic Bay Vineyards | Cutchogue, NY
  • Aug 29, 2026 (Sat)
Reggae Rasta Day @ Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Aug 29, 2026 (Sat)
Create Your Own Gin In The Garden
The Landcraft Garden Foundation | Mattituck, NY
  • Aug 29, 2026 (Sat)
Dan’s White Party
Hallockville Museum Farm | Jamesport, NY
  • 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
  • Aug 30, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Aug 30, 2026 (Sun)
August's Beer, Wine, Tea, & Coffee Package: Katie's Haunted Book Club
Katies of Smithtown | Smithtown, NY
  • Sep 2, 2026 (Wed)
Summer Wine Trail - Fruit Punch-Glass Painting
Aquila's Nest Vineyards | Newtown, CT
  • Sep 3, 2026 (Thu)
Zachys Cellar School: Chardonnay Showdown
Zachys Wine & Liquor | Port Chester, NY
  • Sep 3, 2026 (Thu)
Chell's Charcuterie Class At Ox & Oak Vineyards
Ox & Oak Vineyards | Lebanon, CT
  • Sep 3, 2026 (Thu)
Wood-Fired Pizza Suppers At Stonegate Farm 2026
Stonegate Farm | Newburgh, NY
  • 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 4, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • 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 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 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)
Deep Dive Into Argentina’s Top Terroirs (by Mascota Vineyards, El Esteco, And More!)
Total Wine & More | Multiple Locations, Nearby
  • Sep 12, 2026 (Sat)
  • Sep 13, 2026 (Sun)
Hudson Valley Wine & Food Festival
Dutchess County Fairgrounds | Rhinebeck, NY
  • Sep 12, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 12, 2026 (Sat)
California Uncorked - Napa Valley & Beyond!
Total Wine & More | Multiple Locations, Nearby
  • Sep 13, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • 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 18, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 19, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 20, 2026 (Sun)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • Sep 24, 2026 (Thu)
Bergen Wine & Food Experience
Edgewood Country Club | River Vale, NJ
  • Sep 24, 2026 (Thu)
Singular Sensations - Getting To Know Single Malt
Total Wine & More | Multiple Locations, Nearby
  • Sep 25, 2026 (Fri)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • 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
  • Oct 3, 2026 (Sat)
Live Music At Peconic Bay Vineyards
Peconic Bay Vineyards | Cutchogue, NY
  • 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)
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 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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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.