Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near Springfield, Massachusetts

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Premium Event

Nantucket Wine & Food Festival
  • Wed, May 14, 2025 to Sun, May 18, 2025
Nantucket, MA
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Featured Local Events

Portland, CT

Arrigoni Winery’s Comedy Night Featuring Brian Glowacki

Sat, June 21, 2025

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Portland, CT

Hocus Pocus: Sanderson Sisters Drag Show & Live Music Event

Sat, September 13, 2025

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Chatham, NY

The Annual Hudson Berkshire Wine & Food Festival

Sat, May 24, 2025

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Carmel, NY

14th Putnam County Wine & Music Fest

Sat, August 16, 2025

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Portland, CT

Taste The Rainbow: Arrigoni Drag Show & Live Music Event

Fri, June 6, 2025

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Portland, CT

Live Music At Arrigoni Winery!

Fri, May 23, 2025 to Mon, May 26, 2025

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Nantucket, MA

Nantucket Wine & Food Festival

Wed, May 14, 2025 to Sun, May 18, 2025

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Brooklyn, New York

An Exclusive Afternoon Of Champagne & Conversation With Stephanie Browne

Sat, June 21, 2025

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Portland, CT

Yoga Night At Arrigoni Winery

Wed, May 28, 2025

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All Upcoming Local Events

  • May 14-18, 2025 (Wed-Sun)
Nantucket Wine & Food Festival
Nantucket Island | Nantucket, MA
  • May 18, 2025 (Sun)
LGBTQ+ After-Hike Dinner @ Barrington Brewery (Great Barrington, MA)
Barrington Brewery & Restaurant | Great Barrington, MA
  • May 20, 2025 (Tue)
Whisky Dinner Presented By Firefly’s BBQ + Julio’s Liquors
Firefly's BBQ | Marlborough, MA
  • May 20, 2025 (Tue)
Tutti Wine Tasting
Tutti Quanti Italian Market | Sturbridge, MA
  • May 21, 2025 (Wed)
Local Wine & Dessert Pairing At Lilac Hedge Farm
Lilac Hedge Farm | Rutland, MA
  • May 23, 2025 (Fri)
Live Music With Nick Fradiani Sr
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 23-26, 2025 (Fri-Mon)
Live Music At Arrigoni Winery!
Arrigoni Winery | Portland, CT
  • May 23, 2025 (Fri)
A Night In France Wine Pairing Experience At Hardwick Winery
Hardwick Winery | Hardwick, MA
  • May 24, 2025 (Sat)
  • May 25, 2025 (Sun)
The Annual Hudson Berkshire Wine & Food Festival
Columbia County Fairgrounds | Chatham, NY
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  • May 24, 2025 (Sat)
Prix Fixe Lunch Of Indian Vegan Specialities
India Masala House | Brattleboro, VT
  • May 25, 2025 (Sun)
Live Music With Jon Condie
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 25, 2025 (Sun)
Wine Tasting @ Hank's Restaurant
Hank's Restaurant | Brooklyn, CT
  • May 27, 2025 (Tue)
Cooking Class @ Paradise Hills Vineyard: Shrimp Scampi
Paradise Hills Vineyard and Winery | Wallingford, Connecticut

40% Off All Riedel Glassware

Elevate every sip with perfectly crafted glassware. For a limited time only.

Shop the Sale
  • May 28, 2025 (Wed)
A Tasteful Event, 2025
Litchfield Community Center | Litchfield, CT
  • May 28, 2025 (Wed)
Yoga Night At Arrigoni Winery
Arrigoni Winery | Portland, CT
  • May 28, 2025 (Wed)
Learn To Roll Sushi At The Grey Goat
Grey Goat Farmtique | Branford, CT
  • May 29, 2025 (Thu)
Chell's Charcuterie Rustic, Italian Theme Class At Paradise Hills Vineyard
Paradise Hills Vineyard & Winery | Wallingford, CT
  • May 29, 2025 (Thu)
Exploremos America Del Sur
Total Wine & More | Multiple Locations, Nearby
  • May 30, 2025 (Fri)
Live Music With Arlene Wow
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 31, 2025 (Sat)
Spirits With A Twist - A Flavored Spirits Exploration
Total Wine & More | Multiple Locations, Nearby
  • Jun 1, 2025 (Sun)
Sushi Sunday
17 Fabyan Woodstock Rd | Thompson, CT
  • Jun 1, 2025 (Sun)
Live Music With Lion Child
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 4, 2025 (Wed)
Adventures In International Dining: Formosa
Formosa Chinese Restaurant | Amherst, MA
  • Jun 4, 2025 (Wed)
Pretty In Pink - Rosé Soirée!
Mullahy's Cheese Shop | Hudson, MA
  • Jun 5, 2025 (Thu)
Charcuterie Workshop
Crystal Ridge Winery, Belltown Road, South Glastonbury, CT, USA | Glastonbury, CT
  • Jun 5, 2025 (Thu)
Wine & Chocolate Truffles Pairing At Broken Creek Vineyard
Broken Creek Vineyard and Winery | Shrewsbury, MA
  • Jun 6, 2025 (Fri)
Live Music With Myke Ross
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 6, 2025 (Fri)
Taste The Rainbow: Arrigoni Drag Show & Live Music Event
Arrigoni Winery | Portland, CT
  • Jun 7, 2025 (Sat)
13th Worcester 
Food Truck & Craft Beer Festival
Worcester Common | Worcester, MA
  • Jun 7, 2025 (Sat)
Meet & Taste: Explore Chilean Wines In An Exclusive Tasting With Viña Carmen
Total Wine & More | Multiple Locations, Nearby
  • Jun 8, 2025 (Sun)
Live Music With Airborne Jazz
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 8, 2025 (Sun)
Meet & Taste: Explore Chilean Wines In An Exclusive Tasting With Viña Carmen
Total Wine & More | Multiple Locations, Nearby
  • Jun 12, 2025 (Thu)
Vive La France
Total Wine & More | Multiple Locations, Nearby
  • Jun 13, 2025 (Fri)
Live Music With Gemsong Productions
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 13, 2025 (Fri)
Meet & Taste: Explore Chilean Wines In An Exclusive Tasting With Viña Carmen
Total Wine & More | Multiple Locations, Nearby
  • Jun 14, 2025 (Sat)
National Rosé Day With Whispering Angel
Total Wine & More | Multiple Locations, Nearby
  • Jun 14, 2025 (Sat)
Vive La France
Total Wine & More | Multiple Locations, Nearby

40% Off All Riedel Glassware

Elevate every sip with perfectly crafted glassware. For a limited time only.

Shop the Sale
  • Jun 15, 2025 (Sun)
Live Music With Tony Di & Carla Zipay
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 20, 2025 (Fri)
Live Music With Eran Troy Danner
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 21, 2025 (Sat)
An Exclusive Afternoon Of Champagne & Conversation With Stephanie Browne
B. Stuyvesant Champagne, Brooklyn Navy Yard | Brooklyn, New York
  • Jun 21, 2025 (Sat)
Arrigoni Winery’s Comedy Night Featuring Brian Glowacki
Arrigoni Winery | Portland, CT
  • Jun 22, 2025 (Sun)
Live Music With Donald Gioiella
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 26, 2025 (Thu)
Discover New Wines From The Old World
Total Wine & More | Multiple Locations, Nearby
  • Jun 27, 2025 (Fri)
Live Music With Bernie Gagliardi
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jun 28, 2025 (Sat)
Gin, Vodka & Tequila— A Battle Of The Clear Spirits
Total Wine & More | Multiple Locations, Nearby
  • Jun 28, 2025 (Sat)
Leyden Farm Vineyard & Winery Annual Pig Roast
Leyden Farm Vineyard & Winery | West Greenwich, RI
  • Jun 29, 2025 (Sun)
Live Music With DizzyFish
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Jul 9, 2025 (Wed)
Georgia On My Wine - The Lanchava Collection With The Lanchava Siblings
Total Wine & More | Multiple Locations, Nearby
  • Jul 10, 2025 (Thu)
Under The Tuscan Sun
Total Wine & More | Multiple Locations, Nearby
  • Jul 12, 2025 (Sat)
Under The Tuscan Sun
Total Wine & More | Multiple Locations, Nearby
  • Jul 16, 2025 (Wed)
Georgia On My Wine - The Lanchava Collection With The Lanchava Siblings
Total Wine & More | Multiple Locations, Nearby
  • Jul 24, 2025 (Thu)
Pop Open A Party—Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Jul 26, 2025 (Sat)
Rum For All And All For Rum!
Total Wine & More | Multiple Locations, Nearby
  • Aug 7, 2025 (Thu)
Sip N’ Snack Pairings
Total Wine & More | Multiple Locations, Nearby
  • Aug 9, 2025 (Sat)
Sip N’ Snack Pairings
Total Wine & More | Multiple Locations, Nearby
  • Aug 16, 2025 (Sat)
  • Aug 17, 2025 (Sun)
14th Putnam County Wine & Music Fest
Putnam County Veterans Memorial Park | Carmel, NY
  • Aug 21, 2025 (Thu)
Summertime Sips
Total Wine & More | Multiple Locations, Nearby
  • Aug 23, 2025 (Sat)
Salud! An Introduction To Tequila & Mezcal
Total Wine & More | Multiple Locations, Nearby
  • Sep 4, 2025 (Thu)
California Uncorked—Napa Valley & Beyond!
Total Wine & More | Multiple Locations, Nearby
  • Sep 6, 2025 (Sat)
California Uncorked—Napa Valley & Beyond!
Total Wine & More | Multiple Locations, Nearby
  • Sep 13, 2025 (Sat)
Hocus Pocus: Sanderson Sisters Drag Show & Live Music Event
Arrigoni Winery | Portland, CT
  • Oct 11, 2025 (Sat)
14th Worcester 
Food Truck & Craft Beer Festival
Worcester Common | Worcester, MASSACHUSETTS

Virtual, Online & Other Listings By Locals

  • Jun 9, 2025 (Mon)
WSET Level 2 Wine Online Course & Exam (starting Jun 9, 2025)
Online Class | Hosted by:New England Wine Academy
  • Jul 7, 2025 (Mon)
WSET Level 2 Wine Online Course & Exam (starting Jul 7, 2025)
Online Class | Hosted by:New England Wine Academy

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