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

Chatham, NY

The Annual Hudson Berkshire Wine & Food Festival

Sat, May 24, 2025

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Portland, CT

Arrigoni Winery’s Comedy Night Featuring Brian Glowacki

Sat, June 21, 2025

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Nantucket, MA

Nantucket Wine & Food Festival

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

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Portland, CT

Hocus Pocus: Sanderson Sisters Drag Show & Live Music Event

Sat, September 13, 2025

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Portland, CT

Yoga Night At Arrigoni Winery

Wed, May 28, 2025

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Portland, CT

Live Music At Arrigoni Winery!

Fri, May 2, 2025 to Sun, May 4, 2025

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Portland, CT

Taste The Rainbow: Arrigoni Drag Show & Live Music Event

Fri, June 6, 2025

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Carmel, NY

14th Putnam County Wine & Music Fest

Sat, August 16, 2025

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All Upcoming Local Events

  • Apr 30, 2025 (Wed)
Whiskey Dinner Presented By Firefly’s BBQ + Julio’s Liquors
Firefly's BBQ | Marlborough, MA
  • May 1, 2025 (Thu)
May Wine Glass Paint And Sip At Hardwick Winery
Hardwick Winery | Hardwick, MA
  • May 1, 2025 (Thu)
PLAINVILLE Adult Pizza Making & Wine Tasting Class !
Square Peg Pizzeria | Plainville, CT
  • May 2, 2025 (Fri)
Free Friday Tasting - Equilibrium Brewing ( MC2, Wavelength, Photon)
Highland Wine & Spirits | Berlin, Massachusetts
  • May 2, 2025 (Fri)
Free Friday Tasting - Hampton Water Rosé & Sparkling Rosé
Highland Wine & Spirits | Berlin, Massachusetts
  • May 2, 2025 (Fri)
Live Music With Chris Marolda
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 2-4, 2025 (Fri-Sun)
  • May 9-11, 2025 (Fri-Sun)
  • May 16-18, 2025 (Fri-Sun)
  • May 23-26, 2025 (Fri-Mon)
Live Music At Arrigoni Winery!
Arrigoni Winery | Portland, CT
  • May 2, 2025 (Fri)
Epicurean Series Ode To Spring Featuring Poet Laureate Ed Lent, Madison, CT
Madison Beach Hotel, Curio Collection by Hilton | Madison, CT
  • May 3, 2025 (Sat)
  • May 4, 2025 (Sun)
New England Taco Festival
The Guilford Fair & Fairgrounds | Guilford, CT
  • May 3, 2025 (Sat)
Free Saturday Tasting - Pantalones Tequila (Blanco & Reposado)
Highland Wine & Spirits | Berlin, Massachusetts
  • May 3, 2025 (Sat)
Free Saturday Tasting - Deep Eddy Vodka (Original & Pineapple)
Highland Wine & Spirits | Berlin, Massachusetts
  • May 4, 2025 (Sun)
Live Music With Joe Ladore
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 6, 2025 (Tue)
Celebrity Chef Joe Gatto's Famous Pasta Class!
Duck Soup | Sudbury, MA

40% Off All Riedel Glassware

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

Shop the Sale
  • May 7, 2025 (Wed)
Norwich Rotary's Whiskey, Wine And Cigar Event
Bella Fiore Restaurante | Norwich, CT
  • May 8, 2025 (Thu)
Wine And Cheese - A Guide To Perfect Pairings
Total Wine & More | Multiple Locations, Nearby
  • May 8, 2025 (Thu)
Spring Mushroom Farm Dinner
Hotel Marcel, Sargent Drive, New Haven, CT, USA | New Haven, CT
  • May 9, 2025 (Fri)
Live Music With The Emily Mager Duo
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 9, 2025 (Fri)
Witchdoctor + Paul Gregory’s Beer Dinner
Witchdoctor Brewing Company | Southington, CT
  • May 9, 2025 (Fri)
Charcuterie Workshop With Mommy Salami At Sunset Meadow Vineyards
Sunset Meadow Vineyards | Goshen, CT
  • May 9-10, 2025 (Fri-Sat)
Rosé Rodeo With Janell Sindab
555 Worthington St | Springfield, MA
  • May 10, 2025 (Sat)
14th Annual Rising Point Brewfest
Pratt & Whitney Stadium at Rentschler Field | East Hartford, CT
  • May 10, 2025 (Sat)
At Home In The Whole Food Kitchen: Book Event W/Amy Chaplin & Tamar Adler
HGS Home Chef | Hillsdale, NY
  • May 10, 2025 (Sat)
Wine And Cheese - A Guide To Perfect Pairings
Total Wine & More | Multiple Locations, Nearby
  • May 10, 2025 (Sat)
Edible Tasting - Sat 5/10 Sip & Paint Night
125 W Main St | Plainville, CT
  • May 11, 2025 (Sun)
Mother’s Day Sunday Brunch Workshop With Chef David Wurth
HGS Home Chef | Hillsdale, NY
  • May 11, 2025 (Sun)
Mother's Day Brunch @ Paradise Hills Vineyards
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 11, 2025 (Sun)
Live Music With DizzyFish
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 14-18, 2025 (Wed-Sun)
Nantucket Wine & Food Festival
Nantucket Island | Nantucket, MA
  • May 14, 2025 (Wed)
Midnight Cellars Reserve Wine Dinner
The Barn Princeton | Princeton, MA
  • May 14, 2025 (Wed)
Wine Wednesday Workshop: Magic Of Wine & Food Pairing
Broken Creek Vineyard and Winery | Shrewsbury, MA
  • May 15, 2025 (Thu)
Stages Wine Dinner 2025
Palace Theater | WATERBURY, Connecticut
  • May 16, 2025 (Fri)
Live Music With Eran Troy Danner
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 16, 2025 (Fri)
Chell's Charcuterie Rustic, Italian Style Class And Wine Tasting
Total Wine & More | West Hartford, CT
  • May 17, 2025 (Sat)
Madeira
To be disclosed upon ticket purchase | Wrentham, MA
  • May 18, 2025 (Sun)
Board & Bloom / Charcuterie Class And Wine Tasting
Wine ETC. Simsbury | Simsbury, CT
  • May 18, 2025 (Sun)
Live Music With Brandt Taylor & Carla Zipay
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 18, 2025 (Sun)
LGBTQ+ After-Hike Dinner @ Barrington Brewery (Great Barrington, MA)
Barrington Brewery & Restaurant | Great Barrington, MA

40% Off All Riedel Glassware

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

Shop the Sale
  • May 23, 2025 (Fri)
Live Music With Nick Fradiani Sr
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 24, 2025 (Sat)
  • May 25, 2025 (Sun)
The Annual Hudson Berkshire Wine & Food Festival
Columbia County Fairgrounds | Chatham, NY
Buy Tickets
  • May 25, 2025 (Sun)
Live Music With Jon Condie
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 27, 2025 (Tue)
Cooking Class @ Paradise Hills Vineyard: Shrimp Scampi
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • May 28, 2025 (Wed)
Yoga Night At Arrigoni Winery
Arrigoni Winery | Portland, 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 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)
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)
Meet & Taste: Explore Chilean Wines In An Exclusive Tasting With Viña Carmen
Total Wine & More | Multiple Locations, Nearby
  • Jun 14, 2025 (Sat)
Vive La France
Total Wine & More | Multiple Locations, Nearby
  • Jun 21, 2025 (Sat)
Arrigoni Winery’s Comedy Night Featuring Brian Glowacki
Arrigoni Winery | Portland, CT
  • Jun 26, 2025 (Thu)
Discover New Wines From The Old World
Total Wine & More | Multiple Locations, Nearby
  • 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
  • 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 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

  • May 12, 2025 (Mon)
WSET Level 2 Wine Online Course & Exam (starting May 12, 2025)
Online Class | Hosted by:New England Wine Academy
  • 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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