Wine Tastings, Dinners & Festivals

Wine Tastings, Dinners & Festivals

Near West Springfield, Massachusetts

Submit Your Event

Featured Local Events

Portland, CT

Live Music At Arrigoni Winery!

Fri, September 26, 2025 to Sun, September 28, 2025

View details

All Upcoming Local Events

58 Events listed within 60 miles.

60 miles 30 miles 15 miles
  • Sep 23, 2025 (Tue)
Glendale Ridge Wine Dinner At Wyckoff Country Club
Wyckoff Country Club | Holyoke, MA
  • Sep 23, 2025 (Tue)
Stamp N Sip Cuff Bracelets At Paradise Hills Vineyard
Paradise Hills Vineyard | Wallingford, CT
  • Sep 25, 2025 (Thu)
GLASTONBURY Adult Pizza Making And Wine Tasting Class
Square Peg Pizzeria Glastonbury | Glastonbury, CT
  • Sep 26, 2025 (Fri)
Free Friday Tasting - Vermont Distillers No. 14 Maple Whiskey
Highland Wine & Spirits | Berlin, Massachusetts
  • Sep 26, 2025 (Fri)
Free Friday Tasting - Fuso Wines
Highland Wine & Spirits | Berlin, Massachusetts
  • Sep 26, 2025 (Fri)
Free Friday Tasting - Cayman Jack Canned Margaritas
Highland Wine & Spirits | Berlin, Massachusetts
  • Sep 26, 2025 (Fri)
Live Music With Nick Fradiani Sr
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 26-28, 2025 (Fri-Sun)
  • Oct 3-5, 2025 (Fri-Sun)
  • Oct 10-12, 2025 (Fri-Sun)
Live Music At Arrigoni Winery!
Arrigoni Winery | Portland, CT
  • Sep 26, 2025 (Fri)
Live Music With Scotty At 12 Grapes New Fairfield
12 Grapes | New Fairfield, Ct
  • Sep 27, 2025 (Sat)
Terry McKeon In Concert Celtic Music And Other Favorites
Cameron's Winery & The Back Room Brewing Company | Northfield, Massachusetts
  • Sep 27, 2025 (Sat)
Chef O's Streatery @ Paradise Hills Vineyard
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 27, 2025 (Sat)
Free Saturday Tasting - Surfside Canned Cocktails
Highland Wine & Spirits | Berlin, Massachusetts
  • Sep 27, 2025 (Sat)
Free Saturday Tasting - Ketel One Espresso Martini
Highland Wine & Spirits | Berlin, Massachusetts
  • Sep 27, 2025 (Sat)
Free Saturday Tasting - Handcrafted Cocktails Ft Don Julio & Astral Tequila
Highland Wine & Spirits | Berlin, Massachusetts
  • Sep 28, 2025 (Sun)
Curdside Pickup @ Paradise Hills Vineyard
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 28, 2025 (Sun)
Live Music With DizzyFish
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Sep 28, 2025 (Sun)
Four Corners X Isola Pop-Up Dinner
Isola Wine and Tapas | Kinderhook, NY
  • Sep 30, 2025 (Tue)
Mini Cheesecakes & Sweet Wines Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Oct 1, 2025 (Wed)
Oktoberfest Beer Dinner
Tin Bridge Brewing Co. | Westfield, MA
  • Oct 2, 2025 (Thu)
Left Bank, Right Bank—All About Bordeaux
Total Wine & More | Multiple Locations, Nearby
  • Oct 3, 2025 (Fri)
Live Music With Gemsong Productions
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 3, 2025 (Fri)
Fall Wine Event / A Symphony Of Wine, Charcuterie, & Oysters
1477 Main St | Springfield, MA
  • Oct 3, 2025 (Fri)
Epicurean Dinner With King Of Cocktails Dale DeGroff, Madison, CT
Madison Beach Hotel, Curio Collection by Hilton | Madison, CT
  • Oct 4, 2025 (Sat)
Fall Desserts & Wine Pairing
Aquila's Nest Vineyards | Newtown, CT
  • Oct 4, 2025 (Sat)
Left Bank, Right Bank—All About Bordeaux
Total Wine & More | Multiple Locations, Nearby
  • Oct 5, 2025 (Sun)
Charcuterie Board & Sip
Methuselah Bar and Lounge | Pittsfield, MA
  • Oct 5, 2025 (Sun)
Live Music With The Emily Mager Duo
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 7, 2025 (Tue)
California Lunch By Advanced Food Preparation
Culinary Arts Center Dining Room L294 | Manchester, CT
  • Oct 7, 2025 (Tue)
Encore Fall Dinner With Cato Corner + Carbone's Prime
Carbone's Prime | Rocky Hill, CT
  • Oct 8, 2025 (Wed)
Wine Class Wednesday
Isola Wine and Tapas | Kinderhook, NY
  • Oct 9, 2025 (Thu)
Halloween Candy Cookies And Wine Pairing Experience At Hardwick Winery
Hardwick Winery | Hardwick, MA
  • Oct 9, 2025 (Thu)
Exploring Viral Trends In The Wine & Spirits World
Total Wine & More | Multiple Locations, Nearby
  • Oct 9, 2025 (Thu)
Napa Elevated: An Intimate Wine Journey
Total Wine & More | Multiple Locations, Nearby
  • Oct 10, 2025 (Fri)
Live Music With Chris Marolda
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 10, 2025 (Fri)
Murder Mystery Dinner Theatre
Cameron's Winery & The Back Room Brewing Company | Northfield, Massachusetts
  • Oct 11, 2025 (Sat)
New England Noir Wine Fest (Picnic Table)
Glendale Ridge Vineyard | Southampton, MA
  • Oct 11, 2025 (Sat)
Harvest Sip & Shop
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 11-12, 2025 (Sat-Sun)
New England Noir Wine Festival 2025
Glendale Ridge Vineyard | Southampton, MA
  • Oct 11, 2025 (Sat)
14th Worcester 
Food Truck & Craft Beer Festival
Worcester Common | Worcester, MASSACHUSETTS
  • Oct 11, 2025 (Sat)
Oktoberfest Dinner
Cameron's Winery & The Back Room Brewing Company | Northfield, Massachusetts
  • Oct 16, 2025 (Thu)
Exploremos América Del Sur (Let's Explore South America)
Total Wine & More | Multiple Locations, Nearby
  • Oct 17, 2025 (Fri)
Live Music With Eran Troy Danner
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 17, 2025 (Fri)
Spooky Charcuterie Workshop
Sunset Meadow Vineyards | Goshen, CT
  • Oct 18, 2025 (Sat)
Unlocking Your Home Bar - Essentials For Cocktail Lovers
Total Wine & More | Multiple Locations, Nearby
  • Oct 19, 2025 (Sun)
Live Music With Tony Di & Carla Zipay
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 23, 2025 (Thu)
Port And Beyond: Discover The World Of Dessert Wines
Total Wine & More | Multiple Locations, Nearby
  • Oct 23, 2025 (Thu)
An Exquisite Wine Journey Around Argentina With Mascota Vineyards, El Esteco, And More!
Total Wine & More | Multiple Locations, Nearby
  • Oct 24, 2025 (Fri)
Live Music With Acoustic Mafia
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Oct 30, 2025 (Thu)
Pop Open A Party—Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Oct 31, 2025 (Fri)
Live Music With Myke Ross
Paradise Hills Vineyard and Winery | Wallingford, Connecticut
  • Nov 1, 2025 (Sat)
Pop Open A Party—Great Sparkling Wines
Total Wine & More | Multiple Locations, Nearby
  • Nov 6, 2025 (Thu)
Charity Wine Event
The Woodwinds | Branfordhttps://amity-charitable-trust.square.site/, Ct
  • Nov 13, 2025 (Thu)
Sips Of The Season: A Guide To Holiday Entertaining
Total Wine & More | Multiple Locations, Nearby
  • Dec 4, 2025 (Thu)
Distinguished Reds: A Global Tasting Journey
Total Wine & More | Multiple Locations, Nearby
  • Dec 6, 2025 (Sat)
Distinguished Reds: A Global Tasting Journey
Total Wine & More | Multiple Locations, Nearby
  • Dec 11, 2025 (Thu)
Spiced, Sweet & Everything Neat: Flavored Spirits For Winter
Total Wine & More | Multiple Locations, Nearby
  • Jan 15, 2026 (Thu)
Sip, Savor, And Salud - An Intro To Spanish And Portuguese Wines
Total Wine & More | Multiple Locations, Nearby
  • Jan 17, 2026 (Sat)
Sip, Savor, And Salud - An Intro To Spanish And Portuguese Wines
Total Wine & More | Multiple Locations, Nearby

Share These Listings

Stay Informed

Add Your Listing

By using this website, you agree to our use of cookies. We use cookies to provide a better user experience.