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Winetasting Events and Things to do in Lenox, MA

Learn how to Judge wine like a pro!
Sun, Apr 19, 2:00 PM
Middlebury · Tranquillity Vineyard & Winery
Learn how to Judge wine like a pro!
Sun, Apr 19, 2:00 PM
Middlebury · Tranquillity Vineyard & Winery
Just added
Wine & Climate Change: A Conversation and Wine Tasting
Sat, Jun 20, 6:00 PM
Brattleboro · Brattleboro Museum & Art Center
Just added
Wine & Climate Change: A Conversation and Wine Tasting
Sat, Jun 20, 6:00 PM
Brattleboro · Brattleboro Museum & Art Center
Sales end soon
Grand Spring Wine Tasting at Boutique
Saturday at 1:00 PM
Fishkill · Boutique Wines, Spirits, & Ciders
Sales end soon
Grand Spring Wine Tasting at Boutique
Saturday at 1:00 PM
Fishkill · Boutique Wines, Spirits, & Ciders
Sales end soon
Kindred Roots Presents: The Inaugural Table — New Date Coming Soon
Sunday at 5:00 PM
Albany · 725 Madison Ave
Sales end soon
Kindred Roots Presents: The Inaugural Table — New Date Coming Soon
Sunday at 5:00 PM
Albany · 725 Madison Ave
Just added
2026 Hudson Valley Wine & Food Festival
Sat, Sep 12, 11:00 AM
Rhinebeck · Dutchess County Fairgrounds, U.S. 9, Rhinebeck, NY, USA
Just added
2026 Hudson Valley Wine & Food Festival
Sat, Sep 12, 11:00 AM
Rhinebeck · Dutchess County Fairgrounds, U.S. 9, Rhinebeck, NY, USA
Going fast
Candle Making and Sip at Cooper's Daughter Spirits! (March 27)
Friday at 5:30 PM
Claverack · Cooper's Daughter Spirits at Olde York Farm
Going fast
Candle Making and Sip at Cooper's Daughter Spirits! (March 27)
Friday at 5:30 PM
Claverack · Cooper's Daughter Spirits at Olde York Farm
2nd Annual Wild Cider Cup
Sun, May 17, 12:00 PM
Albany · Nine Pin Cider
2nd Annual Wild Cider Cup
Sun, May 17, 12:00 PM
Albany · Nine Pin Cider
Tea Art Experience - April 4, 3:00 pm
Sat, Apr 4, 3:00 PM
Norfolk · Connecticut-Asia Cultural Center
Tea Art Experience - April 4, 3:00 pm
Sat, Apr 4, 3:00 PM
Norfolk · Connecticut-Asia Cultural Center
Pop-Up! Isola Le Primizie with Guest Chef Jesse Ford
Kinderhook · Isola Wine and Tapas
Pop-Up! Isola Le Primizie with Guest Chef Jesse Ford
Kinderhook · Isola Wine and Tapas
Manchester Vermont Food & Wine Festival
Manchester · The Equinox Golf Resort & Spa
Manchester Vermont Food & Wine Festival
Manchester · The Equinox Golf Resort & Spa
Shaker Lemon Pie Tasting with Navona Catering
Sun, Apr 12, 1:00 PM
Albany · Shaker Heritage Society
Shaker Lemon Pie Tasting with Navona Catering
Sun, Apr 12, 1:00 PM
Albany · Shaker Heritage Society
Albany | The Blu Pizza & Dough-Making Experience
Thu, Apr 2, 7:00 PM
Albany · The City Beer Hall
Albany | The Blu Pizza & Dough-Making Experience
Thu, Apr 2, 7:00 PM
Albany · The City Beer Hall
The Hess Collection Wine Dinner 2026
Saturday at 5:00 PM
Southwick · The Ranch Golf Club
The Hess Collection Wine Dinner 2026
Saturday at 5:00 PM
Southwick · The Ranch Golf Club
Sales end soon
Blend with the Winemaker
Sunday at 2:00 PM
Middlebury · Tranquillity Vineyard & Winery
Sales end soon
Blend with the Winemaker
Sunday at 2:00 PM
Middlebury · Tranquillity Vineyard & Winery
Cupcake Wars
Thu, Apr 23, 5:00 PM
Pittsfield · 639 South St
Cupcake Wars
Thu, Apr 23, 5:00 PM
Pittsfield · 639 South St
Going fast
Small Business, Big Questions: Community Gathering for Women Leaders
Mon, Mar 30, 5:00 PM
Bethlehem · CORAY KITCHEN
Going fast
Small Business, Big Questions: Community Gathering for Women Leaders
Mon, Mar 30, 5:00 PM
Bethlehem · CORAY KITCHEN
EAT, DRINK, & BE HOLYOKE
Thu, Apr 30, 5:30 PM
Holyoke · Holyoke Council on Aging & Senior Center
EAT, DRINK, & BE HOLYOKE
Thu, Apr 30, 5:30 PM
Holyoke · Holyoke Council on Aging & Senior Center
Almost full
PAINT & SIP Sunny Sunflower – Wood Porch Leaner
Sun, May 3, 1:00 PM
Lanesborough · The Venue At Skyline
Almost full
PAINT & SIP Sunny Sunflower – Wood Porch Leaner
Sun, May 3, 1:00 PM
Lanesborough · The Venue At Skyline
Almost full
Paint & Sip
Friday at 6:00 PM
Pittsfield · Tavern At The A
Almost full
Paint & Sip
Friday at 6:00 PM
Pittsfield · Tavern At The A
Hooked Seafood Food Pop-Up!
Sun, Apr 5, 12:00 PM + 16 more
Claverack · Cooper's Daughter Spirits at Olde York Farm
Hooked Seafood Food Pop-Up!
Sun, Apr 5, 12:00 PM + 16 more
Claverack · Cooper's Daughter Spirits at Olde York Farm

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