Head of Westport, Massachusetts Wine Tasting Events, Wine Dinners and Festivals

Featured Local Events

Howard's Spanish Wine Tour 2024

Sun, September 8, 2024

Trip or Vacation

All Upcoming Local Events

Dec 6-9, 2023 (Wed-Sat)

Upcoming Whiskey Raffle - 2nd Drawing December 9th

Highland Wine & Spirits | Berlin, Massachusetts

Dec 6, 2023 (Wed)

Holiday Wine Series: December 6 - Sparkling Wines For The Holidays

Blithewold Mansion, Gardens & Arboretum | Bristol, RI

Dec 6, 2023 (Wed)

Guinness Beer Dinner

Aidan's Pub | Bristol, RI

Dec 6, 2023 (Wed)

Wine Down Wednesday

2377 Washington St | Boston, MA

Dec 6, 2023 (Wed)

Gingerbread Cookie Decorating And Wine Night At The VERVE Hotel, Natick

The VERVE Hotel Boston Natick | Natick, MA

Dec 6, 2023 (Wed)

Champagne Explained!

Commonwealth Wine School | Cambridge, MA

Dec 7, 2023 (Thu)

Free Wine Tasting - Ferrari-Carano And Chateau St Jean Wines

Highland Wine & Spirits | Berlin, Massachusetts

Dec 7, 2023 (Thu)

The Wines Of Piedmont With Alessandro From Ethica Wines In NEEDHAM!

Bin Ends Wine | Needham, MA

Dec 7, 2023 (Thu)

A Toast To The Holidays: PBG Members Holiday Dinner

Liz's Cafe | Provincetown, MA

Dec 7, 2023 (Thu)

Holiday Wine Tastings At Chatham Bars Inn

Chatham Bars Inn | Chatham, MA

Dec 7, 2023 (Thu)

Meet The Makers Dinner: Sarma &; Remnant Brewing

Remnant Brewing - Satellite | Cambridge, MA

Dec 7, 2023 (Thu)

Sparkling Wines Tasting @ Moldova

Moldova Restaurant | Newton, MA

Dec 8, 2023 (Fri)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 8, 2023 (Fri)

Wines Of Piedmont With Alessandro From Ethica Wines In BRAINTREE!

Bin Ends Wine | Braintree, MA

Dec 8, 2023 (Fri)

Raffetto's Palate: Cooking Classes

Stonington Community Center (COMO) | Stonington, CT

Dec 8, 2023 (Fri)

Holday Paint.Nosh.Sip Night- Watercolor, Charcuterie & Wine.

Running Brook Vineyard & Winery | Dartmouth, MA

Dec 9, 2023 (Sat)

Meletti Tasting In NEEDHAM

Bin Ends Wine | Needham, MA

Dec 9, 2023 (Sat)

Angel's Envy Bourbon Bottle Engraving

Highland Wine & Spirits | Berlin, Massachusetts

Dec 9, 2023 (Sat)

FizzFest 2023 In BRAINTREE!

Bin Ends Wine | Braintree, MA

Dec 9, 2023 (Sat)

Spirits Of Maynard Wine And Spirits Holiday Tasting

Spirits of Maynard | Maynard, MA

Dec 9, 2023 (Sat)

Flight Club Wine School @ Georgie's | Holy Wines

Georgie's Wine Shop and Bar | Boston, MA

Dec 9, 2023 (Sat)

Flight Club @ Georgie's Wine | Holy Wines

Georgie's Wine Shop & Bar | Boston, MA

Dec 9, 2023 (Sat)

Meletti Tasting In BRAINTREE

Bin Ends Wine | Braintree, MA

Dec 9, 2023 (Sat)

Wine, Cheese And Charcuterie!

Commonwealth Wine School | Cambridge, MA

Dec 10, 2023 (Sun)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 10, 2023 (Sun)

Blind Wine Tasting 101: Sparkling Wine

525 Western Ave | Boston, MA

Dec 10, 2023 (Sun)

FizzFest 2023 In NEEDHAM!

Bin Ends Wine | Needham, MA

Dec 11, 2023 (Mon)

Fun With Corks & Wine!

Broken Creek Vineyard and Winery | Shrewsbury, MA

Dec 11, 2023 (Mon)

Hand Painted Holiday Plate At Uva Wine Bar

Uva Wine Bar | Plymouth, MA

Dec 11, 2023 (Mon)

Blue Collar Soiree

Topgolf | Canton, MA

Dec 12, 2023 (Tue)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 12, 2023 (Tue)

Women In Wine And The Arts: A Winter Sip & Draw (December 12th)

Vorse House | Provincetown, MA

Dec 12, 2023 (Tue)

2023 Holiday Party

Hotel 1620 Plymouth Harbor | Plymouth, MA

Dec 12, 2023 (Tue)

Belgium In Belmont V2: A Beer Pairing Dinner With Brouwerij St.Bernardus

Trinktisch | Belmont, MA

Dec 12, 2023 (Tue)

Wine & Christmas Cookie Pairing Experience At Broken Creek Vineyard

Broken Creek Vineyard and Winery | Shrewsbury, MA

Dec 12, 2023 (Tue)

Holiday Resin Art Night

The Vin Bin | Marlborough, MA

Dec 13, 2023 (Wed)

A Bruno Christmas Pairing Menu

Boston Winery | Boston, MA

Dec 13, 2023 (Wed)

Holiday Sparkling Wine Dinner

Red Rock Grill and Bar | Upton, MA

Dec 13, 2023 (Wed)

Gingerbread Cookie Decorating And Wine Night At The VERVE Hotel, Natick

The VERVE Hotel Boston Natick | Natick, MA

Dec 13, 2023 (Wed)

St Bernardus 5-Course Beer Dinner At Burgundian

Burgundian | Attleboro, MA

Dec 13, 2023 (Wed)

Wine Tasting & Dinner: Germany!

Uva Wine Bar | Plymouth, MA

Dec 14, 2023 (Thu)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 14, 2023 (Thu)

Wines Of Bordeaux With Beth Von Benz In Needham!

Bin Ends Wine | Needham, MA

Dec 14, 2023 (Thu)

Winter VIP Beer Dinner

Samuel Adams Boston Brewery | Boston, MA

Dec 14, 2023 (Thu)

Edrington Cocktail Dinner In Benefit Of Stone House

Baramor, Union Street, Newton Centre, MA, USA | Newton, MA

Dec 14, 2023 (Thu)

Wine School: Special Sauce: Sagittarius Edition!

Wild Child | Somerville, MA

Dec 14, 2023 (Thu)

Holiday Wine Tastings At Chatham Bars Inn

Chatham Bars Inn | Chatham, MA

Dec 14, 2023 (Thu)

Drew Estate Christmas Dinner

Havana Cigar | Warwick, RI

Dec 14, 2023 (Thu)

Murder Mystery Dinner: Theater Camp

Trident Booksellers & Cafe | Boston, MA

Dec 14, 2023 (Thu)

Exploring Escodo Rojo Wines

Franklin Liquors | Franklin, MA

Dec 15, 2023 (Fri)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 15, 2023 (Fri)

Wines Of Bordeaux With Beth Von Benz In Braintree!

Bin Ends Wine | Braintree, MA

Dec 15, 2023 (Fri)

Festive French Wines With Matt From Cynthia Hurley Wines In NEEDHAM

Bin Ends Wine | Needham, MA

Dec 15, 2023 (Fri)

Italian Dinner With Tiramisu Finale (3-hour Culinary Experience)

Selfup Venue | Boston, MA

Dec 15, 2023 (Fri)

Winter, Watercolors And Wine

290 W Main St | Northborough, MA

Dec 15, 2023 (Fri)

Bewitching Wine Labels And How To Read Them

Commonwealth Wine School | Cambridge, MA

Dec 16, 2023 (Sat)

Festive French Wines With Matt From Cynthia Hurley Wines In BRAINTREE

Bin Ends Wine | Braintree, MA

Dec 16, 2023 (Sat)

Sudbury Wine And Spirits Holiday Tasting

Sudbury Wine and Spirits | Sudbury, MA

Dec 16, 2023 (Sat)

Gospel Concert And Dinner

109 Court St | New Bedford, MA

Dec 17, 2023 (Sun)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 17, 2023 (Sun)

Paint Night At The Wine Store: Winter Buoy Tree

Dunn & Sons Wine | Yarmouth, MA

Dec 17, 2023 (Sun)

Pasta Every Day With Meryl Feinstein

2267 Massachusetts Ave | Cambridge, MA

Dec 18, 2023 (Mon)

Tree Of Life Or Cardinal Resin Suncatcher Workshop At Hometown Tavern

Hometown Tavern | Warren, RI

Dec 18, 2023 (Mon)

Holiday Cheers! A Night Of Creativity, Self Care And Shopping

The Vin Bin | Marlborough, MA

Dec 18, 2023 (Mon)

Smoke Shop BBQ's 2nd Annual Ugly Sweater Holiday Party With Maker's Mark

The Smoke Shop BBQ - Harvard Square | Cambridge, MA

Dec 18, 2023 (Mon)

Keep It UGLY & Be Merry

Chart House | Boston, MA

Dec 20, 2023 (Wed)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 20, 2023 (Wed)

Candle Making Workshop + Wine

House of Art and Craft, LLC | Boston, MA

Dec 20, 2023 (Wed)

Blueprint Spirits Tasting In NEEDHAM

Bin Ends Wine | Needham, MA

Dec 20, 2023 (Wed)

Black Button Bespoke Bourbon Cream Tasting In Braintree

Bin Ends Wine | Needham, MA

Dec 20, 2023 (Wed)

A Bruno Christmas Pairing Menu

Boston Winery | Boston, MA

Dec 20, 2023 (Wed)

Wine Down Wednesday

2377 Washington St | Boston, MA

Dec 21, 2023 (Thu)

Boston Harbor Distillery Tasting In BRAINTREE!

Bin Ends Wine | Braintree, Massachusetts

Dec 21, 2023 (Thu)

Black Button Bespoke Bourbon Cream Tasting In Needham

Bin Ends Wine | Needham, MA

Dec 21, 2023 (Thu)

Wine School: Holiday Treats & Wine Pairing Class!

Wild Child | Somerville, MA

Dec 21, 2023 (Thu)

Holiday Wine Tastings At Chatham Bars Inn

Chatham Bars Inn | Chatham, MA

Dec 21, 2023 (Thu)

Ravioli And Wine Pairing

Boston Winery | Boston, MA

Dec 22, 2023 (Fri)

Italian Dinner With Tiramisu Finale (3-hour Culinary Experience)

Selfup Venue | Boston, MA

Dec 22, 2023 (Fri)

Candle Making Workshop + Wine

House of Art and Craft, LLC | Boston, MA

Dec 22, 2023 (Fri)

Oyster Decoupage Ornaments

Dunn & Sons Wine, Willow Street, Yarmouth Port, MA, USA | Yarmouth, MA

Dec 22, 2023 (Fri)

Boston Harbor Distillery Tasting In NEEDHAM!

Bin Ends Wine | Needham, MA

Dec 22, 2023 (Fri)

Raffetto's Palate: Cooking Classes

Stonington Community Center (COMO) | Stonington, CT

Dec 22, 2023 (Fri)

Paint & Sip

Pure Elegance D’Luxe Event Venue | North Attleborough, MA

Dec 22, 2023 (Fri)

Erev Xmas Eve | Boston 2023

Kowloon Restaurant | Saugus, MA

Dec 22, 2023 (Fri)

Dueling Pianos - Live In The Vault

The Vault Music Hall | New Bedford, MA

Dec 23, 2023 (Sat)

Leyden Vineyards Wine Tasting- Fall/ Winter 2023

Leyden Farm Vineyard & Winery | West Greenwich, RI

Dec 23, 2023 (Sat)

Candle Making Workshop + Wine

House of Art and Craft, LLC | Boston, MA

Dec 24, 2023 (Sun)

The Good Time Brunch And Day Party Estella Lounge

Estella | Boston, MA

Dec 24-25, 2023 (Sun-Mon)

Dancehall Link Soca D' Night B4 Xmas

William E. Reed Auditorium | Boston, MA

Dec 26, 2023 (Tue)

New Bedford Blitz Sccavenger Hunt

Cork Wine and Tapas | New Bedford, MA

Dec 29, 2023 (Fri)

All The Bubbles! Sparkling Wines And The Party Treats That Love Them

Commonwealth Wine School | Cambridge, MA

Jan 10, 2024 (Wed)
Jan 17, 2024 (Wed)
Jan 24, 2024 (Wed)