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The 5 Best Wine Festivals In Massachusetts

Rebecca Hanlon
Last Updated: August 8th, 2023

Your schedule might not allow you to take a long drive to the wine country. So, you can sample some premium wines at a vineyard or winery. Consider satisfying your palate with some superb wines at one of the wine festivals in Massachusetts.

These gatherings have incredible vintages easy on the pocketbook while satisfying the palate with each sampling.

You, your family, and your friends also experience tasty food from spectacular chefs or food trucks, live music, shopping, and artisan work. Other activities might be yoga classes, kid’s zone, and grape stomps.

Top Wine Festivals in Massachusetts

  1. Nantucket Food & Wine Festival
  2. Boston Wine & Food Festival
  3. Worcester Wine Festival
  4. Duxbury Food & Wine Festival
  5. Pioneer Valley Wine & Food Festival
  6. Taste of the Vineyards

1. Nantucket Food & Wine Festival

nantucket food & wine festival

  • Nantucket Island
  • May
  • Nantucket Island, MA
  • Tickets: Single Session: $65.00, Two Sessions: $100.00, Several Package Deals Available

The Nantucket Wine & Food Festival is a week-long affair, with the Grand Tasting weekend the most coveted event for festival goers. You’ll meet winemakers, wine connoisseurs, and alike, thanks to the ambiance and prestige of Nantucket.

Mostly, you’ll want to stay on the island during the fest because your blood alcohol content will demand it for safekeeping. But first, you’ll require a way to get to the island.

The choices are airplane or ferry. Then, find a place to stay accessible through a service called Nantucket Accommodations, a longstanding service that charges $15.00 to find you the perfect room.

The unique events available have tasty food offerings with pairing or cooking demonstrations. Each has a wine theme, so you’ll have plenty of pleasure for your palate and liver.

The Grand Tasting event is the one to attend. Make sure you bring a pen and paper. You can jot down new favorites that are easy on the pocketbook, which you’ll find at your local market.

2. Boston Wine & Food Festival

boston wine & food festival

  • Boston Harbor Hotel
  • January to March
  • 70 Rowes Wharf
  • Boston, MA 02110
  • 617-748-1854
  • Tickets: TBA

Some would say the Boston Harbor Wine Festival is the running wine fest in the country. However, the event has added “food” to its name.

It’s a long festival that spans from January to March. Chef Daniels presented a new program to the festival last year which introduced a spotlight called the Visiting Chef Series. Additionally, events were planned that integrated art, theater, music, and wine.

Highlights included Sunday cocktail jazz brunches, a truffle seminar, and dinner.

3. Worcester Wine Festival

worcester wine festival

  • Polar Park
  • August
  • Worcester, MA
  • Tickets: General Admission: $40.00, VIP: $125.00

Worcester Wine Festival’s Grand Tasting celebrates the best of wine at Polar Park. You’ll see thousands of food and wine enthusiasts and enjoy quality wines from an excellent presentation of vineyards, wineries, and more.

VIP tickets allow you and your friends to taste wines from around the world on the field at Polar Park. Make sure you wear flats and no heels on the grass. VIPs have access to an upstairs area of the Club, where they experience the curated pairing menu with premier wines not regularly available to the public. After the pairing, VIPs are welcome to return to the field until the last call.

The general admission ticket welcomes you and your friends onto the field of Polar Park, tasting wines for over two hours.

Mass Food & Wine hosts the festival at Polar Park and others, like Bubbles & Rose Tasting and Spring Wine Soiree.

4. Duxbury Food & Wine Festival

duxbury food & wine festival

  • Alden House Historic Site
  • September
  • 105 Alden Street
  • Duxbury, MA 02332
  • Wine Stroll Tickets: $60.00 to $90.00

The festival’s board has reimagined the marquee event for this year and may change back the following year.

Take part in the Wine Stroll, produced with the Duxbury Art Association. Walk the grounds of Duxbury’s Historic Alden House. You and your friends will rub shoulders with food-and-wine devoted neighbors as you explore noteworthy wines from around the world.

Although the structure of the festival has changed slightly, what hasn’t changed is its commitment to curating a tasting experience that showcases superior wine.

As you stroll the grounds between tastings, you’ll eat light, tasty bites while appreciating outstanding local art and live music.

5. Pioneer Valley Wine & Food Festival

pioneer valley wine & food festival

  • Brimfield Auction Acres
  • June
  • Brimfield, MA 01010
  • Tickets: FREE to $30.00

Brimfield Auction Acres hosts the annual Pioneer Valley Wine & Food Festival, so you and your friends can try the local wines from the wineries of Pioneer Valley and beyond.

Not only will your palate taste delectable wine, but you’ll also have the pleasure of listening to live music all day. And take in the local farmers’ market and artisans as you sip and stroll.

You can purchase yummy food at the various food trucks.

There is free admission for seniors, military, and children under 12 and free entry to the food festival, farmers’ market, and live music.

Bring blankets and lawn chairs for a relaxing day.

6. Taste of the Vineyards

taste of the vineyards

  • Martha’s Vineyard
  • June
  • 99 Main Street
  • Edgartown, MA
  • Tickets: TBA

“The Taste,” as endearingly known, Taste of the Vineyard, is the most anticipated gathering on Martha’s Vineyard.

You have helped preserve and maintain the island’s most iconic historical landmarks by attending.

Don’t forget to attend the Gourmet Stroll season’s kick-off event. It happens on the first night of the Taste of the Vineyard.

You and your friends can eat, drink, and dance, featuring the island’s finest caterers, restaurants, and beverage purveyors. Ask about the VIP Party!

About The Author

Rebecca Hanlon

Rebecca has been a blogger for over 5 years, before that enjoying a number of jobs to fund her passion for travel. She's taught English as a foreign language, a part-time Barista, a waitress, and a tour guide.

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