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Lenox Wine Festival wine festival in Lenox, Massachusetts
Upcoming · Saturday, September 19, 2026

Lenox Wine Festival

Lenox Wine Festival in Lenox, MA — 4th year, unlimited tastings of international and domestic wines with their importers at Pizzeria Boema. Sep 19, 2026. $35.

Best for couples Best for beginners other 21+ only
Saturday, September 19, 2026
$35, unlimited tastings; food extra
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Quick facts

At a glance.

Dates
Saturday, September 19, 2026
Duration
Single day
Best for
Couples, Beginners
Atmosphere
Casual
Food
Bring or buy nearby
Age
21+ only

The story

About this festival.

Lenox Wine Festival is an afternoon of unlimited wine tastings hosted by Dare Bottleshop & Provisions at Pizzeria Boema, 84 Main Street, in Lenox, Massachusetts, on Saturday, September 19, 2026, and the 2026 event is the fourth year. Tickets are $35 and cover tastings of international and domestic wines poured by their importers, distributors and producers, plus local ciders and craft beers; every wine is sold at festival-only prices for stocking up.

Wood-fired pizza from Pizzeria Boema, cheese boards from High Lawn Farm and shucked-to-order oysters are sold separately. Dare notes that buying through its own site avoids ticket-platform fees. Lenox is the Berkshires town of Tanglewood and Edith Wharton's The Mount, about 2.5 hours from Boston and New York.

Getting there

Location & logistics.

Pizzeria Boema
84 Main Street, Lenox, MA
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What to expect

The experience.

What you'll pour

A mix of varietals from regional producers. Start light, work toward the bigger reds.

The setting

Held at Pizzeria Boema in Lenox. Check the venue page for layout details.

The crowd

Friendly to first-timers — no one is going to quiz you on Pinot. Ask questions, take notes, enjoy.

Worth the trip

Arrive early, hit your must-try wineries first, then wander. That's the move.

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What people are saying.

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Frequently asked

Common questions.

When is the Lenox Wine Festival?
The Lenox Wine Festival is Saturday afternoon, September 19, 2026, at Pizzeria Boema, 84 Main Street, in Lenox, Massachusetts. It is the fourth annual edition, organized by Dare Bottleshop & Provisions; hours are on the ticket page.
What does a Lenox Wine Festival ticket include?
The $35 ticket includes unlimited tastings of wines from around the world plus local craft beer and cider, and the chance to talk with the importers, distributors and producers pouring them. All featured wines are sold at special festival-only prices.
Is food included at the Lenox Wine Festival?
No. Wood-fired pizza from Pizzeria Boema, cheese boards from High Lawn Farm and shucked-to-order oysters are available for purchase during the festival. Tickets bought directly from Dare Bottleshop's site avoid platform fees.

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