Wine, food & community—September 19 in Lenox. Tickets on sale now!
The Lenox Wine Festival is back for its fourth year on Saturday, September 19th, 2026 at The Barn at Pizzeria Boema in Lenox, MA and we’re excited for another unforgettable, feel-good celebration!
Join us for an afternoon of wine, food and community while supporting something close to home.
Each year, Dare Bottleshop proudly partners with the Lenox Library Association through an on-site silent auction, helping fund the Lenox Library and its programming. So as you sip and explore, you’re also giving back to one of our community’s most special resources.
✨ Don’t miss the LLLA Auction! ✨
Get ready to bid on some fabulous baskets filled with specialty wine, yoga gear & props, GOOP, Blue Q, and so much more! 🎁🍷🧘♀️
Whether you’re treating yourself or shopping for the perfect gift, there’s something for everyone. Place your bid and take home a basket you’ll love! 💫
Don’t miss your chance to snag something special! 🛍️✨
Festival Highlights & Experiences
🥂 Unlimited tastings of wines from around the world
🍻🍎 Local craft beer & cider tastings
🤝 Meet & mingle with passionate wine experts, importers & producers
🛍️ Shop featured wines at special event-only pricing
🍕 Wood-fired pizza from Pizzeria Boema*
🧀 Cheese boards by local favorite High Lawn Farm*
🦪 Shucked-to-order oysters*
(*Select food offerings available for purchase)
Giving Back to Our Community
✨ Why You’ll Love It
This is more than a tasting, it’s a celebration of community, a chance to connect with the people behind the wines, discover new favorites, and enjoy one of the most joyful days of the season while supporting the Lenox Library Association.
🔔 Don’t Wait…
🎟️ Tickets are available now for $35 (regularly $45)—for a limited time. Purchase here
This event traditionally sells out, so don’t miss your chance to be part of it.