Where the wine flows, the bass drops, & the energy feels like summer no matter the weather.

At Linganore Winecellars, we’ve never believed great wine (and great vibes) should come with a rulebook. As one of Maryland’s OG wine pioneers, we helped shape the local festival industry long before it was trendy. Our philosophy is simple: craft great wine, price it fairly, and create memorable experiences you’ll want to mark on your calendar months in advance.

What started as a small idea between a few cool people has grown into a beloved Maryland tradition, rooted in the sounds and spirit of Caribbean culture. It’s colorful, it’s high-energy, and yes… “just one glass” often turns into “let me grab a case of wine to-go”.

Our festivals have become the unofficial HQ for reunions, celebrations, and those long-overdue “we need to do this more often” moments. Some guests have been coming back since day one, and honestly, it wouldn’t be a party without them. Because at our core, we’re here to bring people together. Fifty years in, and we’re still pouring, still partying, and still saving you a spot on the dance floor.

We’ve got a lineup that will make you want to party with us all weekend long. (And yes, those wine-fueled dance moves will end up on our Facebook reels later – we promise you look great).

SATURDAY, MAY 23:

DJ Sprang Intl – MC | 10AM-6PM

Pan Masters Steel Orchestra | 11AM-2PM

Image Band | 3PM-6PM

SUNDAY, MAY 24:

DJ Sprang Intl – MC | 10AM-6PM

Pan Masters Steel Orchestra | 11AM-2PM

Eclipse International Band | 3PM-6PM

We may be half a century into this whole wine thing, but we’re continually making changes and additions to continue improving the guest experience! Check out these great new adds and updates for 2026:

• Wine Cocktail Cabana: We heard you loved our seasonal wine cocktails and slushies, so we made it better. Visit our brand new Wine Cocktail Cabana, located right by the stage to make it even easier to keep your glass full and the dance floor packed.
• Expanded Specialty Drinks Menu: At the cabana, in the Tasting Room, and at the Pavilion – enjoy an expanded list of seasonal offerings.
• [2] Complimentary Zero-Proof Drinks for Designated Drivers & Ages 18-20: You’re here to party, sans wine. Enjoy two complimentary non-alchoholic drinks keep yourself hydrated while you dance the day away.
• Housemade Niagara Grape Juice in Bottles: Perfect for kids or grown-up kids, our housemade grape juice is the best way to taste the vineyard without the buzz.

Customize your experience with your choice of General Admission, VIP, Designated Driver, and Early Access ticket options!

General Admission Tickets Include:

• Access into the festival grounds at 9AM
• Keepsake 9oz stemmless wine glass for sampling
• Unlimited sampling of 19 different wines from Linganore Winecellars beginning at 10AM
• Shopping from over 40+ boutique vendors
• Live music from 10AM-6PM
• Bottle sales, glass sales, speciality cocktails & drinks available for purchase from 10AM-6PM
• Cell phone charging stations available on site

VIP Tickets Include:

All of the perks of General Admission, plus:

• Streamlined VIP entry into the festival – no waiting in long lines!
• Bonus VIP gift in addition to the 9oz keepsake glass
• Access into the VIP Hall, which includes air conditioning and indoor restrooms
• Bonus wine tasting of 6 exclusive wines in the VIP Hall

Designated Drivers & Ages 18-20 enjoy discounted tickets, plus will enjoy their choice of two specialty zero-proof beverages at the festival. Linganore Winecellars offers a number of zero proof options for designated drivers and other non-drinkers to enjoy throughout the event.

Early Access Tickets allow ticket holders to enter the festival grounds as early as 6AM. All attendees who wish to enter the grounds at 6AM MUST have an early access ticket type. Early Access ticket holders may exit and re-enter the festival at a later time if they wish. (Yes, we’re okay with you napping in your car. Yes, we’ll have a coffee cart for you. And yes, we’re that excited for the festival too.)

There’s no shortage of great drinks to be had at the Caribbean Wine & Music Festival! With over 40 wines from Linganore Winecellars, craft beers from Red Shedman Brewery, and a handful of seasonal speciality beverages, you’re sure to stay hydrated all day long.

Don’t miss out on fan favorites like Mango Sangria (basically summer in a bottle) or Mountain Red (hello, adult grape juice!). Maybe you’re in the mood for something a little drier – may we suggest Seventh Rosé or Retriever Red? Not sure? Hm. Guess you’ll just have to come to the festival and try them for yourself.