Caribbean Wine & Music Festival 2026

@ 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. SATURDAY, MAY 23:DJ Sprang Intl – MC | 10AM-6PMPan Masters Steel Orchestra | 11AM-2PMImage Band | 3PM-6PM SUNDAY, MAY 24:DJ Sprang Intl – MC | 10AM-6PMPan Masters Steel Orchestra | 11AM-2PMEclipse International Band | 3PM-6PM BUY ON EVENTBRITE MORE FESTIVAL INFORMATION Add to calendar Google Calendar iCalendar Outlook 365 Outlook Live