The DMV Flavor Map, Part 2: Strawberry Fest, Plena, and Artscape Weekend

A long weekend is coming. Here is where to spend it.

We already gave you the first course. Now here is the second—more festivals, more flavors, and a free Afro-Puerto Rican music celebration tucked into a quiet museum town.

Let us get to it.

1. Caribbean Wine & Music Festival (May 23–24)

Location: Linganore Winecellars, Mt. Airy, MD

The event: An island-style getaway in the Maryland countryside. Nineteen wines. Forty-plus vendors. Live music with heavy Caribbean influence.

Did you know? Linganore Winecellars is one of Maryland's original wine pioneers. They helped shape the state's modern festival industry. Early Access tickets let you in at 8 AM if you want first pick of the vendors.

Good to know: The festival runs 10 AM to 6 PM both days. Bring a chair. You will want to stay.

Highlights.

2. Strawberry Jubilee Festival (May 23–31)

Location: Great Country Farms, Bluemont, VA

The event: A week-long celebration of spring harvest. Live music, farm-fresh food, and pick-your-own strawberries straight off the plant.

Did you know? Bluemont was originally named Snickersville until 1900. The town sits at the base of Snickers Gap in the Blue Ridge Mountains, a historic passage used by Native Americans and Civil War generals alike.

Good to know: Call ahead for berry conditions. The farm posts updates on their Facebook page. A quick check saves a long drive.

Highlights.

3. Artscape (May 23–24)

Location: Mount Royal Avenue & North Charles Street, Baltimore, MD

The event: America's largest free arts festival. Art installations, live performances, and a food scene featuring local Baltimore favorites and experimental street eats.

Did you know? Artscape takes over the Mount Royal cultural district, home to the Maryland Institute College of Art (MICA), founded in 1826.

Good to know: It is free. It is crowded. Go early. Take the Light Rail if you can.

Highlights.

4. Strawberry Celebration Day (May 31)

Location: Derwood Farmers Market, MD

The event: A market day dedicated to local berries and strawberry-infused treats. Jams, pies, shortcakes, and maybe something savory if a vendor gets creative.

Did you know? Derwood was once a small crossroads known as Upper Falls. It grew after the B&O Railroad came through. The farmers market is not a new addition—it is the original reason the town exists.

Good to know: The market runs 9 AM to 1 PM. Strawberries sell out. Go early.

Highlights.

5. Puerto Rico in Maryland Festival (May 30)

Location: Sandy Spring Museum, Sandy Spring, MD

The event: A free, family-friendly afternoon celebrating Puerto Rican culture. Live performances of Plena and Bomba—Afro-Puerto Rican music traditions rooted in rhythm, call-and-response, and storytelling. Local artisans, cultural workshops, and authentic cuisine.

Did you know? Sandy Spring Museum sits in a Quaker-founded community that was a stop on the Underground Railroad. The same grounds now host a celebration of Afro-Puerto Rican heritage. History has a way of layering.

Good to know: It is free. No ticket required. Just show up at 17901 Bentley Rd.

Highlights.

6. NVA Thai Street Food & Culture Festival (May 31)

Location: Manassas Museum, Manassas, VA

The event: A deep dive into authentic Thai flavors. Traditional street food stalls, cultural performances, and enough lemongrass to fill a small room.

Did you know? The Manassas Museum sits on a site that was once a major railroad junction—the reason the First and Second Battles of Bull Run were fought nearby. Now the area smells like pad thai instead of gunpowder.

Good to know: The festival runs 11 AM to 5 PM. Bring cash.

Highlights.

The Final Reminder: Takoma Trukgarten (May 30)

Do not forget the home game. Takoma Trukgarten is the annual gathering of local breweries, cideries, and food trucks at the corner of Laurel and Carroll. It is relaxed, family-friendly, and a genuine neighborhood highlight. Dogs welcome. Water bottle refill station on site. No on-site parking—walk, bike, or Metro.

Highlights.

Ready for June?

May is the warm-up. June brings the 5th Annual Taste of the DMV in Baltimore and the first of the legendary crab feasts. More on that soon.

#DMVFlavorMap #PuertoRicanHeritageFest #StrawberryJubilee #Artscape #TakomaTrukgarten

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