Painted in Love, Poured with Purpose

Every May, something special happens on Main Street. The air turns warm, laughter echoes between historic buildings, and our town gathers in celebration of the things that bring us joy—art, wine, music, and each other. But the Downtown Sykesville Art & Wine Festival is more than a good time. It’s a tradition rooted in heart, and this year, its roots run even deeper.

Because this year, every ticket carries a legacy.

We are honored to dedicate the 2025 Art & Wine Festival to the memory of Donna Carol Box—a beloved sister, artist, runner, and creative force whose warmth and compassion touched so many. Donna’s sister, Denise, and Denise’s wife, Leslie, are generously sponsoring the event in her honor and raffling a print of one of Donna’s original watercolor paintings as a tribute to her life and her love of all things handmade and heartfelt.

“This is the old fire truck that used to sit at the entrance of Beck’s,” Denise shared. “It’s a special memory of the town—and a perfect way to celebrate her life and art.”

The painting print will be raffled to support AAMDS, the Aplastic Anemia and MDS International Foundation, an organization that supports individuals and families affected by rare bone marrow failure diseases. Donna battled aplastic anemia with incredible strength and spirit, and this raffle is a meaningful way to raise both awareness and support in her name.

Their chosen tribute line says it all:

“Her Art, Her Heart, Her Legacy. Forever cherished, missed beyond measure.”

“Honestly, it’s twofold,” Denise said. “We aren’t doing the golf tournament this year with the DSC, which is when we would usually raise money for AAMDS. This is an even better way to do something in her memory. She was an artist and loved the town. She would have loved the Art & Wine Festival. And by sponsoring it, we get to share her memory with many more people.”

It’s a powerful reminder that this event is about more than wine and art—it’s about celebrating lives, stories, and the kind of enduring love that keeps memory alive in joyful ways.

Your ticket is more than admission—it’s action.

When you buy a ticket to the Art & Wine Festival, you’re not only signing up for a wonderful day—you’re helping fund the free community events that define Downtown Sykesville:

• Trick or Treat on Main Street
• The Happy-Thon holiday initiative
• Historic preservation initiatives
• Walking tours and public art displays
• The farmers market
• Cultural celebrations, youth programs, and so much more

These experiences are made possible by the Downtown Sykesville Connection, a nonprofit dedicated to keeping our town not only beautiful and historic—but inclusive, welcoming, and alive with possibility. The Art & Wine Festival is one of our largest fundraisers of the year, and the impact of your participation stretches far beyond a single afternoon.

Whether you’re a longtime local, a first-time visitor, or one of the many who discovered Sykesville through a “Best and Coolest Small Towns” list, your ticket helps preserve the very charm that brought you here in the first place.

This festival is also a chance to slow down and connect.

As you sip wines from regional vineyards and explore handcrafted goods from local artists, you’re stepping into a shared experience. You’re meeting the faces behind the booths, bumping into old friends, and maybe—just maybe—seeing the town through someone else’s eyes for the first time.

That’s the kind of everyday magic Donna believed in. And it’s the kind we’re honored to celebrate in her name.

“She’s probably p****d that she’s not here to celebrate with us,” Denise said. “If she were here today, I’m sure she would have a booth at the festival.”

Donna was the kind of person who seemed to excel at everything she touched—from painting to carpentry to being a loyal and loving presence in the lives of those around her. “We’re biased,” Denise said, “but for us, she was everything. A loving wife, mother, daughter, sister, and friend. She loved this town and would have loved how much it has grown. She was interested in all kinds of art, but painting became a passion for her.”

We invite you now to be part of something bigger than a day out—to be part of a movement rooted in creativity, generosity, and homegrown joy.

Tickets are on sale now and do sell out—secure yours today and help us make this year’s festival one to remember:
Purchase your tickets here.

Let’s raise a glass to art, to legacy, and to the kind of town that wraps its arms around both.