Painted in Love, Poured with Purpose

Honoring the Life and Legacy of Donna Box

Every May, something special unfolds on Main Street.

The air softens, music drifts between historic buildings, and our community gathers to celebrate the simple, powerful things that connect us—art, wine, laughter, and shared experience. The Downtown Sykesville Art & Wine Festival has always been about joy. But this year, it carries something even deeper.

This moment carries a legacy.

We are honored to dedicate the 2026 Art & Wine Festival to the memory of Donna Box—an accomplished artist, a signature member of the Baltimore Watercolor Society, and, above all, a person whose warmth, humor, and generosity left a lasting imprint on everyone who knew her.

Donna was full of life in a way that made people feel instantly at ease. Her dry wit could catch you off guard and leave you laughing long after the moment passed. Her creativity wasn’t just something she practiced—it was something she lived. Whether through painting, building, or simply showing up for others, she brought beauty and intention into the world around her.

And she loved this town.

A Legacy You Can See—and Carry Forward

In her honor, Donna’s family is sharing a piece of her artistry with the community she cherished. Throughout the entire month of May, a print of one of Donna’s original watercolor paintings will be raffled—both online and in person at the festival.

Each raffle ticket is more than a chance to take home her work.
It is a direct donation to the Aplastic Anemia and MDS International Foundation (AAMDS), supporting individuals and families facing rare bone marrow failure diseases.

Donna faced aplastic anemia with strength and grace. This effort ensures that her story continues to make a difference.

We invite you to enter the raffle/make a donation “in memory of Donna Box”—to honor her life, support this critical cause, and keep her legacy alive in a way that reflects who she was: generous, creative, and deeply connected to others. The raffle will end 5/31/2026, and the lucky winner will be announced shortly after!

A Place That Holds Her Story

There’s a bench on Main Street that offers one of the best views in town—a place to pause, reflect, and take in the charm of a community that continues to grow while holding tightly to its roots.

It now carries Donna’s name.

It’s a quiet but powerful reminder that the people who shape a place never truly leave it. They live on in the spaces we gather, the stories we share, and the traditions we continue.

More Than a Festival

The Art & Wine Festival has always been a celebration—but it’s also one of the most important ways we sustain the work of the Downtown Sykesville Connection.

Your participation helps fund the experiences that define this community:

• Trick-or-Treat on Main Street
• The Happy-Thon holiday initiative
• Historic preservation and placemaking
• Veteran Banners 
• Public art, cultural programming, and youth initiatives

This Festival connects celebration with purpose.

Because alongside unlimited wine tastings, local art, live demonstrations, and unforgettable moments, there is a deeper thread running through it all—a reminder that joy and remembrance can exist side by side.

A Celebration She Would Have Loved

Donna was the kind of person who didn’t just attend events—she elevated them. She created, contributed, and connected. It’s easy to imagine her here: maybe behind a booth, maybe laughing with friends, maybe quietly observing the beauty of a moment she would later turn into art.

This festival reflects that same spirit.

It’s vibrant. It’s creative. It’s rooted in community.
And it’s exactly the kind of place where her legacy belongs.

Join Us

We invite you to be part of something meaningful.

Come for the wine.
Stay for the art.
Give in memory of Donna.

🎟️ Purchase your festival tickets
🎟️ Enter the raffle/Make a donation “in memory of Donna Box”

Together, we raise a glass—not just to a beautiful day on Main Street, but to a life that continues to inspire it.