Freehand Silhouettes: The 5‑Minute Portraits Bringing History Back to Life

In an age of high‑resolution cameras and AI filters, there’s something quietly magical about a portrait that’s created with nothing more than scissors, paper, and a very trained eye. At Newport’s historic Colony House, that magic comes to life this Winterfest with freehand silhouette portraits by Deborah O’Connor, better known as The Silhouette Lady.​

What Exactly Is a Silhouette Portrait?

Long before photography, families preserved their likenesses as simple black paper cut‑outs, carefully snipped to capture profiles, curls, and collars in surprising detail. These silhouettes were quick, affordable and incredibly personal—think of them as the original “profile pictures,” but with a timeless, gallery‑worthy feel.​

Today, silhouettes have made a quiet comeback as keepsakes for weddings, baby showers, anniversaries and, increasingly, for people who want art that feels more human than a phone screen.​

Inside the Colony House Experience

On Saturday, February 21st, 2026, the Colony House in Washington Square, Newport, turns into a live studio for this old‑world art form. Between 11:30 AM and 3:30 PM, visitors can sit for a portrait that takes about five minutes from start to finish—no cameras, no sketching, no tracing. Deborah works freehand, cutting directly into paper as she studies each profile, translating expression and personality into a single continuous line.​

Silhouettes can be created from live sittings or from photographs, which means shy kids, busy adults and even beloved pets can be captured without stress. Families, couples and pet parents walk away with matching portraits that look stunning framed together on a wall or displayed on a mantle.​

Art, History, and a Little Bonus

Part of the charm of this event is the setting: the Colony House is one of Newport’s most important historic buildings, so you’re getting a piece of living history inside another piece of history. It’s a perfect winter afternoon activity that blends culture, creativity and cozy nostalgia.​

Pricing stays accessible: silhouettes are $30, with additional copies at $15, making it easy to create a set for grandparents or gifts. You can choose from simple black frames (5×7 for $20, 8×10 for $30) or deluxe gold‑leaf frames (5×7 for $40, 8×10 for $60, with the larger frames fitting two silhouettes side by side). And if you’re wearing a Winterfest bracelet, your silhouette sitting also earns you a voucher for a walking tour of your choice—art plus exploration in one go.​

Creative Takeaways for Edge Realty Readers

Why are we spotlighting this in Creative Edge? Because it’s a beautiful reminder that:

• A simple medium can still tell a powerful story.

• Personality doesn’t need pixels to shine through.

• People connect deeply with tangible, handcrafted keepsakes.

For those of us in real estate and creative marketing, silhouette portraits are a great metaphor: the strongest brands and spaces don’t rely on clutter—they rely on clear outlines, character, and a memorable first impression.

If you find yourself in Newport around Winterfest, this five‑minute portrait session might just become one of those small traditions you look forward to year after year.​