From Linda’s Journal
Date: June 29, 2019
Wedding #1
Location: The Barns at Wesleyan Hills, Middletown, CT
Canvas Size: 18 x 24″
Time on Site: 4:30–10:30 PM
Time in Studio: About one month
One lesson from this day: Painting the landscape was the easy part. Painting people would become a lifelong pursuit.
Seven years ago today—June 29, 2019—I painted my very first live wedding.
At the time, I had no idea that saying “yes” to one wedding would completely change the direction of my career. If you had told me that one day I would paint more than 170 weddings, build a business around live wedding painting, and eventually enjoy encouraging other artists who wanted to pursue this path, I honestly don’t think I would have believed you.
Like many good opportunities, this one began with a simple phone call.
A call from a friend
My friend Holly and I had known each other for several years through the Branford Art Center, where we both exhibited our work. I mostly showed plein air landscapes, while Holly created beautiful abstract figurative paintings and was also an incredibly talented muralist. She had been painting two or three live weddings each year and was already booked for June 29th when another inquiry came in from a family in New York looking for a live wedding painter for a Connecticut wedding. Instead of turning them away, she thought of me.
The painting was meant to be a surprise gift from the groom’s brother. Holly told me she normally charged around $1,800, but because this would be my very first live wedding, the family asked if I would do it for $1,500. I didn’t hesitate. I was thrilled. I already had a simple contract and online payment system from my art business, so I sent everything over, they signed the agreement, and just like that, I had my first live wedding booked.
I knew how to paint. What I didn’t know yet was how to paint a wedding.
The wedding was only about a month away, so I spent those weeks researching everything I could find. I studied the websites of other live wedding painters, looked through wedding photographers’ galleries, visited the venue ahead of time, met with the coordinator, walked the property, and tried to imagine exactly where I would stand on the wedding day.
The couple wanted the ceremony painted with the wedding party surrounding them, but they also wanted the first row of family members included—even if it meant painting the backs of their heads. I remember looking at the reference photos and thinking, How am I going to paint all of these people?
Wedding Day arrived
When the wedding day arrived, I got there about two hours early. I didn’t even set up my easel yet because the painting itself was a surprise. Instead, I quietly photographed the ceremony site, knowing the groom’s brother would introduce me when the newlyweds entered the reception.
I’ll never forget the groom’s reaction. As soon as he understood what was happening, he began to cry. In that moment I realized this painting was going to mean far more than I had imagined.
Once I finally set up, I did what felt most familiar—I painted the landscape. Years of plein air painting had prepared me for that part without me even realizing it. Painting the trees, the light, and the ceremony setting felt comfortable. Adding the people was another story.
I began with the bride and groom, keeping them loose and impressionistic, and gradually added the wedding party and eventually dozens of guests. At one point the groom’s mother walked over to watch me. She quietly looked me up and down, studied the painting, and with what I remember as a very skeptical expression said something like, “We’ll see how this turns out.”
Looking back now, it makes me smile. Maybe she sensed it was my first wedding. Maybe she was simply curious. Either way, I just kept painting.
As the evening went on, more guests stopped by. They asked questions, watched the painting develop, and offered encouraging comments. By the time I packed up around 10:30 that evening, I was exhausted, but I was also energized. I drove home thinking about nothing else.
The next morning I walked into my little studio near downtown Branford and couldn’t wait to continue. I honestly thought I’d finish the painting in a week or two. Instead, I spent nearly a month refining every part of it before carefully packing it up and shipping it to New York. The family who commissioned the painting arranged a video call so they could watch the bride and groom open their surprise gift together. Knowing they would have that memory for the rest of their lives was incredibly rewarding.
A few weeks later I wrote a blog post about the experience. At the time, I thought I was simply sharing a project that I had enjoyed. I had no idea that one blog post would quietly become the foundation of my live wedding painting business.
Life certainly didn’t become easy after that first wedding. Just a few months later I had to close my studio because I could no longer afford the rent. Then the pandemic arrived, weddings disappeared almost overnight, and I wondered if that first live painting had simply been a wonderful one-time experience.
Then, in September of 2020, another inquiry came in. That wedding led to another, then another. Before long I had seven weddings booked, then thirty-nine, then forty-four. Looking back now, I realize the business wasn’t built overnight. It grew one commission, one relationship, and one lesson at a time.
Today, seven years later, I can see that my first live wedding painting taught me far more than how to paint at an event. It taught me about serving clients, writing better contracts, preparing well, communicating clearly, pricing my work, recovering from mistakes, refining my workflow, and learning how to balance studio life with painting on location. Every season brought new lessons, and in many ways I still feel like a student.
Over the coming months I’d love to share more of those stories—not because I’ve figured everything out, but because I remember exactly what it felt like to stand behind that easel seven years ago wondering if I was ready.
If you’re an artist who’s thinking about becoming a live wedding painter, I hope you’ll join me as I look back on the lessons, mistakes, unexpected blessings, and small moments that shaped this journey. And if one of these stories encourages you to take your own first step, then sharing them will have been well worth it.
Seven Years Later
Rock Island Lake Club – Sparta, New Jersey
April 12, 2026
This weekend Dean and I had the pleasure of personally delivering this painting to Briana and Eric.
As I looked at this finished piece, I couldn’t help but think back to that very first wedding in June of 2019.
The painting itself is certainly different. My drawing has improved, my understanding of light has grown, and years of painting people have made me much more confident in capturing a couple’s likeness. But what struck me most wasn’t how much my painting has changed—it was everything I’ve learned that has nothing to do with holding a brush.
Today I arrive at each wedding with a refined setup, a well-tested workflow, and years of experience working alongside planners, photographers, DJs, and venue coordinators. I have systems that help me stay organized, contracts that reflect lessons learned, and a studio process that has evolved through many successes—and a few difficult mistakes.
Every wedding has taught me something.
Some lessons were exciting discoveries.
Others were learned the hard way.
Looking back now, I realize that becoming a live wedding painter wasn’t just about becoming a better painter. It was about becoming a better business owner, communicator, problem solver, and steward of the trust that each couple places in me.
As I begin sharing Linda’s Journal, I hope to tell more of those stories—the ones that happen behind the scenes and the lessons that have shaped not only my paintings, but my career as an artist.
