{Jessica & Orlando}

22 Jul {Jessica & Orlando}

Posted at 06:00h in Weddings by Shaun Bollinger

Jessica + Orlando | A Beautiful Wedding at Historic Ashland

Jessica and Orlando were married on May 29, 2026, at the beautiful Historic Ashland, and I have to say—I completely understand why couples love this venue. This was my first time photographing a wedding there, and the gorgeous grounds did not disappoint.

We started the day with some of the sweetest photos of Jessica with her dogs, which was such a fun way to kick things off. From there, she shared a first look with her dad, followed by a first look with Orlando. Both moments were so genuine and emotional. After seeing each other, they took a few quiet minutes to read their private vows, and it was such a special part of the day.

One thing I couldn’t help but notice all day long was the way Orlando looked at Jessica. Every time she walked into the room, he couldn’t take his eyes off of her. It was one of those little things that reminded everyone just how in love they are.

After their beautiful Catholic ceremony, everyone headed back to Historic Ashland for the celebration.

Jessica chose light blue floor-length dresses for her bridesmaids, while Orlando and his groomsmen wore light gray suits. The soft colors were perfect for a late spring wedding and looked beautiful throughout the day.

The reception was so much fun. Their first dance was beautiful, and then came one of my favorite moments of the night—the father-daughter dance. It started out as a traditional slow dance before turning into a choreographed mashup of fun songs that had everyone laughing, clapping, and cheering them on.

Another detail that guests absolutely loved was the live wedding painter. Throughout the evening, she painted Jessica and Orlando’s first kiss, and it was so fun watching everyone stop by to see how the painting was coming along. What an incredible keepsake from their wedding day.

The rest of the evening was filled with heartfelt toasts, great food, lots of dancing, and a packed dance floor. It was such a fun celebration from beginning to end.

Jessica and Orlando, thank you for trusting me to capture such an important day in your lives. It was truly a joy to celebrate with you both, and I wish you a lifetime of love, laughter, and happiness together.