Meet Ashley Cunningham | Wedding Planner

We had the good fortune of connecting with Ashley Cunningham and we’ve shared our conversation below.

Hi Ashley, we’d love to hear more about how you thought about starting your own business?
Starting Thoughtfully Curated Events felt like the most natural next step in my career. I had just wrapped up one of the biggest events of my professional journey—the National Aviation Hall of Fame Enshrinement Dinner—when my client looked at me and said, “Why don’t you have your own company? You were made for this.” That comment stuck with me. The very next day, I sat down and started putting everything into motion. Launching my own business had always been a dream of mine, and that moment gave me the final push I needed to make it real.

What truly sets me apart as a planner is the depth and diversity of my background. Before starting my own company, I spent years gaining hands-on experience in every corner of the event industry—from managing venues in Chicago to working in catering sales, floral design, and full-scale event production. That well-rounded foundation allows me to anticipate and solve issues before they arise, and it makes me a calm, confident leader on event days—someone vendors and clients alike can count on.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
One of the things I love most about wedding planning is the opportunity to bring all of my creative passions together to craft a truly unforgettable day for each couple. From a young age, creativity was always a part of who I was—you couldn’t keep crayons or sketchbooks out of my hands. I was constantly designing, creating, and later in high school, fell in love with capturing small, meaningful moments through film.

My journey into the events world began with my first job at a venue in Chicago. I’ll never forget the first wedding I worked—the emotion of the ceremony, sitting quietly in the back and tearing up as the couple exchanged vows, and then witnessing the pure joy on their faces as they were introduced for the first time. That was my “aha” moment. I realized then that I had the chance to be part of something so meaningful—to celebrate life’s most special moments with people and help bring their vision to life.

To do that well, I invest a lot of time getting to know my couples on a personal level. I love connecting beyond just logistics—whether it’s sharing a meal in their home, observing how they host and what makes them light up. All those little details give me insight into their personalities and love story, which I then translate into a wedding experience that feels deeply personal and completely one-of-a-kind.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
As a proud Colorado native, there’s nothing I love more than sharing the magic of Denver with friends and visitors. This city has so much to offer, and I always enjoy curating a little “locals-only” experience for anyone coming to town.

We’d kick things off with a scenic train ride into the city for drinks at the iconic Union Station. After settling in, we’d head out to Red Rocks for a bit of light hiking and exploring—complete with to-go charcuterie boards, of course. For dinner, Hop Alley is always a favorite, followed by an immersive evening at Meow Wolf. And no Denver night is complete without a sweet stop at Little Man Ice Cream to wrap things up.

Some of my go-to restaurants I love to recommend (and revisit!) include Briar Common Brewery, Safta, Makfam, Snarfsburgers, Buckhorn Exchange, Uchi, and Hey Kiddo. When it comes to activities, a Rockies game is a must, along with a tour at Stranahan’s Distillery, an afternoon in charming downtown Golden, and a relaxing spa day at Monarch Resort and Casino. And naturally, no Colorado experience would be complete without exploring the endless hiking trails that surround us.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I truly believe that success is never achieved alone. I’m incredibly grateful for the community of people who have supported, encouraged, and uplifted me along the way. Their belief in me has played a huge role in shaping the path I’ve taken and the milestones I’ve reached.

That said, my biggest role model has always been my dad. He built a highly successful business from the ground up, and throughout my life, he’s been a constant source of inspiration. He taught me the value of hard work, resilience, and believing in yourself. Most importantly, he always reminded me that no dream was ever too big—and that I was more than capable of achieving anything I set my mind to.

Website: https://www.thoughtfullycuratedevents.com

Instagram: @thoughtfullycuratedevents

Linkedin: https://www.linkedin.com/in/ashley-cunningham-5a352926/

Image Credits
Bridget Burnett Photography, Silk and Sage, Mariana Ziegler Photography, Mallory Munson Photography, Autumn Cutaia Photo