Couple stands underneath the Disneyland Railroad just before a surprise proposal.

Planning of this surprise Disneyland proposal

I’m not alone in the feeling that there’s truly magic in Disneyland. It’s one of my favorite places in the world. The first time I met Bre, I was still living in California and working at Disneyland. It’s even more special that I was able to help her surprise proposal in the Happiest Place on Earth!

Matt came to the resident expert on Disneyland (meaning, me) to help plan his surprise proposal. The castle is always the most classic and obvious choice for a proposal. However, it was being renovated at the time and was completely blocked off with a giant castle-printed tarp. But hakuna matata (it means no worries) because there are plenty of spots to propose besides the castle in Disneyland, and I know every part of the park by heart. While planning we went through a few different options. Matt ultimately decided it was best to go with whatever felt right that day.

Once we met up at the entrance to Disneyland, Matt slipped the ring into my backpack. Then, we ran to grab our first FastPass for the day. After we all crammed into a teacup on the Mad Tea Party, Matt was getting anxious. It was becoming more clear that it might not be a complete surprise. I slipped the ring back and we headed toward Big Thunder Mountain. Along the path, there is an alcove directly underneath another Disneyland classic, the railroad. At the time, it was one of the quietest places in the park, one of the few places without a crowd.

Excited newly-engaged couple embrace after a surprise marriage proposal at Disneyland in Anaheim, California. The surprise Disneyland proposal was photographed by Wind and Sky Photography.
Surprised or not, Bre was more than happy and emotional after Matt popped the question! So thankful I was able to photograph these moments for the newly engaged couple.
Excited newly-engaged couple embrace after a surprise marriage proposal at Disneyland in Anaheim, California. The surprise Disneyland proposal was photographed by Wind and Sky Photography.
Excited newly-engaged couple embrace after a surprise marriage proposal at Disneyland in Anaheim, California. The surprise Disneyland proposal was photographed by Wind and Sky Photography.
Bre took the liberty of drawing out the exact engagement ring she wanted on a napkin from the bar they met working at. Matt searched the internet for the perfect one and it’s safe to say he did a good job based on Bre’s reaction.
Excited newly-engaged couple embrace after a surprise marriage proposal at Disneyland in Anaheim, California. The surprise Disneyland proposal was photographed by Wind and Sky Photography.
Excited newly-engaged couple embrace after a surprise marriage proposal at Disneyland in Anaheim, California. The surprise Disneyland proposal was photographed by Wind and Sky Photography.
Excited newly-engaged couple embrace after a surprise marriage proposal at Disneyland in Anaheim, California. The surprise Disneyland proposal was photographed by Wind and Sky Photography.
Excited newly-engaged couple embrace after a surprise marriage proposal at Disneyland in Anaheim, California. The surprise Disneyland proposal was photographed by Wind and Sky Photography.

I will take any chance I get to go to Disneyland. I absolutely will travel to photograph more surprise proposals here, or even better, a wedding!

Contact me for more information on my availability. I love to help plan proposals, and I’m really good at hiding in plain sight.