Balloons over Waikato 2025: Gail Dryland’s 20-year ballooning journey

Gail Dryland and her team ready to fly Lollipop off on the second to last day of the Balloons over Waikato festival. Photo / Malisha Kumar

After 20 years as a hot air balloon pilot in Waikato, retired dairy farmer Gail Dryland says she’ll “carry on” flying as long as possible.

Dryland was one of more than 20 pilots at the annual Balloons over Waikato festival in Hamilton this week, flying her 6-year-old multicoloured balloon named Lollipop.

She loves being up in the sky and feeling free, “putting on my black gloves and waving down like a queen”, but also feeling how peaceful and therapeutic it is from above.

She’s been flying at the festival for more than a decade. Reflecting on her 20-year piloting journey with the Waikato Herald, she remembers how she “never wanted to be a pilot or own a balloon”.

“The balloons flew over my farm one day and that’s how I first saw them. They landed down the back of the farm, I went over and talked to them, volunteered at the club, and it just snowballed,” she said.

That was 20 years ago.Now, as well as being a member, she’s also been a mentor at the Waikato Balloon Club, championing people to pursue their passions in hot air ballooning.

Gail Dryland, the pilot of the hot air balloon named Lollipop at the 2025 Balloons over Waikato festival. Photo / Malisha Kumar

She said a lot more women were coming into the club and were interested in being a pilot now after seeing her: “Women can do anything.”

Dryland also encouraged her brother to follow her ballooning trail. He has been flying hot air balloons for a decade. an d was also flying the Goldilocks balloon at the festival.

“It’s so lovely ... not many brothers and sisters can fly in the sky together.”

Despite “getting older”, and with all the maintenance and health and safety work that goes into flying a hot air balloon, she’ll “carry on as long as I can”.

Her inspiration for continuing is “the happiness it generates for everyone”.

“I always feel so happy, I love it, but just the enjoyment it brings everyone and not just me ... it’s a very happy thing.

“We love to share it with people, we love talking about it, it’s always fun and it’s happy.”

When asked what she would say to other women wanting to pursue a career in hot air ballooning, she said: “Come down to the club, help some crews, and see if you like it.”

Gail Dryland's hot air balloon Lollipop (right) getting ready to fly. Photo / Shanel Prasad

Malisha Kumar is a multimedia journalist based in Hamilton. She joined the Waikato Herald in 2023 after working for Radio 1XX in Whakatāne.