Some kids face obstacles you can’t always see. For Teddy, school was never a simple path — filled with changes, challenges, and plenty of hard work just to get where he is today. But through it all, Teddy has remained smart, determined, and full of humor — always finding ways to make people smile.
Recently, Teddy got a well-deserved break from life’s struggles — trading classrooms for clouds — when he took his Dream Flight with Above the Clouds. Teddy flew with Chris Steward, one of our dedicated volunteer pilots who helps make these special experiences possible for kids like him. From takeoff to landing, Teddy soared high above the challenges below, experiencing the freedom and confidence that only flight can bring.
At Above the Clouds, we create unforgettable aviation experiences for kids and teens facing adversity — reminding them that no matter how tough the journey has been, the sky is still wide open.
Huge thanks to Chris and to all of our amazing volunteer pilots, donors, and supporters who make Dream Flights like Teddy’s possible. You are helping kids rise above — one flight at a time.
Learn more, nominate a Dream Flyer, volunteer or support: abovethecloudskids.org
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After a week of watching the forecast closely, we’ve made the difficult decision to cancel this Saturday’s Dream Flight Day due to poor weather conditions. Low ceilings, heavy cloud cover, and rain have made it clear that flying safely—and giving our Dream Flyers the full experience they deserve—just isn’t possible this weekend.
We explored the possibility of shifting to Sunday, and we’re incredibly grateful to the pilots and volunteers who offered to adjust their schedules to make that work. Your flexibility and willingness to step up are what keep this program going strong.
Unfortunately, Sunday’s weather isn’t looking much better. The most recent forecasts show conditions improving only later in the afternoon, which would mean a significantly delayed start. That creates challenges not only for our pilots and volunteers but also for several families who simply wouldn’t be able to participate at a later time. Between the limited availability and the forecast uncertainty, we’ve decided that trying to squeeze in a partial day just isn’t the right call.
Instead, we’re turning our attention to the next full Dream Flight Day on Saturday, July 19—and we’re excited to make it one of our biggest yet.
We’re also in the process of adding additional Dream Flight Days in July and August, along with weekday flights to help serve more children on our waiting list. If you’re a pilot or volunteer who has weekday availability, we’d love to hear from you!
✅ Sign up now for the July 19 Dream Flight Day:
Click here to register
We’re grateful for your continued support, your patience, and your passion for helping children experience the joy and wonder of flight. The skies will clear soon—and when they do, we’ll be ready.
But on this special day, Miranda took to the skies instead of the stage, flying with our longtime supporter and first-time Dream Flight pilot Charles Evan in his Beechcraft BE-36 Bonanza. As always, Miranda’s bright personality, endless curiosity, and gift for connecting with others made the day even more special for everyone involved.
At Above the Clouds, we create unforgettable flight experiences for kids of all abilities who are facing adversity — helping them see just how high their dreams can soar.
Huge thanks to Charles and to all our volunteer pilots, supporters, and families who make Dream Flights possible!
After a long stretch of rainy weekends and postponed plans, Above the Clouds finally took to the skies again on Sunday, June 1—and it was nothing short of magical.
We were thrilled to fly nine incredible kids, ages 9 to 16, many of whom had been patiently waiting through multiple reschedules due to weather. These resilient Dream Flyers came from across Massachusetts—and one even made the two-hour journey from Connecticut!
This special day was made possible thanks to the dedication and generosity of 33 amazing volunteers, including:
8 volunteer pilots who donated their time, talent, and aircraft
5 flight coordinators who ensured everything ran smoothly on the ground
And a full team of photographers, joy makers, greeters, and support volunteers who made every moment fun, welcoming, and memorable
We are deeply grateful to everyone who made this day a success. Each smile, high-five, and joyful takeoff reminded us why we do this work—and how powerful it can be for children facing adversity.
We’re already looking ahead to our next Dream Flight Day on Saturday, June 28, and we’re actively recruiting:
Pilots
Flight Coordinators
Photographers
Joy Makers and General Event Volunteers
If you’re interested in being part of the magic, we’d love to have you join us.
Click here to confirm your availability for June 28
Above the Clouds serves children and teens (ages 6–18) who are facing serious adversity—whether it’s illness, disability, the loss of a loved one, foster care, or financial hardship. A Dream Flight is a joyful, one-of-a-kind experience meant to uplift and inspire.
If you know a child who could benefit, we invite you to learn more and apply:
Apply for a Dream Flight
Thank you again to our volunteers, partners, and supporters who continue to help us bring hope and joy to kids who need it most. We couldn’t do this without you!
Unfortunately, while there will be a window on Saturday without rain, the forecast is predicting low clouds between 200–700 feet, which is well below the minimums Above the Clouds sets to fly and provide a positive experience for the children we serve. As a result, we will need to cancel the Dream Flights planned for May 17.
We know this is disappointing—especially after other recent weather-related cancellations—and we are truly grateful for your dedication and flexibility.
We will work with families to reschedule these Dream Flyers to one of the following options:
To those who have already committed to May 31—thank you! We’re looking forward to a great day with about 10 Dream Flyers and 10 pilots, including three first-time pilot volunteers.
If you haven’t yet let us know your availability for May 31, you can do so using the link below:
Click Here to Confirm Your Availability for May 31st Dream Flight Day
Let’s all keep our fingers crossed for better weather at the end of this month and throughout the summer. Thank you again for being part of the Above the Clouds family—your time and commitment mean the world to us.
This powerful segment follows 13-year-old Jake, one of our Dream Flyers, and his flight with volunteer pilot Chris Steward, capturing the joy, confidence, and healing that take flight through our mission. You’ll also hear from Board President Greg Bongiorno and see behind the scenes of a Dream Flight Day in action.
For our team, this moment is especially meaningful. One of our founder Gary Oberstein’s early dreams was to see Above the Clouds featured on Chronicle. We’re proud to have fulfilled that vision—and grateful to share this story with the wider community.
We’re thrilled to announce that Above the Clouds will be featured tonight, May 6 at 7:30 PM on Chronicle, WCVB-TV Channel 5’s award-winning news magazine!
This special episode is all about Taking Flight in New England—from nostalgic balsa wood airplanes made in Wakefield, to space suits built in Worcester (including one worn by astronaut Sunita Williams on her recent mission), to a behind-the-scenes ride aboard the Sky 5 news chopper. The episode also highlights the legacy of a visionary scientist whose early experiments helped shape modern rocketry.
We’re honored to be one of the featured stories.
Our segment follows volunteer pilot Chris Steward, Dream Flyer Jake, and his dad as they take to the skies with Above the Clouds, showing the powerful impact flight can have on children facing serious adversity.
Tune in tonight, Monday, May 6 at 7:30 PM
WCVB Channel 5 – Chronicle
This is a big moment for us—and for the children and families we serve. We’d love for you to watch and share the episode with others who may want to support our mission.
Whether it’s by volunteering, making a referral, or making a donation, you can help bring the joy of flight to even more kids across the region.
Thank you for helping us lift children’s spirits and dreams—one flight at a time.