Winners — Getaway with Ascend
TripDrop Winners

Real trips. Real winners. Every month.

Every month we drop one vacation, anyone can enter, and we announce a real, named winner — right here. No stock photos, no "winner withheld."

Congratulations to the Webster Family — July 2026 TripDrop winner
Winner

The Webster Family

One entry, one name drawn, and a family vacation on the way.

Congratulations to the Cannaday Family — June 2026 TripDrop winner
Winner

The Cannaday Family

One entry, one name drawn, and a family vacation on the way.

Congratulations to the Castleman Family — May 2026 TripDrop winner
Winner

The Castleman Family

One entry, one name drawn, and a family vacation on the way.

Up next

Next month's winner could be you.

Free to enter, one name drawn, a real trip on the way. Get your name in for the August drop — it takes about 30 seconds.

Enter the next drop