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Test Flight: Glasswing Ventures AI Hackathon ($300K In Compute!) - Sponsored by Microsoft Azure & AWS

TFJames Massaquoi
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dateSep 26 – Sep 27, 2026
locationBoston, MA
prize$300,000 in compute
priceTBA
formatIn-Person
organiserJames Massaquoi

about this event

Test Flight is a two-day, in-person AI hackathon, hosted by Glasswing Ventures. One weekend and $300,000 in compute on the line for the team that wins. The theme is Enterprise-Ready AI so you are building something a real company would actually deploy. Judges want measurable ROI and a credible path to production. Clever technology alone does not clear the bar. Glasswing brings the compute, the credits, the on-site engineering, and mentors from leading AI infrastructure partners, so the only constraint is what you can ship before the clock runs out. Saturday you build. Sunday at 2:00 PM the code freezes, you demo live to the panel, and awards go to the teams that turned a hard enterprise problem into something that works.

Apply solo or bring a team (up to 4), and if you are flying solo or short a few people, we will match you with other builders who made the cut. One application per person, even if you are applying together. We review on a rolling basis, so the sooner you are in, the better.

https://glasswing.vc/hackathon-2026/

schedule

Sat 26 Sep9:30 AM - 6:00 PM ET

Main Hackathon Event

Saturday you build.

◍ Boston, MA
Sun 27 Sep9:30 AM - 5:30 PM ET

Main Hackathon Event

Sunday at 2:00 PM the code freezes, you demo live to the panel, and awards go to the teams that turned a hard enterprise problem into something that works.

◍ Boston, MA

prizes

Prize places and values for Test Flight: Glasswing Ventures AI Hackathon ($300K In Compute!) - Sponsored by Microsoft Azure & AWS
PlacePrizeValue
WinnerCompute$300,000
Test Flight: Glasswing Ventures AI Hackathon ($300K In Compute!) - Sponsored by Microsoft Azure & AWSSep 26 – Sep 27, 2026 · Boston, MA · $300,000 in compute
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