We study discovery prospects for a real triplet extension of the Standard Model scalar sector at the Large Hadron Collider (LHC) and a possible future 100 TeV $pp$ collider. We focus on the scenario in which the neutral triplet scalar is stable and contributes to the dark matter relic density. When produced in $pp$ collisions, the charged triplet scalar decays to the neutral component plus a soft pion or soft lepton pair, yielding a disappearing charged track in the detector. We recast current 13TeV LHC searches for disappearing tracks, and find that the LHC presently excludes a real triplet scalar lighter than 248 (275) GeV, for a mass splitting of 172 (160) MeV with $mathcal{L}=rm36,$fb$^{-1}$. The reach can extend to 497 (520) GeV with the collection of $3000,$fb$^{-1}$. We extrapolate the 13 TeV analysis to a prospective 100 TeV $pp$ collider, and find that a $sim3$ TeV triplet scalar could be discoverable with $mathcal{L}=30$ ab$^{-1}$, depending on the degree to which pile up effects are under control. We also investigate the dark matter candidate in our model and corresponding present and prospective constraints from dark matter direct detection. We find that currently XENON1T can exclude a real triplet dark matter lighter than $sim3$ TeV for a Higgs portal coupling of order one or larger, and the future XENON20T will cover almost the entire dark matter viable parameter space except for vanishingly small portal coupling.