  Two Higgs doublet extensions of the standard model, such as supersymmetry,
predict the existence of charged Higgs bosons. We explore the reach for
TeV-scale charged Higgs bosons through their associated production with top
quarks, and their decay to boosted top jets and $\mu_x$ tagged boosted bottom
jets, at a 14 TeV CERN Large Hadron Collider and at a 100 TeV Future Circular
Collider. In particular, we show the moderate $\tan\beta$ "wedge" region of
parameter space cannot be probed at the Large Hadron Collider for TeV-scale
$H^\pm$ because the cross section is too small. However, a 100 TeV future
proton collider can close the wedge region below 2 TeV, and search for $H^\pm$
up to 6 TeV.
