It is widely known that conditional covariances of asset returns chang
e over time. Researchers doing empirical work have adopted many strate
gies for accommodating conditional heteroskedasticity. Among the popul
ar strategies are: (a) chopping the available data into short blocks o
f time and assuming homoskedasticity within the blocks, (b) performing
one-sided rolling regressions, in which only data from, say, the prec
eding five year period is used to estimate the conditional covariance
of returns at a given date, and (c) performing two-sided rolling regre
ssions, in which covariances are estimated for each date using, say, f
ive years of lags and five years of leads. Another model-GARCH-amounts
to a one-sided weighted rolling regression. We develop continuous rec
ord asymptotic approximations for the measurement error in conditional
variances and covariances when using these methods. We derive asympto
tically optimal window lengths for standard rolling regressions and op
timal weights for weighted rolling regressions. As an empirical exampl
e, we estimate volatility on the S&P 500 stock index using daily data
from 1928 to 1990.