Sheesh, with all the people openly having a target of $1000 it's going to take years to get there and crash magnificently the moment it does.
It depends. If Bitcoin hits $1000 for the same reasons it hit $266 in April - pure speculation - then, yes, it will crash dramatically. In fact, it will most likely crash before it gets to $1000, if its based mostly on speculation.
However, if the underlining fundamental values of BTC increase such as:
A. Legitimacy as a true store of wealth - (ETF funds, financial markets treating it as if it is a viable option)
B. Increased adoption and implementation in developing or struggling countries (i.e. relationship with M-pesa/Cyprus)
C. Legitimacy as a currency grows - adoption by large internet companies/off-line retailer brands, etc.
then $1000 could come and go without much ado at all.
It really just depends on how Bitcoin evolves over then next 24 months.