By default Windows Server 2008 firewall blocks ping requests.
To enable please follow the below methods :
1) Open the windows firewall console.
2) Click inbound rules.
3) Find "File and Printer Sharing (Echo Request - ICMPv4-In)" and click enable rule. (if you need IPv6 you will need to enable that too)
Or
Using command line:
netsh firewall set icmpsetting 8