TripleSync with Outlook conduit: Keep your Outlook, Web calendar, and TripleSync calendars all in sync with the push of a button.  Outlook Configuration Details

TripleSync's desktop calendar is designed to keep track and remind you of important events before they occur. TripleSync displays holidays, birthdays, anniversaries, or any scheduled event in a list or on an attractive traditional calendar. Have TripleSync alert you of events when your computer starts, or at any specified time. TripleSync has built-in support for sending e-mail when an event comes up. Have the e-mail sent automatically, or compose it yourself. TripleSync seamlessly integrates the option to attach a personal greeting, recorded using your computer's sound card and microphone. With TripleSync you will never forget an important date again.

Note: Web syncing requires a Brown Bear web calendar version 3.7 or later.