Waiting for OTA updates takes a large amount of patience or you can just manually perform the update. This is not a root process rather the approved update without the wait.
Instructions to manually install Android 2.2 Froyo (FRG22D) on the Original Motorola Droid
- Download OS update from Google
- Rename the downloaded file to update.zip (avoid naming update.zip.zip)
- Copy the file to the root of your microSD Card.
- Power off the phone
- Hold the Power button and the X key on the physical keyboard (This will boot into recovery mode)
- When you see the /!\ triangle with an exclamation point release both keys
- Press the Volume up and Camera button at the same time
- Using the D-Pad (aka mouse pad on the keyboard) select apply update.zip
- Press the D-Pad down
- The update should run and the phone will reboot once completed
This is the same process for updating or installing any ROM on the Motorola Droid. This process is for non rooted phones or those phones running the currently available ROM from Verizon.
[Source DroidLife]