Note: You will need a debug adapter to sideload the OTA which Google offers via invitation only. @breaddisease explains on the XDA developers website how he obtained the debug adapter. Make sure you download the correct image for your specific model of Pixel watch.
Enable Developer Options
Go to Settings > System > About and tap on the build number seven times. You should see a message that says "You are now a developer!"
Enable ADB Debugging
Next, you'll need to enable ADB debugging. To do this, go to Settings > System > Developer options and toggle on the "USB debugging" option. Connect Your Watch to Your Computer
Plug the connected adaptor into the USB port on your PC
On your computer, open a command prompt or terminal window and navigate to the folder where you downloaded the OTA image.
Reboot to recovery to sideload the OTA image
adb reboot recovery
adb sideload <path to the OTA image>
After the flashing process completes, tap 'reboot device now'
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