http://www.limlawmaplefarm.com/

I'm from VT and this is where I get mine, now that our old family connections (and their connections) are all retired and no longer sugaring.

I've bought half gallons or even gallons at MOM before, but I don't know if they have them all the time, and the last gallon I bought there was only available in Grade B. Which many people like, but you specified medium amber, which is Grade A.

Trader Joe's! It's a darker maple syrup, and comes in what looks like a wine bottle.

LLBean has great real syrup with free shipping!

No, I wish I knew where to buy it locally. I just like that you can get large quantities, rather than the pints or small sizes around here. TJ's sells decent syrup, but again it's in pint or maybe quart size at best.
You could look up Southern Most Maple and they may ship to you. They are from Highland and are one of the biggest producers out that way.

As in, drive to Highland County? I have been there before and it's lovely, but I'm looking for a closer source. Do you know anywhere local that sells Highland County syrup?

Highland County. The sell it by the half gallon, and smaller. Don't think they have gallons anymore.

Last fall I bought some amazing maple syrup at a bazaar on the recommendation of a friend, and I'm kicking myself for not buying more. Any idea where to buy really good maple syrup? This one was a medium amber and was so, so tasty.