These maps can certainly make you cross eyed trying to understand how to proceed!
Your best bet is the Hartford signals near magnetic 30. You have a reasonable chance of receiving all the major stations from that market down to WEDH PBS.
The antenna I'd go with would be an Antenna's Direct DB8e. This antenna is designed for UHF (channels 14 and up). You'll notice you have ABC affiliate broadcasting on real channel 10. You are close enough and it is strong enough, there is a pretty good chance you'll receive it with the UHF design. UHF antennas have been known to receive VHF signals if they are strong and close.
I'd get the DB8e on your roof with the best line of sight possible to magnetic 30 (NE).
... and if the CH-10 reception is not satifactory, an Antennacraft Y5713 or Antennas Direct CS5 could be added after the fact.
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If the well is dry and you don't see rain on the horizon, you'll need to dig the hole deeper. (If the antenna can't get the job done, an amp won't fix it.)
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Thanks for the help! I will need to put a plan together and hopefully have this installed in the near future. I have a hip roof, so I think a ridge mount will be the best solution.