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I am right next door in Springfield, and know the issues well: If you upgrade to a Winegard HD-7696P and a rotator like the Channel Master 9521a, you'll have no problems with either the Springfield stations or the Hartford-New Haven stations. An HD-7696P will allow you to see WTNH from New Haven, an ABC station. Be wary of using a preamplifier, however, as WSHM, the low-power CBS affiliate in Springfield is building a new digital transmitter on Minnechaug Mountain just 2-3 miles from your house: using a preamp could cause overloading of the preamp or your TV tuners.
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