Which State Will Elect a Republican Congressman First

[H. Ross Peron]

Connecticut if forced to guess.

[TDAS04]

Connecticut is clearly the best guess.

[Mister Mets]

Connecticut is a good guess.

It's not quite as liberal as Massachusetts, and it has more members of congress (and opportunities in General Elections) than Vermont and Rhode Island.

[solarstorm]

Correct answer: Connecticut

The closest election (out of these four states) was in CT-05 (53% for Esty).

In Massachusetts, the GOP didn't even field a candidate in 6 (six!) out of 9 districts.
Even MA-06, which was supposed to be "competitive" was won by Moulton without any difficulty (in a midterm election with a Republican tsunami!!!).

[Rockefeller GOP]

CT could have a Republican in a good year in one of its more traditionally conservative districts in our current climate ... I couldn't see the other three electing a Republican until the climate is a bit different.  Vermont would be next, but we'd need to be in an era where the GOP is less dominated by social conservatives (maybe a decade or two?).

[Thunderbird is the word]

Connecticut in either Fairfield County (narrowly) or Litchfield County more likely.

[IceSpear]

CT-04/CT-05 could be competitive when Himes/Esty retire. Mass is fools gold. Every single time there's a "competitive seat", the Dems win anyway. Even the scandal plagued Tierney survived when he was left for dead by everyone in 2012.

[Mr. Illini]

CT could have a Republican in a good year in one of its more traditionally conservative districts in our current climate ... I couldn't see the other three electing a Republican until the climate is a bit different.  Vermont would be next, but we'd need to be in an era where the GOP is less dominated by social conservatives (maybe a decade or two?).

Surely one of the central or northeastern Massachusetts districts would go Republican before Vermont, in my mind.

[Sumner 1868]

Vermont was the first in 1854, so they already won.

[President Punxsutawney Phil]

Connecticut is very likely certain for first, because they less than a decade ago actually had a majority Republican house delegation.
Northeastern Massachusetts after that, then Vermont or Rhode Island (I'm not sure who'd be last).

[The Other Castro]

CT 5th is the correct answer

[President Punxsutawney Phil]

Well in 2005-6, CT had Rob Simmons (CT-2), Chris Shays (CT-4), and Nancy Johnson (CT-5).  Shays was the only one to survive the 2006 midterms, but then fell thanks to the Obama tsunami.  So CT-4 was the last to elect a Republican.
CT-4 has a PVI of D+5, and CT-5 has a PVI of D+3.  So your guess should be on spot.

[Attorney General, LGC Speaker, and Former PPT Dwarven Dragon]

Connecticut. Then probably Massachusetts (the 9th district, probably). Then Vermont.