Dewey '44-Kerry counties

There were 173 counties in these states that voted for Dewey in 1944 and then voted for Kerry in 2004.

Alpine, CA
Imperial, CA
Lake, CA
Mono, CA
San Benito, CA
Santa Cruz, CA (122,084)
Sonoma, CA (220,690)

Adams, CO (136,672)
Boulder, CO (159,257)
Clear Creek, CO
Gilpin, CO
La Plata, CO
Pitkin, CO
Saguache, CO
San Juan, CO
Summit, CO

Fairfield, CT (400,967)
Middlesex, CT
Tolland, CT

Alexander, IL
Calhoun, IL
Champaign, IL
Fulton, IL
Henderson, IL
Jackson, IL
Knox, IL
Mercer, IL
Peoria, IL
Putnam, IL
Whiteside, IL

LaPorte, IN
Marion, IN (320,838)
Monroe, IN

Buchanan, IA
Chickasaw, IA
Clarke, IA
Clayton, IA
Clinton, IA
Des Moines, IA
Fayette, IA
Floyd, IA
Jackson, IA
Jefferson, IA
Jones, IA
Lee, IA
Linn, IA
Mitchell, IA
Muscatine, IA
Story, IA
Winneshiek, IA

Douglas, KS

Carter, KY
Magoffin, KY

Aroostook, ME
Cumberland, ME
Franklin, ME
Hancock, ME
Kennebec, ME
Knox, ME
Lincoln, ME
Oxford, ME
Penobscot, ME
Somerset, ME
Waldo, ME

Baltimore County, MD (353,479)
Charles, MD
Howard, MD (133,810)
Montgomery, MD (415,225)

Barnstable, MA (132,148)
Dukes, MA
Franklin, MA
Middlesex, MA (688,960)
Nantucket, MA
Norfolk, MA (331,137)
Plymouth, MA (233,297)

Arenac, MI
Ingham, MI (133,053)
Isabella, MI
Kalamazoo, MI (119,783)
Lake, MI
Oakland, MI (641,977)
Saginaw, MI (102,852)
Washtenaw, MI (173,264)

Blue Earth, MN
Fillmore, MN
Lac qui Parle, MN
Nicollet, MN
Rice, MN
Winona, MN

St Louis County, MO (542,983)
Ste Geneviève, MO

Big Horn, MT

Cheshire, NH
Grafton, NH
Merrimack, NH

Bergen, NJ (400,244)
Essex, NJ (289,348)
Union, NJ (203,387)

Guadalupe, NM
Mora, NM
Santa Fe, NM
Socorro, NM
Taos, NM

Broome, NY
Columbia, NY
Franklin, NY
Nassau, NY. (618,343)
Niagara, NY
Onondaga, NY (214,625)
Queens, NY (605,062)
Rensselaer, NY
Schenectady, NY
St Lawrence, NY
Suffolk, NY (638,712)
Tompkins, NY
Ulster, NY
Westchester, NY (395,770)

Sioux, ND

Ashtabula, OH
Athens, OH
Erie, OH
Franklin, OH (525,827)
Lucas, OH (220,430)
Monroe, OH

Benton, OR
Hood River, OR
Lane, OR (185,872)
Washington, OR (231,308)

Bucks, PA (319,816)
Delaware, PA (284,538)
Erie, PA (125,898)
Lehigh, PA (145,091)
Montgomery, PA (399,591)

Washington, RI (62,632)

Buffalo, SD
Clay, SD
Corson, SD
Day, SD
Dewey, SD
Shannon, SD
Todd, SD

Kenedy, TX

Addison, VT
Bennington, VT
Caledonia, VT
Lamoille, VT
Orange, VT
Orleans, VT
Rutland, VT
Washington, VT
Windham, VT
Windsor, VT

Arlington, VA (94,650)
Fairfax, VA (461,379)

San Juan, WA

Adams, WI
Buffalo, WI
Crawford, WI
Dunn, WI
Eau Claire, WI
Grant, WI
Green, WI
Iowa, WI
Jackson, WI
La Crosse, WI
Lafayette, WI
Pepin, WI
Pierce, WI
Rock, WI
Sauk, WI
Trempealeau, WI
Vernon, WI

Teton, WY

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Viewed from 2020, this is actually a somewhat eclectic group of counties. 58 (a little over a third) voted for Trump twice: Alexander, Calhoun, Fulton, Henderson, Knox, Mercer, Putnam, and Whiteside, IL; LaPorte, IN; all the Iowa counties save Linn and Story; Carter and Magoffin, KY; Aroostook, Franklin, Oxford, Penobscot, and Somerset, ME; Arenac, Isabella, and Lake, MI; Fillmore, Lac qui Parle, and Rice, MN; Ste Geneviève, MO; Franklin, Niagara, St Lawrence, and Suffolk, NY; Ashtabula, Erie, and Monroe, OH; Corson and Day, SD; and all the counties in Wisconsin save Eau Claire, Green, Iowa, La Crosse, Rock, and Sauk. Several others voted for Trump in 2016 but not in 2020 (most notably Saginaw, MI and Erie, PA); and of those that stuck with both Hillary Clinton and Joe Biden, several more trended Republican in both elections (such as Rock, WI, and Lake, CA).

On the other hand, many of the counties, especially the largest ones (the ones that cast over 100,000 votes in 2004 are in bold), are integral parts of the new Democratic coalition, and became more Democratic in the Trump years, such as Fairfax, VA (and Arlington, VA, which cast just under 100,000 votes in 2004); the two inner-most Main Line counties in Pennsylvania; Boulder, CO; Washington and Lane, OR; Sonoma and Santa Cruz, CA; Oakland, Ingham, and Washtenaw, MI; Franklin, OH; Baltimore, Howard, and Montgomery Counties, MD; Bergen, Essex, and Union, NJ; Fairfield, CT; Champaign, IL; Marion and Monroe, IN; Westchester and Nassau, NY; Douglas, KS; and St Louis County, MO. 

Of course, at 60 years, the span between 1944 and 2004 is the longest one we're using here between elections for 'darkest hour' comparisons. (In contrast, from 1924 to 1948 is 24 years; from 1932 to 1968, 36 years; from 1952/1956-2000, 44-48 years; from 1984 to 2012, 28 years; and from 1996 to 2016, a mere 20 years. Crisitunity considered using 1964 as the Republican reference year vis-à-vis 2008, a span of 44 years.) 

Partly, this is out of necessity. Like the Democrats since 1992, the Republican Party embarked from 1948 through 1988 on an extraordinary period in which, with one exception, they never lost a presidential election badly. The one exception--Goldwater in 1964--was not simply a bad defeat, but one in which Goldwater largely drew on atypical sources for what support he did get. A number of counties cast their first Republican vote in decades (in some cases, ever) for him, even as a number of usually loyally Republican counties turned against him. 

1992 and 1996 are too recent as reference points for 2004 to tell us that much (although there are Bush Sr '92-Kerry counties and Dole-Kerry counties). 

Even 1944 has some problems; 1940 and 1944 were both, like 1964 (if to a lesser degree), 'atypical' elections. In 1940 and 1944, isolationist sentiment shore then-typically Democratic states such as Colorado from the Democratic coalition (even whilst leaving in states that had voted to re-elect Hoover, such as New Hampshire, Connecticut, Pennsylvania, and Delaware). In 1948, with isolationism no longer a motivating factor for voting Republican, Colorado and Wyoming returned to the Democratic fold even as Dewey ran the first truly close election for the Republicans nationally since 1928 (and in doing so carried every state that had voted to re-elect Hoover). Truman, despite only narrowly winning nationally, did something Franklin Roosevelt had been unable to do in his two decisive wins in 1940 and 1944: '[sweep] the Mountain West'. At the time, the Mountain West was a base for the Democratic Party, at least when it was nationally competitive; Peter F. Galderisi and Michael S. Lyons wrote of the historical 'attachment of the Mountain West to the Democratic Party' as 'preced[ing] the New Deal realignment' and tracing back to 'the candidacy of William Jennings Bryan'. And Arthur Paulson notes that 'the west was essential to Democratic victories when they occurred' between 1896 and the Great Depression (and although it obviously wasn't essential to FDR's second two victories, Paulson also writes that there was a 'secular realignment of 1948 through 1960', before which elections correlated more closely with 1896 than with 1996, and after which the reverse was true).

There are a great many counties that voted in the pattern Roosevelt '32-Roosevelt '36-Willkie '40-Dewey '44-Truman '48, which one would not normally expect. Some of the counties on the above list that followed such a pattern were Saguache, CO, San Juan, CO, Chickasaw, IA, Des Moines, IA, Lee, IA, Winneshiek, IA, Lac qui Parle, Nicollet, and Winona, MN, Ste Genevieve, MO, Monroe, OH, Buffalo and Todd, SD, and Buffalo, Crawford, Dunn, Iowa, La Crosse, Lafayette, Pepin, Pierce, Trempealeau, and Vernon, WI. Several further counties defected from the Democrats only in 1944, still nevertheless going against a considerable national trend to switch back to Truman in 1948: Clear Creek, Pitkin, and Summit, CO, Alexander, IL, Taos, NM, Lucas, OH, Day, SD, and Adams, Eau Claire, and Jackson, WI. With a few exceptions (such as Todd, SD, Monroe, OH, and Ste Geneviève, MO), however, most of these counties either had a typically Republican character before 1932, or went on to have a typically Republican character for a period after 1948 (or, in some cases, both). (To date, Ste Geneviève County has voted for only four losing Republicans: Willkie in 1940, Dewey in 1944, Romney in 2012, and Trump in 2020. Monroe County, Ohio has voted for only five: Willkie in 1940, Dewey in 1944, Nixon in 1960, Romney in 2012, and Trump in 2020; and has even given Democrats their biggest raw-vote margin in Ohio in 1860, 1864, and 1924.)

In fact, the Dewey '44-Kerry counties illustrate two trends that occurred in the decades following the FDR administration. One is the trend of suburban areas shifting to the Democrats, a trend that has continued and intensified. But the other is the trend of rural and working-class areas that stayed Republican during the New Deal, perhaps because of a 'Yankee' background (or a unionist background in states such as Kentucky), transitioning to the Democrats between the 1940s and the 1980s before returning to the GOP in the 2010s. In many of the cases where Truman won a county that FDR had carried in the '30s but lost in the '40s (especially in the Upper Midwest), he was the first losing or narrowly-winning Democrat to carry it. Many of these counties went back to being Republican after 1948, but eventually became more reliably Democratic at some point during the Cold War period. They formed a remnant of Democratic strength in rural America that subsisted through the 2012 election, one that was increasingly recognised as such in the 20th century. In 2004, for example, Bob Woodward remarked that 'the new centre of the Democratic Party might be the Midwest'. In 2016, after the defection of Wisconsin and Pennsylvania (and likely of Michigan) from the Blue Walll had become apparent, Ron Brownstein, the originator of the Blue Wall, allowed that 

Their [Democrats'] success in presidential races since 1992 has depended in part on an act of political levitation: they have run slightly better among working-class whites in the Midwest than they have anywhere else in the country.

And on election night 2016, both Bill Hemmer and Steve Kornacki drew attention to the difference in sheer acreage in Wisconsin and Michigan that was blue that night vs. in 2012. While Obama didn't win a majority of either state's counties in 2012, he did in 2008--and Minnesota, Wisconsin, Michigan, and Iowa were the only states between the Appalachians and the Rockies in which Obama won a majority of the counties in 2008. (In contrast, Bill Clinton had won a majority of the counties in Tennessee, Arkansas, Louisiana, South Carolina, Missouri, and West Virginia in 1996, and Carter had won a majority of the counties in every Southern state save Maryland--but not in Michigan or Iowa--in 1976.)

Of one of the Dewey '44-Kerry counties that has gone on to vote for Trump twice--Isabella, MI--Michael Tracey pointed out that it had given Bernie Sanders his highest vote share in his upset win in the 2016 Michigan primary. He pointed to Sanders' loss of the county in 2020 as evidence of the cratering of Sanders' rural support in 2020 relative to 2016 due to his acceptance of the imperatives of 'professional leftists'.