70. Ulster County, N.Y.
Largest city: Kingston
Merely mentioning “Woodstock” can ignite arguments 40 years after the 1969 concert. Of course, the concert wasn’t actually held in Woodstock, but the original intention to hold the event here wasn’t a coincidence: Woodstock has long been an artist colony attentive to alternative lifestyles. Ulster County is located at the base of the Catskills, once part of the Borscht Belt of Jewish summer resorts. It gave Obama 60 percent of the vote.
69. Albemarle County, Va.
Largest city: Charlottesville
Charlottesville is an independent city, but the county seat of surrounding Albemarle County is Charlottesville. Just as well, sicne the two entities are basically one and the same. Thomas Jefferson, a native of the county, set up his last great project in Charlottesville — the University of Virginia. The university dominates the economy and culture of the county. The county correspondingly leans Democratic, and Charlottesville is more liberal than the county itself.
68. Kauai County, Hawaii
Largest community: Kapa’a
Kauai is the farthest west of the main Hawaiian islands. The main settlement here is Kapa’a, where most of the retail and tourism is located. This is the first of three Hawaii county units on the list, all of which are similar politically and demographically. It was Democratic even before Hawaiian-born Barack Obama ran in 2008, giving John Kerry 60 percent of the vote during a strong showing for incumbent George W. Bush.
67. Hawaii County, Hawaii
Largest city: Hilo
The entire chain of Pacific islands known as Hawaii is so designated due to the largest, most eastern island in the area being named Hawaii. It is now commonly referred to as the Big Island to avoid confusion with the rest. The second city of Hawaii is Hilo, the largest city on this island (though it is not formally incorporated). The island tends to have more of an anti-development ethos as compared to the rest of the islands.
66. Maui County, Hawaii
Largest community: Kahului
Maui County is comprised of a few islands in the middle part of the Hawaiian Islands. The economy of the islands was once mostly based on sugar cane production. Now, the economy is almost entirely based on tourism. It also includes the island of Molokai, most famous for the leper colony Father Damien de Veuster attended to. The islands making up the county gave native son Obama 76 percent of the vote.
65. Albany County, N.Y.
Largest city: Albany
America’s most dysfunctional state government (at least east of California) meets in Albany, a mid-sized city in the upper Hudson River Valley. Its status as the state capital means that the presence of permanent state bureaucrats tilts the county to the left. It anchors a metro area (encompassing Schenectady and Troy) that is larger than many realize.
64. Cumberland County, Maine
Largest city: Portland
Portland is the largest city in Maine, and is one of the most prosperous communities in the state. The city where the prohibition movement began (Portland mayor Neil Dow passed the first prohibition bill in 1851) is now home to a great many microbreweries. Maine was a longstanding Republican state that has become Democratic as the Republicans have come to be defined as a Middle American party. Mainers rejected legalizing same-sex marriage last fall.
63. Cheshire County, N.H.
Largest city: Keene
Western New Hampshire takes its cues from neighboring Vermont instead of its conservative heritage. The largest town here is Keene, which is a college town with more than one-fourth of its population students. This creates a typical university-left setting, and the county unit gave Obama 63 percent. This comes in a sort of county that never voted for Democrats until the 1990s.
62. Yolo County, Calif
Largest city: Davis
Cal Davis is the largest campus in the University of California system, making it bigger than the better-known UCLA and Cal Berkeley. Davis is a liberal mecca of the sort that passes resolutions declaring the city a “nuclear free zone.” This is part of the Sacramento suburbs, and it is actually more Democratic than Sacramento County. This is interior California’s most liberal county.
61. Middlesex County, Conn.
Largest city: Middletown
Middlesex County is generally non-descript, with no real tourist attractions though Wesleyan University is located in Middletown. Katherine Hepburn and her family made their estate in Old Saybrook. The county is generally in the middle of Connecticut’s party spectrum. On the plus side, there’s no barriers to getting hitched with your partner.
Check back tomorrow for the 41st-60th most liberal-friendly counties in America.