Originalism and Brown:
Perhaps the most powerful objection to adopting an original meaning approach to constitutional interpretation is that such an approach would be inconsistent with the result in Brown v. Board of Education. For most, regardless of ideology, any theory of interpretation that does not get Brown correct, is unacceptable, almost by definition. The perception that Brown is inconsistent with originalism is nurtured by Brown itself, in which Chief Justice Warren stated that the evidence of whether originalism supported the outcome was inconclusive. This came after the Court held the case over for further briefing on the historical question.

Some originalists deal with the problem of Brown by invoking precedent. Other originalists who, like me, are generally skeptical of precedent (see my essay on originalism and precedent here), cannot go that route (though our approach to originalism would not have any awkwardness rejecting the precedent of Plessy).

Most scholars today know of Michael McConnell's work on school desegregation and originalism, though it seems not to have made much of a dent in the criticism. A concise summary of the originalist response to this repeated charge (including that by Judge McConnell) is presented by Edward Whelan in Brown and Originalism: There's more than one way to get it right. Here is how it starts:
The Left's "killer" argument against an originalist reading of the Constitution is that adherence to the original meaning of the Fourteenth Amendment purportedly would not have yielded the just result — the end to the evil of segregated public schools — mandated by the Supreme Court's landmark 1954 ruling in Brown v. Board of Education. Margaret Talbot's interesting but flawed profile of Justice Scalia and originalism in a recent issue of the New Yorker (which I wrote about here) is typical: The only "way to get to Brown," she asserts, is "to embrace the 'living Constitution.'"
In my experience, scholars who are not originalists typically do not do originalist analysis very well. In part, this may be because they are attempting by their historical analysis to discredit originalism or at least neutralize an originalist outcome with which they disagree. Perhaps the biggest problem is that, not being originalists, they are not altogether careful about what an originalist argument entails—especially as original intent originalism has been largely abandoned in favor of original meaning originalism. (This may partially account for the Court in Brown finding the historical evidence inconclusive.) Whelan ends his essay on a similar note:
The legitimacy of originalism as the only proper method (or class of methods) of constitutional interpretation inheres in the very nature of the Constitution as law and does not depend on the results that originalism yields. Originalists will have disputes among themselves. But those who seek to discredit originalism by hiding behind Brown . . . should hardly be presumed sound arbiters of how originalism should apply.
This essay makes a good introduction for law students about to take constitutional law, but students should definitely read Michael McConnell's articles as well:
Originalism and the Desegregation Decisions, 81 Virginia Law Review 947 (1995) and
The Originalist Justification for Brown: A Reply to Professor Klarman, 81 Virginia Law Review 1937 (1995).
[Both are on Westlaw and Lexis, of course, but if someone sends me on-line links to these article, I will add them to this post later.]

Update:Those with a heinonline subscription can click here for the McConnell article.