By all means see Williamsburg. That is, really, the home to so much of our early history. William and Mary College (the oldest college in the country, designed by ChristopherWren, where many of our founders and their families attended).
See some of the plantations and homes of our presidents. Shirley Plantation, about 400 years old; Mount Airy; Warsaw; Tappahannock; Marlbourne; Ampthill; Berkeley; Westover; Evelynton; the home and plantation of the 10th president, John Tyler (Sherwood Forest).
There are many places where battles were fought between American Indians (natives) and the new European Americans; Civil War battles. This is probably the most historic area in the country. You will see the historical St. James River.
The first Thanksgiving in America was held at Berkeley plantation. When we were there, you could only see the downstairs portion as there were residents upstairs. When we visited Sherwood Forest once, they were preparing for public TV shoot and only part of the house was available but it was worth the visit as we got to see all downstairs and hear the history of the home. This was the biggest presidential family at the time (of course the Kennedys are bigger but that is not immediate family as the President Tyler had two wives and was very prolific with each).
At Williamsburg, you can see many, many historical sites including the Governor's House, the Wythe house, the Wren building.
Others of interest are the first White House of the Confederacy in Richmond (I think the settled WHoC was in Montgomery, Al); St John Episcopal Church in Richmond, where Patrick Henry delivered that famous speech on "Give me liberty or give me death."
I loved that I could be in Williamsburg and feel the presence of Thomas Jefferson, George Washington and step back in a time when our country was beginning and yet it was in more turmoil than it is now and to see that it all turned out.
Oh, you could spend months there and never see it all.
The Steeplechase is October 25, if per chance you are interested or plan to attend.
ABOUT YOUR ORIGINAL QUESTION: I have found that slacks, a blouse and a sweater will do well throughout the day, starting with the sweater in the morning and putting it over your shoulders before noon until dark; if you are sightseeing, which you most likely weill wish to do, wear jeans, a long sleeve shirt over a short sleeve shell or top for early morning and evening but you may want to remove the long sleeve shirt and tie it around your waist during peak temperatures from around 10 a.m. to 4 p.m.
Of course, I recall one year that it snowed (unseasonably). Cool mornings, warm days (especially if you are walking and sightseeing) are usually the way it works. I believe October is the normally the dry (Indian summer) kind of weather.
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