I didn't have time to watch any episodes today, so I don't have any new reviews to post this evening. So, instead...
...*drum roll even though you have already read the subject line*....
-Days spent on each case include the day after they solve them, if it is shown in the episode.
-Day counts assume one driving day in cases when the boys hear about the case and must travel to the location, unless otherwise stated.
-Day counts count partial days as full days (meaning if an episode starts late at night, that night counts as a day)
Either July 19th or August 5th, 2006 - John Winchester Dies. In My Time of Dying takes place over 4 days, assuming that Sam has a day of rest in a hospital bed, before we see him check up on Dean and John, in Missouri (from Devil's Road Map on S2 DVD). The second to last day of the episode is August 4th, 2006. We see this by looking at Dean's heart monitor when they restabalize him. There is a conflict in the monitors on this show, as John's monitor says that it is July 19th 2006, when they declare him to be dead (at 10:41am); however, if you listen to the DVD commentary, you find out that this episode was filmed the week of July 19th - which means that John's monitor reflects the day of filming, rather than Dean's monitor that reflects an unrelated day. (As episodes are usually put together during an 8 day period, it's unlikely that they were still filming this episode on August 4th).
Early or Mid August (after, but close to, the 12th), 2006 - the boys have been at Bobby's for a week, when Sam finds an old message on John's phone, which in turn leads them to the Harvelle's Roadhouse. They spend 4 days (including the day Sam finds the message) working at jobs at a carnival in Medford Wisconsin, where Everybody Loves a Clown except for Sam.
Unknown - Sam and Dean spend 3 days exploring a possible hunt in Red Lodge, Montana, where they meet Gordon, a hunter with a particular Bloodlust for vampires. (The Impala is fully repaired, so we can assume that this episode takes place a considerable amount of time after the previous one, however, given that the next episode takes place at the very end of August, we'll have to assume that Dean got the impala all fixed up in only two weeks - apparently the car has the same magic healing powers as the boys do - and that the next episode follows closely on the heels of this one.)
~August 29th - The Winchesters head to Illinois (oddly, according to The Devil's Road Map on the S2 DVD, Mary Winchester's grave is in Illinois and not in Lawrence, Kansas), where they spend 4 days teaching us that Children Shouldn't Play With Dead Things. (Angela Mason dies on August 22nd - date on her cellphone; the boys arrive in town a week later - Sam says she "died last week", and four days after her funeral - Dean says "she was buried four days ago".) (Special note: The temporary gravestone marker also has dates on it, however they are out of sink with both the date on Angela's cellphone when she dies, and also with what year it is, so they are disregarded for the purposes of this timeline).
Sept, 2006 - A vision leads Sam and Dean to travel to Guthrie, Oklahoma (and two stops at The Roadhouse). They spend 3 days (2 days and 1 night) in this episode, and only one day and a morning in Guthrie. In Guthrie, they meet Andy, who has abilities like Sam. (Sam says his abilities started "about a year ago," which can be interpreted as meaning a little under a year.) (Simon Said).
Sept, before the 28th, 2006 - Following immediately after the previous episode, Jo sends Sam and Dean on a hunt to Philadelphia for 8 or 9 days. (The invitation one of the victims gets in the mail is for a party on Thursday Sept. 28th, this happens on the fourth day of the episode.) (Note: 2 days have been added to the count, as it's nearly a 24 hour drive between Nebraska, the presumed location of the Roadhouse, and Philadelphia) (No Exit)
Unknown - October most likely - Sam and Dean spend four days in Baltimore, Maryland, where they become The Usual Suspects in a series of murders. One day to hear about the job and go to Baltimore, 24 hours in police custody, one day is experienced through flashbacks, and then one day is presumably spent getting the Impala back once they escape.
November 2006 - Sam and Dean track some bizarre deaths in Greenwood, Mississippi, for about 5 days, and encounter a Crossroads Demon. (Crossroad Blues)
Late November 2006 - Sam has a vision that leads him and Dean to River Grove, Oregan, for 3 days (one driving day) where they find the word Croatoan craved into a tree and discover that the town is infected with a demonic virus. (See Hunted notes for details on date)
Late November/Early December 2006 - Immediately following the events of Croatoan, Sam strikes out on his own, stops at the Roadhouse, and then heads to Lafayette, Indiana, only to end up Hunted by Gordon. The episode spans at least 6 days, 4 of which we see, at least 2 of which are spent driving. (The dead guy's prescription bottles read 23/10/06 and are nearly full. It is said that he was killed "about a month ago" and Eva says her abilities started "about a year ago".)
January 2007 - Sam and Dean stay at an Inn in Cornwall, Connecticut, that is filled with interesting Playthings. The episode takes place over 4 days (1 added for travel from Peoria, IL to location). (Sam says that they've been looking for Eva for a month, which means that a month has passed since the previous episode and this one).
Unknown - The boys run into trouble with the law again, when they are trapped in a hostage situation with a Shapeshifter in Milwaukee, Wisconsin. The episode takes place over exactly 3 days, because the boys are already in Milwaukee at the beginning of the episode. (Nightshifter)
Unknown (mid-January*) - The boys investigate Houses of the Holy in Providence, Rhode Island, where they debate the existence of angels. The episode takes place over exactly 2 days, as the boys are already mid-investigation when it begins. (*Fr. Gregory's tombstone says 2007, and the other priest says that he died 2 months ago...but we know that Roadkill takes place on February 22nd, yet the two episodes between this one and Roadkill consume nearly a month's worth of days, which would mean that this episode would have to take place before January 22nd in order for the numbers to work out. So, either this takes place in mid-January and the tombstone is wrong, or events in the series are shown out of order and Houses of the Holy takes place AFTER Roadkill, I suppose the choice is yours, but personally I prefer to keep things in episodic order - so I believe this episode takes place mid-January and the tombstone date should be ignored.)
Unknown - Poor Sam was Born Under a Bad Sign and goes missing for "over a week" (departing from West Texas) and eventually leads Dean on a 3 day chase (assuming it takes within one day for Dean to reach Sam when he calls at the beginning of the episode) that goes through Duluth, Minnisota, and ends in South Dakota. (This means that by the end of the episode, at least 17 days have passed, since the last episode left the boys in Rhode Island, yet Sam disappeared from West Texas...that's AT LEAST 4 days of travel, I think, if not more.)
Unknown - The boys tell Bobby some Tall Tales when they encounter a Trickster in Springfield, Ohio. Bobby helps them for either 1 or 2 days, and there are 4 days worth of flashbacks (excluding the flashbacks that happen on the day Bobby arrives), which brings us to a total of 5 or 6 days. We know it's only been a short time since the boys left Bobby's, since he says "it's nice to see you again so soon."
February 22nd, 2007 - Sam and Dean spend a night with Molly in Nevada (or Western California - according to The Devil's Road Map on the S2 DVD) trying to find the grave of a farmer who ended up as Roadkill. The events of the episode take place over only one night, but through flashbacks we can guess that the boys probably spent at least 3 days researching the case beforehand.
Unknown - Dean's happy to discover a werewolf in San Francisco, California, until it spends 4 days ripping Sam's Heart out metaphorically.
Unknown - Still in California, the boys head down to LA to check out a haunted movie set for at least 5 days, possibly a full week. (Hollywood Babylon)
Unknown (End of March beginning of April possibly) - Sam and Dean are arrested in Arkansas, in order to check out a haunting at a local prison. The episode takes place over at least a week, and the boys are incarcerated at the prison for at least 4 days. (Due to the complexity of the set up, and the fact that the boys were called there on a favour, we can guess that there would have been a substantial number of days of research and planning before the beginning of the episode.) (Folsom Prison Blues).
Unknown - Dean learns What Is And What Should Never Be one night, when he encounters a Djinn in Joliet, Illinois. (Although Dean experiences several days inside his wish, in reality it's only a few hours.) The boys are still freaked out by cop cars, so we can guess that this may be their first stop since escaping prison in Arkansas.
Early May, 2007 - All Hell Breaks Loose (I&II) when Sam disappears from a roadside cafe and ends up in Cold Oak, South Dakota. Dean takes 24 hours to find him, but by then the damage is done. Part II picks up a estimated 2 days later and spans 2 days. In total, including the missing estimated two days, the two parts span 4 days (the first day of Part II being the same day as the second of the two missing days). (Another timeline has the date as May 2nd, but I do not know the reasoning behind the exact date, though the episodes do occur in early May - Sam tells Eva that she's been mising for 5 months - so it's possible, but a horrible Birthday for Sam IMO).
Just to reiterate:
Mainly, my goals for this timeline were:
1)Finding dates using only information provided by the episodes.
2)Keep track of how many days the boys spend in each episode.
As I worked on it, two lesser goals occurred as well:
1)Figure out where they are -mainly for the purposes of estimating driving time.
2)Try to work the episode title into a sentence - because it's fun!