I would choose Monterey for all of the stated reasons plus: I have been to upstate New York and the Monterey Peninsula, and I prefer Monterey.
How almost?
No Poco?
I could have gone either way, but after looking at the artist & set lists, I’d say Monterey. Unfortunately, I didn’t actually go to either, even though I was in the San Francisco Bay area at the time.
And my ancestors didn’t come over on the Mayflower, either. I guess you could say my family has a history of missing the boat.
gimme the “24 Hour Technicolour Dream” or “Christmas Night Of Earth” anyday!
No Y. Woodstock was the second gig for CS&N (“We’re scared shitless!”), not CSN&Y.
Y was there. He just wasn’t in the film.
Woodstock for me. My favorite band was there, though by all accounts, they kind of sucked.
I sit corrected. Never knew that.
Regarding Lou Rawls and Hugh Masekela, YMMV. Also, I think it would’ve been interesting to catch Otis Redding and Laura Nyro just to see if the reaction to her set was as negative as it allegedly was.
On a related note, one advantage Monterey had over Woodstock was the fact the former in terms of music was more eclectic and diverse. I don’t think it wouldn’t have hurt Woodstock if they had a bit more soul or jazz in their line-up. Unfortunately, Otis Redding wasn’t around by then but I could easily imagine, for example, acts like Aretha Franklin, the Staples, or even Miles Davis on the bill.
Monterey didn’t have Sha Na Na, so I guess Woodstock for me.
A lot of the preferences seem to be based on whether you look at the events as musical experiences vs historical experiences.
Having been at Woodstock, I certainly wouldn’t swap it for Monterey. Regardless of any considerations of musical quality or comfort, Woodstock was just much more historically and culturally significant. And while the rain and mud were uncomfortable enough at the time, they added to the lore.
And yeah, there is the “bragging rights” aspect. Almost everybody knows about Woodstock; many fewer are familiar with Monterey.
What, no Altamonte option? I wanna see the show where they actually hired the Hell’s Angels for security! (I guess it must be one of those “It was the '60s, you had to be there” things.)
Oh man oh man. . .I actually listen to music from Woodstock on a regular basis, but the event itself kind of played out like a happy disaster - all that traffic, mud, bad acid 
, lack of facilities, and IIRC, a shortage of food & water. OTOH, Monterey is freakin’ Monterey, which considering that places I have lived, would be a great place to visit even without the added benefit of great music.
The Butterfield Blues Band, The Who & Jimi Hendrix were at both, so that’s great. I guess if I had to choose by music, it would be Woodstock, but choosing by having to actually live through the experience, I guess I’d have to go with Monterey.
The performances at Monterey were far better.
Monterey was the festival that could have been better than it was… Paul had hoped that the Beatles would play their farewell concert there.