Outdoor Berkshires/Hudson Valley/Catskills wedding -- which summer month is best?

Honestly, it will be hit or miss. There have been times we have had very cool mild summers and also disgusting hot summers. If you are in the Catskills, it might be a little cooler because of the elevation. 4 pm or even a little later will be better temp wise, cause around 2-5ish is going to be your warmest part of the day.

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I see you edited your original post. June would not be too chilly. June is actually pretty nice overall. Especially early June. You're probably looking at temps in the mid-70's.. occasionally in the low 80's. Of course a few freakish days here or there though, can't guarantee anything with weather :-/ lol

It's kind of hard to generalize about the weather; a year ago Halloween up was up to my knees in snow right outside of Woodstock....it's kind of impossible. Best advice? Shoot for late June but always, always have a plan B. (And a Plan B might be not only for rain, but for cold/wind/very, very hot....anything that makes it hard for guests to enjoy how beautiful this area is.)

I agree... Late June/early July is probably your best bet out here.

I love the catskills! I think May or June would be your best bet for a outdoor wedding in NY it won't be too hot then. Aug/July will be super hot to be outdoors all day. IMO

We are doing october bc of this .... I hate the heat and my FH has terrible allergies in the spring and I didn't want him to be miserable at his own wedding. I would have preferred sept but I had 2 friends getting married in that month (though one has since switched but our date is already locked in now)