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Holiday weekends work very well. But it depends on the holiday. I think Memorial Day and Labor Day weekends are great wedding weekends. If you ask any wedding industry person, we all are always booked on those weekends pretty quickly. Now that being said, many vendors will charge a little more because it's a holiday - especially if you live in a touristy area. It takes more time out of their day and often they have to pay their staff more for holiday rates.
It always surprises me how many couples get married over the Thanksgiving holiday.
the decision is ultimately yours to make. but here are my thoughts. i attended memorial day weddings in the past 2 years. as much as i love seeing my friends getting married, part of me still recend it being a holiday weekend. memorial day is the first holiday weekend since president's day in FEB!!! alot of people make plans to travel, which from what I heard from the 2 brides that they did see a higher number of declines due to guests traveling instead of attending the wedding.
i also had the choice of holding my wedding this memorial holiday and i chose a later date from my own experience.
I think holiday weekends are great if most of your guests are traveling, but if a lot of them are local, you run the risk of them being bitter that you're "wasting" a potential getaway weekend. A lot of people plan to go out of town during holiday weekends, often with family, so they might be missing out on something else if that's when your wedding is. BUT if your wedding IS a fun vacation away, then I think it's so much more convenient that people won't have to take a day off of work to get there. So I say do whichever one you prefer for yourself, because you can't please everyone. :-)
We are getting married memorial day weekend this year, chosen for many reasons, including the fact that the number 24 is both of our lucky number! So when this date came up, we both fell in love. I thought having it on a holiday weekend would be great.
Since then I have heard some complaints. I suppose some people would rather spend their holiday on holiday instead of at my wedding. Now my nephew is getting married on July 4th, and it sucks. We always have a big party on July 4th, now we have to spend the whole weekend doing his wedding stuff (my daugther is one of 3 flower girls). I don't know why we didn't pick July 4th, I think it was that I didn't want to honeymoon on one of the bussiest vacation weeks of the year. But I kind of regret it.
To make our May 24th date worse, it falls right at the end of school years while finals are going on, so some people that would really love to come, can't make it because of finals. And then we find out his 17 year old daughter, who is one of our bridesmaids, will be missing the counties track meet (and she is in first place this year) as well as her junior prom. Makes me feel like a lot of people resent coming to my wedding. But it is too late to change it.
But I still love the date! Just wish others did too.
Good points candi and bluebell. Memorial Day is a better holiday than Thanksgiving or Christmas, as there are fewer family commitments you are potentially interfering with. However it is right before graduation, right in the middle of finals for a lot of people, so students, teachers, and parents of high school/college seniors are going to be super busy already. It is true that having the extra day off might make travel easier. The holiday also makes plane tickets more expensive, hotels more expensive, and travel much more difficult in general. And I agree that people who have a traditional Memorial Day activity - we generally go camping although not this year as we will be too busy getting ready for our own wedding - are going to have to forego their normal plans in order to attend. Because of those things, some people who would normally have trouble attending from OOT may be more able to come, and some people may choose to opt out because they have other things going on. You just have to realize that and understand that you may have some guests who choose not to attend for all the various reasons already discussed.
Holiday weekends are tricky. On the one hand, with the Monday holiday, people may not need to take time off work and can spend more time at the wedding location if they are out of towners. However, that involves traveling on a holiday weekend, which can be both more expensive and more time consuming than travel at other times.
Like Candi1024 above, some people have yearly traditions around certain holidays that can be disrupted by weddings. While your wedding will happen once, weddings tend to come in packs, so multiple holiday weekend weddings can be a pain and cut into those weekend getaways.
That said, you should pick a date and a location that *you* are in love with. Let others decide if they want to make the trip or not, but please don't guilt them if they opt not to do so.
I agree that you can't plan your wedding around everyone else's schedule. If your guests truly want to be there they will make it regardless of what day it is. Ultimately, it's your decision.
As a side note though...Smithtown and Wading River are pretty far into Long Island. If most of your guests are from out of town and you anticipate them to stay for a few days, you may want to consider what exactly they are going to do in Long Island. Unless of course you plan for them to head into the city...anyways just a thought...
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Thanks for all the comments, everyone! As far as I know, my fiance and I are the only ones out of our family and close friends who go away every year for Memorial Day weekend, so I hope (and don't think) I will be infringing on anyone else's vacation plans! I know for my close family though, even if they had to miss a 3-day weekend they would be delighted to be at our wedding. Since my family will be driving from Maine, Virginia and Upstate NY, that's an extra day of work they don't have to take off. And I definitely wouldn't hold it against any of our friends for not being able to make it because of other plans. I plan to send Save-the-Dates out a year in advance to avoid any last-minute travel/logistical/price hiking issues. A few of my friends are teachers, so they will have the 3-day weekend but don't think it will interfere with any exam schedules for them. One of my cousins/groomsmen is in college so he'll be done with school by then and then my two younger cousins will be juniors in high school so I know it might be tough for them but no tougher than a different 2-day weekend in May. We definitely don't want to go into June or July (we originally started out looking at March and April!), so I think some school problems will be unavoidable regardless.
MissBlueBear, you make a great point about location and what people will do all the way out East in LI. One of the reasons we liked MDW instead of a regular weekend for East Wind is that there are vineyards, outlets, beaches and golf near Wading River, so it could be kind of like a mini destination wedding weekend. I am Polish, so we always have a BBQ/picnic-type thing the day after the wedding (called "poprawiny"); so a pro for having the 3-day weekend is that everyone would be able to stay for that and not have to worry about driving back home on Sunday. Hmmm... good points either way but I think I'm feeling a little more confident now. Thanks so much for all the great feedback -- you are all awesome!! 
I'm having my wedding on Labor day weekend and so far the feedback has been good. People like the fact that they have an extra day of travel. The only advice I'd give is to let people know as far in advance as possible to prevent people from making plans (even if not a vacation per se).
We're having a Memorial Day weekend wedding this year (Sunday the 25th) and we've had mostly a good response. There are several families who won't be able to make it because they have graduations/conferences/vacations that had been scheduled, but most of our family and close friends are going to make it. Our vacation is a destination for 90% of our guests and since it's not your typical destination wedding (mountains not the beach) we've put together a full weekend of activities to make it worth their while - hiking, touring the Biltmore, a barbecue, and brunch. We did send out save the dates about 8 months in advance which I think is very important for anyone doing a destination wedding especially on a holiday weekend. Since we booked the hotel so far in advance we were able to get a discount on the normal rate for our guests but the airlines have been more expensive - whether it's the cost of gas or because it's a holiday weekend I don't know. All in all, if most of your major players don't make big plans for the holiday and you give them enough notice I think you'll have a nice response and if you're wedding isn't enough of an event for them to change their plans then you have to be OK with that. At this point, I'm just glad for any no's since more people are coming than we thought and now everyone who says no is money saved.
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It sounds like it will make sense for your guests and for you--go for it!
I don't think it would have worked for us for a number of reasons--lots of people would have plans, not everyone has the same holidays (Cdns/Americans/Quebec/English Canada/overseas), etc. But, I have gone to a couple holiday weddings where the fact it was a holiday weekend didn't make any difference to me (American T'giving and I live in Canada, Victoria Day when I wasn't working a normal job); for other people, they meant that they couldn't come, for others, it meant that they could. In both cases, I think it made a lot of sense for the B&G.
I think it's an awesome weekend! Our wedding is on May 30, 2009 and I feel like this:
I'm going to invite all the people I would like to share the day with.
IF the people I invited, really want to share the day and help us celebrate a milestone in both our lives: THEY WILL COME.
And if they don't... then perhaps it's time to re-evaluate the friendship with said people.
Save the Dates and invitations are going out w/ plenty of anticipation, so that people may make arrangements to be there. Of course, last minute emergencies cannot be avoided - and one must be understanding of said emergencies. However, I don't feel that a planned family vacation or weekend getaway is an emergency. The invitations were sent - and they still chose to take their vacation.
That's my 2 cents.
I'd also like to add to this post. =) I considered a Labor Day weekend wedding for this year: August 30th. When I was considering dates and places, my brother specifically told me, "don't do that to people!" I was pretty pissed off, since 90% of my guest list is coming in from out of town and I figured it would help people out by having the extra day. And besides, he never goes away! Haha. The place we ultimately decided on didn't have that day available anyway, and we went with September 27th. So bottom line, you pick the place that you want with the date that works for YOU and the important people, parents, etc. I agree with MsVanessa, if people really care and want to be there, they will be. Otherwise, it's a good way to cut down the final bill. =D Haha, I know that's awful, but that was something I was thinking about since ours is getting out of hand! But good luck, and save the dates are wonderful, no matter when the wedding is!
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Ooh!! And one more thing: we went to a Memorial Day weekend wedding last year, 5/26/07 and loved it! We don't normally go away for it, but it was great to come home on Sunday and still have another day to relax before going back to work. You know when you go away on the weekend and feel like you lost your weekend? The whole thing flies by. So that made it a bit nicer. Ok, I'm done. =) Good luck!
Im yes and no on this one! We have attended 2 weddings the last 3 memorial day weekends. I missed my "holiday", but didn't have to take time off work or whatever to travel. But I have to disagree with MsVanessa, if you choose a popular travel time for your date, you gotta be prepared some people wont come. I know it is hard to take the declines without becoming defensive, but its going happen and you gotta be prepared! Not every "no" is a personal attack, sometimes it is just a no! :)
Just wanted to see if anyone had any thoughts on this thread from last year!!
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Hi! My FI and I have to make our final RH decision by Wednesday morning and it is a doosie. We've been trying to decide between Watermill in Smithtown, LI and the Estate at East Wind in Wading River, LI... and it is SUCH a tough choice!!! We even went back to see both of them again yesterday, which unfortunately didn't make the decision any easier! I've heard great things about both, and each one has its pros and cons. I think the decision right now will come down to date options. EW has Saturday 5/23/09 available which is the Saturday of Memorial Day Weekend, and Watermill has Saturday 5/30/09 (the weekend after MDW) available. We both have a ton of guests coming from out of town, so...
How do guests feel about holiday weekend weddings? Is it a Good idea? Bad idea? I need help!!