What Happens if It Rains on Your Wedding Day? A Destination Wedding Expert Explains | WDP Ep 86

🎧 Listen to learn:

• What to do if rain is in the forecast on your wedding day
• Why destination weddings require experienced local vendors
• How to create an unforgettable wedding weekend experience
• Why every outdoor wedding needs a weather backup plan
• How family history shaped one of Oregon's most unique wedding venues
• What couples should look for when choosing a destination wedding venue

What happens if it rains on your wedding day? In this episode of Wedding Day Podcast, host Sonja Babich, CEO of Iron Diamond Media, sits down with Kathleen Crook-O'Donnell, president and owner of Crook Point, to discuss destination wedding planning, navigating unpredictable weather and creating unforgettable celebrations along Oregon's breathtaking coastline.

As the steward of her family's seventh-generation property, Kathleen shares how Crook Point evolved from a cherished family retreat into one of Oregon's premier destination wedding venues. She reflects on unexpectedly entering the wedding industry, building upon decades of family hospitality and creating a place where couples can celebrate with stunning ocean views, private lodging and immersive weekend experiences.

The conversation also explores the realities of planning an outdoor wedding, from preparing for changing coastal weather and building reliable contingency plans to assembling an experienced vendor team that can confidently navigate the unexpected. Kathleen explains why destination weddings are about so much more than a beautiful backdrop—they're about creating meaningful guest experiences, thoughtful logistics and lasting memories that extend far beyond the wedding day.

Transcript

SPEAKER_01 0:00

Welcome to Wedding Day Podcast with your host, Sonia Babbage, CEO of Iron Diamond Media, a leading wedding resource featuring seven localized wedding brands across the country. Hi everybody, Sonia here with Wedding Day Podcast. We're here at the beautiful Ritz Carlton here in Portland. And I'm sitting here with Kathleen Crook O'Donnell. She is the owner of Crook Point here in southern Oregon. And it is stunning. We have done a style shoot there, actually. Amanda Jean did it, and it's absolutely amazing with the big rock in the ocean. And I'm just so honored that you're here with us and made the drive six-hour drive beyond the podcast.

SPEAKER_00 0:39

Thank you. Thank you for having me. It's truly an honor.

SPEAKER_01 0:41

Yeah. Thank you. Well, seven generations have owned this property through the years, and you have it now, which is amazing. But it was your grandfather that came over. Did I read this right? How what's the story? How he got this property?

SPEAKER_00 0:59

So back in uh the middle, the middle of the 1800s, my third great-grandfather. Um, I think the story goes that there was too many people in the Midwest in Illinois, and so he wanted to move out where there were less people. And so he got on horseback and um got on the Oregon Trail train. I believe he traveled with another family that his one of his sons actually married into. Oh, okay. And a little bit of my research of genealogy. My dad was always a buff. And so um came out west when the whole the major, major push was in 1852, and then too many people in the upper Willamette Valley, so he went all the way through the state, actually into California, and then settled up in southern Oregon. So the first to settle in the and the first white settler in that area in our little valley. So and this is so beautiful. And how many acres is it? We have um, I always think I'm a little humble about it, but um, we have about 3,000 acres. And it's on the coast, just over two miles of coastline, and we're lucky in Oregon. So Oregon beaches are public, but we don't have to provide public access over private land. So if people rent Crook Point and their homes, our homes there, then the beaches are essentially private unless someone boats in, but no one does because it's so remote. Yeah, and it's probably too high to get you can, but it's but it's just it's a it we're we're halfway between two little local communities called Gold Beach and Brookings. Brookings is becoming more of a hot spot um on the southern Oregon coast, it's a little more well known. Let's get in a little bougie and a little more cultured, and um, and so we're 15, 20 minutes from town from either direction. Oh, so it's if there's places to stay, places.

SPEAKER_01 2:45

You know what? That's closer to my target, to my house. So that's nothing.

SPEAKER_00 2:49

Although it's a bit of a drive. If you forget something, you have to go back to town. Yeah, it it can be arduous sometimes, but um, once people load up on all their stuff from local to grocery store, then they come to Crook Point, um, get comfortable in one of our eight homes and just be immersed in the space.

SPEAKER_01 3:08

It's so like a storybook, like uh just a beautiful storybook. And like it sounds like you can paint your wedding day however you want it to be on your property, like not a lot of rules, just rent it for two and a half days. Yes. Um, if you want, of course, um, and really let your dreams fly on the property. Is that correct?

SPEAKER_00 3:29

Absolutely. So we've my family's been renting um homes since the 70s and even before that. But the 70s was when my parents actually started that. My mom would do it in the summers when um when she was um when not teaching, so it was her summer um activity um to help supplement. And um, and so the lodging's always been a part of our family and doing a little bit of hospitality. And so when when people will want to come for events, they'll be able to um stay at one of the houses. Stay at one of the houses if it's a small event, then it's curated based on whatever their wishes, if they want to have an informal barbecue, or if they want to have a brunch, or if you want to rent out everything and have a big event. Um, it can be scattered, you know, across the property. But um, it's really personal. And we have lots of because of the homes, there's lots of flexibility in what what fits your not just your event size, but what fits like your vision and what sort of um what you're looking for.

SPEAKER_01 4:30

Yeah. So what's in right now is experience and your property is literally definition of an experience. Yes. So um, but it's also cattle ranch. They so what does that mean? Is there cows? Mm-hmm. Oh wow.

SPEAKER_00 4:45

There are cattle. We have about um, I think we have about 80 head of moms of cow of female cows. So when we're calving now, or um have our most of our calves are born at this point, but um, so we have about 150 head of cattle running around, but they're on the east side of the highway. Okay, they don't interfere with the wedding day festivities. There's one house on the east side, our Mervia State House. And so sometimes they'll come in the morning and hang out, and then you can tell them to go home and they'll go up to the main up above. Go home. So go home. Go home. So sometimes guests are a little surprised.

SPEAKER_01 5:22

So you kind of dove more into the weddings recently, right? Like relatively like immersed in it. And was that a couple years ago? When did you decide to take that leap?

SPEAKER_00 5:32

So I jumped in as sort of an accident. Um, in 2017, a family member had passed, and she is my it's my brother's wife. Um, she was running our lodging um hospitality. We had done weddings over the years, sort of like word of mouth, and the community or vacationers would want to come back and get married. They're like, it's so perfect. There's houses and beach, and it's just beautiful. And so we knew um weddings were something that we should look into. And then after she passed, um, my family asked me to help out. And so it was my side hustle with my full-time job in San Francisco. And so I had planned my own wedding in San Francisco, and so I started researching and sort of started my journey there in 2018. Oh, we did our website and found pictures of weddings that had happened and sort of created, you know, yes, we do weddings and and then just did it organically.

SPEAKER_01 6:24

Yeah, well, that's usually how it's and you find your it's like a passion project at first, and then you're like, oh, this is like I can see this forever. Um so what is the largest wedding that you've done on the property and what's the smallest? Because I can like you said, micro weddings are kind of a fun thing to do, but I'm sure you get some interest to do a big tent wedding probably on the property.

SPEAKER_00 6:45

We do. We've had, we've had, we we do more than just weddings. We'll do corporate events and retreats as well. But our biggest event was probably 280. Okay. So, and the lawn is our main Archwalk main lawn is huge. It's over 40,000 square feet of grass.

SPEAKER_01 7:01

Okay.

SPEAKER_00 7:01

So you could do even bigger, but we're set up with event rentals to do about like 280 to 300, depending on what they're looking for. And for a small event, we'll have elotements of just two people and they'll ask for some event rentals, and we'll help them, you know, we'll help curate what vendors to to use. Um, we have a preferred list, but you know, we're always gonna give advice if if they ask. Um, and they'll rent out a house and have a romantic moment in the Redwoods or on the corridor or on our property. Umstone point was where they where your the style shoot was.

SPEAKER_01 7:42

And you see the big boulder in the ocean in the distance. It's just like it doesn't even look real. And that's what you look at every single day, which is just like crazy. Like, I feel honored to know you. That's your world.

SPEAKER_00 7:57

It's it is. I mean, I one of again, because of our family history and sort of just the way things happened, where my I knew my family needed help, it was a really natural leap for me with my corporate experience. But every or where our main lawn is, which is um your team had looked at a little bit, but the style shoot was over at our at our cove and sandstone point. Um, but where the main lawn is, is where my grandmother's house was, and she helped raise us. Um, I spent every day after school from kindergarten through sixth grade, and every major family gathering for ours family was there. Yeah, and so it's there's just something so special. There's this energy that um, and I'm not like an energy person, but um you just when you minute you come around the turn, it just it just feels so good. Yeah, and then you have the the roar of the ocean when you open your car door, and I don't know, it's it just the sense of calm. Oh yeah, I need a couple of things. It just it's it just weddings and gatherings are so they're just meant to be there. Yeah and I I and so it happened to con, you know, the opportunity came and my family need help on it, but it was more around like organically, like what makes sense in each space, and how do we how do we make it just easy and inviting and such?

SPEAKER_01 9:18

It's awesome. Well, Mike, how many people just have in general a bucket list to get to the organ post? And this is your daily life, and now there's opportunity to actually make it happen and have a wedding celebration there, which is like creme la creme, you know. So more of what people know about you. I'm just like honored to like spread the word, and but this style shoot that we did that Amanda Jean and my creative director and editor, like it's outer space, so everybody has to check it out because it's like helps just paint the picture and the beauty, and it's just so organic. Like, there's not much that you really have to do because it's just so naturally beautiful.

SPEAKER_00 9:54

Well, your team also did with Amanda Jean, did an amazing job. The editorial was so um organic but so elevated, which I feel is you know, it it it was such a beautiful fit because you can still have that rustic, natural, outdoorsy experience, but you can still feel like it's you know, you can be decked out and in a tux and in a beautiful gown, and it's and it doesn't look out of place.

SPEAKER_01 10:19

Yeah. So, okay, on your property, do you require a wedding planner or what, or do you have a coordinator, or like what's the ideal? What's the image like the picture?

SPEAKER_00 10:27

We do require that you have at least a day of coordinator. We're remote. Um, we're six hours from Portland, it's a seven, eight-hour drive from San Francisco. Um, there is a really great um local airport you can get into really easily about 50 minutes away in Crescent City. But um it's you need it's really helpful to know the space, know the vendor team, you know, choices and understand how that really works. So it's really important as in any wedding, and and as a former wedding wedding planner professional yourself, like it helps to have someone help you with that, but also who just knows the players, depending on what you're looking for.

SPEAKER_01 11:04

And probably your big player is weather, right? Like, how does weather partake like in your area? Like, how does it I'm sure it's a curveball? Like it gets the organ coast, yeah. And like it was any wedding, like minute let's say even Minnesota, like you can't you have your day's gonna happen regardless. And I people go, you don't watch the weather? I'm like, no, because I'm still gonna get the bride down the aisle. Yeah, I'm like, the show's gonna happen. Um, yeah, is Mother of Nature gonna give me a curveball? Yeah, but my blood pressure is gonna get it high a little bit.

SPEAKER_00 11:33

Yeah, that's why you have a good vendor team back up and you and you know who to call. Exactly. We have an amazing vendor that's um a few hours away that has tents, so um, we actually just we're they're gonna we're recommending that a couple put a call to them even for this upcoming weekend because there's a little bit of rain coming, so they might need a backup.

SPEAKER_01 11:51

And that's just showing that you care. And again, you're the on the coast.

SPEAKER_00 11:54

So I mean, so it's understanding how to how to help navigate and knowing the right weather apps um for smaller events um up to 50, we can actually move it indoors. Um, our largest home from a square footage can handle 50 people inside. Oh, that's great, along with a dancing bar area as well. So that really provides that flexibility in a backup plan. This weekend we we might be moving the reception up.

SPEAKER_01 12:21

I heard I'm like, we got this heat wave right now, and then you're like it might be changing. So yeah, well, and it's good to have those backup plans, and it's realistic in any wedding, any location, to know your plan B and your plan C with weather. Absolutely if you're planning anything outside. That's just it's just the way it is. It's just the way it is in any state. So, um, but you have your plans and you have your backups and you have those pros that got your back, so that's good. And again, they want to be at your property, like they're not gonna say no technically to a sale, right? And protect that wedding day.

SPEAKER_00 12:52

We'll actually have um the wedding, the the the tent rental company has called me in the past because um weather was not looking good and there were tentative holds, and they would call us and say, I you know, what's I think you guys are gonna, I think you're gonna need it. We want to make sure you guys are covered because of the relationship, and I'll help uh counsel the couple through. And now our venue manager, she she takes on that that role for me, but um, and make sure that they know like they're gonna need to make a decision to make sure their event is gonna be wonderful and comfortable and enjoyable.

SPEAKER_01 13:30

You're just gonna say yes because you want to make sure your wedding day is perfect, yeah. Um, but you also said that your weddings only happen between May and October.

SPEAKER_00 13:38

For the most part, yes. Um, it's just risky um in the winter. We don't have a dedicated large space yet. We're working on it, we're working on um putting in a new uh event pavilion, but it's a a slow process. It's a business like money doesn't grow on trees. Yes, that's for sure. Um, and so most of our events, um, I would say larger, like more full full service weddings are gonna be in um middle of May, usually starting around Memorial Day, and then they'll go through mid-October, so once the end of October.

SPEAKER_01 14:11

You do a lot of weddings in between them. When you told me how many you do, I went, oof, da, you got your running shoes on during this time. And that's and the also the part of like thinking about during that time is the maintaining of the property to make sure it's always staying beautiful. Like that's a lot of work. And you say 3,000 acres?

SPEAKER_00 14:27

That's a lot of work. It is a lot of work. So in the summer months, this is our largest, um, our team's the largest that it's ever been during the main season. We have 20 people on staff.

unknown 14:38

Wow.

SPEAKER_00 14:38

And then in off-season, it's about 12 to 13 year round. And and even if we're not that busy, um, we're lodging, we have lodging so year-round. So we definitely have guests that come and stay with us. But um, we have that's when we're doing all of our projects to figure out what we need to improve upon, what maintenance and like upkeep we need to do. Um, it is we're just as busy in the winter as we are in the summer, but um, so it's it's a balance. Yeah, well, and it's teamwork. We have an I'm I'm so fortunate. I feel like it's everyone, and I think I believe the team feels this way too, that um it's an extended family, they're a part of the crook family. Um I am I am so blessed as um someone who's running an organization that I have so much faith and trust and appreciation in all of my and all of our team members. Um housekeepers are the most important. If we don't have clean houses, then we can't you can't run a resort. And so um respecting and acknowledging everyone's effort is so is so key and um and making sure everyone has a voice. So I feel we we we just had our staff meeting on the way up when I was we were driving up this morning. Yeah, and um it was just it's it's fun, it's entertaining for the most part, sometimes not always, you know, it's always colorful at times too.

SPEAKER_01 15:58

But we have but it's yeah, but you're sharing the memories together too, and I'm and especially when it's like a uh family-owned business, you should pay attention when you're doing those tours, and you can pay attention of the the bond of every the team. Like you can tell like the smiles to each other, and you can tell the nonverbals right away if everybody's getting along or not. And so it is important to feel the energy right away in that tour when you're picking your perfect venue. So, but again, who couldn't be happy working weddings on your property? It's such a dream. Thank you. Yeah. Well, thank you so much for being on the podcast.

SPEAKER_00 16:34

Thank you, Sonia. Again, it was really an honor. We're excited for the adventure.

SPEAKER_01 16:39

Well, thank you everybody for tuning into Wedding Day Podcast.