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Smith Rock State Park Private Residence Summer Wedding Bend, Oregon

Holly + Henry

By Ashleigh Cropper

March 30^th, 2025

Holly + Henry's Wedding At Monkey Face Ranch

There is nothing quite like a wedding at a private estate! I have found after ten years of capturing weddings that it's always a personal favorite because there is so much history and personal connection and that was definitely the case with Holly and Henry!

Smith Rock State Park (one of the most epic places in Oregon and the West Coast) was the backdrop of what Henry's family, who owns the property, calls Monkey Face Ranch. It is the only property that is grandfathered into the state park land! Needless to say, it's an epic location and incredibly charming...just scroll through this wedding as evidence!

The couple chose this location because this was where Henry proposed to Holly and they have numerous amazing memories here! It is also Henry's absolute favorite place in the whole world!

As you scroll through this incredible wedding, I wanted to point out some stunning details with their day that must be noted.

-All designs, signage, invitations were watercolor and created by Holly's mom, Ann! She is an amazing painter and put so much work into this personal touch for her daughter's wedding day.

-Holly wore her late Nana’s diamond earrings and her late great-grandmother’s diamond around her neck as a way to incorporate loved ones who are no longer with them. I always find these details to be so dear and sweet.

-Henry’s grandmother, Dottie Schoonmaker, bought Monkey Face Ranch in the 1970’s, and the family has been lovingly caring for and enjoying it ever since. Both Henry’s parents and his brother and sister-in-law were married there, too.

Smith Rock State Park Private Residence Summer Wedding Bend, Oregon

About Holly + Henry

Henry and Holly originally met in their college years, through Holly’s cousin and Henry’s childhood good friend, Joe. Holly always had an eye for her cousin’s friend, Henry, and vice versa. The two had sparks flying at a cabin weekend in Black Butte Ranch with a group of friends in 2016.

Life plans happened and Henry went off to Thailand for a year to teach English and Holly starting a Masters program in Seattle. It would be a few years before they would find their way back to each other.

They didn’t rekindle and start dating until 2020, just before the pandemic hit. Having increased remote work flexibility, Henry and Holly were able to spend extended periods of time together in each of their family’s central Oregon vacation homes: Black Butte (Holly’s family) and Monkey Face Ranch (Henry’s family).

Henry and Holly live together in Seattle, where Henry coaches lacrosse and works in the lumber industry and Holly manages an integrative wellness clinic. They love a jog or walk around Lake Union for coffee, take advantage of Seattle’s proximity to the outdoors, and enjoy exploring the city’s ever-evolving food and bakery scene.

About The Ceremony

On one of the hottest days of the summer in August, everyone gathered to celebrate these two!

The ranch has an upper and lower locations. They wanted everyone to take a little hike down to the lower pasture for the ceremony, and then come back up for the reception and party for the evening.

Monkey Face Rock, a famous rock climbing location within Smith Rock State Park and an overall well known rock structure was the backdrop for the ceremony, and it sure was stunning!

As you walked down to the ceremony site, there was signage telling the tale of their love story along the way. At the bottom, guests would be greeted by a close family friend playing the piano under the apple trees.

Ken (Holly’s uncle, Henry’s childhood basketball coach) officiated the wedding, sharing loving and fun stories about Henry and Holly as kids, teenagers, and now adults and how their paths seemed to keep crossing and crossing until the timing was right to make it official.

Florals

Roots Wild once again created the most beautiful arrangements for Holly and Henry's day. If you don't know much about Roots Wild, let me just say Eliza is simply incredible! She and her partner have a farm right around the corner from the state park and grow their flowers! She uses sustainable farming practices and creates these custom pieces with her premium seasonal blooms!

Eliza, the florist, suggested a half-arch ground floral arrangement in lieu of an arch, so that Monkey Face would have center stage in the backdrop. It was the perfect recommendation to highlight the amazing location!

The florals were Holly’s favorite part of the entire design, The floral design extended from the point where guests arrived, along the path to the ceremony site, and all the way back to the cocktail hour and reception site, where the farm tables were adorned with sweet bud vases and floral arrangements. The cocktail cabin was decked with a large floral and greenery installation. The bouquets were flower forward with a mix of lush fresh flowers and gorgeous dried, earthy florals all grown a couple miles from Smith Rock State Park at Roots Wild flower farm. The color palette was mostly neutral with some pops of rust and other muted tones. The florals perfectly accented the already beautiful landscape and Smith Rocks canvas.

Reception

After the ceremony, guests then made their way back up the path to the lawn next to the house, where cocktail hour and the reception took place.

On the menu was the most delicious paella prepared out of giant paella pans on site.

For dessert, Bonta Gelato’s restored 1957 scoop truck pulled up and guests enjoyed a scoop of gelato along with a chocolate chip cookie (fresh baked by Holly’s aunts).

On the property, there is a small structure, which Henry’s family has lovingly named the “half-house.” It was used for their cocktail bar and was adorned with gorgeous florals by Roots Wild.

Guests enjoyed their meals and drinks through dinner, where Holly’s dad made everyone cry, and Henry’s brothers made everyone fall out of their seats laughing.

After dinner, Henry and Holly kicked off the dance party with something special they’d been working on - a light and fun choreographed dance to The Best by Tina Turner.

A tradition in Holly’s family is to bring all the family on the dance floor to dance to We Are Family by Sister Sledge’s. Everyone joined and danced the night away with Smith Rock in the background!

Final Thoughts

I asked Holly and Henry about some highlights and favorite moments when reflecting on their wedding day! I love to hear what stood out to the couples and here are some of what they said, along with some advice to share for future couples:

"There is no feeling quite as surreal and special as standing at the altar, in front of all your favorite and most cherished people, reciting your thoughtfully written vows and hearing the carefully curated words from the person you are choosing to spend your life with in return. There were laughs, tears, and all the feels. It was magical and unforgettable."

"The dance floor was so much fun and never had a dull moment. One of Holly’s best friends curated the most epic playlist for the entire evening (highly recommend having your most music savvy friend do this!). At multiple times during the night, Henry’s high school and college lacrosse teammates and friends hoisted both Henry and Holly in the air - full body tosses. Terrifying but oh so fun!

Advice for other couples:

"Savor every single second. Nothing can prepare a bride or groom for how fast this day goes. It’s over in a flash! Every single moment during this day (and the days leading up) is so very special. Cherish the people, the place, the details, the conversations, the laughs, and everything in between. "

"Let the small stuff go! Your guests will not notice an out of place piece of signage! The day is about celebrating you and your person, the love you share, and the adventure you’re committing to together. To have all your chosen people in one place, surrounded by love and celebration, is seriously the most special and beautiful experience.”

"Take a pause - step back from the party, look out at everyone who has traveled near and far to be with you and celebrate you on your day. Appreciate the community you’ve built and soak in how special that very moment feels."