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A Curated Montana Celebration | Caitlin + Grant

If you're wondering how to entertain guests with multiple, personalized events, while also creating lasting memories for your family and friends, then you're going to want to read Caitlin's beautiful recapture of how their wedding week celebration unfolded in Paradise Valley. Photography by Font & Figure.


"We met through a coworker of mine and good mutual friend, Sydney. Grant had been asking Sydney about me; Sydney finally mentioned this guy, Grant. "Would you be interested in meeting him?" I told her, "Sure, why not?" I was having a single girl summer and wasn't looking for anything, but I was always open to a new adventure. I joined Grant, Sydney, and some other friends for dinner and live jazz at Walker's on a Sunday. We made each other laugh the whole night. I remember walking out and thinking, "Wow, this might really be something."

The next weekend, I invited Grant to a party at my house. I told him it started at 7 PM and he arrived exactly at 7 PM. But we were 24 years old! "Party starts at 7 PM" means "show up at 9." He walked in as we were still getting our house ready for the party, and looked terrified that no one else was there yet. I had insisted he bring his guitar, and the party ended with a particularly unruly jam session that involved a trombone and a French horn. Poor neighbors.

The next night, we happened to be at the same party at someone else's house. I got there late and hadn't eaten dinner. Grant found some hot dogs for me in the host's fridge and cooked them for me over the fire. We ran around laughing and having a fun time.

After that, Grant learned that I had never eaten pizza in Billings and asked to take me on a "pizza date" to try every good pizza place in town. I thought this meant one date with lots of different locations (a slice per stop). Grant meant many consecutive dates. He picked me up for the date in his truck and had Italian music playing (because it was on theme). We sat at Pug Mahon's and ate pizza from Guido's, and every time there was a lull in conversation, Grant whipped out a sheet of fun facts he had written down about the history of pizza. Afterwards, we went and drank whiskey on the outdoor chapel pews at Rocky. The rest was pizza history!"


"I had a trip planned to New York with my best friend Sydney (same Sydney as above) to visit my sister Mae. Grant secretly planned with Sydney and Mae to fly out to New York in the middle of their weekend together and surprise me in Central Park. My sister cut through the park under the ruse that we were "going to brunch." I had absolutely no idea and did not ask a single question about why we were taking an unusually circuitous route to get to brunch. We came around a corner and Grant was standing there, waiting. After getting engaged, we went on a bit of a pub crawl around New York and then met my whole family for a celebratory dinner."


"I never felt particularly beholden to traditions when it came to thinking about our wedding. I felt so much creative energy around the challenge of figuring out how to make a day that felt like us - both in experience and in aesthetic. And it was so much work, but I had FUN doing it and it felt so worth it. We felt a lot of freedom to make choices that felt right to us, whether it was around the entertainment or ignoring certain traditions or shopping for all the groomsmen's shirts at Montana Vintage. Our day felt like "us" and that felt really right and really special.

Grant and I sat down early on and talked about what our priorities in planning were. We decided easily and quickly that the day was for and about our guests. Our family, our friends, and our shared community. We figured that we could've gotten married privately if it was really about us ... but in a way, he and I already felt married in a deep and spiritual way. So the purpose of this day was to gather the people in our lives and share this with them, invite them into it, and give them a really loving, meaningful, and fun as f*** experience. We wanted the wedding experience to be a gift to them and an expression of gratitude.

We knew we wanted to get married in Montana. Grant was born and raised in Billings, and has lived in Montana his whole life. I grew up in Baltimore, but I've been in Billings since 2015. Montana has been such an important part of my life, and our story as a couple is here. Plus, my family and friends from back east love visiting. I knew they would get a kick out of making the trip, especially to an area as beautiful and special to us as Paradise Valley. We've spent a lot of time in Paradise Valley over the years, and feel like we know the valley well - so it felt much easier to find and choose vendors in the area, and also to plan a really fun and beautiful series of days.

Our wedding was almost a week long ... we packed the week full of celebrations, hard work, arts and crafts, outdoor activities, opportunities to learn something local about the area, you name it. We knew a lot of people were making big trips to be there, and we wanted to give them an experience that felt worthwhile. We also wanted to create a real window into the state we call home - what's special about it, what Montana culture is like, a taste of our community and the community that makes up this state. "One small town with very long streets," isn't it?

We kicked the week off with a BBQ for both of our immediate families. We both come from exceptionally loving families that we're really grateful to have and be a part of. We also recognized that our wedding was a joining of the families, and wanted to kick the whole week off with an acknowledgment of that. My family got to run around (and get bossed around) by Grant's five wild nieces; the magic was there and everyone was feeling it. The next day, we invited the entire wedding to float the Yellowstone River with us. It was huge - almost 40 people showed up! We had our close friends "captain" each float, and teach the East Coasters a thing or two about a Montana river adventure.

My aunt, Lena Wu, designed and arranged all the floral arrangements for our wedding. She put in WORK, and it felt so special to have a family member take the lead on this. On Thursday night, under Lena's direction and discerning eye, my bridesmaids and I ran over to Bozeman and picked all the flowers for our bouquets from Calliope Flowers, a flower farm in the area. Lena assigned us each a color to pick, and let us loose with shears. It was a gorgeous evening and felt intimate to get to pick our bouquets ourselves.

On Friday, we hosted a pickleball tournament at the Livingston Civic Center. My family loves sports, and has a particular history with racquet sports. It felt like a way to weave my family's competitive, athletic side into the week - and also something unusual (as far as weddings go) that would help people break the ice with each other. My aunts, Alicia McConnell and Louise Finnegan, and my brother, David Cromwell, ran the tournament. Again, it was huge - something like 65 people turned out! Most to play, some to spectate. We served mimosas, told people to come in costume, and gave out awards for the best costume, best sportsmanship, WORST sportsmanship (!!), fanciest footwork. We also ran an actual bracket and celebrated the winning, championship team. To no one's surprise, the final match wound up as my sister and her partner against my parents ... and my parents won the whole thing.

On Friday afternoon, we arranged for our guests to take tours of a local ranch. Learning about agriculture and working with many of the amazing people who produce our food has been a big part of my work at Northern Plains Resource Council and my time in Montana overall. I've been so grateful for my connections to that community and the ways I've been invited to share in that world. We wanted to invite our guests to do the same by taking a tour of Barney Creek Livestock. Barney Creek is run by Pete and Meagan Lannan, fourth generation ranchers who raise grass fed beef and use a regenerative management approach to build healthy soil and take care of their community and environment. We met Meagan in 2021, when my siblings were visiting town, and the chemistry was off the charts! We loved her instantly — and we thought our guests would, too. And they did! Grant's grandfather wanted to sign on as a ranch hand after the tour. We also thought that many of our guests from outside of Montana wouldn't have as much natural exposure to local agriculture, and that it would be a really special opportunity to show them that part of our life, our community, and our state.

We served barbeque from Follow Yer Nose (we are obbbsessssed with their BBQ) for our rehearsal dinner, and let anyone attending the rehearsal dinner share a toast or some words if they wanted to. It was really special to get to hear from more people and in a more intimate setting than we might've gotten just at the wedding. My dad, siblings, and grandfather sang "Home on the Range" for us with gorgeous harmonies; there was not a dry eye in the room. My grandfather toasted my grandmother, who was back home in Baltimore and unable to make the big trip. Grant's grandfather offered some words and choked up while doing so. Both sets of our parents offered really moving insight into what they see in our relationship. We felt so lucky and bowled over by the love from our family and friends.

On Friday night, we hosted all of our guests for welcome drinks at the Old Saloon in Emigrant. The Old Saloon is a favorite spot of ours. Grant has played his own music there, many of our friends who are musicians play shows there regularly, and it's always not-too-rowdy-but-just-rowdy-enough. There was a great band playing, and our guests flooded the place and tore up the dance floor. Practice for tomorrow!

The wedding itself .... what to say, my goodness. I chose our wedding colors straight from the colors of a Montana landscape - the dusky blue of mountains in the distance as the light starts fading and the sun is slipping behind them. A sandy yellow that looked like a blur of durum wheat across the horizon. I wore embroidered blue boots with white toes under my dress, because they felt like me. My dress was the perfect marriage of a Western, prairie aesthetic and some high drama. It was a statement piece, but also bohemian, soft and relaxed, but also maximalist. I loved wearing it and felt like exactly myself.

Grant and the groomsmen got ready in downtown Livingston at the Murray. My bridesmaids and I got ready on site, in a big room with floor-to-ceiling windows at Stoneflower. I tie-dyed sets for my bridesmaids in our wedding colors - yellow and blue - for everyone to wear as we got our hair and makeup done. The morning felt full and busy but so relaxed; my bridesmaids were buzzing around and Grant's nieces even stopped by for a visit (they loved seeing the "big girls").

The bridesmaids wore mismatched dresses of their own choosing in yellows and blues; some were solids and others floral. The groomsmen wore pearl snap shirts in either dusky yellow or dusky blue. I found most of the shirts at Montana Vintage and ordered a few on Etsy. Grant hand-strung new leather into vintage bolo ties he picked up at Montana Vintage, and gave them as gifts to his groomsmen.

I went to the ends of the earth to find the right hair and makeup artists. I wanted my hair to feel like a slightly more polished version of my natural hair; I wasn't looking for a cookie cutter look that didn't feel quite like me. Celeste from Parlour Livingston got the vibe immediately, in a deep and intuitive way. And Payton from PS Artistry gave me the peachy, natural, bridal glow of my dreams.

Grant and I did a first look, but I pranked him first! I had one of his groomsmen, Keller Paulson, tap Grant on the shoulder, dressed in a vintage wedding dress from the 80s that I found at High Trash Boutique in downtown Livingston. Grant went white as a sheet when he turned around. We did a REAL first look after that, but I think it took Grant a bit to fully recover from that moment...... there's an incredible shot Allison took of all my bridesmaids watching this from a window and laughing hysterically. It's the little things!

I did a first look with my whole family after that. They're all criers, so they were all weeping. I remember my brother saying, "Hi, beautiful" in a shaky voice and we all lost it after that. My whole family is really close and they were all so central to my day (and to who I am as a person). It felt special to have a quiet moment with just the five of us before the more public celebration began.

We fell in love with Stoneflower. We originally found the venue because we were floating the Yellowstone the summer prior, and floated down the river to the sounds of a happy wedding coming from somewhere up above on the bank. We spotted a tent but not much else. I dropped a pin, and came back to visit it in the fall. We wanted to get married on a ranch property, but not something that felt too manicured, gleaming, or not true to our understanding of or experience in Montana. Stoneflower fit the bill exactly. Suzie Stenberg, who manages the venue, is the third generation of her family on the property, and it was her grandfather's ranch. There's a creek running through the property, the field we held our reception is in typically used for livestock, and there were tractors and farm equipment parked at every corner of the place. We loved that the place had a history and real family roots, and we loved the less manicured look of a working ranch.

I walked down the aisle with both of my parents, to a favorite anthem, "River" by Patty Griffin. It goes: "Isn't she a river / She doesn't need a diamond to shine / You can't really have her / But you can hold her for a time" "You don't need to save her / or teach her to behave, just let her arms unwind / Ever-changing and undefined / She's a river." To me, it spoke to a concept of love that is deeply independent, not co-dependent, not contingent on being rescued or saved or changed, but always growing, always changing - the kind of love that Grant gives me every day.

Cocktail hour, reception, dancing - it was all a blur. Grant's mom, Valerie Jones, planned and set up an absolutely amazing "kid's area" for the kids to have their own fun and something to do. They blew bubbles, played with toys, colored with crayons, and ran around the whole wedding covering people with stickers. It was an absolute highlight, and our family and friends with young kids raved about having something to keep the kids occupied.

Grant and his mom danced to "Forever Young" by Bob Dylan, and my dad and I danced to "Wild One" by Faith Hill. We did a call-and-response style dance, where I made up a move, and he had to imitate me. We kept it going as the moves escalated and got harder and harder, and then switched into some square-dance style moves and promenaded around the entire tent - through and outside the tables. It brought down the house; the tent was LOUD with laughs and hollers, cheering us on.

The main event was, without a doubt, our band - Laney Lou & the Bird Dogs. They're favorites of ours and we'd seen them live quite a bit, as had many of our friends and Montana community. Grant opened for them at a show they played in Billings. So we felt a special connection to them, and also had a ton of confidence in their ability to get a whole crowd moving with incredible originals (harder to do than we realize! Everyone loves covers!). The dance floor was FULL and it didn't take any work to get it that way. We also know our friends and family... they're a good time. The floor was truly thumping, and people old, young, and kids were out there for hours.

Partway through Laney Lou's set, Grant surprised me by hopping up on stage and pulling his guitar over his head. The band backed him up as he played and sang "Angel From Montgomery" by John Prine. It's the first song I ever asked him to learn and the first song he ever played for me - special to both of us and such a moving surprise.

The next day, my whole family took a dip in the Yellowstone River, we signed our marriage license, and the neighbor's cows got out. The perfect end to a weekend that felt like us.

I learned that weddings, if anything, are an exercise in letting yourself accept and receive an intense amount of love. We did our best to stay SO present, not panic about how much love we were being given or how much we were being ACTIVELY loved, and just let it happen - just open ourselves up. That'd be my advice to other couples. Plan your day around the love you're going to give. You'll end up spending your whole wedding receiving it right back." –Caitlin, the bride


Photography | Font & Figure (#MBV)

Catering | The Ugly Onion

Dresses & Menswear | Anthropologie Weddings (bridal gown), various brands (bridesmaid dresses), thrifted vintage or from Etsy (men's shirts)

Her Boots | @momonewyork_

Floral Design | Bride's aunt designed, flowers were handpicked from Calliope Flowers in Bozeman

Gifts & Favors | The bride hand tie-dyed sets for the bridal party to get ready in and gave them crocheted bags; the groom bought vintage bolo ties and re-strung them on new leather for groomsmen

Makeup | PS Artistry

Day-of Coordinator | The Anchor G

Event Insurance | Leavitt-Great West Insurance

Stationery | Designed by bride but the art was by Abigael Tripp, Here Studio of Missoula

Travel & Transportation | Party Bus Rentals LLC


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