Three Matches Later: A Pine Grove Wedding in Roxbury
Rachael (she/her) and Heather (she/her) didn’t just find each other once. They found each other three times, across three different apps, before finally making it to a first date that almost didn’t happen. What followed moved quickly, not because they rushed it, but because it clicked in a way neither of them expected.
They got married in Roxbury, New York, with 140 guests they chose carefully. No obligatory invites, just the people who had been part of their lives and relationship. The weekend included a mountain-top rehearsal dinner, a pine grove ceremony led by Heather’s mom, and a barn dance floor that ended in a full-room singalong to “Pink Pony Club.”
You matched across three dating apps before a yes, tell us more about falling in love.
We matched on Tinder, then Bumble, then Hinge – three apps, same person. At our third match, Rachael finally said it: “Alright, this is the third app. We need to go out. How’s next Friday?” Even then, the date didn’t happen due to an urgent family obligation. A month later, Heather reached out again, and this time, we made it happen. The date was insanely good. Heather told her best friend that Rachael hadn’t emotionally exhausted her (the highest compliment), and Rachael texted her cousins, “If I don’t marry this one, I’m dying alone.”
We tried to follow timelines at first, but they didn’t stand a chance. We moved in sooner than planned, spent every day together, and learned how healthy a relationship could be. Heather soft-launched her feelings by declaring love for Rachael’s dog, Elton, while Rachael took a little longer to name what she felt, but once she did, everything shifted. Even when we said we’d get engaged “next year or the year after,” Heather’s mom didn’t buy it. She was right.
In June 2024, Rachael proposed on the memorial grave of her ancestor, Elizabeth Howe – the first woman hanged in Salem – a moment that honored the long history of women persecuted for “witchcraft” and the many people whose resistance made our love possible. It felt like a way of acknowledging those who came before us and paved the way.
Our big love is now shared with our menagerie of fur babies Lily, Elton, Modotti, and Dahlia – all thrilled to have two moms.
Tell us more about wedding planning, and how trusting an ‘inclusive’ vendor unravelled.
Honestly, we were shocked by how easy planning felt. Our visions aligned so naturally, and the team at Roxbury Barn + Estate handled so much, from the venue to catering and desserts. Most of our vendors even came through their recommendations.
The only real snag came the week leading up to our wedding, and it was a big one. After over a year designing custom femme suits, everything unraveled at the final fitting. Unfinished pieces, major sizing issues, and being refused entry to even try them on the night before we left for our wedding. It was incredibly frustrating, especially as queer clients trusting an “inclusive” vendor.
Thank goddess for community. A close friend shut down her seamstress shop to help us, and with some last-minute problem-solving (and an overnighted top that somehow fit perfectly), everything came together. Truly, without her, Rachael wouldn’t have had something that fit her body or reflected her gender expression, and that’s not something anyone should have to risk.
Tell us more about Roxbury Barn and Estate, and why it was a perfect New York wedding venue
Rachael first found Roxbury Barn + Estate nearly ten years ago while working as a wedding photographer and helping a friend venue hunt. The pine grove stuck with her. When it came time to plan our wedding, she pulled it up again, thinking maybe we’d find something similar closer to Philadelphia. Heather said, “Well, why not just do it there?!”
Since our people are scattered everywhere anyway, travel was inevitable, and the second we visited, we knew that place was it. The wooded mountainside, pine grove ceremony, outdoor pavilion, carriage barn, bonfire… it had everything, and somehow felt even more magical in person.
Casper and Roger, the owners, have built something really special. The whole team felt kind, celebratory, and genuinely invested, like we were in this little magical bubble, surrounded by good people who attract good people.
Tell us about building an intentional wedding guest list.
Our guest list landed at about 140 people, and we were very intentional. No obligatory invites, no prioritizing family over chosen people, just those who had been pivotal in our lives and in us finding each other. If we hadn’t spoken recently, they weren’t on the list.
What we didn’t expect was that some people who had quietly held onto their bigotry would make it known once invitations went out. It was tough, but it also clarified everything. After that, our decline rate was only about 6%, and everyone we deserved to have showed up for us, traveling to be there.
That approach became a filter, and honestly, we couldn’t recommend it more. The people in that space were fully there, fully supportive, and full of genuine care, and that’s one hell of a good feeling.
You chose Marilyn Lamanna Photography as your inclusive wedding photographer, and Ramble Free Photography for Super8 film, how were they?
Our queens! We found Marilyn Lamanna Photography on Instagram, and Rachael (a photographer and photography historian) immediately knew she was it, someone who works with film and treats the day as art. Marilyn blew us away. She’s whimsical, dynamic, entirely unique, and somehow made two people who are not comfortable in front of a camera look completely at ease.
As the wedding got closer, we realized we needed video, but not just anything. Super8, and someone who would collaborate seamlessly with Marilyn. She recommended Hannah of Ramble Free Photography, who just happened to have availability before moving to Perth!
Hannah and her partner Brent captured everything so beautifully. Now we get to experience the day, and everyone we love, in motion forever.
How did you lean into some of your favorite things; tarot and theatre?
Our love story was the blueprint, and quite literally the Lover’s Tarot card, which Heather kept pulling before we met. Everything about the day was built around synchronicity, intuition, and the feeling that something bigger was at play. We wanted natural elements, meaningful objects, and symbols of our lives woven throughout the space.
We leaned all the way in: a full-scale, theatrical version of our story. We even created a Playbill as our program, treating the day like a production. Set design, casting, music, all of it. Think deep reds and regal purples, black and gold, crystals and stones filled with meaning, and a soundtrack shaped by artists like Stevie Nicks, Brandi Carlile, and Annie Lennox.
Heather was the vibes director, Rachael brought it to life (three art degrees at work), and together it became exactly what we wanted. Something immersive, intentional, and a little bit magical.
Your wedding was DIY – how was that?
Nearly everything was either custom or DIY. We sourced a few things from Etsy (like neon signage), but most of the details were made by us, from laid paper folios and dried flowers to calligraphy and vintage stamp collages for our invites.
One of our favorite pieces: pressed-flower dinner nameplates, each hiding a personal letter sealed with wax from a stamp we bought the day we got engaged in Salem. We also brought in rugs from our home, our crystal collection, tarot cards, and made custom woodblock robes for our inner circle.
Rachael designed all the signage and the Playbill, and we used red and purple throughout to represent each of us. Splitting everything based on our strengths made it feel seamless, and very, very us.
Walk us through the wedding day.
We started the weekend with a mountain-top rehearsal dinner at Bovina Farm & Fermentory, long tables, incredible food, local wine, house-made beer, and all our favorite people. The next morning was slow and easy: getting ready together at Roxbury Barn + Estate with our inner circle and Heather’s mom (our officiant), who helped us both get dressed. Then an hour in the woods for photos and Super8 with Marilyn Lamanna Photography and Ramble Free Photography before keeping everything else relaxed and present.
The ceremony was everything to us. Set in the pine grove at Roxbury Barn + Estate, rooted in nature and our Celtic ancestry, with our community surrounding us in a half-moon. Elton made his entrance in a purple Billy Porter-inspired tuxedo gown, and Heather’s mom married us, one of the most meaningful parts of the day. We called in the elements, heard readings from Mary Oliver and Oscar Wilde, exchanged vows, and walked back down the aisle to Maggie Rogers, covered in lavender and rosemary, surrounded by florals from Sticky Petal Farm.
From there: a quiet moment with cocktails, then straight into hugs, dinner, and speeches (which were incredible), with food by Roxbury Barn + Estate. The dance floor in the barn, led by Matt + Hillz, completely surprised us. It ended up being one of our favorite parts of the night. By the final song, “Pink Pony Club,” it felt like everyone was singing together while we danced in the center. Ending the night with a bonfire and s’mores, surrounded by people who truly showed up for us, felt like the perfect close, everything aligned, and so, so us.
What are some of the moments that meant the most?
The ceremony was hands down one of the best parts of the day. We put so much into making it feel like us, letting go of any traditions that didn’t fit, and once it started, we were fully present in it all.
The dance floor in the carriage barn was another standout — totally unexpected, but magical and liberating. By the final song, “Pink Pony Club,” it felt like everyone was singing together while we danced in the center, surrounded by our people.
And honestly, one of the most special things was watching our worlds collide. We seated people intentionally, not by “sides,” and seeing new friendships form between people who might never have met was everything.
And, one last shout out for your dream team?
Truly, our vendors made the magic possible. Marilyn Lamanna Photography and Ramble Free Photography are dreams. We feel so lucky to have their work in our home forever. And the team at Roxbury Barn + Estate built something really special, creating a space that felt genuine, caring, and incredibly talented from start to finish.
Leah Detreville and Kristina Ugenti from Roxbury Barn + Estate created food and desserts our guests are still talking about, and their coordinator Danielle somehow pulled everything together behind the scenes (we’re sure things came up — we just never knew about them!). Trusting their recommendations was one of the best decisions we made.
Marcy from Sticky Petal Farm brought our witchy floral vision to life, and Matt + Hillz turned our chaotic music taste into the best dance party ever, even pointing us toward Bovina Farm & Fermentory for our rehearsal dinner. Honestly, everything, and everyone, was perfect.
Captured by Marilyn Lamanna Photography
Celebrant Lisa McMasters
Ceremony Venue Roxbury Barn + Estate
DJ Matt + Hillz
Florist Sticky Petal Farm
Hair Stylist Chelsea B Canfield
Rings Hidden Spaces & Braverman Jewelers
Transport Premiere Transportation
Rehearsal Dinner Bovina Farm & Fermentory
Videographer Ramble Free Photography
