This Old Barn, Dayton Maine Barn Venue
- Brick + Tides
- Nov 4
- 8 min read
Updated: 5 days ago
When Cheryl and Dale Wilkinson first stepped inside the centuries-old barn on Dennett Road, they didn’t just see decay — they saw history worth saving. The beams were hand-hewn, the floors uneven, the air thick with memory. Years of renovation later, This Old Barn stands again in all its rustic glory: a 202-year-old structure now alive with weddings, laughter, and the steady pulse of family effort.
How an Old Farm Became a Barn Venue
The Wilkinsons didn’t set out to be venue owners. In 2015, when a neighbor offered to sell them the land across the street—an old farmhouse and a battered barn—Cheryl and Dale “jumped at the opportunity,” thinking first about their children and the chance, as Cheryl put it, that they might “someday settle down, right across the street.” Horses and open space were the original dream.
Then someone toured the property and suggested it would make a beautiful wedding barn. The idea grabbed Cheryl by the shoulders. “Someone had put the seed in my head and I couldn't sleep for three days… I loved it.”
What followed was not a quick flip, but a long, careful rescue. “It took five or six years to renovate,” Cheryl says, describing nights and weekends, a “paperwork process with the town of Dayton,” and the slow choreography of stabilizing a 19th-century frame for a 21st-century purpose. The barn’s first wedding came in 2021; this fall, they finished their fifth season.
Saving a Barn That Looked Unsalvageable
When the Wilkinsons first walked through the doors, even they wondered whether the building could be saved. “We looked at each other, whether we should just burn it. It was pretty much sideways. Part of the floor was gone. The exterior had holes in it, gaping holes.” Dale—who owns an excavation business—saw a path forward. “He just chipped away at… securing the structure, getting it upright,” Cheryl says, until the barn was “restored” and standing proud again.
Their stewardship isn’t just about craftsmanship; it’s about lineage. The previous owners told Cheryl the barn was built by the Dennett family—namesake of Dennett Road—when this hill was part of a dairy farm. She thinks of them often: “I just appreciate what they must have gone through."
There’s also a personal thread that runs back to Dale’s childhood. As a kindergartener, he visited a farm with a red barn on a class field trip. The image seared into him—proof, maybe, that first loves can be built of timber. Years later, when it came time to name their place, he reached for another early imprint. He’d grown up watching Bob Vila and This Old House on PBS, marveling at the revival of old structures. “What about This Old Barn?” he asked one day. Cheryl didn’t hesitate: “I absolutely love it. It's got to be.”
From Bankruptcy Files to Wedding Vows
For nearly two decades, Cheryl’s professional life ran on a very different track. She managed a law firm that handled bankruptcy cases—necessary work, but heavy, empathy-soaked, and emotionally exhausting. “I went from… people that were at rock bottom… It was a heavy… I take on people's emotions,” she says.
The barn offered a seismic shift in emotional climate. “Now I’m working at someone's happiest time of their life. It's made all the difference in the world for me. Physical, emotional, mental well-being. It's amazing. I love it.” The words land with relief and gratitude. She’s quick to add that she loved her former colleagues, but the day-to-day of weddings suits her nature. “I am a hopeless romantic. I love love… I just have to pinch myself… it's wonderful just to be a part of peoples love story.”
A Family Business, Root to Rafter
The rescue and relaunch of This Old Barn became a family project in the truest sense. Cheryl’s son helped Dale with structural work and with building the bridal cottage tucked behind the barn. Her daughters work events and, like their brother, have grown up seeing what patience, grit, and pride look like when they’re nailed into place.
There’s a wider circle, too: “I hire a lot of local high school kids that are eager to work. You're only as good as your team,” Cheryl says. “My team is all very warm, very helpful, very loving and nurturing. I have two or four people per event and they're amazing.”
The cottage itself is a love letter to the property’s past. When the old farmhouse had to come down, Dale pulled and saved its hand-hewn beams. He repurposed those 200-year-old timbers into the cottage so that a five-year-old structure would feel as if it had grown there over generations. Cheryl lights up describing the result—rustic, fairytale-calm, exactly what she imagined when she told Dale, simply, that couples needed a place on site to get ready.
Inside the barn venue, a protected patch of original flooring remains—a quiet relic that connects dancing feet to the Dennetts’ work boots. It’s a reminder that past and present don’t just coexist here; they hold hands.
A Community of Makers and Doers
Ask Cheryl about vendors and she’ll give you a roll call of hardworking small businesses that bring the place to life—barbecue smoke curling into the evening, florists filling mason jars with wildflowers from nearby farms, a mobile food truck pulling up like a friend. “Mac's Barbecue, Above and Beyond Catering, OreNell's, Bliss… Rustic Taps and Catering is amazing… a lot of local farms… People are doing a lot of wildflowers… supporting your local small businesses, especially your farms.”
Even the bar service is a family affair: “My bar service, B+M Spirits… who I'm exclusive with now is actually… my brother and my sister-in-law!"”
Moments You Carry Forever
Every wedding is singular—its own choreography of nerves, toasts, and tears—but a few stories have lodged in Cheryl’s heart. One September afternoon this year, a well-known local businessman, recently diagnosed with ALS and now wheelchair-bound, watched his daughter come down the aisle. The entire barn seemed to breathe with him. “There wasn't a dry eye in the place… it was beautiful.”
On another day, a beloved Biddeford teacher and longtime football coach toured the property; later, his son was married here, and the celebration doubled as a reunion of hometown affection. Cheryl, born and raised in Biddeford, still glows when locals choose the barn.
And then there was the couple who loved Pixar’s Up so much they brought a hot-air balloon to the back field for a full-hearted theme wedding. “I have pictures. It was well done… like you were inside the movie UP.”
The barn makes room for more than vows, too. Two of the Wilkinsons’ kids had their senior proms here—they donated the space. Couples sometimes come back with new babies to take photos where their families began. It’s hard to imagine a more literal illustration of legacy.
Why the Work Matters
For Cheryl, the deepest reward is simple and profound: caretaking a historic place while becoming part of other people’s most joyful memories. “It's knowing that… my husband and I, are part of their story… This Old Barn is always going to be a part of their story.” She can already see the future: parents turning down a quiet country road with their kids and saying, This is where we got married.
That future seems likely, if the guest book is any indication. Many couples come from around southern Maine, but plenty find their way here from Massachusetts, New York, Connecticut, and New Hampshire—and even farther afield. Cheryl still smiles about the inquiry that arrived from Hawaii. Often, it’s a tie to Maine—a college romance at UNE or UMaine—that pulls people back to say their vows on a hill in Dayton, Maine.
Life Beyond the Barn Door
When the season slows and the doors rest on their hinges, the Wilkinsons head for Little Sebago Lake, where winter means snowmobiling, skating, and ice fishing; summer means boating, fishing, and wakeboarding. Cheryl loves a good meal—“Yolked” in Windham is a favorite—and a good walk, whether in Clifford Park or along a quiet beach. One of her favorite rituals is hunting for sea glass with her daughter, who turns the finds into Etsy art. It’s a small thing that feels like the rest of Cheryl’s life: noticing beauty, saving what’s worth saving, and turning it into something meant to be shared.
The Barn That Isn’t an Object
If there’s a single sentence that explains everything about This Old Barn, it might be the one Cheryl offers almost apologetically, as if she worries it will sound too sentimental: “I don't feel like the barn is an object at all. I call her she… I just want to take care of her.” The pronoun matters. It signals respect and responsibility. It’s also a clue to why the space feels different the minute you step inside: the people who run it have built their lives around honoring what’s here.
That honor shows up in details—the saved beams, the preserved floorboards, the way the wind moves through the rafters—and in choices: a seasonal calendar that respects old wood; a cottage built to calm jittery mornings; a staff hired as much for warmth as for hustle.
It shows up, too, in the way the barn has knit the Wilkinsons together. What began as a rescue mission became a family enterprise, and then something more—an inheritance in motion. Cheryl says it out loud near the end of our conversation, and you can hear how much it means: “It's just such a sense of pride
that it's, it could be a legacy… Hopefully for our family's generation to come, and someday it'll be 302 years old, God willing.”
What Comes Next
Cheryl’s vision for the next five, ten, twenty years isn’t about expansion or trends. It’s about continuity—more wonderful couples, more tours that end with someone falling in love with the place, more weekends where the hills echo with laughter and a fiddle line. “We just keep wonderful weddings going, meeting new couples, sharing our property and our rustic barn with them… I just love, love. I love romance… I just hope it continues to be a part of more love stories to come.”
Writer’s Note
When our conversation ended, Cheryl smiled softly and said, “She’s like a person to us — we even call her ‘she.’”
That line never left me. And so, it felt only right to let the barn have the final word.
A Love Letter from This Old Barn
To the Wilkinson Family — with gratitude.
Dear Cheryl, Dale, Baylor, Blake, and Brynn,
It’s me — the old red barn on the hill. I’ve been standing here for more than two centuries, weathering snow, sun, and time itself. I’ve seen plenty come and go, but none like your family. You didn’t just patch me up — you brought me back to life.
Dale, your strength gave me life I’d almost forgotten. Cheryl, your care filled my walls with light again. The kids — their laughter still dances around my rafters on quiet mornings. Together, you gave me a second chance to be useful, beautiful, and full of joy.
I’ve hosted weddings, music, and the kind of laughter that sticks to wood grain. I’ve stood proud, watching love begin again and again under my roof. And through it all, I’ve felt your fingerprints in every detail — the kind that say, we did this together.
So, thank you — for the mending, the lifting, the bracing, the dreaming.
And thank you, most of all, for not burning me to the ground. Honestly, I wouldn’t have blamed you — but I sure am glad you didn’t.
With quiet appreciation -
This Old Barn
Video by Biddeford Videographer and Photographer - Tim Holt / @BiddefordForBreakfast
Call This Old Barn: 207.602.8284
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