Megan Osteen was in the early stages of building her home—and she had all the experience necessary, as a fifth-generation member of her family’s lumber supply company—but she needed the land cleared first. Enter Zack Todd. “Zack’s business card came across my desk,” Megan remembers. “His business completed the site work before I could start the building process.” His company laid the foundation for Megan’s house, and that laid the foundation for their love story. 

The duo dated for five years—all the while Megan’s house was being finished—until Zack proposed one Christmas Eve at John’s Island Club in Vero Beach, Florida. “My family has been going to the club for Christmas Eve dinner since I was eight years old,” Megan says. “I grew up taking family pictures in front of the big Christmas tree there, so that is the exact spot Zack popped the question. He knew how important family values are to me, so he made sure my family was present during the proposal.” 

The couple is outdoorsy and nature-loving; they wanted their wedding to represent that. “Zack is a true Southern man; he loves to fish and doesn’t leave home without his boots,” Megan says. “I grew up riding horses and have always loved the calming aspect of nature.” On Cumberland Island in Georgia, where they decided to say, “I do,” wild horses roam free, and nature and wildlife are the stars. They felt most at home at Greyfield Inn, the same venue where John F. Kennedy Jr. and Carolyn Bessette held their reception. 

“The wedding vibes Zack and I wanted were Southern and simple, but also classy and elegant—a wedding that was less about grandeur and focused more on our love and eternal commitment to one another,” Megan shares. Over The Moon Editor’s Pick Planner Victoria Ann Events brought their vision to life and Releve Films captured it all on video.

Welcome bags were personalized with each guest’s monogram and held handwritten notes from the bride and groom; at the reception, linen dinner napkins were embroidered with guests’ names. The details were intimate, while the decor, artfully curated by Liz Stewart Floral Design, was understated. “We did not want to take away from Greyfield Inn and Cumberland Island’s natural beauty.”

Megan looked to her venue’s most famous bride, Carolyn Bessette, for fashion inspiration. “Carolyn was a fashion icon in the 1990s; she was chic, elegant, timeless, and classic,” Megan says. “This is exactly what I wanted in my wedding dress.”

The bride worked with bridal stylist and fellow Over The Moon Bride Sam Levis of The Bold & Bridal to recreate Carolyn’s look with modern updates, adding lace stockings and sleeves to a clean Lee Petra Grebenau dress. She wore Christian Louboutin block heels (Cumberland Island’s paths are made of mostly crushed shells), a something-borrowed-and-blue Van Cleef & Arpels bangle, and a flowery veil.

The morning of the wedding, Megan wore a Hill House Home dress and got primped by Down the Isle, as wild horses grazed outside the inn. “I remember looking out the window after I finished my hair and makeup and seeing two horses roaming right outside,” she says. “It was calming and helped ease my nerves. The horses could not have been more magical.” (The creatures also turned up for the bride and groom’s wedding portraits.) 

Later that day—October 14, 2023—Megan and Zack exchanged vows in front of 50 guests beneath a massive oak tree on the lawn, silver moss blowing in the wind. As she walked down the aisle, “time stopped,” Megan says. “As soon as we locked hands at the end of the aisle, Zack and I immediately felt the nervousness go away. We felt comfortable and just so happy.”

The bride’s uncle officiated and started by asking her and Zack to look out at each audience member. “By keeping the guest list small, we ensured that every person present held a significant place in our hearts and lives,” Megan reflects. “When we looked around, we felt just that.”

Just like the Kennedys, Megan and Zack hosted an intimate reception dinner on the porch of Greyfield Inn. Head chef Jada Veljkov served a three-course meal of vegetables grown in the inn’s island garden, strip steak, and vanilla bean wedding cake. “The candlelit dinner was dreamy and magical, and after dinner on the front porch, we moved the party to the south lawn,” Megan says. Brick pavers became a makeshift dance floor as country singer and songwriter Brian Sutherland played “Sweetest Love” for the newlyweds’ first dance.

Later in the night, a Dart Collective DJ took the stage. “We had light-up flower crowns and glow sticks,” Megan says. “We opened up the dance floor by handing out the blow-up stick horses and playing ‘Pony’ by Ginuwine.” 

After the reception, some guests headed off to bed, while others joined Megan and Zack around the fire pit and sang and danced and laughed. “It was a perfect ending to the best day of our life,” the bride says. “I told Zack from the beginning that what we may lose in numbers—since we only had 50 guests—we will make up for in authentic experiences and deep connection. There was no shortage of joy. Everyone was genuinely excited to celebrate our love and marriage, and that feeling was absolutely incredible.”