Ashley & Jason’s Intimate Outdoor Wedding at Sugarland

How They Met

While Ashley hails from Plymouth, Wisconsin, Jason was born and raised in South Africa until he was 18, then moved to London, England, for 20 years before landing in Milwaukee. The two met through the OK Cupid dating app, which Ashley downloaded and deleted 24 hours later, deciding it wasn’t for her. “However, Jason’s message still came through.” Thank goodness it did.

The two met in Grafton on a Tuesday night, despite both being under the weather. “We met again that Friday, and that is where we fell in love. We knew at that moment we were meant to be.” When the two got engaged, it took a village. “Jason knew that part of my heart was left in Africa after a mission trip in 2017,” Ashley says. “So he worked with multiple jewelers around the world and his family in South Africa to have a custom ring made with an African diamond.”

A Global Proposal

The couple planned a trip to Australia for Jason’s birthday in February of 2020. While there, Jason arranged to climb to the top of the Sydney Harbor Bridge, overlooking the Sydney Opera House, on Valentine’s Day—which is also his birthday. “Once we got to the top, he got down on one knee and asked for my hand in marriage.”

Pandemic Wedding Planning

Jason and Ashley went through a roller coaster of wedding planning in 2020. First, they set the date for July 11th at Sugarland in Wisconsin. When Covid hit and Jason’s family were unable to travel, they decided to fly to Hawaii with the kids for a July 7th elopement. But Hawaii then announced they were requiring a two-week quarantine upon arrival until August—so they pushed back the elopement date to August 18th. August came, and Hawaii extended their quarantine, so Ashely and Jason canceled everything. “We decided on an elopement-style wedding here in Wisconsin for August 25th at our original location, Sugarland—just us and the kids and a couple of witnesses.”

Now, Jason and Ashley are working to plan a Wisconsin reception as well as a trip to South Africa to celebrate with Jason’s family. “We went from canceling three wedding dates to now trying to plan three weddings and receptions. It has been stressful, but we have learned to roll with the punches.”

An Intimate Wedding at Sugarland

Ashley and Jason said their vows under the old oak tree on the Sugarland property on a Tuesday afternoon. “It was incredibly intimate with only six chairs put out for the children and our witnesses.” Ashley found her gorgeous gown at Amelishan Bridal. “I had my photographer/witness get me into my dress.” She did her own makeup and her daughter’s makeup that day.

That morning, the bride and groom met just around the corner from each other, so as to be together, but not see each other. “We held hands around the corner. Jason’s parents had sent items to fulfill the ‘something old, something new, something borrowed, something blue, and a sixpence in your shoe.’ There were lots of tears shed, feeling the love from him and a family an ocean away.”

For photos after the ceremony, Jason and Ashley just stayed on the Sugarland property, which has plenty of picturesque land, a river, a beautiful barn, and a fountain. The reception consisted of setting up a table under the old oak tree with white candles and food brought in from Sugarland’s restaurant, Old Feed Mill. “Jason came up with a wonderful idea of celebrating wedding traditions from different cultures from different time periods.”

Decor-wise, Ashley turned to Well Dressed Tables to bring her vision to life. “I enjoy simple, earthy, and elegant romance. So we had soft flowers with a burlap runner and minimal decorations, letting the setting speak.”

The Start of Ever After

What’s next for Jason and Ashley? In addition to celebrating their marriage with friends and family, this globetrotting couple is hoping for an epic honeymoon. “We’re waiting for Covid to really calm down. We love to travel the world, having already gone to Mexico, England, South Africa, and Australia. We would love to go to Peru to Machu Picchu and sidetrack to the Amazon rainforest.”