Alyssa moved to Virginia in 2009 to work as a nurse in trauma medicine. Ben was working as Flight Paramedic and Police Officer in Fairfax, Virginia. Alyssa met Ben on a ride along in the helicopter, and the two hit it off.

In 2012, the pair were married at Holland Lake, in the Swan Valley, Montana, and a year later landed in Bozeman, Montana. On the way to Bozeman they picked up their first baby, a German Shepherd puppy who they named Hilo after the location closest to where Ben proposed to Alyssa. Medicine was still the main practice of both; Alyssa working in the ICU, and Ben pursuing a Post Baccalaureate in Pre-medicine.

In 2014, Alyssa and Ben planned to travel. They traveled to Ireland, Italy and New Zealand. In Italy, they tasted amazing wines and in New Zealand they worked for room and board on a vineyard. This is where the dream to grow cold hardy grapes in Montana was born.

In 2017, they welcomed their first baby and three weeks later planted their first vines in their vineyard. In 2019, they welcomed their second baby, finished planting their vineyard and made their first harvest.

Flathead River Vineyard is currently one acre under vine located in Dixon, Montana. The cultivars include two varieties of white grapes: Itasca and La Crescent, and two varieties of red grapes: Crimson Pearl and Frontenac.

Ben and Alyssa started making wine in 2016, and built their winery next to their vineyard. They named it Watchdog Winery after their watchdog, Hilo. She continues to watch everything that happens on and around the vineyard and winery.