Fleetwood Farm Leesburg VA Wedding

Rachel and Steven’s wedding weekend at Fleetwood Farm Winery celebrated love, family, and jaw-dropping design. Their love story began during the pandemic, flourished around their shared passions for athletics and ambition, and culminated in an extraordinary 3-day wedding celebration at Fleetwood Farm Winery.

As fate would have it, after embarking on a global quest to find the perfect black diamond engagement ring, Steven learned that the ring would be delivered on a day of profound significance: the anniversary of Rachel’s adoption into her family. In a beautiful gesture, Steven discarded his original proposal plans and seized the opportunity to commemorate this special date by getting down on one knee with Rachel’s horse, Gameboy, standing witness. As an added homage to her adoption date, the couple then decided to plan their wedding for the same weekend, one year later.

Drawing inspiration from Rachel’s black diamond ring and the couple’s shared love for modern design and horses, Jessica Ashley Events blended clean lines, sleek aesthetics, and equestrian charm to create a brilliant fusion of rustic-chic elegance. Highlights included a roaring twenties-inspired welcome dinner, a horse competition ring branding and escort display, custom acrylic signage, stacked china tablescapes of marble and monochrome, hand-painted marble bar insets, a champagne dress performer, and surreal floral installations by Darling and Daughters. The full weekend of events concluded with a luxury biscuit truck send-off.