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.
The Rehearsal Dinner
The Wedding Day
The Farewell Brunch
Vendor Credits:
Photography: Molly Lichten Photography
Venue: Fleetwood Farm Winery
Planning & Design: Jessica Ashley Events
Florals: Darling and Daughters
Hair & Makeup: MAB Artistry
Stationary: Emily Baird Design
Gown: Ava Laurenne Bride
Shoes: Bella Belle Shoes
Bridesmaids Dresses: Azazie
Groom’s Tux: Emporio Armani
Rentals: Something Vintage, Maison de Carine, BBJ La Tavola, Select Event Group, DC Event Rentals, Blissful Design and Decor
Custom Bar Inserts: Lindale Studios
Drapery: Fabrication Events DC
Champagne Dress: Tip Top Tap Truck
Catering: Design Cuisine
Cake: Fluffy Thoughts Cakes
DJ: Dan Goldman Events
Officiant: Ceremony Officiants
Trees: Plants Alive
Transportation: Dulles Limousine
Food Truck: Biscuit Batch
Featured in The Knot print in the Winter 2024 National Edition
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Explore More Virginia Wedding Venues
If you’re still searching for the perfect Virginia wedding venue, I’ve put together a guide featuring some of my favorite venues throughout Charlottesville, Northern Virginia, and beyond.
→ Best Virginia Wedding Venues for Timeless Celebrations
If you love the idea of a Virginia vineyard or countryside wedding, you may also enjoy:
→ Pippin Hill Farm & Vineyards wedding in Charlottesville, Virginia
→ Stone Tower Winery wedding in Leesburg, Virginia
→ Early Mountain Vineyards wedding in Virginia wine country
→ Great Marsh Estate wedding venue in Virginia
Planning Your Fleetwood Farm Winery Wedding
Fleetwood Farm Winery is a beautiful choice for couples dreaming of a Virginia wedding that blends vineyard charm with a refined, personalized experience. With its scenic landscapes, elegant spaces, and welcoming atmosphere, the venue offers endless possibilities for celebrations that feel both elevated and true to each couple.
If you’re planning your Fleetwood Farm Winery wedding, I’d love to hear what you’re envisioning!

















































































