Come for the
wine
Stay for the
experience
A stone walkway surrounded by nature at an outdoor winery in Leesburg, Virginia.
A hand with a watch pouring a glass of red wine into a stem glass at a Leesburg, Virginia winery wedding venue.
An exterior view of Fleetwood Farm Winery's front entrance from hydrangea plants on the property.

The Vineyard

Come soak in the sunshine on the expansive lawn. Sip fireside in the tasting room. Stroll the gardens at any time of year. Indulge in fresh, seasonal fare on the Grand Terrace. We created Fleetwood to share a phenomenal selection of wine in a space where everyone feels relaxed and well cared for.

FLEETWOOD’S HOURS & POLICIES
Plan
Your Visit in Advance

Much deliberation, time, and energy has gone into cultivating a space that inspires serenity and relaxation. Our team works hard to preserve our pristine gardens and beautiful setting so you can come and enjoy it. Because of this, Fleetwood Farm Winery is a 21 and over space Wednesday through Saturday. Children are welcome on Sundays. Thank you for understanding.

Winery Hours

Monday | Closed
Tuesday | Closed
Wednesday | Closed
Thursday | Closed
Friday 12-9
Saturday 11-8
Sunday 11-6

A bottle of pinot noir rested next to two wine glasses and a charcuterie board at a Leesburg winery with food.
21+ only l Except Sundays

While we ask that all guests are 21 and over during the week, children are welcome on Sundays. We look forward to welcoming the whole family.

Blonde woman in a hat walking through a stone archway at Fleetwood Farm Winery, an indoor-outdoor wedding venue & winery in Leesburg, VA.
No outside food or drink, please.
(Exceptions made for celebratory desserts.)

We think you’ll be surprised by all we have to offer here! Our food menu features an ample selection of seasonal fare, with delightful options for every palate and dietary/allergic restriction. Our expansive wine collection also includes hard cider and non-alcoholic options.

A flight of six different wines lined up on a board next to a flatbread pizza at a winery with live music in Loudoun County, Virginia.

For more answers to commonly asked questions, please visit our FAQ section.

FAQs
RESERVATIONS
Three women seated at an outdoor patio area at an outdoor winery with food near Ashburn, Virginia.
Reserve Your Space
Heading to Fleetwood with a group?

We’re happy to set aside tables for your group, whatever the size. Please reach out to reserve your space and we’ll determine how we can best help.

EVENTS
Live Music, Trivia and More

There’s always something happening at Fleetwood, from live music and Friday night trivia to wine club gatherings, seasonal menus, and special events. Come explore the beautiful grounds, visit the historic Manor House, and experience all that Fleetwood has to offer.

Join our newsletter and you’ll be the first to know what’s happening among the garden and grapes.

Group seated at a large wooden table inside of Fleetwood Farm Winery in Leesburg, Virginia.
Events
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Galentine’s Night at Fleetwood
Girls just wanna have fun! Grab your girls and join us at Fleetwood for a Galentine’s Night with @yourlocalbestiesdc and influencer Mai Tang on February 13th from 6-9PM! Featuring women-owned […]
An exterior view of a historic manor house that is highlighted in Fleetwood Farm Winery's historic winery tours.
Family Days
Family Days Coming Soon
A band playing live music at Fleetwood Farm Winery in Leesburg, Virginia.
Live Music
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Luke Andrews
Spend your afternoon unwinding with Luke Andrews, whose versatile setlist offers a little something for everyone. Enjoy a blend of country, folk, indie, Americana, blues, jazz, and soft classic rock—all delivered with a cozy, coffeehouse vibe. Pair the music with your favorite Fleetwood wine and make it a relaxing day to remember!
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David Goodrum
Join us for an afternoon of music with Dave Goodrum, a Leesburg-based solo acoustic artist performing hits from the ’70s to today. Blending rock, blues, funk, pop, and more, Dave brings a fresh mix of favorites from John Mayer to Johnny Cash, plus creative mashups and deep cuts that keep every set unique. You won’t want to miss this great live performance!
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Dan Barry
Dan Barry is a singer-songwriter who blends rock, jazz, folk, and soul into a sound that’s entirely his own. His live performances guide listeners through both familiar favorites and deeper cuts, all highlighted by his percussive guitar style and impressive vocal range. Dan’s dynamic sound will set the perfect tone for a relaxing day at Fleetwood!
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Lindsay Austin Duo
Spend your afternoon with the Lindsay Austin Duo, bringing their signature blend of acoustic charm and smooth harmonies to Fleetwood. Perfect for a laid-back day with great wine, their performance offers an enjoyable mix of songs to set the mood. Relax, unwind, and let their music be the perfect backdrop to your weekend!
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Laura Cashman
Join us for an unforgettable afternoon with Laura Cashman, a powerhouse vocalist and Best of Loudoun 2024 Finalist! Known for her unmatched energy and crowd engagement, Laura brings a wide-ranging setlist of hits from the 70s to today, along with a few original songs. With her dynamic performances and acoustic guitar, Laura creates a fun, entertaining, and memorable experience. Don’t miss the chance to enjoy her incredible talent while sipping your favorite Fleetwood wines!
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Grayson Moon
Grayson Moon, a talented singer-songwriter blending soulful vocals with contemporary guitar and electronic vibes. Drawing inspiration from legends like Sam Cooke and Elvis Presley, Grayson creates a unique Indie-Soul experience that’s sure to captivate. With a background in classical voice and a passion for genre-blending soundscapes, Grayson has become a crowd favorite on stages across the East Coast. Don’t miss this opportunity to enjoy his soulful artistry in Fleetwood’s enchanting setting!
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Zach Jones
Zach Jones is a Northern Virginia–based musician known for his versatile solo acoustic sets. His performances blend classics and modern favorites—from The Beatles and Neil Young to John Mayer, Dave Matthews Band, The Black Keys, Noah Kahan, and more—plus a few original songs. A regular performer at local breweries, wineries, and private events, Zach brings an engaging acoustic sound wherever he plays. We’re excited to welcome him to Fleetwood!
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Scott Kurt
Scott Kurt brings a unique blend of Southern grit and Rust Belt rock to his signature country sound. Influenced by artists like Eric Church, Jon Pardi, Luke Combs, and Tom Petty, he delivers authentic, guitar-driven performances rooted in strong storytelling—evident in his single “American Man,” which reached the iTunes Country Top 40. His hard work and talent have earned him opening slots for major country acts including Cole Swindell, Montgomery Gentry, Jimmie Allen, Eli Young Band, Kip Moore, and Easton Corbin. Scott’s powerful mix of country and rock is the perfect fit for a great day at Fleetwood!
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David Thong
David is a seasoned DC-area musician who has been performing since age nine. Known for his versatility, he blends influences from pop, rock, reggae, hip-hop, and indie, and has played everything from vocals and rhythm guitar to drums, bass, and keys. He’s currently working on his solo debut Doux-Amer with Nathon Haddon of Haddon Records and also founded the nostalgic alternative rock DJ series Back To The 90s. David has shared the stage with artists like Weezer, Ryan Cabrera, Ash, Ballyhoo!, and Ozma, and has performed at major venues including Nationals Park, The Fillmore, Union Stage, and Jammin’ Java. Come enjoy a great afternoon of live music with David at Fleetwood!
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Shane Hines
Join us for an incredible live performance with Shane Hines, a powerhouse singer-songwriter and producer whose music bridges pop, rock, country, and Americana. With years of experience writing and producing alongside top Nashville talent, Shane brings grit, honesty, and emotion to every song. A John Lennon Songwriting Contest finalist and acclaimed performer, his sound blends heartfelt lyrics with polished musicianship. Get ready for an unforgettable afternoon of live music!
A close-up of a Fleetwood Farm Winery employee pouring a glass of wine.
Tastings & Classes
Tastings & Classes Coming Soon
A smiling, excited representative of Barton Smart Trivia, representing trivia night events at Fleetwood Farm Winery in Leesburg, VA.
Trivia Night
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Trivia – February 20
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Trivia – February 27
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Trivia – March 6
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Trivia – March 13
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Trivia – March 20
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Trivia – March 27
Two women seated on yoga mats in a field, representing winery events & classes available at Fleetwood Farm Winery in Leesburg, VA.
Wellness
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Sip & Surrender Sound Bath Experience
Join us at Fleetwood Farm Winery for a 60-minute immersive sound bath, followed by a refreshing glass of wine of your choosing as we honor renewal and intention for the […]
Food + drink
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Join the Club!

Fleetwood Wine Club members get special access to the new wines we release each quarter, discounts on wine, exclusive early access to private ticketed events, and other membership rewards.

Members receive:
  • Four bottles of wine per quarter at 15% off retail value
  • 15% discount on wine and retail purchases
  • Advanced notification, access and discounts for ticketed Fleetwood events
  • Private quarterly wine pick-up events with tastings and food
  • Complimentary glass of wine for you and a guest every visit
Want to learn more? Become a member and start taking advantage of the perks immediately! We’ll be in touch.
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