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 vine 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.

Hours & Policies Reservations Events Menus Wine Club
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. Please refer to our Fleetwood Google Business page for holiday hours and special closures. Thank you for understanding.

Winery Hours

Monday | Closed
Tuesday | Closed
Wednesday | 3-8
Thursday | 3-8
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
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Reserve Your Space
Heading to Fleetwood with a group?

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

Make a Reservation Contact us
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.

Sign Up
Group seated at a large wooden table inside of Fleetwood Farm Winery in Leesburg, Virginia.
Events
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F45 Workout Class in the Meadow
Aug 15 | 10:00 am – 11:00 am
Start your Saturday with movement, fresh air, and beautiful views at Fleetwood Farm Winery! Join F45 for a complimentary outdoor workout in our Meadow, surrounded by lush gardens and vineyard […]
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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Benjamin Weimer
Jul 19 | 1:30 pm – 4:30 pm
Join us for an afternoon of live music with Benjamin Weimer, a talented and down-to-earth performer bringing an incredible mix of rock, pop, and country classics to life. From timeless hits by Johnny Cash and Tom Petty to favorites by Green Day and Lynyrd Skynyrd, Benjamin’s versatile repertoire has something for everyone. Grab a glass of wine, kick back, and enjoy an afternoon of great music in the relaxed ambiance of Fleetwood. Don’t miss it!
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Ryan Sill
Jul 25 | 1:30 pm – 4:30 pm
Spend your afternoon with Ryan Sill, a talented singer-songwriter and finalist from The Voice Season 7. Known for his smooth pop vocals blended with the soulful edge of blues and rock, Ryan brings a captivating performance to every stage. Currently producing his debut album, Ryan’s music is available on all streaming platforms. Don’t miss the chance to enjoy his incredible sound while sipping your favorite Fleetwood wines!
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Gary Smallwood Duo
Jul 26 | 1:30 pm – 4:30 pm
Join us for an afternoon with Gary Smallwood, a seasoned musician whose soulful, guitar-driven sound blends classic rock, blues, country, and funk. Performing professionally since age 16, Gary has shared the stage with legendary acts like Robin Trower, The Marshall Tucker Band, and Bret Michaels. With over 200 shows a year, his passion and talent shine through every performance, bringing decades of experience and a love for all styles of music to the stage. Don’t miss this incredible live show!
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Dan McGuire
Aug 1 | 1:30 pm – 4:30 pm
Dan McGuire is a talented guitarist, singer, and bandleader based in the Frederick, Maryland area, known for delivering engaging live performances at weddings, wineries, and corporate events throughout Virginia, Washington D.C., and Maryland. Whether performing solo acoustic sets or with the Dan McGuire Group, he brings an energetic mix of music spanning multiple decades and genres, creating the perfect atmosphere for any occasion. We’re excited to welcome Dan McGuire to Fleetwood and look forward to sharing his incredible live music with our guests!
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Shane Gamble Duo
Aug 2 | 1:30 pm – 4:30 pm
Join us for an afternoon of music with Shane Gamble, a Maryland native blending Country, Rock, Pop, and Americana into a sound that’s uniquely his own. With a career that includes a Top 10 single on SiriusXM’s The Highway and his acclaimed album American Heart, Shane’s music captures the essence of heartfelt storytelling and raw energy. Often compared to legends like Tom Petty and Bruce Springsteen with a modern twist, Shane’s performance is sure to leave an impression. Don’t miss this chance to experience his soulful voice and passionate guitar in the intimate setting of Fleetwood!
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Dan Gallagher
Aug 8 | 1:30 pm – 4:30 pm
Dan Gallagher is one of the most in-demand musicians in the DMV, known for his skill as a bassist, guitarist, and vocalist. With years of national touring, local performing, and studio work, he brings professionalism and talent to every stage—earning praise from collaborators, including Phil Kominski of Freestyle Events, who calls him “the epitome of a true, hard-working musician.” We look forward to welcoming Dan to Fleetwood for an afternoon of exceptional live music!
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Scott Kurt
Aug 9 | 1:30 pm – 4:30 pm
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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Laura Cashman
Aug 15 | 1:30 pm – 4:30 pm
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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Benjamin Weimer
Aug 16 | 1:30 pm – 4:30 pm
Join us for an afternoon of live music with Benjamin Weimer, a talented and down-to-earth performer bringing an incredible mix of rock, pop, and country classics to life. From timeless hits by Johnny Cash and Tom Petty to favorites by Green Day and Lynyrd Skynyrd, Benjamin’s versatile repertoire has something for everyone. Grab a glass of wine, kick back, and enjoy an afternoon of great music in the relaxed ambiance of Fleetwood. Don’t miss it!
event-category-2
Ryan Sill
Aug 22 | 1:30 pm – 4:30 pm
Spend your afternoon with Ryan Sill, a talented singer-songwriter and finalist from The Voice Season 7. Known for his smooth pop vocals blended with the soulful edge of blues and rock, Ryan brings a captivating performance to every stage. Currently producing his debut album, Ryan’s music is available on all streaming platforms. Don’t miss the chance to enjoy his incredible sound while sipping your favorite Fleetwood wines!
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 – July 24
Jul 24 | 6:30 pm – 8:30 pm
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Trivia – July 31
Jul 31 | 6:30 pm – 8:30 pm
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Trivia – August 7
Aug 7 | 6:30 pm – 8:30 pm
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Trivia – August 14
Aug 14 | 6:30 pm – 8:30 pm
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Trivia – August 21
Aug 21 | 6:30 pm – 8:30 pm
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Trivia – August 28
Aug 28 | 6:30 pm – 8:30 pm
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Trivia – September 4
Sep 4 | 6:30 pm – 8:30 pm
Two women seated on yoga mats in a field, representing winery events & classes available at Fleetwood Farm Winery in Leesburg, VA.
Wellness
event-category-6
F45 Workout Class in the Meadow
Aug 15 | 10:00 am – 11:00 am
Start your Saturday with movement, fresh air, and beautiful views at Fleetwood Farm Winery! Join F45 for a complimentary outdoor workout in our Meadow, surrounded by lush gardens and vineyard […]
Food + drink
MENUS
Our
offerings

In keeping with our mission to have something for everyone here, you’ll find delicious options for every palate and lifestyle – from our selection of premium local, regional, and global wines, even including non-alcoholic options, to our full menu that features traditional, gluten free, vegetarian, and vegan fare. And of course, they pair perfectly together.

A veggie flatbread on a wooden table at a Virginia winery with food near me.
Food
Locally Sourced, Locally Loved
VIEW MENU
Six bottles of Fleetwood Farm Winery wine lined in a row on a wooden barrel at an outdoor winery in Virginia.
Wine
Sip + Savor
VIEW MENU
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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, food, 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
  • 20% discount off wine cases (including events)
Want to learn more? Become a member and start taking advantage of the perks immediately! We’ll be in touch.
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Already a member? Click here to login.
An exterior side view of a manor house on the property of a winery wedding venue with gluten free food.

Every Sip
Has a Story

Learn about our story.

Our Story
Pink hydrangeas blooming at a garden winery & outdoor event venue in Loudoun County, Virginia.

Frequently Asked
Questions

For more information please visit our FAQ page.

Winery FAQ