ILIANDI- Live Music
Join us for an afternoon of live music with ILIANDI at Two Twisted Posts Winery! Enjoy their soulful vocals and acoustic favorites while you relax with award-winning wines, beautiful vineyard views, and great company.
Karaoke Michelle
Ready to take the mic? Join us for an afternoon of karaoke fun with Michelle at Two Twisted Posts Winery!
Open mic karaoke from 2–5 PM
Laid-back, family- and pet-friendly setting
Good times with great people!
Wine and Wigglebuts
Wine & Wigglebutts
A beloved annual event supporting Boykin Spaniel Rescue, inspired by our first winery dog, George, and the rescue pup who followed—Mojo. Since 2019, this dog-loving celebration has brought together wine, wagging tails, live music, food trucks, vendors, raffles, and silent auctions to raise funds for rescue dogs in need.
With help from local merchants, pet vendors, and the Boykin community, the event has raised $3,000–$6,500 each year through raffles, auctions, and merch—no ticket sales required. Past highlights include dog demos, fun games, and incredible grand prizes like wine-country getaways.
We’re excited about the possibility of bringing this meaningful, tail-wagging fundraiser back and continuing to support an amazing rescue that’s close to our hearts.
Jes Jams
Enjoy the piano and amazing voice of Jess Jams live from 2-5pm. You don’t want to miss this talented singer and songwriter.
Mark Cullinane
Spend the evening at Two Twisted Posts Winery with live music from Mark Cullinane! Enjoy his engaging acoustic performance featuring a mix of classic favorites and contemporary hits while you sip award-winning wines and relax among the vines.
TTP Wine Club Pick-up Party
Two Twisted Posts Wine Club Pick up
Come enjoy this months featured wines and barrel tasting with the winemaker
Please call to reserve your pick of time. RSVP Required.
1-1:40 pm
2-2:40 pm
TTP 2026 Ghostly Grapes 5K & 10K Trail Run/ Walk
5K &10K Trail Run /Walk/ Wine. Delight in this trail run along Short Hill Mountain and enjoy a glass of wine at the end. Register in advance for a discount.
Wine/ Food/ Beer/ Music/ Beautiful Views/ Costumes/ Prizes/ T-shirts and More!
We hope you can join us!
TTP Wine Club Pick-up Party
Two Twisted Posts Wine Club Pick up
Come enjoy this months featured wines and mini food pairing with the winemaker
Please call to reserve your pick of time. RSVP Required.
1-1:30 pm / 1:30- 2pm/ 2-2:30pm
Jason Frye
From 2–5 PM, enjoy live music by Jason Frye, a singer-songwriter with a truly unique and distinctive style all his own. Fun and soulful, Jason has been entertaining audiences throughout the Mid-Atlantic with his colorful lyrics and heartfelt delivery.
Brahman Noodles
Live music by Brahman Noodles playing blues funk! This improvisational acoustic jam style creates a laid-back yet high-energy atmosphere, full of rhythm, soul, and originality.
Live acoustic jams with funky, feel-good energy
Great Wine/ Snacks/ Beer/ Views
Live Music
There's no better way to spend an afternoon than with great wine and live music. Join us as we stay open late to enjoy local musicians, beautiful vineyard views, and a relaxing atmosphere perfect for gathering with friends and family. Whether you're enjoying a favorite vintage or discovering something new, live music makes every visit to Two Twisted Posts Winery even more memorable.
John Benjamin
Join us for an afternoon of live country music with John Benjamin! A Virginia-based touring artist, John brings authentic country sound, heartfelt originals, and crowd-favorite covers to every performance. Relax with a glass of wine, take in the vineyard views, and enjoy great music in a beautiful setting.
Peach Festival -Vendors, Music, Food, and More
Peach Festival at Two Twisted Posts Winery!
Celebrate summer with juicy peaches, refreshing peach sangria, and a day full of sweet vibes! Enjoy live music on the patio with the Blast Daddies Band, local vendors, delicious food, and family-friendly lawn games all afternoon.
Great music • Tasty bites • Peachy sips
Kids and pets welcome — bring the whole crew!
Sip, snack, and play your way through the perfect peachy day at the winery!
Karaoke Michelle
Ready to take the mic? Join us for an afternoon of karaoke fun with Michelle at Two Twisted Posts Winery!
Whether you're a seasoned performer or just in it for the laughs, this is your chance to show off your talent, sip some delicious Virginia wine, and enjoy a fun, relaxed vibe in the vineyard.
Open mic karaoke from 2–5 PM
Laid-back, family- and pet-friendly setting
Good times with great people!
Pride DrAG Celebration
Raise a final glass to Pride! Sip With Pride brings inclusive wineries, LGBTQ+ artists, drag and live performances together in one elegant day at Two Twisted Posts Winery. Join us to celebrate love, community, and creativity—sip thoughtfully, cheer loudly, and toast to a future where every person has a place. Drag Show and wine festival ticketed event: https://sip_with_pride.eventbrite.com
Father Day Celebration
Celebrate Dad! Bring your fishing pole and fish our pond, play some corn hole, hike our trail through Short Hill Mountain, and sit back and relax with a cold beer or a delicious glass of wine!
Jed Duvall as Sir Paul
Jed Duvall as Sir Paul McCartney – Live at Two Twisted Posts Winery from 2–5 PM for an unforgettable afternoon with Jed Duvall, the award-winning tribute artist whose spot-on recreations of music legends leave audiences amazed.
Enjoy great wine, timeless music, and a fantastic time in wine country!
$5 door charge – Reserve your spot now!
Wayne Snow
OPEN LATE- Grab Dinner from Between the Hills and join us for a soulful afternoon with Wayne Snow, a talented singer-songwriter whose smooth, heartfelt sound is sure to please every guest.
First Friday with Visit Loudoun
Live in Leesburg? Join us!
Enjoy a complimentary tasting from Two Twisted Posts Winery at the Visit Loudoun Visitor Center during Leesburg's First Friday.
Pride in the Vines
Pride in the VInes - Loudoun County
Celebrate love, community, and great wine with Pride in the Vines, Loudoun Wineries & Winegrowers Association’s month-long Pride Month passport experience in DC’s Wine Country®. Throughout the entire month of June, guests are invited to visit inclusive wineries across Loudoun County, collect passport stamps along the way, and toast to Pride and inclusivity. Earn stamps at participating wineries, and once you’ve collected 10 stamps, you’ll be entered into a raffle to win wine-related prizes from our winery partners.
We are OPEN -Memorial Day
Open all day today
Join us for a glass of wine, sit back and take in the surroundings and reflect.
TTP Wine Club Pick-up Party
Two Twisted Posts Wine Club Pick up
Come enjoy this months featured wines and vineyard tour with the grape grower
Please call to reserve your pick of time. RSVP Required.
1-1:30pm, 1:30-2pm, 2-2:30pm
Jim Steele
A splendid time is guaranteed for all!
Jim Steele grew up listening to a variety of musicians and genres that have played an influential role in shaping his signature sound.
For some, music is just a way to let out a little bitof energy, but for Jim it’s so much more than that– it’s a way of life. Bringing happiness and creating memories is what drives him.
Paint & Sip
Join us for Paint & Sip! Enjoy guided painting instruction, wine, and a beautiful scenic atmosphere. Click Purchase Tickets to view this month’s featured art. Posted 30days out.
2026 Winery 5K/10K Run
5K &10K Trail Run/ Walk along the base of Short Hill Mountain at the edge of our winery and enjoy a glass of wine at the end. Race event led by Bishops Events with a course made by fellow runners and winery owners. We are excited for this years expanded course and fun event planned. We hope you can join us!
Run/ Wine/ Music/ Food Truck/ Beer
Mother's Day Brunch
Mother’s Day Brunch
Celebrate Mom with a beautiful afternoon of wine, delicious food, and vineyard views
$65/pp Kids meal available
Reserve your spot -Space is limited
Karaoke Michelle
Ready to take the mic? Join us for an afternoon of karaoke fun with Michelle at Two Twisted Posts Winery!
Open mic karaoke from 2–5 PM
Laid-back, family- and pet-friendly setting
Good times with great people!
Kristin Eyerman
Live music with Kristin Eyerman
Join us with a fun keyboard performance live on the patio from 2-5 PM
Jason Frye
From 2–5 PM, enjoy live music by Jason Frye, a singer-songwriter with a truly unique and distinctive style all his own. Fun and soulful, Jason has been entertaining audiences throughout the Mid-Atlantic with his colorful lyrics and heartfelt delivery.
Paint & Sip
Join us for Paint & Sip! Enjoy guided painting instruction, wine, and a beautiful scenic atmosphere. Click Purchase Tickets to view this month’s featured art. Posted 30days out.
Ralph Baez
Join us at Two Twisted Posts Winery for a relaxing afternoon of smooth vibes and great wine!
Live music by Ralp Baez from 2–5 PM. His smooth, soulful sound sets the perfect tone to unwind, sip, and soak in the beauty of the vineyard.
Mo & Mary Mac
Join us from 2–5 PM for an afternoon of live music with Mo & Mary Mac, a popular and dynamic duo based in Virginia. Featuring pianist and singer Mo Safren alongside Mary Mac, they are known for their smooth harmonies, original songs, and high-energy performances.
Karaoke Michelle
Ready to take the mic? Join us for an afternoon of karaoke fun with Michelle at Two Twisted Posts Winery!
Open mic karaoke from 2–5 PM
Laid-back, family- and pet-friendly setting
Good times with great people!
The West Virginia Banshee
Live Music at Two Twisted Posts Winery
Join us for a special afternoon performance by The West Virginia Banshee, bringing a powerful, sweet, and savory voice straight from the hills of West Virginia. Blending notes of blues, rock, and folk, this is a set you won’t want to miss.
Time: 2–5 PM
Location: Two Twisted Posts Winery
Come relax, sip, and enjoy an unforgettable live music experience.
Easter Egg Hunt (Adults & Kids!) (Copy)
Join us at Two Twisted Posts Winery for a fun-filled Easter egg hunt for both kids and adults.
Hunt for colorful eggs across the grounds and keep an eye out for the Golden Egg, which comes with a special prize for the lucky finder.
Bring your baskets, your friends, and your festive spirit. It’s going to be a great day for everyone.
John Benjamin
John Benjamin
New album “Tenfold” on all streaming platforms under “John Benjamin Weimer”
Nashville Artist
Guided tasting with the winemaker
Taste the medal winners
Enjoy a guided tasting with the winemaker featuring our Governor’s Cup winning wines. Learn about the craft, the story, and the flavors that earned top honors.
Guided tasting with the winemaker
Taste the medal winners
Enjoy a guided tasting with the winemaker featuring our Governor’s Cup winning wines. Learn about the craft, the story, and the flavors that earned top honors.