Join Two Twisted Posts Winery and Bishop’s Events for our annual 5K/ 10K, Trail Run/ Walk/ Wine Halloween vineyard race benefiting Boykin Spaniel Rescue! Enjoy rolling hills, Short Hill Mountain views, and Halloween props along the course. Wear a costume for a chance to win a fun prize!

Bring friends and family, then stay for Acoustic Soul, live from 11 AM–2 PM, plus beer and wine.

How to register: Visit our Race Roster registration page, click Register.

Wine/ Food/ Beer/ Music/ Beautiful Views/ Costumes/ Prizes/ T-shirts and More!

We hope you can join us!

https://raceroster.com/events/2026/117507/ghostly-grapes-5k-and-10k-at-two-twisted-posts

Join us at Two Twisted Posts Winery for an electrifying live performance by GianPalomo!

Born from the high-octane roots of Twisted Flags, this raw acoustic duo—Gianpiero on guitar and Paloma on vocals—brings the fire with a sound that fuses AC/DC grit and Stevie Wonder soul.

Great wine • Killer music • Beautiful wine country

Dean Kern Live at Two Twisted Posts Winery
2–5 PM | Farm Tour Fun

Make Two Twisted Posts part of your Farm Tour plans! Join us for great wine and live music with Dean Kern, a talented musician whose love of Go-Go, Soul, Funk, Blues, and Rock shines through in every performance.

Take a break from exploring, settle in with your favorite glass, and enjoy an afternoon of music in wine country.

Come for the Farm Tour, stay for the wine and music!.

Live Music & Bold Flavors at Two Twisted Posts Winery!

Todd Brooks bringing smooth country vibes and heartfelt tunes to the vineyard. 5-8pm

Order from Between the Hills Catering and have it delivered to your seat! Enjoy wine, music and delicious food.

• Menu Link: https://www.betweenthehillsevents.com/

Celebrate National Coming Out Day! Today we celebrate love, acceptance and the courage it takes to be true to oneself. Whether you’re coming out at LGBTQ+ or showing support for loves ones, this day is a reminder that everyone deserves to live authentically and be embraced for who they are. We will have a DJ, unforgettable dance party and Drag Show.

Special Drag Performance | 2–5 PM

$10 entry at the door
Sip on our finest Virginia wines while enjoying vibrant performances and a warm, inclusive atmosphere.

Whether you're out, coming out, or simply standing proud in support – this event is for YOU. Let’s toast to authenticity, community, and living life out loud.

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!

Spend the afternoon 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.

Paint & Sip 1-3pm

Sign up now for this fun event with paint instruction, wine, beer, and a beautiful scenery. Click on purchase tickets to reserve your spot now.

Join us at Two Twisted Posts Winery for an electrifying live performance by GianPalomo!

Born from the high-octane roots of Twisted Flags, this raw acoustic duo—Gianpiero on guitar and Paloma on vocals—brings the fire with a sound that fuses AC/DC grit and Stevie Wonder soul.

Great wine • Killer music • Beautiful wine country

Talented singer and songwriter. Join us from 2-5 for great music, great vibes, great wine and a great time.

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.

Jed Duvall as JED- Get ready to shake, rattle, and roll with Jed Duvall—one of the region’s premier tribute artists!

Great music, amazing food, and an unforgettable experience — bring your friends and enjoy the show!

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!

Join us Saturday from 2–5 PM for an afternoon of timeless tunes with Will Shepard — a talented singer-songwriter known for his soulful renditions of classic favorites. Relax with a glass of wine and enjoy the rich, live sounds of one of the area's finest musical talents.

Don’t miss it — great wine, great music, and great vibes await.

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

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.

Enjoy the piano and amazing voice of Jess Jams live from 2-5pm. You don’t want to miss this talented singer and songwriter.

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.

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!

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.

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.

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

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.

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 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!

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!

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

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 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!

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.