Event calendar
Live Music feat. Matt Andrus
Friday May 29th
Start your weekend off the right way with live music from 5-8PM!
05:00 PM - 08:00 PM
Live Music feat. Mark Croft Band
Saturday May 30th
Mark and his crew are back at the winery from 3-6PM to ensure you are thoroughly entertained! With a glass of wine in hand and your foot tapping to the music you're sure to enjoy the day to the fullest!
03:00 PM - 06:00 PM
Live Music feat. Taylor & Von
Sunday May 31st
Closing out another weekend with one of the coolest duos around!? Sign us up - Taylor and Von are going to be rocking our stage from 2-5PM.
02:00 PM - 05:00 PM
National Cheese Day
Thursday June 4th
We love 'cheesy' holidays like this! Join us for National Cheese Day June 4th!
11:00 AM - 06:00 PM
Live Music feat. Too Sick Charlie
Friday June 5th
The drinks are cold, the music is live, and the weekend is here! Join us Friday from 5–8 PM for a fun night filled with great tunes and even better company. 🎸
05:00 PM - 08:00 PM
Live Music feat. John Masino Band
Saturday June 6th
Nothing says weekend like live music and your favorite drinks. Join us Saturday, June 6th from 3-6 PM for an afternoon of music, laughter, and good times! 🎸✨
03:00 PM - 06:00 PM
Live Music feat. Tapestry
Sunday June 7th
🎸 Sunday Funday Starts Here 🍷
Join us this Sunday from 2–5 PM for live music, delicious drinks, and laid-back vineyard vibes.
The perfect excuse to relax before the new week begins! ✨
02:00 PM - 05:00 PM
Live Music feat. Britton & Sarah Music
Friday June 12th
🎶 Friday Night Vibes
Nothing says weekend like live music and your favorite drinks. Join us Friday from 5–8 PM for a night of music, laughter, and good times! 🎸✨
05:00 PM - 08:00 PM
Live Music feat. Alpha Romeos
Saturday June 13th
🎸 Saturdays Are Better With Live Music 🎶
Join us Saturday, June 13th from 3–6 PM for an afternoon of live music, delicious drinks, and relaxing weekend vibes.
Kick back with your favorite wine or cocktail, enjoy great company, and let the music start your weekend off right! 🍷✨
03:00 PM - 06:00 PM
Live Music feat. Lake Collective
Sunday June 14th
🎶 Live Music Sunday, June 14th 🎶
Wrap up your weekend with us! Enjoy live music from 2–5 PM, your favorite wines, and a relaxing afternoon with friends and family. 🍷☀️
02:00 PM - 05:00 PM
Live Music feat. Markus J
Friday June 19th
🍷 Live Music Friday, June 19th 🎶
The drinks are cold, the music is live, and the weekend is here! Join us Friday from 5–8 PM for a fun night filled with great tunes and even better company. 🎸
05:00 PM - 08:00 PM
Live Music feat. Elizabeth Mary Band
Saturday June 20th
🎶 Saturday Music 🎶 Enjoy your weekend with us! Join us Saturday, June 20th from 3–6 PM for live music, great drinks, and the perfect Saturday afternoon atmosphere. Grab your friends, sip your favorite wine or cocktail, and enjoy a night of great tunes and good vibes. 🍷🎸
03:00 PM - 06:00 PM
Father's Day
Sunday June 21st
Treat your dad and join us for Father's Day! We're open 10-6PM with live music feat. Van Dwellers from 2-5PM.
10:00 AM - 06:00 PM
4th Of July
Saturday July 4th
We're open on the 4th so come celebrate with us!
10:00 AM - 09:00 PM
National Wine and Cheese Day
Saturday July 25th
Join us on National Wine & Cheese Day July 25th!
11:00 AM - 09:00 PM
National IPA Day
Thursday August 6th
Come grab a beer with us on National IPA Day!
11:00 AM - 06:00 PM
National Prosecco Day
Thursday August 13th
Start your night with some bubbly for National Prosecco Day!
11:00 AM - 06:00 PM
National Rum Day
Sunday August 16th
Join us on National Rum Day on August 16th!
11:00 AM - 06:00 PM
National Fajita Day
Tuesday August 18th
Come grab some sizzling goodness for National Fajita Day!
11:00 AM - 06:00 PM
National Whiskey Sour Day
Tuesday August 25th
It's National Whiskey Sour Day! Come down and let our awesome bartenders make you a great Whiskey Sour!
11:00 AM - 06:00 PM
National Red Wine Day
Friday August 28th
It's National Red Wine Day! Come enjoy a glass from our excellent selection!
11:00 AM - 09:00 PM
Live Music feat. Chasing Denver (TICKETS REQUIRED)
Sunday September 6th
Chasing denver is back with a splash from Fort Myers, FL! They will be playing from 3-6PM with Brian Matteson opening for them from 11-2PM! We highly encourage everyone to bring their own lawn chairs. No coolers are permitted and all backpacks will be checked as carry ins are not allowed.
https://baileysrunvineyard.ticketspice.com/chasing-denver-september-2026
03:00 PM - 06:00 PM
Grape Stomp 2026
Saturday September 12th
Join us for our 7th Annual Grape Stomp at Bailey's Run Vineyard & Winery on September 12, 2026!
Everyone who plans to stomp must pre-purchase tickets online. A team = 2 people; one who stomps the grapes and the other gathers juice. The team who produces a specific amount of juice the fastest will be the winner. The registration fee includes stomping competition, commemorative T-shirt per team member and 1 drink ticket good for a glass of wine or beer. Fastest teams then compete in the FINAL CRUSH. Winners of the FINAL CRUSH will receive a bottle of wine per team member.
Following all competitive stomping heats we will have:
- Best Team Costume Competition
We will also have one "Petite" heat where the teams consist of one adult and one child participant. The "Petite" heat will begin promptly at 11:00AM on the main stage with the adult heats starting right after the Petite's are done. We will have live music after the stomp from 3:00 - 6:00 PM.
** Any registrations after 8/15/26 will NOT be guaranteed a Grape Stomp T-shirt.
https://baileysrunvineyard.ticketspice.com/grape-stomp-2026
11:00 AM - 03:00 PM