2026 Live Music Schedule

We host live music on the lawn every SATURDAY & SUNDAY April-October as well as every FRIDAY June-September. Additionally, there are select weekday & special events during the winter months that also feature live music. All scheduled music is weather dependent.

May

Saturday, 5/9 - Joe Nester, 12:00-4:00 pm

Sunday, 5/10 - Adam McCue, 12:00-4:00 pm

Saturday, 5/16 - Paul Wilkinson, 12:00-4:00 pm

Sunday, 5/17 - Katelyn Christine, 12:00-4:00 pm

Saturday, 5/23 - Chris Despo, 2:00-5:00 pm

Sunday, 5/24 - Bill Hake, 1:00-4:00 pm

Monday, 5/25 - Rick Caldwell, 1:00-4:00 pm

Saturday, 5/30 - Joe Vandetty, 12:00-4:00 pm

Sunday, 5/31 - Greg Jones, 12:00-4:00 pm

June

Friday, 6/5 - Chris Despo, 5:00-7:30 pm

Saturday, 6/6 - Brooke DiCaro, 2:00-5:00 pm

Sunday, 6/7 - Nicole Zell, 1:00-4:00 pm

Friday, 6/12 - Joe Nester, 5:00-7:30 pm

Saturday, 6/13 - Adam McCue, 2:00-5:00 pm

Sunday, 6/14 - Bill Hake, 12:00-4:00 pm

Friday, 6/19 - Ashley Sweetman, 5:00-7:30 pm

Saturday, 6/20 - Bill Hake, 2:00-5:00 pm

Sunday, 6/21 - Greg Jones, 1:00-4:00 pm

Friday, 6/26 - Jason Ager, 5:00-7:30 pm

Saturday, 6/27 - Chris Despo, 2:00-5:00 pm

Sunday, 6/28 - Rick Caldwell, 1:00-4:00 pm

July

Friday, 7/3 - Joe Nester, 1:00-4:00 pm

Saturday, 7/4 - Bill Hake, 2:00-5:00 pm

Sunday, 7/5 - Nicole Zell, 1:00-4:00 pm

Friday, 7/10 - Paul Wilkinson, 5:00-7:30 pm

Saturday, 7/11 - Adam McCue, 2:00-5:00 pm

Sunday, 7/12 - Rick Caldwell, 1:00-4:00 pm

Friday, 7/17 - Joe Vandetty, 5:00-7:30 pm

Saturday, 7/18 - Greg Jones, 12:00-4:00 pm

Sunday, 7/19 - Brooke DiCaro, 1:00-4:00 pm

Saturday, 7/25 - Jason Ager, 1:00-4:00 pm

Sunday, 7/26 - Bill Hake, 1:00-4:00 pm

Friday, 7/31 - Chris Despo, 5:00-7:30 pm

August

Saturday, 8/1 - Greg Jones, 12:00-4:00 pm

Sunday, 8/2 - Nicole Zell, 12:00-4:00 pm

Friday, 8/7 - Chris Despo, 5:00-7:30 pm

Saturday, 8/8 - Paul Wilkinson, 2:00-5:00 pm

Sunday, 8/9 - Brooke Dicaro, 12:00-4:00 pm

Friday, 8/14 - Adam McCue, 5:00-7:30 pm

Saturday, 8/15 - Greg Jones, 2:00-5:00 pm

Sunday, 8/16 - Rick Caldwell, 1:00-4:00 pm

Friday, 8/21 - Ashley Sweetman, 5:00-7:30 pm

Saturday, 8/22 - Joe Nester, 2:00-5:00 pm

Sunday, 8/23 - Bill Hake, 1:00-4:00 pm

Friday, 8/28 - Rick Caldwell, 5:00-7:30 pm

Saturday, 8/29 - Adam McCue, 2:00-5:00 pm

Sunday, 8/30 - Chris Despo, 1:00-4:00 pm

September

Friday, 9/4 - Brooke Dicaro, 5:00-7:00 pm

Saturday, 9/5 - Joe Vandetty, 2:00-5:00 pm

Sunday, 9/6 - Nicole Zell, 1:00-4:00 pm

Monday, 9/7 - Allison Landon, 1:00-4:00 pm

Friday, 9/11 - TBD, 5:00-7:00 pm

Saturday, 9/12 - Bill Hake, 2:00-5:00 pm

Sunday, 9/13 - Adam McCue, 1:00-4:00 pm

Friday, 9/18 - Joe Nester, 5:00-7:00 pm

Saturday, 9/19 - TBD, 2:00-5:00 pm

Sunday, 9/20 - Ashley Sweetman, 1:00-4:00 pm

Friday, 9/25 - Jason Ager, 5:00-7:00 pm

Saturday, 9/26 - Chris Despo, 2:00-5:00 pm

Sunday, 9/27 - Bill Hake, 1:00-4:00 pm

October

Saturday, 10/3 - Ryan Laliberte, 12:00-4:00 pm

Sunday, 10/4 - Nicole Zell, 1:00-4:00 pm

Saturday, 10/10 - Adam McCue, 2:00-5:00 pm

Sunday, 10/11 - Greg Jones, 1:00-4:00 pm

Saturday, 10/17 - Joe Vandetty, 12:00-4:00 pm

Sunday, 10/18 - Rick Caldwell, 1:00-4:00 pm

Saturday, 10/24 - Jason Ager, 2:00-5:00 pm

Sunday, 10/25 - Allison Landon, 12:00-4:00 pm

November

No music scheduled at this time

December

No music scheduled at this time

We are open to new talent on a limited basis as we generally work with a select group of local professional musicians. If you are interested in performing as part of our Live Music on the Lawn series, please note that inquiries can be made via email to our Event Coordinator Kait@pennswoodswinery.com. Please include a link to where we can view past performances as well as your availability. We will reach out if we have a date available & feel the you are a good fit.