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.

March

Saturday, March 14th - Chris Despo, 1:00-4:00 pm

Sunday, March 15th - Adam McCue, 1:00-4:00 pm

Sunday, March 29th - Brooke Dicaro, 11:00-3:00 pm

April

Saturday, April 4th - Ashley Sweetman, 11:00-3:00 pm

Saturday, April 25th - Greg Jones, 12:00-4:00 pm

Sunday, April 26th - Tim Williams, 12:00-4:00 pm

May

Saturday, May 2nd - Jason Ager, 2:00-5:00 pm

Sunday, May 3rd - Nicole Zell, 1:00-4:00 pm

Saturday, May 9th - Jeff Kessler, 12:00-4:00 pm

Sunday, May 10th - Adam McCue, 12:00-4:00 pm

Saturday, May 16th - Paul Wilkinson, 12:00-4:00 pm

Sunday, May 17th - Katelyn Christine, 12:00-4:00 pm

Saturday, May 23rd - Chris Despo, 2:00-5:00 pm

Sunday, May 24th - Bill Hake, 1:00-4:00 pm

Monday, May 25th - TBD, 1:00-4:00 pm

Saturday, May 30th - TBD, 12:00-4:00 pm

Sunday, May 31st - Greg Jones, 12:00-4:00 pm

June

Friday, June 5th - Chris Despo, 5:00-7:30 pm

Saturday, June 6th - Brooke DiCaro, 2:00-5:00 pm

Sunday, June 7th - Nicole Zell, 1:00-4:00 pm

Friday, June 12th - Joe Nester, 5:00-7:30 pm

Saturday, June 13th - Adam McCue, 2:00-5:00 pm

Sunday, June 14th - Bill Hake, 12:00-4:00 pm

Friday, June 19th - Ashley Sweetman, 5:00-7:30 pm

Saturday, June 20th - Bill Hake, 2:00-5:00 pm

Sunday, June 21st - Greg Jones, 1:00-4:00 pm

Friday, June 26th - Jason Ager, 5:00-7:30 pm

Saturday, June 27th - Chris Despo, 2:00-5:00 pm

Sunday, June 28th - Rick Caldwell, 1:00-4:00 pm

July

Friday, July 3rd - Joe Nester, 1:00-4:00 pm

Saturday, July 4th - Bill Hake, 2:00-5:00 pm

Sunday, July 5th - Nicole Zell, 1:00-4:00 pm

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

Saturday, July 11th - Adam McCue, 2:00-5:00 pm

Sunday, July 12th - Rick Caldwell, 1:00-4:00 pm

Friday, July 17th - TBD, 5:00-7:30 pm

Saturday, July 18th - Greg Jones, 12:00-4:00 pm

Sunday, July 19th - Brooke DiCaro, 1:00-4:00 pm

Saturday, July 25th - Jason Ager, 1:00-4:00 pm

Sunday, July 26th - Bill Hake, 1:00-4:00 pm

Friday, July 31st - TBD, 5:00-7:30 pm

August

Saturday, August 1st - Greg Jones, 12:00-4:00 pm

Sunday, August 2nd - Nicole Zell, 12:00-4:00 pm

Friday, August 7th - Chris Despo, 5:00-7:30 pm

Saturday, August 8th - Paul Wilkinson, 2:00-5:00 pm

Sunday, August 9th - Brooke Dicaro, 12:00-4:00 pm

Friday, August 14th - Adam McCue, 5:00-7:30 pm

Saturday, August 15th - Greg Jones, 2:00-5:00 pm

Sunday, August 16th - Rick Caldwell, 1:00-4:00 pm

Thursday, August 20th - TBD

Friday, August 21st - Ashley Sweetman, 5:00-7:30 pm

Saturday, August 22nd - Joe Nester, 2:00-5:00 pm

Sunday, August 23rd - Bill Hake, 1:00-4:00 pm

Friday, August 28th - TBD, 5:00-7:30 pm

Saturday, August 29th - Adam McCue, 2:00-5:00 pm

Sunday, August 30th - Chris Despo, 1:00-4:00 pm

September

Friday, September 4th - Brooke Dicaro, 5:00-7:00 pm

Saturday, September 5th - Jeff Kessler, 2:00-5:00 pm

Sunday, September 6th - Nicole Zell, 1:00-4:00 pm

Monday, September 7th - Jeff Kessler, 1:00-4:00 pm

Friday, September 11th - TBD, 5:00-7:00 pm

Saturday, September 12th - Bill Hake, 2:00-5:00 pm

Sunday, September 13th - Adam McCue, 1:00-4:00 pm

Friday, September 18th - Joe Nester, 5:00-7:00 pm

Saturday, September 19th - TBD, 2:00-5:00 pm

Sunday, September 20th - Ashley Sweetman, 1:00-4:00 pm

Friday, September 25th - Jason Ager, 5:00-7:00 pm

Saturday, September 26th - Chris Despo, 2:00-5:00 pm

Sunday, September 27th - Bill Hake, 1:00-4:00 pm

October

Saturday, October 3rd - TBD, 12:00-4:00 pm

Sunday, October 4th - Nicole Zell, 1:00-4:00 pm

Saturday, October 10th - Adam McCue, 2:00-5:00 pm

Sunday, October 11th - Greg Jones, 1:00-4:00 pm

Saturday, October 17th - TBD, 12:00-4:00 pm

Sunday, October 18th - Rick Caldwell, 1:00-4:00 pm

Saturday, October 24th - Jason Ager, 2:00-5:00 pm

Sunday, October 25th - TBD, 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.