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.

July

Friday, 7/24 - Joe Nester, 5:00-7:30 pm

Saturday, 7/25 - Jason Ager, 12:00-4:00 pm

* Wheels & Wine Car Show

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

* Lobster & Bubbly

Friday, 7/31 - Pending, 5:00-7:30 pm

August

Saturday, 8/1 - Greg Jones, 2:00-5:00 pm

Sunday, 8/2 - Nicole Zell, 1:00-4:00 pm

Friday, 8/7 - Rick Caldwell, 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, 12:00-4:00pm

* Ferragosto

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

* Food Truck Pop Up: The Haven Social

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

* Lobster & Bubbly

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

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

* Food Truck Pop Up: The Haven Social

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

* Lobster & Bubbly

October

Friday, 10/2 - Jason Ager, 5:00-7:00pm

* Paws in the Vineyard

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

*25th Anniversary Party

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

*25th Anniversary Party

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

* Harvest Celebration

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

* Harvest Celebration

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

* Harvest Celebration

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

* Harvest Celebration

Saturday, 10/31 - Chris Despo, 12:00-4:00pm

* Halloweekend

November

Sunday, 11/1 -Adam McCue, 1:00-4:00pm

* Halloweekend

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.