Ease into the evening with the easygoing acoustic sound of Justin Singleton. From 4:30–7:30 PM, sip your favorite wines, unwind on the lawn, and enjoy a laid‑back spring night at Chesapeake Manor Vineyard.
#winetasting
Live Music! Michael Waskey @ Chesapeake Manor Vineyard
Kick off your weekend with Michael Waskey live at the vineyard on April 24, 4–7 PM. His mix of originals and crowd‑pleasing covers creates the perfect backdrop for wine, sunshine, and Friday vibes.
Live Music! Chris Sacks @ Chesapeake Manor Vineyard
Experience a beautiful spring Sunday at Chesapeake Manor Vineyard as Chris Sacks performs from 1–5 PM. His warm, coastal style pairs perfectly with vineyard views and a relaxing day of wine.
Live Music! Shredded Cheddar @ Chesapeake Manor Vineyard
Spend your Saturday afternoon at Chesapeake Manor Vineyard with live music from Shredded Cheddar on April 18 from 2–6 PM. Their upbeat acoustic‑rock style pairs perfectly with spring weather, handcrafted wines, and our relaxed Eastern Shore atmosphere.
Live Music! Michael K @ Chesapeake Manor Vineyard
Join us on Saturday, April 4th from 2–6 PM for live music with Michael K, an award‑winning songwriter known for his dynamic performances and rich musical style. When he’s not rockin’ with the band, Michael brings the same energy and talent to his solo and duo shows—including his popular collaborations with Todd Kreuzburg. Settle in with a glass of wine and enjoy an afternoon of great music at the vineyard.
Live Music! Daphne Eckman at Chesapeake Manor Vineyard
Experience an intimate performance by Daphne Eckman on Friday, April 3rd from 4–6 PM. Her expressive voice and thoughtful lyrics create a warm, atmospheric set that feels right at home among the vines. Sip, savor, and enjoy a beautifully crafted musical evening.
