Join us Friday from 3–7 PM as Anna Burgess brings her warm, soulful style to the vineyard. Sip something you love, take in the bay breeze, and settle into a beautiful spring evening outdoors.
#winetasting
Live Music! Steve & Victoria 1pm-4pm
Join us on Saturday, May 2 from 1–4 PM as Steve & Victoria bring their smooth harmonies and acoustic charm to the vineyard. Settle in with a glass of wine, enjoy the spring breeze, and spend a relaxing afternoon on the Shore.
Live Music! Nyte Jazz 4:30-7:30
Settle in for an evening of smooth, soulful jazz at Chesapeake Manor Vineyard. Nyte Jazz brings laid-back grooves and rich melodies to the vineyard — the perfect soundtrack for sipping wine, sharing a pinsa, and watching the sun set over Kent Island. Grab a glass, find your spot, and let the music carry the night.
Live Music! Justin Singleton @ Chesapeake Manor Vineyard
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.
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.
