Upcoming Events
Events
Calendar of Events
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Friday
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Saturday
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Sunday
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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.
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Parker Barrow, the blues-infused Southern rock band led by husband and wife duo Megan Kane (vocals) and Dylan Turner (drums), supported by the formidable Alex Bender (guitar), and band Will Tipton (Guitar), Kyle Priber (Bass), & Eric Safka (Keys), is a powerhouse group, taking the stage by storm – boasting a distinctive musical style. Forged […]
$10
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2 events,
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Kick off your Saturday with Steve & Victoria live at Chesapeake Manor Vineyard on May 2, 1–4 PM. Their blend of acoustic favorites and soulful vocals pairs perfectly with good wine, good company, and a beautiful spring day.
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Sip through our lineup, relax into the sunset, and enjoy the perfect pairing of wine and music. |
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Join us for a relaxed wine‑tasting afternoon with live music by PJ & Neal on Sunday, May 3, 1–5 PM. |
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PRESSING STRINGS Hailing from Annapolis, Maryland, Pressing Strings is a powerhouse trio–led by guitarist and vocalist Jordan Sokel–has earned a loyal following with their genre bending blend of blues, rock, and folk, wrapped in soul-stirring storytelling and toe tapping grooves. Their music resonates with the emotional grit of blues, the laid back swagger of folk, […]
$20
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1 event,
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In 2026, The Wailers celebrate the 50th anniversary of Rastaman Vibration, one of Bob Marley & The Wailers’ most influential albums. The 50 Years of Positive Vibrations tour honors this landmark release with select cuts alongside the timeless classics that continue to unite generations. Released in 1976, Rastaman Vibration carried reggae’s message of resistance, spirituality, […]
$45
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Ease into the weekend with a glass in hand as Anna Burgess brings her soulful acoustic sound to the vineyard this Friday from 3–7 PM. |
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Celebrate the past and future of Kent Island on Kent Island Day - Saturday, May 16th! Join us in the center of Historic Stevensville for a vibrant celebration of our community heritage. From 10 a.m. to 4 p.m., the streets come alive with local artisans, unique vendors, delicious food, live music, and a community parade. […]
Free
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Spend your Saturday afternoon with a glass in hand as Bobby Hensley brings his smooth acoustic sound to the vineyard from 2–6 PM. Settle into your favorite pour, explore a new flight, and enjoy an easy, wine‑soaked afternoon surrounded by good music and great company.
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Spend your Saturday afternoon with a glass in hand as Bobby Hensley brings his smooth acoustic sound to the vineyard from 2–6 PM. Settle into your favorite pour, explore a new flight, and enjoy an easy, wine‑soaked afternoon surrounded by good music and great company. |
1 event,
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Spend your Sunday afternoon relaxing at the vineyard with Michael Waskey and his easygoing acoustic sound from 1:30–5 PM. Settle in with a glass of your favorite pour, enjoy the breeze off the bay, and unwind with a slow, scenic day of wine, music, and good company. |
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Ease into the weekend with live music from Alex Peters this Friday from 4–7 PM. His smooth acoustic style pairs perfectly with a glass of wine and a relaxed afternoon at the vineyard.
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THE PHOENIX WITHIN (NYC, USA) The Phoenix Within is an independent NYC-based alternative prog-rock band, that incorporates diverse elements and styles of rock into their boundless heavy soundscape. The band is fronted by Omar Feliciano and is backed by Nick Narlis on bass guitar, John Narlis on guitar, and drummers James Narlis and Steve Khan. […]
$12
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3 events,
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Join us Saturday from 1–4 PM as Guava Jelly brings warm, rhythmic energy to the vineyard. Sip your favorite pour and enjoy a laid‑back afternoon surrounded by music and bay‑breeze views.
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Kick off your Saturday night with Justin Singleton live from 4:30–7:30 PM. Expect a mix of favorites and originals, perfect for sipping, snacking, and easing into the evening.
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Brickyard Road has their sights set on being the best Lynyrd Skynyrd Tribute in the world. Now, after Twenty-Five years and over a dozen talented players contributing to the success the band has achieved, we’re glad to say our current lineup is the best we’ve ever had y’all! Our band leader Rob says, “This is […]
$15
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Enjoy a slow, scenic Sunday with Justin Ryan live from 1:30–4:30 PM. Pair the music with your favorite pour and take in a peaceful afternoon surrounded by vineyard views. |
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Kick off your Friday with Dave & Ginger performing live from 3–7 PM. Settle in with your favorite pour and enjoy a fun, feel‑good mix of classics and crowd favorites.
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EMO Prom is a full-on throwback dance party celebrating the angst, anthems, and eyeliner-soaked bangers of the early-2000s emo era, performed live by EMOtional Support. Known for high-energy, crowd-driven shows that turn the entire room into a sing-along, EMOtional Support brings the emotion, nostalgia, and chaos that made these songs unforgettable. Dress to impress in […]
$10
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Join us Saturday from 1:30–5:30 PM as Michael Miller brings a lively mix of favorites and originals to the vineyard. A perfect soundtrack for sipping, snacking, and easing into the weekend. |
1 event,
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Spend your Sunday afternoon with the Chesapeake Sons Duo, performing live from 1:30–4:30 PM. Settle in with a glass, enjoy the breeze, and unwind with an acoustic set rooted in local Eastern Shore charm. |