June 2025
It’s Blueberry Season!
June, July, & August
Enjoy delicious blueberry specials in the tasting room all summer including our seasonal Blueberry Wheat Ale, Blueberry Cider, Blueberry Lemonade Wine Slushies as well as menu items highlighting this favorite fruit including our popular Blueberry Flatbread, Baked Brie, & more! We’ve teamed up with SugarBear Ice Cream again this year to bring back the fan favorite, Blueberry Sunshine, lemon ice cream swirled with blueberry coulis! It’s a sweet treat you won’t want to miss this summer!
Virginia Oyster & Wine Celebration
Every Friday
Kick off the weekend with us! Just 5 miles from the Downtown Mall, join us for a celebration of Virginia oysters and wine every Friday night this season.
Pair your oysters with a glass of sparkling Blanc de Blancs or enjoy our many other food options paired with a variety of gold medal winning wines. We also offer juice flights and cheese boards for the kids. There is something for the whole family at Eastwood.
Live Music
June 6: John Kelly
June 13: Eli Cook
June 20: Liz Barnes Trio
June 27: Matthew O’Donnell
July 4: Matthew O’Donnell
July 11: Eli Cook
July 18: FarAway
July 25: Matthew O’Donnell
Reservations are not needed to visit the winery. Join us for oysters, wine, and live music Friday evenings!
Eastwood After Dark
Every Saturday
Join us for upbeat & fun bands every Saturday night! Gather your friends and family and join us for live music that you’ll want to dance to! Or sit back and enjoy your favorite beverage and delicious food.
Live Music
June 21: Cake Fight
June 28: Tara Mills Band
July 5: Kat & The Travelers
July 12: Stillhouse Sound
July 19: Jackson, Pendergrass, & Townsend
July 26: Blue Healer
Reservations are not needed!
Paint & Sip
Wednesday, June 11 & Sunday, June 29
Grab a glass of wine (or your favorite drink!) and let your creativity flow in our relaxed and fun Paint & Sip class. Whether you’re an experienced artist or a first-time painter, the talented instructors of Blue Ridge Brushes will walk you through the painting process as you create your own masterpiece. Enjoy a welcoming environment where you can laugh, relax, and let the brush strokes come naturally. Sip and unwind with friends or meet new ones. No experience needed—just a passion for creativity and a desire to have a good time!
Join us for a memorable evening of art, drinks, great food, and good vibes. You’ll leave with a beautiful painting to take home and a great experience to remember!
Father’s Day Market + Live Music
Sunday, June 15th
Looking for the perfect way to spend Father’s Day? Join us at Eastwood for a festive afternoon filled with local flavor, live music, and fun for the whole family!
Father’s Day Market | 12:00 PM – 5:00 PM
Explore a vibrant selection of handcrafted goods and artisan products from local makers. It’s a great opportunity to find something special — for Dad or yourself!
Live Music | 1:00 PM – 4:00 PM
Enjoy lively entertainment from the talented Matthew O’Donnell, bringing high-energy tunes and a great atmosphere for all ages.
Bring Dad, bring the kids — and make some memories together at Eastwood this Father’s Day. We look forward to celebrating with you!
Juneteenth Celebration
Thursday, June 19
Celebrate Juneteenth with a special wine & ice cream tasting along with live music all day! Curious about Juneteenth food traditions? Looking for a unique way to honor the day? Join Black Women Who Wine and SugarBear Ice Cream at Eastwood on Thursday, June 19.
Location: The Veranda Bar at Eastwood
Time: Pairings available from 12:00 PM to 3:00 PM
Live Musical Performances
Jen Tal & Jamal Millner Duo | 12:00 PM – 3:00 PM
Meisha Herron | 5:00 PM – 8:00 PM
Wine & Ice Cream Pairing
SugarBear Cherries Jubilee Ice Cream
Zora Chloe 2023 Dark Fruit
A robust dry red blend of Merlot and Petit Verdot
We’re open until 8 PM!
Enjoy our full menu all day, including bottles of Zora Chloe 2023 Dark Fruit.
SugarBear Ice Cream available while supplies last!
Come for the wine & ice cream, stay for the music, community, and meaningful celebration of Juneteenth. See you there!
Live Music & Music Bingo
Thursday – Sunday Every Week
Join us for the popular Eastwood After Dark featuring upbeat, danceable music on Saturday nights from 5-8pm (in addition to our more mellow Saturday afternoon music program). Eastwood also hosts a range of live performances by talented local and regional musicians every Thursday and Friday night and many Sundays. See Winery Calendar For Details