October 2026
Fall at Eastwood
October is the perfect time to gather at Eastwood as we celebrate Virginia Wine Month and all the magic of fall! From cozy Porch Nights and our weekly Virginia Oyster & Wine Celebrations to Music Bingo, Paint & Sip, and one unforgettable Harvest Party weekend, there’s something for everyone to enjoy. Join us on Halloween and get into the spooky spirit with family-friendly fun and a special Halloween edition of Eastwood After Dark. Come raise a glass, enjoy the season, and make October memories with us!
Harvest Party Oyster Roast
Saturday, October 17
Harvest Party Market & Fall Family Day
Sunday, October 18
Paint & Sip
Sunday, October 25
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!
Halloween at Eastwood
Saturday, October 31
Porch Nights at Eastwood
Every Thursday
There’s something about a porch at golden hour that makes the world slow down in the best possible way. At Eastwood Farm and Winery, we’re leaning into that feeling all season long with Porch Nights — our weekly Thursday gathering featuring outdoor live music and an easygoing atmosphere. Grab a seat on our covered veranda or at one of our many picnic tables, relax with the sparkly lights overhead, fireflies in the fields, and a glass of porch-sipping wine in hand – join us for your new favorite Thursday tradition.
Live Music
October 1: Solo Steve
October 8: Sharif
October 15: Michael Clem
October 22: Ty Burkhardt
October 29: Michael Bergamo
Bring the family, the dog, a few friends, or just yourself. No reservations, no cover — just good music, good company, and spring evenings done right.
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
October 2: Eli Cook
October 9: Michael Tice
October 16: Matthew O’Donnell
October 23: Matthew O’Donnell
October 30: Lenny Burridge
Reservations are not needed to visit the winery. Join us for oysters, wine, and live music Friday evenings!
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
