Live Music & Wine Club Day
Program Details & Spotlights
Join Fifty-Third Winery & Vineyard for a special day of live music, delicious food, and award-winning wines. Richmond singer-songwriter Nate Oyler will perform acoustic country hits from 1:00 PM to 4:00 PM, while Willie's Waffles food truck serves mouth-watering options. Non-club members are fully welcome to purchase tickets and enjoy the relaxing vineyard vibes. Sample a flight or share a bottle of local wine with friends on the outdoor patio.
For Lake Anna locals and weekend visitors looking to trade the wakeboards for wine glasses, a quick trip down to Louisa is always a treat. Fifty-Third Winery & Vineyard is hosting a spectacular Live Music & Wine Club Day, offering the ultimate afternoon escape. Tucked away in the rolling countryside just a short, scenic drive south of the lake, this local gem is known for its sustainably grown grapes, modern-rustic tasting room, and highly welcoming southern hospitality. Whether you are a seasoned club member or a curious newcomer, this event is designed to celebrate the very best of Virginia's thriving wine culture.
The highlight of the afternoon kicks off at 1:00 PM when Richmond's own singer-songwriter, Nate Oyler, takes the outdoor stage. Known for his soulful delivery and rich acoustic arrangements, Oyler will be playing a crowd-pleasing set of country hits and acoustic favorites through 4:00 PM. His warm, organic sound is the perfect soundtrack for a lazy afternoon spent lounging on the spacious patio, glass of award-winning estate wine in hand, as the autumn breeze rustles through the nearby vines.
To satisfy your cravings, the beloved Willie's Waffles food truck will be parked on-site, serving up their famous, mouth-watering creations. Think golden, crispy-on-the-outside, fluffy-on-the-inside waffles topped with a variety of delicious savory and sweet options. Pairing a warm, decadent waffle with one of Fifty-Third's crisp whites—like their acclaimed Viognier—or a bold, spicy Cabernet Franc is an unexpected culinary match made in Louisa heaven.
While this day is a special celebration for Fifty-Third's dedicated Wine Club members, the winery is rolling out the red carpet for the public as well. Non-club members are fully welcome to purchase tickets, grab a tasting flight, or buy a bottle to share with friends. It is a fantastic, low-pressure opportunity to "test-drive" the winery experience, chat with the knowledgeable staff, and soak in the relaxing, tight-knit community vibe that makes the Lake Anna region so special.
Why You Should Attend
- Exceptional Local Pours: Taste your way through Fifty-Third’s award-winning, estate-grown Virginia wines.
- Live Acoustic Vibes: Enjoy three solid hours of live country and acoustic classics from Richmond artist Nate Oyler.
- Unique Food Truck Eats: Indulge in sweet and savory creations from Willie's Waffles, the perfect comfort food pairing for a crisp afternoon.
- The Perfect Day Trip: Just a short drive from Lake Anna's shores, offering a peaceful vineyard setting and a great change of pace.
Insider Tips for the Perfect Visit
- Arrive Early for Prime Seating: The tasting room opens at 11:00 AM, but the music starts at 1:00 PM. Arrive early to secure the best spots on the outdoor patio or a shady table under the trees.
- Bring Your Lawn Chairs & Blankets: If the patio fills up, the winery has plenty of lush, open lawn space perfect for setting up your own premium picnic spot.
- Sample a Flight First: If you are new to Fifty-Third, order a tasting flight when you first arrive to discover your favorite varietal before committing to a full glass or bottle.
- Bring the Whole Crew: The outdoor areas are family-friendly and leashed-dog-friendly, so feel free to bring your kids and four-legged companions along for the fun!
⚓ Local Visitor Navigation Tips & Parking
Tickets are $17 per person and include a custom wine tasting, a food coupon for the food truck, and access to the live music. Outdoor deck and lawn seating are available, but bringing your own lawn chairs is highly recommended.