📜 A Little History First

This mountaintop vineyard has been in the Jackson family for generations, originally an apple orchard. In 2008, Mike and Sabrina Jackson began planting grapes with a vision to produce European-style wines that could thrive at high elevation. After nearly a decade of growth and planning, Point Lookout Vineyards officially opened in 2018 as a winery, event space, and tasting destination.

The name comes from the land’s past as a Civil War-era lookout, and today it still lives up to the name. The views stretch for miles. The property is also home to World’s Edge Meadery—but we’re just not mead people, so we skipped it.

🗺️ Where They Fit in the AVA

Point Lookout is part of the Crest of the Blue Ridge – Henderson AVA, established in 2019. The AVA recognizes the area’s unique elevation, soil, and cooler mountain climate—perfect for vinifera grapes. Sitting at 2,900 feet, Point Lookout is one of the highest vineyards in the region and played a key role in helping define the AVA. The elevation contributes to the crisp acidity and structure in their wines—especially the reds we tasted.

Entrance for Lookout Point
Closer look at entrance

🌄 The Setting & Vibe

Even the parking lot has vineyard views. The tasting area is open-air and relaxed, with large wooden tables and chairs set up on a covered patio. It’s casual and mostly self-serve. You order your flight at the counter, then find a table and go at your own pace. No pressure, no frills—just a laid-back way to take in the scenery and enjoy the wines.

Looking out at Lookout Point
An overview of the winery
Lookout Point views over our shoulder as we are selecting our wine

🍷 What We Tasted

We went straight for the six-wine flight. Our group chose a mix of mostly reds:

Merlot – Soft and dry, with notes of plum and cherry Where Shadows Play – Earthy, dry red blend with structure Cliffield – Bold, dark fruit blend with a long finish Bliss – Lighter and fruit-forward—easy to sip Pavilion – Smooth and balanced. A nice middle ground Petit Verdot – Inky and full-bodied. Stood out Cabernet Sauvignon – Classic and strong, with a smooth finish

My tasting arrived

Everyone picked their own combo, but we all found something we liked. We ended up buying bottles of Where Shadows Play, Pavilion, and Cliffield to bring home.

Glenn buying 2 truffles (check out the view)

🍫 Chocolate Truffle Pairing

We passed on the pizza and saved dinner for later in Hendersonville, but we couldn’t resist the truffles. Glenn started off with just two, but then Tim spotted a discount for buying six—and showed up with a tray full. Tracie immediately burst out laughing with a full-on “WTH” moment, and without missing a beat, Glenn sprang into action to balance out the collection. We ended up with a full sampler: salted caramel (both dark and light), blueberry, strawberry, hazelnut, Kahlua, coconut, and plain dark chocolate.

Tracie pointing out the imbalance of chocolate

The truffles were rich and just indulgent enough. The Cabernet and Petit Verdot paired especially well, making the whole tasting even more fun.

🛍️ Extras

There’s a small retail section near the tasting bar, but I wasn’t impressed. They barely had any T-shirts, and the merchandise felt like an afterthought—nothing that made you want to browse or bring home a souvenir.

The Merch wasn’t great

⭐ Final Take

Overall, we liked this winery. The views alone are worth the drive. It had a relaxed, open-air setting with casual vibes and solid wines. We’d rank it as our 3 or 4 of the trip. Not the top, but definitely one we’re glad we didn’t miss.

⛈️ A Wild Ending

Just as we were finishing up, a crazy storm rolled in—wind, lightning, and fast-moving clouds. The staff quickly lowered the clear vinyl sides of the patio, and we stayed dry, watching it all unfold from our table. It made for a pretty dramatic send-off, and somehow just added to the memory of the place.

Plastic sides down & Tim is in no hurry to leave