đ 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 landâs 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 Worldâs Edge Meaderyâbut weâre just not mead people, so we skipped it.
đşď¸ Where They Fit in the AVA
Point Lookout is part of the Crest of the Blue Ridge â Henderson AVA, established in 2019. The AVA recognizes the areaâs unique elevation, soil, and cooler mountain climateâperfect 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 winesâespecially the reds we tasted.


đ 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. Itâs 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 frillsâjust a laid-back way to take in the scenery and enjoy the wines.




đˇ What We Tasted
We went straight for the six-wine flight. Our group chose a mix of mostly reds:
Merlot â Soft and dry, with notes of plum and cherry Where Shadows Play â Earthy, dry red blend with structure Cliffield â Bold, dark fruit blend with a long finish Bliss â Lighter and fruit-forwardâeasy to sip Pavilion â Smooth and balanced. A nice middle ground Petit Verdot â Inky and full-bodied. Stood out Cabernet Sauvignon â Classic and strong, with a smooth finish

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.

đŤ Chocolate Truffle Pairing
We passed on the pizza and saved dinner for later in Hendersonville, but we couldnât resist the truffles. Glenn started off with just two, but then Tim spotted a discount for buying sixâand showed up with a tray full. Tracie immediately burst out laughing with a full-on âWTHâ 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.

The truffles were rich and just indulgent enough. The Cabernet and Petit Verdot paired especially well, making the whole tasting even more fun.
đď¸ Extras
Thereâs a small retail section near the tasting bar, but I wasnât impressed. They barely had any T-shirts, and the merchandise felt like an afterthoughtânothing that made you want to browse or bring home a souvenir.

â 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. Weâd rank it as our 3 or 4 of the trip. Not the top, but definitely one weâre glad we didnât miss.
âď¸ A Wild Ending
Just as we were finishing up, a crazy storm rolled inâwind, 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.

