A $400 Day Trip From Asheville That Ends With Wine and a 4,232-Foot View

By Jon Tharp, Broker  ·  August 4, 2026

There is a grassy bald about 30 minutes southeast of Asheville where you can see all the way into South Carolina on a clear day, and a new package out of a downtown bed and breakfast will get you there before lunch and pour you a glass of local wine by mid-afternoon. Bearwallow Mountain rises to 4,232 feet above the Hickory Nut Gorge in Henderson County, reachable from downtown Asheville by way of US-74A through Fairview and then up Bearwallow Mountain Road.

Pinecrest Bed & Breakfast on Cumberland Avenue is offering the trip as an add-on to a stay. Guests get a homemade breakfast at the inn, then head out with private guide Dave of Hike Bike Kayak Asheville for the morning climb. In the afternoon, Dave drives the group about 30 minutes south to Marked Tree Vineyard in Flat Rock for a guided tasting. It starts at $400 for up to four guests and runs through November 25, 2026.

What makes Bearwallow Mountain worth the hike?

Most summits in Western North Carolina are wooded to the top. You climb for an hour, arrive, and find yourself standing in a stand of oaks with no view at all. Bearwallow is the exception, and locals have known it for a long time.

Cattle have grazed the open grassy bald at the top for generations, which is why the trees never took over. There is a fire tower up there and views that run in almost every direction, out over the gorge toward Chimney Rock and Lake Lure and south toward the state line. The trail from the gap is about a mile with a few hundred feet of climbing, and there is a gravel service road for anyone who would rather take a steadier grade.

The Conserving Carolina land trust holds a conservation easement on the summit, which is the only reason any of this is open to the public.

Is Henderson County actually a wine region?

It is. The federal government approved the Crest of the Blue Ridge Henderson County AVA in 2019, one of the newest American Viticultural Areas in the country and the one covering the high-elevation vineyard land around Hendersonville and Flat Rock.

Elevation is what sets it apart. Vines here sit well above where most Southern wine grapes grow, and the cooler nights slow ripening in a way that holds onto acidity. The result is wine with more structure than people expect from North Carolina.

Marked Tree Vineyard is one of those vineyards. The tasting room looks out over the surrounding ridges, and Flat Rock itself has been a mountain retreat for well over a century, going back to the Charleston families who came up to escape the Lowcountry summers. Carl Sandburg spent his last 22 years there. The Flat Rock Playhouse still runs a full season.

Who is this kind of trip really for?

Anyone who wants a full day in the mountains without renting a car or figuring out which vineyard is worth the drive. That describes a lot of visitors, and it describes plenty of second-home owners hosting family for a weekend too.

The private guide piece matters more than it sounds. Dave knows the trail conditions and the back way between Fairview and Hendersonville when US-74A backs up. That local knowledge is most of what you are paying for.

Fall dates tend to go first. Leaf season on that side of the county runs roughly mid-October through early November, and the package is subject to guide availability, so anyone eyeing an October weekend should book well ahead.

What does this say about the area?

Ten years ago, a day trip like this would have been harder to assemble. The vineyard was younger and the appellation did not exist. The Bearwallow trail also had less public access than it does now. All of that changed within about a decade.

That is the pattern across a lot of Henderson and Buncombe County right now. Land trusts open up access and small producers get good enough to build a reputation. The people who live here get a better place to spend a Saturday, and the visitors follow.

If a day that starts on a mountain bald and ends on a vineyard deck sounds like something you would want within a half hour of home, Jon Tharp is glad to talk about what that looks like around here.

 

Frequently Asked Questions

How hard is the hike to Bearwallow Mountain?

Bearwallow is one of the more approachable summits in the region, which is part of why it works as a guided outing for mixed-ability groups. The main trail climbs roughly a mile from the gap at Bearwallow Mountain Road to the top, gaining several hundred feet along the way. There is also a gravel service road to the summit that trades switchbacks for a steadier grade. The payoff is a grassy bald with a fire tower and open views in nearly every direction, which is unusual in a region where most summits are wooded and viewless. Most reasonably fit hikers finish the round trip in about two hours.

Where is Marked Tree Vineyard and what makes the Crest of the Blue Ridge appellation different?

Marked Tree Vineyard sits in Flat Rock in Henderson County, about 25 minutes south of Asheville just off I-26. It is one of the vineyards inside the Crest of the Blue Ridge Henderson County AVA, the federally recognized appellation approved in 2019 that covers the high-elevation growing area around Hendersonville and Flat Rock. Elevation is the whole story here. Vines planted well above the elevations of most Southern wine country get cooler nights and a longer hang time, which tends to produce wines with more acidity and structure than the region's reputation suggests. The tasting room's deck view of the surrounding ridges does not hurt either.

What is included in the Summit to Sip package and how do I book it?

The package is booked as an add-on when you reserve a room at Pinecrest Bed & Breakfast at 249 Cumberland Avenue in Asheville, not as a standalone tour. Pricing starts at $400 for up to four guests and covers private transportation for the full day, the services of guide Dave from Hike Bike Kayak Asheville, a light snack at the summit, and the guided tasting at Marked Tree Vineyard. Breakfast at the inn comes with the stay. The offer runs through November 25, 2026, and is subject to guide availability, so booking further ahead matters during leaf season and on fall weekends.

What is the drive time from Asheville to Bearwallow Mountain and Flat Rock?

Bearwallow Mountain sits above the Hickory Nut Gorge in Henderson County, roughly 30 to 35 minutes southeast of downtown Asheville by way of US-74A through Fairview and up Bearwallow Mountain Road. Flat Rock is about 25 minutes south of Asheville on I-26, and the drive between Bearwallow and Flat Rock runs another 30 minutes or so through Hendersonville. That geography is what makes the one-day pairing work. You can stand on a mountain bald in the morning and be on a vineyard deck by early afternoon without spending the day in a car.