Some days deserve more than a map and a to-do list. Summit to Sip is Pinecrest’s private guided day tour — a morning hike to one of the most spectacular open summits near Asheville, followed by an afternoon wine tasting in the Blue Ridge’s newest designated wine appellation. Your guide, Dave of Hike Bike Kayak Asheville, handles the driving, the local knowledge, and the logistics. All you have to do is show up for breakfast.
How the Day Unfolds
After a plated breakfast at Pinecrest at 9 AM, Dave arrives to pick up your group for a private day in the Blue Ridge. With room for up to four guests in his vehicle, this is as intimate as a guided tour gets — no crowds, no strangers, no schedule to keep up with but your own.
The drive south on I-26 covers about 25 miles, winding out of Asheville and into Henderson County as the mountains open up around you.
The Hike: Bearwallow Mountain
The morning is spent on Bearwallow Mountain, a 4,232-foot summit in the Upper Hickory Nut Gorge area. The trail is a 2.1-mile loop — roughly one mile of steady climbing through hardwood forest, gaining about 600 feet of elevation, followed by a return on a gravel forest road. No backtracking required.
The payoff at the top is one of the best open-summit views in the region. The trail breaks out of the trees onto a sweeping grassy bald where the Blue Ridge unfolds in every direction — Mount Mitchell visible to the north, Mount Pisgah to the east, ridgelines layering into the distance. Cattle graze the summit meadow in warmer months, adding to the pastoral quiet of the place.
A light snack is provided at the summit. Linger, take it all in, and let Dave tell you what you’re looking at.
For a full trail description, directions, and tips, see our Bearwallow Mountain trail guide.
The Wine: Marked Tree Vineyard, Flat Rock
From the trailhead, Dave drives you south into the Crest of the Blue Ridge AVA — North Carolina’s newest designated wine appellation, and one of the most scenic in the Southeast. Marked Tree Vineyard in Flat Rock sits at 2,300 feet on the Eastern Continental Divide, where the views from the outdoor patio pick up almost exactly where Bearwallow left off.
The tasting experience at Marked Tree is guided and unhurried. Choose from a Seasonal Flight or an All-Red Flight — we recommend the Seasonal Flight paired with the cheese board and charcuterie. The estate produces award-winning wines from European vinifera grapes: Cabernet Franc, Petit Verdot, Grüner Veltliner, and more. If the afternoon calls for a second glass on the patio, there’s no rush.
Tasting fees and food are paid directly at the vineyard.
The Details
Summit to Sip is a private tour for one to four guests. Dave adapts the pace and the day to your group — whether that means a longer summit break, an extra stop on the way home, or simply more time on the Marked Tree patio.
What’s included:
- Plated breakfast at Pinecrest at 9 AM
- Private pickup and return at Pinecrest B&B
- Guided hike of Bearwallow Mountain with Dave of Hike Bike Kayak Asheville
- Summit snack
- Private transportation and local commentary throughout the day
- Afternoon visit to Marked Tree Vineyard, Flat Rock
Pricing: Starting at $400 for a four-hour private tour. Additional hours available at $100/hour.
Tasting fees and food are paid directly at Marked Tree Vineyard.
Tours run approximately 4.5 to 6 hours depending on pace. Available select days — contact Pinecrest to check availability and reserve your Summit to Sip day.
Notice: Trail and road conditions near Bearwallow Mountain can change with weather and ongoing storm recovery. Before heading out, check Conserving Carolina’s Bearwallow Mountain page for the latest access and trail status. Use the Edneyville approach via I-26 — avoid Route 74/74-A through Gerton.
Frequently Asked Questions
What should I wear for Summit to Sip?
Comfortable hiking shoes or trail runners are ideal for Bearwallow Mountain. The trail is well-maintained but includes rocks, roots, and log stair sections. For the winery visit, smart casual is the right call — you’ll feel at home on the Marked Tree patio in anything from jeans to sundresses.
How strenuous is the hike?
Bearwallow Mountain is rated easy to moderate. The climb gains about 600 feet over roughly one mile, with a steady grade rather than any steep scrambles. Most guests in average fitness complete it comfortably. If you have concerns about mobility or stamina, just mention it when you book and Dave can advise.
How many people can join the tour?
Summit to Sip accommodates one to four guests in Dave’s private vehicle. It’s designed as a couples or small group experience — not a group tour.
Are tasting fees included in the price?
Tasting fees and food at Marked Tree Vineyard are paid directly at the winery. Guided flights start at $25 per person. We recommend the Seasonal Flight with the cheese board and charcuterie.
What if the weather is bad?
Western North Carolina weather can be unpredictable. Dave monitors conditions and will work with you to reschedule if the day isn’t suitable for a mountain hike. The Marked Tree visit can also stand on its own if needed.
How do I book Summit to Sip?
Contact Pinecrest directly at innkeeper@pinecrestbb.com or call (828) 281-4275 to check availability and reserve your date. Summit to Sip is available on select days and subject to Dave’s availability.