How Cabins Helped Fund a Red River Gorge Land Acquisition

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What if you could apply the principles of ski-in, ski-out to climbing? No sketchy roadside parking, no long approach with a heavy pack. Just a rap right off the (literal) deck. “Climb-in, climb-out” isn’t yet an actual amenity in real estate lingo, but it’s fast becoming popular along the cliffs of Kentucky’s sprawling Red River Gorge (RRG).

In the case of Ian Teal, a real estate developer and prolific businessman based in the RRG area, he rappels from his front porch to a crag with around 30 developed routes. At the end of the day, he takes an easy 5.6 back up and jumps in the hot tub. With 150 cabins for rent under his thumb and up to 200 more climbing-adjacent lots for sale, his climb-in, climb-out cabin business is booming—and it just got a lot bigger.

Teal town

Teal had been coming to the Red since he was a 12-year-old Boy Scout. Back in the early 2000s, he was a ship captain conducting oceanographic research, looking for a place to get away when he was on land. In 2006, he bought his first cabin near the Red. But when Teal started searching for a local company to manage his new property, he discovered that no property management companies yet existed in the area—so he started his own.

Nearly 20 years later, Teal owns the largest cabin rental company in the RRG, which stretches across five counties: Lee, Powell, Wolfe, Menifee, and Estill. He also owns a couple hotels, some restaurants, a zipline company, and the Gorge Underground boat tour company, among other ventures.

Teal is also active around the cliffs of the Red. Last year, he worked with the Red River Gorge Climbers’ Coalition (RRGCC) to set up a recreational easement along the cliffline under his Cliffview property. He also provided much of the hardware for the Cliffview area development, and has bolted some routes himself. “I find it to be pretty enjoyable and very freeing,” Teal says. “It’s quite cool to think that people will be climbing on this [route] forever.”

Then, this past February, Teal played a critical role in the largest ever land acquisition by climbers in the country.

How the Ashland deal went down

The RRGCC had been eyeing the climbing potential around the Ashland Wildlife Management Area since 2002. After failed efforts to negotiate climbing access, the property suddenly came up for sale in 2023.

The parcel in question spanned 2,506 acres. The RRGCC primarily set its sights on around 700 acres with over 14 miles of cliffline featuring high-quality climbing potential. Originally, according to RRGCC Executive Director Billy Simek, they had inquired about buying smaller parcels. But the seller refused to subdivide the land and only wanted to deal with one buyer. The price tag for all that acreage? Around 15 million dollars.

So RRGCC set about rallying its donors and community. Funding started to come through—a massive contribution from the Ventura Family of Miguel’s Pizza (that would gain them a chunk of the land), federal conservation-oriented grants, and the support of many climbers who love the Red. However, they were unable to raise the necessary funds with traditional land trust partners and through this initial fundraising push.

“We had tried what I would call a more typical conservation approach,” says Daniel Dunn, Eastern Regional Director of Access Fund, which helped facilitate the deal. “Ultimately, that was not successful and the project sort of went dormant.”

For two years, the RRGCC wasn’t able to muster enough resources to buy the land. This meant they risked losing the entire cliffline to a different buyer who could care less about climbing access. Rumors began circulating about other buyers. One even held that Dolly Parton planned to make the purchase.

Finally, toward the end of 2023, Teal, a longtime supporter and existing partner of the RRGCC, got involved. Eventually, he ended up bringing the biggest chunk of change to the table—and a creative idea. The RRGCC and Teal would orchestrate a simultaneous closing: Teal would take out a loan to purchase the 2,506 acres, then immediately sell the 718 acres with climbing to the RRGCC. Teal would subdivide the rest of the land and sell it as parcels for his cabin business.

Teal needed to put seven million toward the purchase. To take out a loan for five million, he had to find two more as a down payment. To raise the money, he pre-sold a number of lots to climbers. “Anyone who bought [a lot] on the front end got a really good deal,” he says.

While Teal seems a little stressed about making his $30,000 monthly payments on the loan he took out, he says he ultimately feels good about how the deal went down. “There was a lot of trust on both sides,” he says of working with RRGCC. “Everybody’s super happy.”

Climbing below, cabins above

The new Ashland area will now experience two simultaneous forms of development: climbing routes down low, and cabins up top.

Below, local routesetters are getting to work bolting new routes along the 14-plus miles of added cliffline. According to the RRGCC, routesetters have submitted 90 new routes and there are probably another 100 fresh routes for which developers have yet to file paperwork. This is on top of the 100 or so bolted routes that existed prior to the February land acquisition. With nearly 300 routes in the works—and significant potential for more—Ashland is poised to become a climbing destination in and of itself.

Teal has bolted a few of these routes himself, along with his friend Noah Tal Kaufman. A Denver resident, Kaufman bought his climbing cabin from Teal and comes to the Red twice a year to climb and develop new routes. The rest of the year, he rents out his cabin and donates the proceeds to nonprofits like RRGCC and Access Fund. Recently, he’s been putting up new routes—from 5.9s to 5.13s—in the Cave Fork Recreational Preserve part of the Ashland area.

Meanwhile, RRGCC has been busy preparing to expand climber infrastructure, including parking areas, access trails, and belay bases. Aside from this infrastructure, the RRGCC is focused on preserving the land around the climbing. This is in keeping with its mission to conserve the environment across climbing lands, but it’s also an obligation tied to some of the conservation-based grants it received to purchase the land.

Dunn with Access Fund says it worked out well that the most critical ecosystems happen to coexist within the climbing landscape, versus around the development lands above. “In Kentucky, the top land and bottom land are very different ecosystems,” Dunn explains. “A lot of the core conservation values and the climbing happen in the bottom, adjacent to the creeks and streams that define the region. We really were adamant about owning that so that we can protect it.”

Climb-in, climb-out cabins for sale

Above those work-in-progress cliffs, Teal is dividing out the presale parcels to the climbers who invested early. He’s already started selling more parcels across the 800 or so acres of the Highlands—how he’s started referring to the area—that he plans to develop, as well as putting in water and electricity. To allow climbers to park and walk through lots to access climbing, he plans to create easements. And as he’s done in Cliffview, in the coming years, he anticipates building a network of mountain biking trails through the area as another recreational amenity.

As he develops the Highlands, Teal emphasizes that he wants to preserve the natural beauty of the area. “We’re very aware of not wanting to overdevelop,” Teal says. So 800 acres doesn’t equal 800 lots. He estimates he’ll sell between 100-125 parcels in the Highlands. While he will sell some lots sized between an acre and an acre-and-a-half, he will also sell some as large as 20 or 30 acres to help conserve the open space feel above the climbing. The price tag? Between $40,000 and $125,000, depending on location and size. Teal still has about 50 to 75 lots for sale in Cliffview as well.

So who will be buying these coveted climbing cabins? Probably not locals. Teal says they’re not interested. “Locals here are typically generational,” Teal explains. “They inherit part of the farm or they get an acre and they build a house on that acre. So the idea of a local person spending 100k on a lot—there’s very few who would do it.”

But Simek suggests there are very few locals who could afford it. According to Pete Fingerson executive director of the Powell County Tourism Commission, the cost of housing has become much less affordable for locals. Since Fingerson and his wife moved to the area in 2018, he says housing prices have “skyrocketed.” According to Zillow, the median listing price for homes in Powell County has risen from around $83,000 in 2018 to around $162,000 in 2025. He’s seen quite a few locals move away due to the rising cost of living—and the lack of long-term rentals available.

Fingerson adds that there are a few affordable housing apartment complexes in Powell County, but that “the Powell County Housing Authority doesn’t even have a waiting list anymore, because it was getting so long.”

The other issue is that Kentucky is more or less the Wild West when it comes to development. Fingerson explains that basically no zoning laws exist. Developers and property owners can do whatever they want when it comes to short-term rentals.

According to Fingerson, on an AirDNA list of areas with the highest demand for short-term rentals and the lowest supply, the Red River Gorge recently held the number one spot. Teal cited this statistic as well. Like other outdoor-centric communities and towns with great recreational amenities, Fingerson says this part of Kentucky saw demand for permanent residences and short-term rentals soar during the pandemic. According to Realtor.com, between 2019 and 2023, the RRG saw the second highest growth rate for vacation rentals in the country, with a 216% increase in demand.

As real estate booms in this corner of Kentucky, it’s worth noting that compared to mountain towns out west or major cities, by comparison, housing remains “extremely affordable,” according to Fingerson. “You take $250,000 in California and you can get six pieces of grass,” he remarks. “Out here, it could get you a home, 30 acres, and a creek.”

According to U.S. Census data, 69% of housing in Powell County is owner-occupied, as opposed to being held as a second home or offered as a short- or long-term rental. In Lee County, the location of the new Ashland climbing area, 75% of housing is owner-occupied. For comparison, Summit County, Utah—where Park City is located—has an owner-occupied housing rate of under 20%. Boulder County, Colorado, is 62.5% owner-occupied. And in New Paltz, New York, a gateway town to the Gunks, only 28% of housing remains owner-occupied.

So while the housing and development situation may not yet be extremely problematic, the concern is that the RRG area is headed down the path of gentrification. “With that influx of new rentals over the last few years, we are starting to see somewhat of a saturation point,” Fingerson says. “Growth is great and we welcome it, but we also need to ensure that our local infrastructure can sustain that growth.” He adds that it’s also about retaining the “local flair” the RRG community is known for and that visitors seek out when they visit.

In addition to concerns about affordable living, local climber and farmer Alex Petit says that the proliferation of cabins impacts her climbing experience in the Red. She describes a beautiful route up an arete called No Place Like Home (5.11c): “Somebody built a cabin—a two-story glass mansion—on that cliffline. Cabins are coming up everywhere. They’re right on top of each other.”

Petit says that the unchecked development takes away from “the beauty of climbing” and “being immersed in nature.” Simek agrees that throwing up a hundred or more cabins that will largely become short-term rentals and second homes can erode “some of that local character” for which the Red is known. For his part, Teal sees the local vibe as “super positive” right now. “It’s kind of like Christmas,” he says. “You wake up one day and there’s all these additional routes all over the place. There are already 3,000, and we’re adding to that number.”

With 200-some employees of his own, Teal understands the importance of affordable housing for his workforce—though he doesn’t see it as a “huge problem” yet. That’s one reason why he’s planning to build a $10 million climbing gym and fitness complex with attached affordable apartment units for his employees. “A lot of the money from sales of these lots will go toward building that,” Teal explains. He adds that this fitness-housing complex would be his way of giving back to the community—not anything he wants to profit from. Currently, he does provide housing to a handful of his managers.

Ultimately, Petit doesn’t hold much against Teal. She acknowledges that he is a capitalist succeeding in a capitalist system—”a microcosm in the macrocosm,” as she puts it. She does have one hope for how he moves forward with the Highlands: She says it would feel like a “small victory” if he opted to only develop around 25% of the available lots. But really, she just wants her community to be more intentional about shaping their future: “There needs to be some idea of whether this is a place we want to live in 30 years when it becomes suburbia.”

Climbers and developers: Better together?

“Is this the future of conservation, where you have to make a deal with a wealthy donor and hope that they’re the next Yvon Chouinard?” asks Petit. The answer? Maybe.

Whether you view the Ashland deal as a positive example of the power of creative partnerships, or just the sort of ‘cross-the-aisle compromise necessary to get anything done these days, surely, an acquisition this massive holds some interesting takeaways.

One learning seems to be that reaching across the proverbial aisle—even if there are separate end goals at play—can be an effective strategy. While it’s clear that Teal, as a climber himself, is interested in expanding climbing access, he surely also saw financial potential in the acquisition of 100-some more lots. After all, these are lots that his booming multifaceted business will sell, then probably develop, and ultimately manage as short-term rentals down the line.

RRGCC could have declared its mission misaligned with that of a developer. But then it would also be missing a massive opportunity to further its own mission of protecting climbing access and conserving land. Because if there’s one thing most folks seem to agree upon down in Kentucky, it’s this: The Ashland deal likely wouldn’t have happened without Teal’s involvement. After some initial waffling, all sources in this story indicated that it’s unlikely the RRGCC would have secured those 718 acres of climbing lands without Teal.

Dunn felt that adapting “to meet the challenge at hand” was crucial to success. He decided to lean into the creative partnership approach and pivot to an “if you can’t beat ‘em, join ‘em” mentality. “Let’s get them on our team,” he says of developers or other unlikely partners. “Let’s convince them that a healthy climbing area with a healthy ecosystem—rather than a degraded one with trees cut down or altered hydrology—is better for the climbers and their business model.” Dunn maintains that though Teal played the largest financial role in the deal, RRGCC and the climbing community remained “in the driver’s seat.”

Another takeaway is that we may see more local climbing organizations partnering with real estate developers in the future. Of course, negotiating with real estate developers is nothing new. From North Carolina’s Hound Ears to Stone Fort in Tennessee, Access Fund and local climbing organizations have worked with development interests in the past to advocate for access.

But Dunn says that in the Southeast and Eastern U.S. where he works, he’s “definitely seeing an uptick” in working with developers. More and more, projects involve a “closer than usual” partnership with a developer. And it’s not always Dunn approaching developers to advocate for access. A few times now, they’ve proactively come to him to say, ‘Hey, I just bought this land and I think there’s climbing on it. Want to work with me on it?’”

Simek agrees that the model they employed for this deal “opened a window.” He explains that while the RRGCC would generally prefer a like-minded nonprofit or land trust partner, “that’s not always realistic these days.” Beyond looking at traditional partners for future acquisitions, he says partnering up with developers gives the RRGCC another option to draw upon. “This remains a good framework for something that we can do down the line and that other local climbing organizations could also look into,” Simek says.