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Wisconsin’s Inn at Wawanissee Point 

By Brian E. Clark

Dave Holdener, who runs the luxurious Inn at Wawanissee Point near Devil’s Lake State Park with his wife, Trudy, likes to boast that he has the best view in Wisconsin from the huge picture windows on the south side of his lodge.

Others might dispute that claim. But there’s no denying that the vista out over Lake Wisconsin to the rolling countryside and forests beyond is stunning.

To top that off, you can see all the way (approximately 30 miles) to the domed state capitol building in Madison – with the aid of powerful binoculars Holdener keeps in the expansive living room of the Wawanissee, which means “beautiful” in the Ho-Chunk language.

Holdener, a 70-year-old native of Chicago, has a decades-long attachment to the Baraboo Hills where the inn is located.

The view from the Inn. Photo Brian E. Clark.

He spent many weekends camping with family and friends on the acre of land his father bought there in 1965. They explored the surrounding territory and would sometimes walk several hundred yards to a lovely knoll and gaze out over the surrounding terrain and the Wisconsin River Valley 800 feet below.

“The view from that spot was mesmerizing, and it still is,” said Holdener. Their four-bedroom, 10,000-square-foot B&B is perched on that same bluff that Holdener first visited more than 50 years ago.

Sometimes, Holdener said, he can still feel the presence of his father, who died from a heart attack near the B&B at age 55.

The first time I visited the inn was in September, two years ago. The colors were turning, which made it a great time to stay and visit nearby Devil’s Lake State Park, Parfrey’s Glen State Natural Area or hike on trails that wind through the 42-acre Wawanissee property.

Holdener, who played football at the University of Wisconsin-Madison during the 1969-70 season said he saw a sign in 1980 where the B&B sits that said the undeveloped land was for sale.

He was in no position financially to buy the property, but he called the real estate agent out of curiosity and told him his family’s connection to the knoll.

The realtor called back the next day and said the owner, Vaughn Conway, wanted to meet Holdener, who nervously awaited the meeting.

“He didn’t want the property to be subdivided,” Holdener said. “He was looking for someone who would be a steward of the land that he loved. Because I had little money, he gave us a land contract deal and it all worked out.”


Innkeepers Trudy and David Holdener, who run the Inn at Wawanissee in the Baraboo HIlls north of Madison, WI. Photo Tish Lafferty.

The next year, they built an access road to a lookout point and cleared a path to the property’s free-flowing spring.

The following year, they moved the Holdener outhouse from across the road, and spent the next 16 years camping, trail blazing, tree planting and hosting what Holdener called “memorable family gatherings.”

One Fourth of July weekend, 150 people gathered on the knoll. They also built a volleyball court, plus a small bunkhouse for stays when the weather was bad.

By the mid-’90s, they were planning what they thought would be their dream home, to showcase the vista and accommodate family and friends, he said. They began construction in 1998, but it wasn’t until several years later when they were staying at a small B&B in northern Wisconsin that the idea to run an inn took hold.

“We looked at one another and said, ‘Maybe we should think about this B&B thing,’ ” Holdener said. “At the time, we were just building it for ourselves. And if you took down the few signs we have, you still wouldn’t know the difference.

“So we went to an innkeepers’ gathering, where they do a good job of trying to talk you out of the idea,” he said.

The couple had a background in the hospitality industry, so they (somewhat) knew what they were getting into. He’d worked for hotels and Trudy, a native of Germany, had been a flight attendant for  Lufthansa airline.

“The biggest complaint among innkeepers was the lack of privacy because they’d converted a mansion or a farmhouse and ended up spending their lives in a 12-foot-by-14-foot room,” he said.


The Inn at Wawanissee Point in summer. Photo Brian E. Clark

So the Holdeners made sure that had plenty of space for themselves in a lower-level, 3,000-square-foot apartment. And six years later after breaking ground, they opened their inn.

“It’s been 16 years and it’s flown by,” said Holdener, who noted that his brother and father-in-law, Louie Hastreiter, did much of the lovely woodwork at the inn.

“Louie was a master cabinet maker in his native Bavaria before moving his family to Chicago in 1956. He hand-picked all the red oak he used for the 42 doors, numerous columns and the detailed crown molding throughout the Inn. He also did the beautiful marquetry (decorative wooden inlay) portraits and thresholds on the main level.”


Handcrafted door at the inn. Photo Brian E. Clark.

Holdener’s late brother crafted the stairwell, barrel roofs, radius balcony and kitchen cooktop and hood. Sadly, he died before the inn was complete.

When I stayed at the inn in 2019, Holdener pointed out a  picturesque farm, complete with a red barn, in the woods not far from Lake Wisconsin below the B&B. Even though it was late September, the sumac trees and shrubs beyond the edge of the lower lawn were turning red.

That late afternoon — following a hard cider with Holdener and two other guests — I went for a walk on the mile-long Ringling Trail (named for the famed circus family from the nearby town of Baraboo) with the innkeepers’ two large, enthusiastic Mastiffs.

The pooches bounded along the trail that circumnavigates the property and looped back to me as the sun set in the west. Soon it was dark and I was glad I had their company while I navigated my way back to the inn.

I spent the night in the Bird’s Nest room in the southwest corner of the B&B, which has lovely views of the valley below. It’s named in honor of Wisconsin’s legendary wildlife artist Owen Gromme, and some of his prints adorn the room.


The author, snowshoeing. Photo Tish Lafferty.

I made a promise to myself during that initial visit that I’d come back to snowshoe on the grounds.  It took me until this March, but the wait was worth it.

After a pleasant night’s sleep in the  Native American-themed Tepee Room and a delicious breakfast prepared by Trudy, photographer Tish Lafferty and I set out on the Ringling Trail past a fir tree planted by Trudy’s late aunt.


Snowshoeing and brandy. Photo Brian E. Clark.

The snow-covered path wound through the woods and we stopped at a bench where the Holdeners had left a small bottle of cherry brandy – from Trudy’s native village in Bavaria – to warm guests up.

I’ve got a feeling I’ll be back. Perhaps next winter to celebrate New Year’s Eve – if not sooner.

More information: The Inn at Wawanissee Point, E13609 Tower Road, Baraboo, is about 200 miles north of Chicago and 110 miles west of Milwaukee. Room rates vary depending on the day of the week and the season. Special packages are also available. Call (608) 305-2263 or see innatwawanisseepoint.com.


Brian E. Clark

Brian E. Clark is a Madison, Wisconsin-based writer and photographer who contributes to the Chicago Tribune and LA Times on a regular basis. He also writes a weekly travel column for the Milwaukee Journal-Sentinel.  A native of Iowa, Clark is a University of Colorado, Boulder, graduate who focuses on adventure travel. He’s a veteran whitewater kayaker and skier who has lived in Norway, Sweden, Brazil and Bolivia. He worked for newspapers in Washington State and California for 25 years, including the San Diego Union-Tribune, before returning to the Midwest. He manages to head back West several times a year when he’s not off in other corners of the globe. Or poking around Wisconsin.

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