Humble Beginnings
âI donât think the cows would mind being closer to the water!â In that moment of simple Norwegian stubbornness, Olaf Treland set a family standard of preserving what was truly important. Four generations later, what began as a simple saw mill on a cattle farm, has now grown into the four separate luxury resort properties that make up Treeland Resorts.
Great-grandpa Olaf came from Norway with his wife, Esther, and their two children. After a short period in Iowa, they moved up to Two Harbors where he started his own logging operation. The state logging companies did not want to go out into swamps to get the tall pines for telephone utility poles. Olaf got a strong team of horses and a sled, and did the work they werenât willing to do. In the process, he made a lot of money. So, in 1914, he packed up his family again, moved to Hayward, and bought land on what is now the famous Chippewa Flowage. The land itself used to be farmland, âbecause there was water thereâ. Later it became fishing cabins, with outhouses out back. They still keep a few just for nostalgic purposes â ânot used, just history!â The old hand pump is still there as a conversation-piece.
A Heritage of the Heart
Treeland Resorts is about more than just cabins, condos, and modern amenities. Certainly, the facilities are superb. Theyâve put a tremendous amount of thought and resources into creating one of the finest resorts in the country, providing you with just about every luxury, comfort, and convenience you could think of. But, the resorts are more than just a business. âThey are a family heritageâ, says Cheryl Treland. âItâs just what we do as a family. You grow up as kids here. You play here, work here. The resort is like an extension of our family. Itâs part of who we are. Itâs in our blood!â
Visit www.TreelandResorts.com, and youâll be impressed with the quality, beauty, and variety of activities that they offer you. Browse the gallery of photos, and youâll very quickly get the sense that itâs about something more, something deeper, and something far more important than just cabins on a lake. Treeland Resorts is all about the lost art of just being there, without the demands of a busy schedule. Whether youâre grilling steak on the deck, or wieners on a stick, itâs not about getting the meal cooked, but about relaxing, and sharing the real feast â friendship, fun, and connection with people you love and enjoy! Itâs about playing cards on the deck while the meatâs being grilled, purely because you have a better time doing that, than anything else. Camaraderie creates consistency through lifeâs changes, sharing a treasure across generations! Thatâs Treeland! You can enjoy everything modern, while looking back, and asking with intrigue, âHow have things changed?â
Changes
Treeland Resorts has seen many changes. First it was electricity and pumps, then heat. Thirty years ago nobody asked for A/C, now everybody asks, and every unit has it. Now itâs all gas log fireplaces, resulting in instant aesthetics without filling up a room with smoky logs.
People donât even fish the same! They used to get up early and stay from dawn till far past dark, six days a week. Now they take a day trip to the Apostle Islands, shoot the breeze on the pontoon, and fly across the lake with a 40-horse motor and a high-speed hull, âjust to see the dam, and maybe stop for a burger on the way back!â Itâs what doesnât change that makes it special â The land, the lakes, the beautyâŚthe spirit of friendship and serenity that pervades the areas that surround âthe Great Chipâ!
In 1923, eleven creeks and nine natural lakes became âthe Flowageâ, just east of the fork in the Chippewa River. With 17,000 acres of water, over 140 islands, and very little development, it became Wisconsinâs largest wilderness lake and the third largest lake in the state. The State asked Olaf if he wanted to sell Moss Creek, the land he owned on the north side of the Flowage. But, he refused! The land under the bay in front of his land got flooded, and his cows got closer to the water. Bob Cammack, a railroad engineer, came up from Chicago in 1928 and bought six acres on the east side of the bay to start a fishing camp. He was inspired by the tall majestic pines that grew there at the time, and wanted to name the area âTreland Pinesâ. To avoid confusion with the Treland family name, Olaf insisted he add an âeâ. It eventually became known as âBob Cammackâs Treeland Pines Resortâ. Apparently, Olaf liked the idea of a fishing camp. In 1938, he told his cows to move over, and built one just like it â Treland Cabins, with one âeâ. That was the first of the Treeland Resort properties, and today, the original homestead still stands on that site.
Passing on the Legacy
Second generation ownership began with his son in 1963, when Oscar Treland and his wife, âJohnnieâ, bought out their father. Oscar was a WWII veteran pilot, having served twenty-three years in the Air Force. Starting in the winter of 1964, he began building a few new cabins every year. In the second year he turned a deer cabin into the main lodge, adding a ping pong table and a pool table. By 1968 he had built it up to twelve cabins.
For estate planning purposes, Oscar and Johnnie incorporated the resort. In 1979, the buzzword had become âCottagesâ. So, they changed the name of the original family resort from Treland Cabins to Treeland Cottages, Inc.
Friends Forever
The third generation became involved in 1982 when Harold and his wife, Jan, his sister Cheryl, and a friend, Jane Bidwell, bought out Treeland Pines from the Cammacks next door. The three friends were young, ambitious, and worked hard at modernizing Treeland Pines. For the first five years, they all worked full-time jobs, and 100% of the revenue went back in to repairs and improvements.
In 1986 Harold, Jan and Cheryl bought out their parents and siblings. They went under land contract to keep the Treeland Pines name, putting both Treeland Pines and Treeland Cottages under the banner âTreeland Resortsâ, and running them as a single resort. It was at that time that they built the marina. Permits were applied for and received from the DNR to excavate and build the harbor in front of the resort. They started pontoon and fishing boat rentals, with an array of modern âluxuriesâ, like swivel seats, live wells, and locators. The boats were rented not just to their guests, but to anyone using the lake.
Every winter the family still gets into new projects. In 1991, they expanded with ten live-in & cook-in motel suites. These spacious suites sleep four, with decks on the front, and have a real Northwoods feel. The Trelandâs opened up twenty-one new insulated units for year round use, put in a luxurious outdoor heated pool, and added a full blown restaurant onto the main lodge.
Second Site
In 1997 they bought a second property. Winter had been tough. With almost no snow, they started seasonally closing the bar, the restaurant, and some units at the main resort. But, still they kept growing. It was natural that they had to, because as each new generation came on board, the families of their guests grew as wellâŚand they kept coming back, year after year! So, Cheryl and her sister, Linda, bought land on the southeast corner of the Chippewa Flowage. They built 6 ultra-modern units with hot whirlpools & internet access, and established the new site at Oak Shores.
Oak Shores was originally intended for couples, but in the summer months they found them filled with families. So, by 2001, they had expanded three more units, and added an in-ground pool.
Still Growing
In 2002, the Trelands built Timber Cove. Now in its fourth generation, the family bought eight acres along three hundred feet of shoreline, about a mile by water from the original homestead. Here they built thirteen year-round vacation homes and this modern and luxurious resort was finished in 2003.
Two years later, in 2004, they purchased Patâs Landing Resort, about three hundred yards north of Oak Shores. Fourteen old fishing cabins gave way to the first condominium units in Sawyer County â twenty-one units, with an in ground pool, a main lodge, and a bar, on one of the best pieces of land on the Chippewa Flowage.
Start a Family Tradition
At Treeland Resorts, the different properties cater to different personalities. Itâs very uncommon to see people renting just one unit, as three or four generations of families come together and take up six or eight units at a time. Some of the people who come to stay had their grandparents staying here when Great-grandpa Olaf had the resort. For most itâs a tradition, like Christmas! Coupleâs come for the romance of the fall colors. Guys come for the fishing and golf. In the old days, they would take a trip to the dump at dusk, to watch the bear in the headlights. Now the bear might show up on your deck, because you didnât clean your grill properly.
Even with gas prices up, Treeland Resorts is still a destination of choice. Youâre only a tank of gas away from Chicago, Minneapolis, and Milwaukee. Itâs easily accessible, and the perfect place to come to for a family vacation. There are fewer and fewer family resorts these days. Treeland Resorts continues to preserve a consistent legacy in the face of persistent changeâŚa timeless treasure of memories and tradition, across generations!

