Sugarloaf Ski Resort is located directly south of Lake Michigan, sitting around 30 minutes northwest of Traverse City, an hour and 10 minutes north of Cadillac, and 2.5 hours north of Grand Rapids, Michigan.

The origins of Sugarloaf date back to the 1930s. In 1935, Leelanau County inherited the original 20 acres that encompassed Sugarloaf Hill from a deceased farmer. While the land was open to the public, it wasn't until the late 1940s that downhill skiing was introduced at Sugarloaf, with a single rope tow and a small warming hut. The new winter park at Sugarloaf officially opened on January 1st, 1947, drawing many local skiers. Featuring several ski runs and a ski jump, Sugarloaf proved to be extremely popular. By 1950 the ski area installed two additional rope tows. In 1951 the rope tows at Sugarloaf were upgraded from diesel engines to electric ones and two new rope tows were installed. This was the era when many new ski areas were being developed and Sugarloaf was right at the forefront. By the late 1950s a new tavern at the base was constructed and dancing was offered every weekend.

In 1961, considerable interest was expressed by several parties in developing Sugarloaf as a year-round resort. By September of 1964, developers had acquired over a thousand acres encompassing Sugarloaf and announced a development plan. This plan included the construction of two double chairs, a J-bar, 10 ski runs, and an 18,000 square foot day lodge. The total cost was estimated to be over $2 million. At the forefront of the development was Jim Ganter, who formed the Sugarloaf Corporation which financed the construction. Carl Barber, formerly at Boyne Mountain, was announced to be the new general manager.

By December of 1964, the new Sugarloaf Resort opened to the public with much fanfare. A large modern snowmaking system ensured ample snow coverage and the ski school boasted five instructors. At this point in time the skiable terrain at Sugarloaf consisted of the front face served by chairs 1 and 3 as well as the J-bar.

In 1966, Sugarloaf announced the development of an 18-hole golf course adjacent to the ski hill. The mountain also announced the development of 20 hotel rooms which would be built onto the day lodge. In the summer of 1967, Sugarloaf installed a third Hall double chairlift on the backside, now known as chair 6, serving four runs. This chair provided access to much needed intermediate terrain and further solidified Sugarloaf's position as one of the top resorts in the Midwest.

By October of 1967, the developers unveiled the general master plan for the land, which included the sale of many townhomes and cottages that would face the ski hill or golf course. Additionally, an airstrip at Sugarloaf was constructed and private flights between Sugarloaf and Detroit were advertised. The late 1960s truly were the start of the mass development of ski resorts around Michigan. All across the state, resorts such as Boyne Mountain, Boyne Highlands, Caberfae, and Nub's Nob were installing lifts, building hotels, and expanding skiable terrain.

In 1968, the lodge at Sugarloaf was further expanded with an additional 30 hotel rooms and a new restaurant and bar. A heated indoor swimming pool was also constructed and the airstrip was lengthened to 4,000 feet. At this point in time Sugarloaf was doing so well that their yearly lift ticket sales were increasing over 100% from previous years. The ski resort was well known for its precariously steep frontside runs, which included the famed Awful Awful run.

In 1969, Sugarloaf installed yet another Hall double chair on the backside, now known as chair 5. This lift opened up several intermediate options as well as an extremely steep run known as Awful Awful Awful, or AAA for short. In 1970 the resort added another nine holes to their golf course. Additionally, a new snowmaking system was designed by the resort's general manager to replace the original Larchmont system. This new snowmaking system increased the resort's capacity by over 100%.

By 1972, the resort installed a fifth Hall chair on the backside, serving advanced and intermediate terrain including the famed Manitou 2 run. This lift is now known as chair 4. While a warm winter in 1973 caused a loss in excess of $300,000, the resort still continued to expand, constructing a 31-unit townhome complex in 1973. By 1976, Sugarloaf constructed a $350,000 conference center as well as a huge addition to the base lodge cafeteria.

By 1979, the resort announced construction of 100 additional hotel rooms, which would bring the sleeping capacity to 1,000 people. Sugarloaf was so busy at this time that they started to implement dynamic ticket pricing. Weekday lift tickets were $8 and weekend lift tickets were raised to $15, which was at this point the highest price in the state. While the ski resort saw 20% fewer skiers that year, they saw a 6% increase in spending for the season.

However, while Sugarloaf experienced record revenues throughout the 1970s, the winters of 1979-80 and 1980-81 were extremely warm, causing a severe drop in business. Sugarloaf had intended to fund the 100-room expansion through the sale of Economic Development Corporation bonds, however the bonds were not sold because of rising interest rates and slumping economic conditions. Thus Sugarloaf defaulted on its construction debt to Empire National Bank and filed for Chapter 11 bankruptcy in April of 1981.

In March of 1982, Harold Van Arnam stated that he had reached an agreement to purchase all assets of Sugarloaf, however the courts did not approve this deal. In December of 1982, Traverse West Incorporated, a wholly owned subsidiary of Empire National Bank, took over operations of the resort. The winter of 1982-83 was all around a disaster, with revenues of ski resorts throughout the state down as meager snowfall and warm temperatures were prevalent.

In 1983, Sugarloaf was finally sold to a group of investors headed by John Sills, who stated the need to increase the resort's summer business. Backed with a Farmer's Home Administration loan of over $2 million, Sugarloaf carried out several improvements including new run clearing and expanded snowmaking. Thankfully, the 1983-84 ski season went on to be one of the best snow years on record, with Sugarloaf experiencing a huge boom in visitation.

Throughout the 1980s, not much changed at Sugarloaf. The resort continued to upgrade snowmaking equipment and installed night lighting on virtually all of the terrain. They also embraced the emerging sport of snowboarding with open arms at a time when many other resorts shunned it. In 1989, Sugarloaf installed a new Leitner-Poma triple chair between the J-bar and chair 3. This lift provided access directly from the ski lodge to the hill and further helped reduce lines at the resort. This would end up being one of the last larger capital expenditure projects undertaken at Sugarloaf.

Throughout the 1990s, Sugarloaf experienced several good and several bad snow years. However, as resorts across the region such as Boyne Mountain continued to modernize with new lifts, hotels, and snowmaking, Sugarloaf stayed much the same as it always had. However, in 1995 the ski resort did undertake the development of a second golf course designed by Arnold Palmer. The course wrapped around the backside of Sugarloaf and featured 18 holes, officially opening to much fanfare in April of 1996.

In 1997, following a poor snow year and several unpaid debts, John Sills surrendered Sugarloaf to Empire National Bank. In November of 1997, Sugarloaf Resort was bought from the bank by Remo Pauli under his company Hotel Group International. Pauli created a wholly owned subsidiary, Mountain Management Corporation, to manage the resort. Pauli did not hold on to Sugarloaf for long, as in 1999 he put Sugarloaf back on the market. Pauli stated that running a ski resort was not within his area of expertise. This came after Pauli failed to obtain a liquor license, which caused problems attracting business groups and conferences.

While there were several parties interested in purchasing the resort, no deal went through. By October of 1999, Mountain Management Corporation filed for Chapter 7 bankruptcy, with over $1.2 million in unpaid bills held by 107 creditors listed. Despite the pending bankruptcy, Sugarloaf continued to operate for the 1999-2000 ski season as a Denver-based management group took over the reins. Sugarloaf closed on March 1st, 2000 after a warm winter.

In June of 2000, Huntington National Bank, which had acquired Empire National Bank, sued Sugarloaf to foreclose a mortgage it held on the property. Huntington National Bank stated that it was owed more than $3 million on its original $4 million loan. The bank also stated that Pauli was behind on state property and Employment Security Agency taxes. Sugarloaf did not operate for the 2000-01 ski season.

In December of 2000, a local businessman Doug Nanny announced intentions to lease the ski hill, eventually converting it into a family conference center. Nanny did not end up operating the resort, as Pauli still somehow ended up with the ski resort. Pauli did end up reopening in 2002, operating it from January until March. While only the three frontside lifts were open, a new restaurant was opened in the lodge and the hotel was reportedly open for business.

However, by April of 2002 a court ruled in favor of Huntington National Bank and ordered Sugarloaf to be auctioned off. A citizens group titled Friends of Sugarloaf formed to try and raise enough funds to purchase the sinking resort. Though the auction was scheduled for July of 2002, a last-minute pause took place as Pauli stated that he had found a buyer. The buyer turned out to be a Florida real estate firm titled Sugarloaf 2002 Limited Corporation, which also happened to be owned by the wife of Remo Pauli. The company closed on the resort in November and stated intentions to eventually reopen the resort once litigation had been resolved.

However, Sugarloaf sat vacant until 2005, when local resident Kate Wickstrom purchased the resort from Polselli. Wickstrom sold off the two golf courses and started renovations to the lodge. She envisioned the revamped Sugarloaf as a destination resort for snowboarders with multiple snowboard parks that would bring in a lot of business. Wickstrom announced that the bar and restaurant would reopen in 2006 and the frontside would hopefully reopen for the 2006-07 ski season. The reopening obviously did not happen and Sugarloaf continued to sit abandoned. In 2013, Wickstrom reportedly transferred the property back to Pauli.

In 2016, Jeff Katofsky, a Californian attorney, purchased Sugarloaf and announced plans to reopen the mountain. Katofsky reportedly purchased the property without even visiting it or understanding the state it was in, paying $3 million for the property using the business name Sweetbread Limited Corporation. Katofsky also removed all the chairlifts, though the lodge remained standing. However, despite Katofsky's grand plans for the property, nothing ever materialized. In 2020, he sold the property to an undisclosed buyer.

In 2021, the undisclosed buyer started the removal of the former lodge and hotel. At this point the building was in extremely rough shape and not at all salvageable. Demolition was completed in 2022 and virtually nothing remains of the property. It is unclear what the future holds for Sugarloaf, but it is unlikely that it will ever be a ski resort again.