All the trails at Saddleback are named after famous fishing flies created in Rangeley by anglers Carrie Stevens, Bud Wilcox, and Dick Frost.

It was awarded the “Best in Maine” ski resort for 2022, 2023 and 2024 by Down East Magazine, beating out the larger mountains of Sunday River and Sugarloaf.

Updates since the Arctaris Impact Fund purchase include RFID scanners at the new Rangeley quad lift, a new mid-mountain lodge, EV charging stations, A-Frame condominiums, repaved mountain road, high-speed residential internet, affordable on-mountain employee housing, and mountain biking trails.

The lower mountain consist of 18 beginner trails, and is serviced by the South Branch Quad, and the Sandy Rope Tow.

In 2007, the Maine Land Use Regulation Commission approved Saddleback's 10-year development plan, which calls for a major expansion of lifts, trails, vacation homes, and other facilities.

[4] In the summer of 2008, Doppelmayr constructed a fixed grip quad to replace the Kennebago t-bar at the top of the ski area, along with new trails.

The Kennebago quad provided easy and faster access to the high-elevation advanced terrain with views of the lakes and Western Maine Mountains.

Of 400 acres of land, the mountain was placed on the market for $12 million, that include ski trails, lifts, the base loge and the surrounding 121 condominium units.

During the summer of 2015, the Saddleback owner, Mark Berry, announced in a release that the ski resort would not open for the 2015–2016 season unless the outdated and slow Rangeley double (GMD Mueller) was replaced; costing them nearly $3 million.

[6] As the year progressed into 2016, Saddleback officials said they were not opening for February school vacation week, keeping its patrons concerned and sending the future of the mountain into uncertainty.

Critics also questioned Monsour's intentions after he was quoted in Maine news reports as saying he was motivated by the EB-5 program that offers foreigners permanent residency if they invest in certain U.S. real estate projects.

[7][8][9] In March 2019, the Arctaris Impact Fund based in Boston made an undisclosed offer to purchase Saddleback Mountain.

Federle owns a Saddleback condo and Shepard has strong interest in preserving the mountain and its role in the economy of the region.

In February, it was announced that Rangeley would be replaced by a new high speed quad constructed by Doppelmayr, accompanied by lodge upgrades, new snowmaking, and a fair ticket pricing approach.

During February, March, and April 2020, the COVID-19 pandemic caused massive disruption to the ski industry and global economy, however, Saddleback announced that their investments were moving forward as expected, with the opening date scheduled for December 15, 2020.

Saddleback had released a plan to open in late November, however the date revised to December 15, due to delays in completing the new Rangeley quad.