1935-36: The CCC and Windsor Outing Club opened the Mt. Ascutney Trail. At 5,400 feet in length, this intermediate trail immediately captured the interest of skiers throughout the region, as did the nearly completed Ascutney auto road nearby.
1946: A group of people including Catharine “Kip” Cushman, Bob Bishop, Dick Springer, Bob Ely, Robert Hammond, and Dr. Peter Patch worked together to get lift served skiing on Mt. Ascutney. Composed of tiered rope tows, two slopes, and a few trails, the Mt. Ascutney Slopes development was likely located at the present day bottom of the Brownsville Trail on Route 44.
1947-48: The rope tow operation was relocated west to the present location of Mt. Ascutney Resort. The improved operation included diesel rope tows, many new trails, night skiing, and snowcat served skiing (via a 3.5 mile ride in a Tucker machine on the other side of the mountain).
1948-49: Another rope tow was added.
1949-50: After a poor season, Ascutney found itself in bankruptcy for the first time. Cushman’s brother, Percival Ranney, purchased the area and handed it back over to Kip.
1955-1956: George Dunning took over as manager of Ascutney for a season, and Ascutney was sold to John Howland shortly after.
Circa 1957: Mt. Ascutney Ski Area, Inc. company was formed by Howland, with Walter Paine becoming the first outside shareholder. The capital injection funded significant improvements for the 1957-58 season, including a 2,250-foot T-Bar and Larchmont snowmaking equipment.
1959-60: Ascutney attempted to install a Larchmont chairlift in the vicinity of its novice area. Operating on a track, the lift was plagued with mechanical problems. After being marketed for the 1960-61 season, the lift was quietly removed.
1962-63: After narrowly avoiding bankruptcy, West Slope Area was developed for the season, served by a new T-Bar. Also around this time, Walter Paine (publisher of The Valley News), became principal owner in the ski area, keeping John Howland on as General Manager.
1963-64: Ascutney expanded upward with a new Hall double chairlift, increasing the area’s vertical drop from 620 to 1,470 feet. In addition, a novice T-Bar was added and a new lodge built.
1968-69: Night skiing was expanded and a mid-station added to the double chairlift, allowing for novices and intermediates to access easier terrain. In addition, the Novice T-Bar was relocated to a new slope between the double chairlift and Main T-Bar.
1970-71: The Sunrise Mountain area opened, featuring novice and intermediate terrain serviced by a new Hall double chairlift.
1972: Walter Paine sold the 820-acre ski area to a group led by John and Sarah Giles. Apart from some real estate development, Ascutney ski area did not change much during the 1970s.
1981: The Giles sold the ski area to Dr. Ronald Massa in July of 1981.
1983: Mt. Ascutney Ski Area Corp. filed for Chapter 11 bankruptcy. That summer, a group named Summit Ventures, Inc. purchased Ascutney and began an aggressive 10-year investment plan. The main shareholders included Joseph Grano Jr., Lou Guido, Daniel Tully, and Ira Lampert.
1984-85: In conjunction with the development of 100 condos, two new triple chairlifts were installed, expanding the ski area downward to the new Village Area. In addition, significant investments were made in snowmaking and grooming.
1986-87: The summit double chairlift was upgraded to a triple, giving Ascutney a top to bottom modern lift system.
1990-91: While the area was able to operate during the Winter, creditors forced it into liquidation that spring.
1993: Steve and Susan Plausteiner purchased Ascutney at auction, beating the owners of Smugglers Notch and an equipment liquidator. Ascutney reopened in December of 1993.
2000: $3 million was invested, including a new high speed detachable quad. Capping the five-year expansion campaign, the new North Peak development resulted in nearly 300 more vertical feet of terrain above the top of the triple chairlift. Unfortunately, debt was growing.
2008: Dan Purjes’ MFW Associates was commencing foreclosure proceedings on the ski area. Two years later, the Plausteiners sold their share in Ascutney to Purjes, who then unsuccessfully attempted to liquidate the area that summer. That fall, word spread that Ascutney would not operate in 2010-2011.
2012: Crotched Mountain, NH announced it had purchased the high speed quad. The refurbished lift debuted as the “Crotched Rocket” in December of 2012. Fixed grip chairlifts still remain standing at Ascutney.
2013: The area was reportedly auctioned to MFW Associates in early November 2013. While the title was reportedly free and clear, the area remained idle for a fourth consecutive season during the winter of 2013-2014.
2014: While MFW Associates initially had hoped to reopen the ski area, it was unable to find a financially viable plan. Instead, the triple chairlifts were sold to Pats Peak and removed during spring and summer 2014.
2014: On October 14, 2014, West Windsor voters approved the purchase of 469 acres of Ascutney, as well as the former base lodge.
2015: The base lodge caught on fire January 8.
2015: Non-profit organization Ascutney Outdoors was formed, and installed a rope tow as the beginnings of bringing back lift-service to Mt Ascutney ski area.
2018: A used t-bar was donated to Ascutney Outdoors and will be installed for use for the 2018/2019 winter season.