Okemo was founded in 1955 by a group of local businessmen. Operations officially began January 31, 1956 with four inches of snow and trails serviced by two Poma surface lifts. The lower poma cost 20 cents per ride, while the upper one cost 60 cents. The early 1960s saw the introduction of four more Pomas, and the first chairlift, the Sachem double, was introduced in 1965. Along with all of these improvements, Okemo began to offer slopeside lodging starting in 1961. In 1963, Okemo purchased its first groomer, a Tucker Sno-Cat model. Snowmaking was first used, starting with the lower part of the mountain, in 1966.

The 1970s brought tough times for Okemo. There were fires, floods, and competition from the West. In 1982, the owners decided to sell the resort rather than go into bankruptcy. Tim and Dianne Mueller purchased the resort on August 2, 1982. While the resort was in danger of going bankrupt and the facilities were outdated, the Muellers wanted to preserve the historic feeling. They kept the name Okemo, which they claim is Native American for "All Come Home", although there is no evidence as to which Native American language this comes from. Certain trail names also continue to preserve this sentiment, such as Chief, Tomahawk, Wardance, Sachem, and Arrow, all of which are present on today's trail map.

Since 1982, Okemo has grown in many different ways. The facilities have been expanded in every aspect, including new chairlifts, trails, lodges, and snowmaking. Since purchasing Okemo, the Muellers have also acquired Mount Sunapee Resort in Newbury, New Hampshire and Mount Crested Butte in Crested Butte, Colorado.

On December 6, 2008, the Muellers sold Okemo, Crested Butte and Mount Sunapee to CNL Lifestyle Properties, Inc. in a lease-back deal valued at over $130 million dollars. CNL now owns the underlying assets of the resorts, while the Muellers will continue to run the resorts as usual.

The base of Okemo stands at 1,144 feet (346 meters) above sea level, and the summit is 3,344 feet (1,019 m). This gives Okemo the largest vertical drop in southern Vermont, 2,200 feet (670 m). The mountain has a total of 119 trails spread across 632 skiable acres (2.52 km²). Trail difficulty is almost evenly divided between novice, intermediate, and advanced/expert. A paved road that runs along the mountainside is used as a ski trail in the winter, making it Okemo's longest trail at 4.5 miles. Mountain Road can be driven during the summer and has parking spots for scenic viewing of the valley.

96% (605 acres) of the trail area is covered by snowmaking, the highest percentage in the East. The snowmaking pond has a total water capacity of 155 million gallons. In addition, the quality of the grooming is ranked sixth in the nation by SKI Magazine readers.

The trails built as each new part of the mountain have had some sort of theme, such as the Native American names on the main mountain and the astronomy-related names at the top of Jackson Gore. The following lists all of the trails by rating and name, alphabetically:

The trail sidewinder, Ph. Henry Gray

See also: Okemo Trail Map

Okemo has 12 chairlifts, including five high-speed detachable quads, four fixed grip quad chairs, and three triples. There are seven surface lifts, of which five are carpets, one is a poma in the beginners' area, and one is a t-bar that takes riders to the top of the halfpipe. These lifts combined to give the mountain a total uphill capacity of 33,450 people per hour.