Two notable geographic features in Orleans County are beautiful Lake Memphremagog, which reaches north into Canada, and rugged 3,862-foot Jay Peak, the home of a ski resort that receives the highest average annual snowfall of any mountain in the eastern United States.

Lake Memphremagog was a renowned Indian tribal fishing and hunting area. It is still prized for those purposes today, as well as recreation. The lake is 30 miles long and one to four miles wide with about two-thirds of it in Canada.

Jay Peak is one of the major summits of the Green Mountains traversed by the Long Trail, the oldest long-distance hiking trail in the United States. The Long Trail extends 272 miles from the Massachusetts state line to the Canadian border.

Another historical man-made feature that stands out in Orleans County is the Bayley-Hazen Military Road, built during the American Revolutionary War to provide an invasion route to Canada. It was never completed or used for that purpose, but it was instrumental in the settlement of the county. The 54-mile road began south of the Northeast Kingdom in the town of Newbury on the Connecticut River and ran north through Greensboro, Craftsbury, and Albany to Hazen's Notch near the Canadian border in Westfield. Some local roads follow portions of the original Bayley-Hazen route. Greensboro and Craftsbury, located next to each other at the southern tip of Orleans County, were the first towns settled in the county.

Due to its proximity to Canada, Orleans County’s history is peppered with dangerous and colorful tales of smuggling to and from Canadian markets, beginning with the Revolutionary War and extending through the War of 1812 and the liquor prohibition era of the 1920s and early 1930s.

Orleans County was the site of several memorable early 19th century events: the 1810 Runaway Pond incident in Glover that sent a torrent of water roaring from that town through Barton, Brownington, Coventry and Newport to Lake Memphremagog; a hurricane in 1815 that caused extensive property damage and crop losses; and damaging cold weather in 1816, which became known as the year with no summer. Northern Vermont and southern Quebec were particularly hard hit in 1816.

Today, Orleans County is bisected by Interstate 91, the major north-south road in eastern Vermont. The county’s most populated towns, Newport and Derby, straddle the southern end of Lake Memphremagog at the international border with Canada.