Orwell is bordered by the town of Shoreham to the north, Whiting to the northeast, Sudbury to the east and southeast, and Benson to the south.

Mount Independence, elevation 306 feet (93 m), is located in northwest Orwell, overlooking Lake Champlain and the town of Ticonderoga.

[4] Vermont Route 22A runs through the town, leading north to Vergennes and south to Fair Haven, where it continues into New York.

While those soldiers billeted at Fort Ticonderoga enjoyed comparatively splendid conditions in the French-style fort, Mount Independence proved a trying and difficult environment for its small cadre of revolutionary defenders, who frequently returned to their farms in the surrounding countryside to tend to their homesteads.

[6] The fortress was passed between the British and Colonials, until it was eventually abandoned at the cessation of hostilities on the northern front of the war.

However, these bright times would be marred by several major tragedies that coincided with the attempted industrialization of the area's farmlands in the 1870s, when several young men were lost in a thresher accident near what is now the intersection of Main Street and Route 22A.

This tragedy was keenly remembered by the community, which banned industrial farming later that year in a special town meeting.

Orwell attempted in the late 1990s to obtain a franchised fast-food restaurant, as a vital link in the food availability between Whitehall, New York, and Vergennes, Vermont, but the residents of the surrounding townships blocked the move, claiming it would upset the rural beauty of the western Vermont countryside.