Sit on the Left side of the plane for the best views on flights from Boston to Portland. Left side wins at both ends of the flight. Over the Rockies and Great Basin the views are broadly similar on both sides, but the Boston departure and Portland approach both strongly favor left for the most iconic landmarks.

During takeoff from General Edward Lawrence Logan International (BOS), sit on the Left side for the best views. Logan's most common departure is runway 22L/22R heading southwest, then aircraft turn northwest. A left seat gives you Boston Harbor, the downtown skyline, and the Charles River basin as you climb out over the city. Right side faces the open Atlantic with little of interest. Notable sights include: Boston Harbor and its islands, downtown Boston skyline, Charles River and Cambridge, Fenway Park area.

When landing at Portland International (PDX), sit on the Left side for the best views. PDX typically lands on runway 28L/28R approaching from the east, meaning the aircraft tracks westward over the Columbia River Gorge. The left side faces south toward Mount Hood and the Portland metro, while the right side looks north into Washington state with less dramatic terrain. Left is the clear winner. Notable sights include: Mount Hood (11,249 ft) to the southeast, Columbia River below, Portland city grid, Mount St. Helens on the distant northern horizon.

The flight from General Edward Lawrence Logan International (BOS) to Portland International (PDX) takes Approximately 5 hours 30 minutes to 6 hours.

The flight tracks roughly along the 44th parallel. Notable features include the Adirondacks and Lake Ontario early on, then the Great Lakes southern shore, followed by the flat agricultural expanse of the upper Midwest, the Missouri River valley, the Northern Rockies over Montana or southern Idaho depending on routing, the Snake River Plain, and finally the Blue Mountains of eastern Oregon before descending into the Columbia River basin.