Seasonal decorations and events, such as the town Christmas tree, are located at the station.

Main Street comprises historic two to four-story edifices with retail businesses, such as a theatre, museum, book store, pharmacy, antique shops, clothing stores and banks.

[4] Also listed on the National Register are the Garrett County Courthouse and Hoye Site.

[5] The hotel was a major tourist attraction until it was torn down in the early 20th century.

[clarification needed] One of the most prominent and historic churches in Oakland is St. Matthew's Episcopal Church, where U.S. Presidents Ulysses S. Grant, James Garfield, Grover Cleveland, and Benjamin Harrison have all attended services.

Oakland, owing to its high elevation and valley location, is among the coldest and snowiest locales in the state of Maryland, and has a warm-summer humid continental climate (Köppen Dfb).

According to weather data tallied between July 1, 1985, and June 30, 2015, for every location in the National Oceanic and Atmospheric Administration's official climate database, Oakland is the snowiest place in the state of Maryland with an average of 106.1 inches or 2.69 metres of snow per year.

33% of Oakland's residents were of German descent, 11% English, 11% Irish, 6% Italian, 2% Dutch, 2% French, 2% Polish, 2% Scottish, 2% Scotch-Irish and 2% Swedish.

People of Swiss, British, Welsh and Hungarian descent each comprised 1% of the population.

[15] The Oakland post office is home to a Depression-era mural, Buckwheat Harvest, painted by American artist Robert Franklin Gates.

Gates was funded by the Treasury Section of Fine Arts to complete the mural as part of President Franklin Roosevelt's New Deal.

Gates was probably inspired by Garrett County's strong tradition of growing buckwheat.

Heading south, US 219 briefly passes through Mountain Lake Park and connects with U.S. Route 50 before entering West Virginia.

MD 39 heads northwest to West Virginia, while MD 135 heads east, connecting to Maryland Route 560, Maryland Route 38 and Maryland Route 495, as well as the towns of Mountain Lake Park and Deer Park, before entering Allegany County near the town of Luke.