Oakland: Railroad History, Trails and Culture

Get to know Oakland through a range of themes: railroad history, historical exhibits, trails and cultural offerings. To start planning, consider whether you’re more interested in a historic building and its collection or would like to set aside time for an outdoor trail. Each route and visitor offering has its own focus.

Railroad History and the Region’s Past

The restored B&O station, built in 1884, is now home to the Oakland B&O Museum. It displays local and regional railroad artifacts, bringing together the historic station building and the railroad collection. The museum is open daily from 10 a.m. to 3 p.m.; on some days, hours may be extended, depending on the availability of volunteer staff. Check current hours before your visit.

The Garrett County History Museum features exhibits about the founding of Garrett County, the county’s history and the lives of its residents in earlier times. The museum also has themed rooms on early industry and a faithful reconstruction of the interior of an early log cabin. Its topics range from the county’s history to industry and a reconstructed living space.

Trails and Different Perspectives

The Glades Biking/Walking Trail starts at the Town of Oakland parking lot by the Asa McCain Walking Bridge. The one-mile, lighted trail passes historic Washington Spring. The 88 Bridge Trail has different features: it connects to the Glades Park Loop Path, is seven-tenths of a mile in each direction, and runs from Glades Park to the 88 Bridge site and the Civil War blockhouses.

This information allows for a direct comparison: lighting and the route past Washington Spring are key landmarks on the Glades Trail; for the 88 Bridge Trail, they are the connection to the Loop Path and the historical destinations listed. You can choose between the trails based on the features described, rather than comparing them by length alone.

Another option is the Oakland, MD Walking Tours. The five different tours each offer a slightly different perspective on the town. Unlike the trails, whose descriptions specify a starting point, length, route or destinations, these tours focus on the variety of perspectives on the town.

Events and Cultural Offerings

The 59th annual Autumn Glory Grand Feature Parade takes place in downtown Oakland on Saturday, October 10, 2026, at 1:00 p.m. Event dates and programs may change, so check the details as you plan your trip. Oakland’s Autumn Glory Festival is a four-day festival; its dates and program may also vary.

In the Oakland Arts & Entertainment District, The Gallery Shop gives local visual artists a place to present and sell their art. Monthly special exhibitions are planned year-round, featuring talks, workshops, demonstrations and entertainment. If you’d like to plan for a specific event, check the dates for your stay. Our Town Theatre offers a variety of plays and other theater experiences; if you’re planning to attend a performance, it’s also a good idea to check the current schedule.

Discover more destinations: Accident, 4, Bloomington and Lonaconing.

Return to the main travel overview: Garrett County.