Cumberland under angular clouds. Cumberland, Maryland. August 30, 2026, 6:34 pm.
I build camera time into my trips because I don't have the income to travel just to photograph. My trip to Oakland and Cumberland, Maryland, was unique because I was transporting my dad’s ashes for burial, so you know, there was no emotional pressure. The gravesite is a four-hour drive from home, and I needed to be there by 12:30 pm. The night before, I got home from work around 11:30 pm, went to sleep around 12:30 am, and woke up shortly after 5:00 am. A nap is unrealistic. I plan to stop in Oakland, Maryland, to eat and compose myself before going to my dad’s burial. The gravesite is in Terra Alta, West Virginia, a twenty-minute drive away. I knew I wouldn’t want to drive home afterward, so I booked a one-night stay at a boutique hotel in Cumberland, Maryland, to drive home the next day. I scouted both areas on Google Maps to make a rough plan for what to photograph in Maryland.
Oakland, Maryland:
I spent about an hour in Oakland, Maryland, walking through its picturesque historic district. Some of my photos look like postcards. Incorporated as a town in 1862, Oakland was one of Maryland's first designated Main Streets. The B&O Railroad's initial expansion brought prosperity to the area, as evidenced by the remaining historic buildings and Victorian architecture. The town currently draws history buffs and outdoor enthusiasts, but with only two small motels, you will likely need to stay elsewhere.
Oakland B&O Museum_01. Oakland, Maryland. August 30, 2026, 10:56 am.
Oakland B&O Museum_03. Oakland, Maryland. August 30, 2026, 11:09 am.
Oakland, Maryland Skyline. Oakland, Maryland. August 30, 2026, 11:24 am.
Garrett County History Museum. Oakland, Maryland. August 30, 2026, 11:15 am.
Oakland B&O Museum_02. Oakland, Maryland. August 30, 2026, 11:32 am.
Oakland, Maryland Museum Signs. Oakland, Maryland. August 30, 2026, 11:26 am.
Garrett County Courthouse & Jail. Oakland, Maryland. August 30, 2026, 11:48 am.
Music & Bait. Oakland, Maryland. August 30, 2026, 11:44 am.
Oakland Bike Shop. Oakland, Maryland. August 30, 2026, 11:03 am.
Red Car. Oakland, Maryland. August 30, 2026, 11:54 am.
Cumberland, Maryland:
Vacationing in more famous areas is often a better bargain. You really need a compatible personality to enjoy shabby chic. I love nature, mountains, local flair, and the charm of imperfection. I hope my spending helps the local economy. I may seem well off to a local, but back home I am one of them.
Cumberland, a major 19th-century transportation and industrial hub in the Appalachian Mountains, known as the "Gateway to the West”, was once Maryland's second-largest city. After World War II, industries restructured and concentrated operations in eastern coastal cities. According to the 2023 American Community Survey, Cumberland is one of the poorest cities in the United States, ranking 707th out of 935 metropolitan and micropolitan areas in per capita income. Tourism has a long way to go to revitalize the area.
Courthouse & Bridges. Cumberland, Maryland. August 30, 2026, 6:45 pm.
Cumberland, Maryland Tourist Trap. Cumberland, Maryland. August 30, 2026, 6:55 pm.
I admire the efforts to make Cumberland more attractive, but the tourist-centric Canal Place Historical Park blends the aesthetics of an amusement park and a board game. A more subdued styling would better support the serious history themes. However, the adjacent historic downtown has beautiful murals to discover on buildings and in alleys.
Historic Downtown Cumberland_01. Cumberland, Maryland. August 30, 2026, 7:05 pm.
Cumberland Downtown Perspective. Cumberland, Maryland. August 30, 2026, 7:24 pm.
The Wills Hotel_01. Cumberland, Maryland. August 30, 2026, 7:22 pm.
Steeple – Emmanuel Episcopal Church. Cumberland, Maryland. August 30, 2026, 7:00 pm.
Ghost Signage. Cumberland, Maryland. August 30, 2026, 7:26 pm.
Historic Downtown Cumberland_02. Cumberland, Maryland. August 30, 2026, 7:14 pm.
Games and a haircut. Cumberland, Maryland. August 30, 2026, 7:21 pm.
Footer’s Dye Works. Cumberland, Maryland. August 30, 2026, 6:40 pm.
Western Maryland Railway Cumberland Station_01. Cumberland, Maryland. August 30, 2026, 6:49 pm.
Western Maryland Railway Cumberland Station_02. Cumberland, Maryland. August 30, 2026, 6:57 pm.
Western Maryland Railway Cumberland Station_03. Cumberland, Maryland. August 30, 2026, 7:03 pm.
When I visit small towns and cities, I often wonder where I would work and live. Most of the time I don’t see the answers when I am there. Google Maps reveals museums, parks, current employment centers, residential areas, and the husks of past prosperity. Searching YouTube for info about an area surfaces real estate agent videos, dash cam driving tours, and cautionary resident-made content.
Cumberland's Historic District and museums show efforts to preserve its heritage. The buildings and businesses are wonderful, and I hope tourism attracts more development without pushing the struggling locals out. I have yet to see a luxury real estate-driven economy do any favors for the working class. The jobs a Whole Foods grocery store brings to an area do not replace a large industry and its supply-chain and service satellites. Companies that want to build data centers will exploit cheaper real estate and perks for access to water and power, but they don't require a large, diverse workforce.
The middle ground that benefits all parties in former boomtowns remains undiscovered. Maybe an adjacent commercial area can be developed without gentrifying the historic center and turning locals into residents of an inconveniently located modern workcamp. Visually, a wealthy part of town and low-income housing outside of town don't imply upward mobility.
Communities must vote for better economic outcomes or accept subservience to the wealthy without representation. Culture war politics do not create jobs or make poverty go away. People need clean air, water, and food. Education, housing, and healthcare should be within reach. Unless you are wealthy, your situation will not change unless you vote for economic change.
If you have the means, consider small towns for your vacations. Learn some history and see a place as it is. Help improve your fellow citizens' lives. Resist politics that sell nostalgia. History is often ugly, so if it does not glorify oppression, resist ignoring or erasing history that is disturbing. Like family, you can’t choose your past. Make the best of it, and work toward a future you can be proud of.
I’ll be posting the supplemental photo blogs over the next month or so as I complete them in order: 2026 Boutique Hotels, 2026 Pics from Parks, and 2026 Townscapes. Each blog will cover the locations in more detail and include about two dozen photos. This process is a test run for future photo blogs, so please feel free to comment or email me feedback. Some photos will be available for purchase as fine art prints, cards, puzzles, and other merchandise. Let me know if you have any favorites.
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