South Main Street Historic District
Eleven buildings and a World War I memorial fill two blocks of Oregon’s central business district, which was added to the National Register of Historic Places in 2000 and, according to its nomination, “retains a high level of historic integrity in setting, materials, feeling, association, and design. … [This] grouping of late 19th and early 20th century commercial buildings [is] immediately recognizable as a downtown.”
The historic district is on the 100 blocks of South Main and Janesville Streets, forming one corner of a triangle. The World War I memorial is the focal point where the two streets meet. The buildings were constructed between 1877 and 1915, and the memorial, thought to be one of the first erected after World War I, was added in 1920.
The earliest Oregon businesses were operated out of log cabins nearly 40 years prior to when the village, then known as Rome Corners, was incorporated in 1883. At that time, 29 businesses were located in and around today’s historic downtown. While the addresses of the historic buildings have changed somewhat, local businesses are still housed in the buildings.
Dan and Elizabeth Donoghue own The Chocolate Caper (105 S. Main Street) and Kickback Café (107 S. Main Street). Their businesses have been in the McDermott Building since 2014 and August 2021, respectively. “We love getting to be a part of the history of Oregon, being able to take something old and use it in a modern way,” says Dan. “There was so much craftsmanship that went into our building, like floor joists 3 inches thick and 12 inches on center. I never have to worry about the floor collapsing as I bring in equipment for The Caper.
“A nice surprise when renovating the space for the Café was finding the original floor, in good shape and clean, below seven layers. We were happy that we could match the original finish. Some people like to lean away from the history of a building; we want to lean into it. We feel like we are more integrated into the village by having our businesses in a historic district.”
Bergey Jewelry (111 S. Main Street) has been in the Cowdrey Tailer Shop building (built in 1878) since 1972. It’s among the longest-surviving commercial buildings in Oregon. Called the White House because it was originally built of cream brick thought to have come from a brickyard east of Oregon, the building has been faced with red brick. The original name can be seen in a white stone inlay on the building’s façade.
Jill Hoff took over the business four years ago from her father, who bought and restored the building to its original look, including a wood floor and raised ceiling. Jill likes being in the historic district, saying, “People will comment on the historic character of the building. It reminds them of a jewelry store they shopped at when they were younger—even down to the antique cash register. However, we just use it as a cash drawer now since the largest amount it can handle is $99.99.”
Built in 1898, Dad’s Barber & Hair Shop (114 Janesville Street) and the commercial vernacular-style building housing it are owned by Curtis Kneifl. A barber shop had been sited there since 1943. Before then, several other barbers, a harness maker, and the saloon for the Hausman Brewing Company were in the building. Curtis says the building originally had a second floor, but that was destroyed by fire and not replaced.
Curtis cautions those considering opening a business in a historic district to know what they want to do with the outside of the building. There are regulations that apply in historic districts set by local historic preservation commissions. Renovation plans require approval.
Next door to Dad’s is Cutler Financial Group (116 Janesville Street), an investment management and retirement planning company. As a CERTIFIED FINANCIAL PLANNER™ professional, owner Levi Cutler has been in his present location for five years. Levi is from Oregon and relocated to the downtown. “Oregon’s historic downtown is a core part of the community. There are people always on the move. We like being where the action is.”
Katie Ace, also from Oregon, is the owner of Ace’s Main Tap (121 S. Main Street). The commercial vernacular-style building was constructed in 1880 and updated in 1907 and 1940. This building and the one next door were erected for Isaac Howe, a doctor who moved from Vermont. A drugstore, a grocery store, and a general store were former occupants. Katie’s uncle owned the bar for 20 years before her father, Kevin Ace, took over in 2014. Katie worked for her father, who trained her to eventually run the bar; she took over when Kevin passed away in 2018.
“I love the vintage, older look of the building,” says Katie. “When you go down into the basement, it feels like you’re passing through a train tunnel, a concrete archway lined with bricks. I like this location. People driving through our downtown stop because there are different businesses to explore here.”
Doris Deits has been in business with Peaceful Hearts (123 S. Main Street) for 20 years. “Being next to other established businesses was beneficial to my business getting noticed and accepted into the community when we first opened.” As the building owner, Doris says, “There’s a comfort to being in an old building and having renovated, remodeled, repaired, or repainted every square inch of it. I have a more intimate relationship with this building than most business owners have. I feel more rooted and grounded here.”
In February 2022, The Ready Set restaurant and bar (113 S. Main Street) opened in part of what is the Oregon Masonic Hall. The building was listed previously on the National Register of Historic Places in 1992. An eclectic commercial design built in 1898, the hall is the “oldest and most enduring of a number of clubs that have been a characteristic feature of the social life of Oregon from its founding days to the present,” according to the Register nomination. “[It] is the best preserved of surviving reminders of the most prosperous period in the village history.”
Nate Herndon, one of the restaurant partners, felt welcomed into the community with its locally sourced seasonal food and cocktail offerings. His favorite feature of the building is the pressed-metal ceiling. Two bathroom doors came from the state Capitol. Nate says the interior of the building has been opened up so patrons can see into the kitchen.
History repeats itself. Oregon’s businesses prosper, and the buildings remain lovingly cared for by their current owners.
Jeanne Engle is a freelance writer.
Owners who renovate historic district commercial buildings may be eligible for state and federal tax credits. Information is available from the Wisconsin Historical Society’s State Historic Preservation Office.
(608) 261-9582