Although the uphill side of Deadwood's Main Street seems like a natural area for development, the neighborhood didn't get its start until the turn of the century, thanks largely to two factors: gunpowder and the stubbornness of Deadwood's first property-rights advocate.
As commercial development sprung up along the banks of Whitewood Creek in the mid to late 1870s, the land along Deadwood Creek remained largely industrial. Considered the outskirts of town, it was here that slaughterhouses, brick kilns and powderhouses were constructed. These buildings laid along the Gayville Toll Road, which connected Deadwood with the mining camps further up the gulch. Since explosives were critical to mining, powderhouses were especially prolific; in fact, two of them sat at the current intersection of Main Street and Highway 14A. Because these buildings were deemed a public safety hazard, very few houses were built along the toll road.
Development also was halted by the Grantz Reserve, a large piece of property along the toll road owned by miner Otto Grantz. When the county moved to upgrade the road for development, Grantz refused to allow the "trespassing" workers access. Although city officials attempted to compensate Grantz, the miner refused to relent, even erecting fences and digging a ditch through the street. In 1897,
Mayor Sol Star deposited a sum of money in Grantz's bank account while he was out of town, cut down the fences, filled in the ditch and reopened the road. A slightly more legal agreement was reached in 1898.
A number of large bungalows, Tudor cottages, Colonial Revival homes and other architectural beauties were quickly erected on Grantz's former property. Water lines and paved sidewalks were added in 1903 and 1904, making the Upper Main neighborhood Deadwood's most modern and attracting the wealthy elite. Merchant John Hunter, Doctor Felix Ashcroft and James Nelson, who managed what was to become the Broken Boot Gold Mine, all had homes here.
More than any other neighborhood, the Upper Main area was built to last. Construction of new homes in the neighborhood continued into the 1960s, when a new four-lane highway finally relieved the neighborhood's traffic.