The Wettest Dry Town in Alaska

Anchorage in 1920 was a town of about 1,900 souls — railroad workers, merchants, adventurers, and drifters who had washed up at the end of the rail line. It was a rough place, barely five years old, still more camp than city. And despite Alaska's bone-dry prohibition laws, it may have been the wettest town in the territory.

The problem — or opportunity, depending on your perspective — was geography. Anchorage sat on Cook Inlet, with hundreds of miles of unpatrolled coastline. Boats could land almost anywhere. To the south, Seward connected to the Lower 48 by steamship. To the north, the wilderness offered infinite places to hide a still. Prohibition in Anchorage was less a law than a suggestion.

This is the story of how a tiny frontier town became a smuggler's paradise — and how it got a neighborhood named Bootlegger's Cove.

Dry Before the Nation

Alaska went dry on January 1, 1918 — nearly two years before the 18th Amendment imposed Prohibition on the rest of America. The territory's voters had approved the ban in 1916, part of a progressive movement that saw alcohol as the root of frontier lawlessness. If Alaska was going to become civilized, the thinking went, it needed to sober up.

The law was strict. Selling alcohol was illegal. Manufacturing alcohol was illegal. Even possessing alcohol became illegal under subsequent legislation. The only legal booze was for medicinal purposes, available by prescription — a loophole that doctors exploited enthusiastically. Otherwise, Alaska was supposed to be bone dry.

Nobody told the drinkers. Or rather, everyone told them, and they didn't care. Anchorage was a railroad town full of men who worked hard and expected to drink hard. They weren't going to let a law passed by do-gooders in Juneau change their habits. If alcohol was illegal, they would simply obtain it illegally.

"Prohibition in Anchorage was a joke from day one. You could get a drink anywhere if you knew who to ask. And everybody knew who to ask."

— Anchorage old-timer, Oral history, 1960s

Forty Speakeasies

By 1920, Anchorage — population 1,900 — had between 30 and 40 operating speakeasies. That's roughly one speakeasy for every 50 residents. The establishments ranged from back rooms in legitimate businesses to dedicated drinking halls that made only token efforts at concealment. Everyone knew where to get a drink. The only question was which establishment you preferred.

The speakeasies operated semi-openly. Raids happened occasionally — the federal marshal would swoop in, arrest a few people, pour out some liquor, and leave. Within days, the speakeasy would reopen. The fines were minor, the demand was constant, and the profits were too good to abandon. Prohibition enforcement in territorial Alaska was woefully understaffed.

The clientele was democratic. Railroad workers drank alongside businessmen. Construction crews shared tables with clerks. In a town where everyone knew everyone, the speakeasies became social centers — places to hear news, make deals, and escape the brutal routine of frontier life. The liquor was often terrible, but it was liquor.

Quality varied wildly. Some speakeasies served genuine imported whiskey, smuggled from Canada or the Lower 48 at considerable expense. Others served "hooch" — locally distilled moonshine that could range from drinkable to deadly. More than a few Anchorage residents went blind or died from badly made liquor. It was a risk drinkers accepted.

The Cove

The neighborhood now known as Bootlegger's Cove earned its name honestly. A natural indentation in Cook Inlet's shoreline, the cove offered protection from observation and easy access to the water. Boats carrying contraband cargo could land at the cove under cover of darkness, offload their goods, and disappear before anyone was the wiser.

The geography was ideal for smuggling. High bluffs screened the beach from town. The inlet's massive tides created windows when boats could approach and depart quickly. The cove was close enough to downtown for easy distribution but isolated enough to avoid casual detection. It was, in smuggler's terms, perfect.

Liquor arrived by multiple routes. Some came from Canada, shipped down through Southeast Alaska and transferred to smaller boats for the final run to Anchorage. Some came from the Lower 48, hidden in the cargo of steamships arriving at Seward and trucked north. Some was manufactured locally, in stills hidden throughout the surrounding wilderness. All of it flowed through distribution networks that centered on the cove.

The name "Bootlegger's Cove" wasn't used publicly until after Prohibition ended — nobody wanted to advertise the illegal trade while it was ongoing. But everyone knew what the cove was for. The first documented use of the name in print came in 1933, right after repeal, when the smuggling days could finally be acknowledged openly.

The Phantom Swede

Every Prohibition town had its legendary bootleggers, and Anchorage's was the "Phantom Swede." The nickname referred to a smuggler — or possibly several smugglers — who operated with apparent impunity throughout the 1920s. The Phantom Swede was said to run liquor from Canada, landing cargo at remote beaches and distributing throughout the territory.

Details about the Phantom Swede are scarce and contradictory. Some accounts describe a single Swedish immigrant who operated a sophisticated smuggling network. Others suggest the name was applied to multiple bootleggers, a collective alias for whoever was running liquor at the moment. The truth has been lost to time and deliberate obscurity.

What's clear is that major smuggling operations existed, and that they were remarkably successful. Federal agents made occasional busts but never dismantled the networks. The liquor kept flowing. The speakeasies stayed supplied. Someone was winning the cat-and-mouse game, and the authorities were the cats.

"Anchorage was a wide-open town. Prohibition was observed mostly in the breach."

— Steve Haycox, Alaska Historian

The Bounty System

Anchorage authorities, desperate to enforce the unenforceable, resorted to unusual measures. The city offered $5 bounties to anyone who reported the location of an illegal still. This was real money in 1920s Alaska — a day's wage or more. The bounty system was designed to turn neighbors into informants.

The primary informants turned out to be children. Kids would roam the outskirts of town, following suspicious smells and activity, and report their findings to authorities in exchange for the reward. It was a strange economy — children earning pocket money by ratting out moonshiners, moonshiners trying to bribe the children into silence.

The bounty system worked, sort of. Stills were busted with some regularity. But new stills appeared as fast as old ones were destroyed. The demand was too strong, the profits too good, the enforcement too weak. The bounty system made Prohibition marginally more inconvenient for bootleggers, but it didn't make Anchorage dry.

Repeal

National Prohibition ended on December 5, 1933, with the ratification of the 21st Amendment. Alaska, which had gone dry before the nation, stayed dry slightly longer — territorial prohibition wasn't repealed until 1934. But when legal liquor finally returned, Anchorage celebrated with enthusiasm.

The speakeasies became legitimate bars. The bootleggers found other work — or, in some cases, became licensed liquor distributors. Bootlegger's Cove kept its name, a permanent reminder of the town's wet history. The Prohibition era entered local legend, a colorful chapter in Anchorage's rough-and-tumble past.

The neighborhood of Bootlegger's Cove is now one of Anchorage's most desirable residential areas. Multi-million-dollar homes line the bluffs where smugglers once landed their cargo. The tony address belies its disreputable origins. Real estate listings mention the scenic views; they generally don't mention the illegal liquor trade that gave the place its name.

Anchorage was born during Prohibition and spent its first decades thoroughly, enthusiastically drunk. Forty speakeasies served 1,900 people. Smugglers landed contraband at a hidden cove. The Phantom Swede ran liquor from Canada. Children earned bounties for reporting stills. The law said Alaska was dry, but Anchorage never got the message.

Today, Bootlegger's Cove is a prestigious address, home to lawyers and executives and oil company managers. The bluffs that once sheltered smugglers now shelter expensive homes with expensive views. The name remains, a fossil from a wilder era, when Anchorage was young and rough and absolutely determined to drink.

The next time you're in Anchorage, raise a (legal) glass to the bootleggers. They built this city as surely as the railroad workers did. They just did it one bottle at a time.