The Oaks midway, or, as it was called at various times between 1905 and 1925, the “Avenue,” the “Trail,” or the “Jolly Midway,” housed numerous amusements, some that changed from year to year. The following, in rough order by date of arrival, are some of the most significant.

Chilcoots Pass (aka The Bumps)
This bumpy slide was a common ride in amusement parks across the country. It was named after a steep and hazardous Yukon pass that brought miners into the gold fields during the Klondike Gold Rush of 1897. Advertisements from 1905 called the Chilcoots Pass “the king of funmakers” and commented how spectators were greatly amused as they watched the “victims” tumble down the massive slide.

Chute the Chutes
The “Chutes” helped The Oaks to establish itself as a full-fledged amusement resort in 1905, as most major parks on the East Coast and in the Midwest had a similar contraption. Flat-bottomed boats that seated twelve passengers left a platform seventy feet in the air to slide down a chute into a shallow pond. During the park’s first year, patrons climbed wooden stairs to reach the platform, but in 1906 a moving staircase made the trip easier. By 1908, an advertisement featured a couple riding the boat to the top of the platform. A caption summarized the improvement: “Up You Ride, Down You Slide.” Fire destroyed the popular ride in 1920, but a new “Chutes” took its place the following year. In the Twenties, “Monkey Mountain,” located in the middle of the Chutes pond, was the home to the Oaks’ monkeys and bears.

Giant Whirl Flying Machine
Long chains connected boats to a forty-foot structure and swung riders over the Willamette River. The Whirl was originally located at the entrance to the Lewis and Clark Exposition, but The Oaks secured a contract to operate the ride in July of 1905. Soon thereafter its concessionaire moved it to its permanent Portland location - between the Tavern and the Bathhouse at The Oaks.

Ikeda’s Mid-Air Slide
“The most magnificent amusement device in the world,” according to one 1905 advertisement, this aerial trolley carried passengers over the Chutes in baskets which hung from a cable high in the air.

Mystic Maze
One of The Oaks’ very first concessions, the wooden building that housed this maze attracted customers to the confusion inside with its respectable, crisp-white paint job.

Laughing Gallery (aka Temple of Mirth)
This traditional fun-house, according to the sign out front, made “the old feel young and the young feel gay.” It was one of the park's prize attractions during the resort's first year of operation.

Hale’s Tours of the World
Hale’s Tours was once one of the largest theater chains in the nation. At The Oaks starting in 1906, patrons sat in Pullman locomotive cars and watched a moving picture screen that simulated the scenery they would view if they were truly passengers. Clanking wheels, train whistles and other sound effects added to the sensation.

Figure Eight
This wooden rollercoaster was the park’s first, having opened for business in 1906. It was named for its sharp curves. Advertisements in 1912 indicate that its name changed to the Blue Streak that year.

Gregg Carousel
It cost $20,000 to purchase this attractive carousel, a popular feature for children and adults alike. Lightning struck the carousel in 1915, damaging its motors and giving its operator a minor electric shock. In the 1920s it was replaced by the Herschell-Spillman Carousel that still exists in the park today.

The ZigZag Staircase
This moving staircase threw all who dared to climb it in various directions.

Old Mill
The Old Mill came to The Oaks in 1906. It was named for the Dutch mill wheel that seemed to propel boats through tunnels, caves, and scenes depicting various worldly places. While its scenery changed from year to year, its concessionaire totally renovated it and opened it in 1915 as Mystic River. The new boat ride included exciting special effects that made passengers feel as though they were falling down rapids, dashing under waterfalls, and even sinking. Romantic couples who cherished such rides were not disappointed, as one advertisement read, “Let it be told in a whisper, there are dark, yes dark places galore in the course of the half-mile trip.” The water ride was again renovated in 1924 and advertised as the Ye Old Mill.

The Tickler
Round wooden tubs rolled back and forth down an incline, throwing seated patrons into one another. The Tickler appeared at the park at least as early as 1908.

Ferris Wheel
The Oaks was home to various Ferris wheels throughout its history, beginning in 1905. Advertisements proclaimed that an updated wheel in 1918 would rival the Chutes in popularity.

Joy Wheel
The Joy Wheel was another contraption designed to make its riders lose balance and crash into one another. Patrons tried to remain on the large rotating disk for as long as possible before being spun off. A 1910 advertisement made note of a “jolly wheel,” but 1911 was the first year that this ride was advertised as the “Joy Wheel.”

Barrel of Fun
This barrel-shaped building was a favorite with the kids from 1913 onward. Surprises inside included skeletons that popped out of corners and air jets from the floor that lifted the skirts of unsuspecting girls. The exit from this concession was a long slide from a second-story window.

Hilarity Hall
When Hilarity Hall premiered at the park in 1918, Manager Cordray asserted that inside patrons would find “everything to make you laugh, whether you are ten or forty.” The Hall contained moving staircases, sinking floors, and spinning chairs.

Miniature Railroad
The addition of a new Miniature Railroad was the main attraction of the park’s 1916 opening day. The gauge of the track was only a foot wide, and the engine only the size of a man’s fist, but the train took youngsters around the park – through a tunnel and under trees – just like a regular train. In a dedication ceremony on May 13, 1916, young “Bobby” Bollinger, who years later owned and managed The Oaks, had the honor of placing the golden spike along the tracks.

Kentucky Derby
Boys and girls competed with one another as they pulled levers that controlled toy horses. Oaks patrons began racing at the Kentucky Derby in 1919.

Dodgem
Spectators enjoyed watching the frustrated drivers of the Dodgem cars. While steering wheels and gear shifts gave the illusion that the motorcars could be controlled, the cars went in every direction but the one the drivers sent them. Dodgem came to the park in 1919.

The Whip
The Whip, which took passengers in buggies around a circular track, came to the park in 1920. Articles touted the new feature as “the ride with a kick in it” and remarked that it was enjoyed by younger folk and a “good percentage of the adventurous of more mature years.”

The Merry Mix-Up
Manager Cordray toured the nation’s amusement parks in December of 1924 to find new rides. The following season he introduced this device that sent patrons sailing through the air in individual swings which were attached to a rotating tower.

Caterpillar
Introduced to The Oaks in the early Twenties, the cars of this coaster traveled in a continuous loop around a bumpy track. A canvas canopy stretched over the cars once the ride gained full speed, making the attraction a favorite among young couples.

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