In the days immediately following the Civil War, North Avenue marked the northern limits of the then young city of Milwaukee and a Sunday visit to North Point was an ambitious picnic jaunt. But Charles Andrews, proprietor of the Newhall House, saw the pleasant lake vistas stretching northward and determined to open up these vistas to the people of Milwaukee. In 1863 he formed the Lake Avenue Turnpike Co. and obtained a state charter to operate a toll road. Built at a cost of $50,000 the new road was opened in the fall of 1872. Starting at what is now Lafayette Place it followed the lake front to the present Silver Spring Drive. The road was unique in one respect-it had only one toll gate and that at the city, or the south, end. As the city grew the lower part of the road was abandoned and the owners donated the land to the city. The toll gate moved progressively northward to Bradford Avenue, a point north of Edgewood Avenue and finally to Capitol Drive {formerly Atwater Road and Mineral Spring road).

Andrews toll road was the first incentive for the development of the North Shore. One John Luck opened a small tavern near the North end-a sort of "First and Last Chance"-and the progenitor of the famed Whitefish Bay Resort of later years. Lueddeman's on the Lake (now Lake Park), the old Milwaukee Country Club and numerous road houses and picnic grounds were early developments. The last part of the road was sold to the county for $15,000 in 1915 and the entire length of Lake Drive became the public thoroughfare it is today.

Steel Rails first came to the North Shore in 1874 through a fluke. The Milwaukee, Lake Shore & Western, building southward along the lake shore from Manitowoc, had planned to use the tracks of the Milwaukee and St. Paul Railroad on the west bank of the Milwaukee River for their right-of-way into Milwaukee. But somehow they did not make arrangements until tracks had been laid as far as the old Dickman farm, several blocks from the site of the Milwaukee Country Day school. An official of the MLS&W called on Alexander Mitchell of the Milwaukee & St. Paul but got a prompt turn-down from the canny Scot who couldn't see why his road should give a hand to a competitor. The chief engineer of the new road saved the day with a novel idea born of necessity. "Why not strike for the lake front and come down the bluff near North Point to a terminal on the lake front?" The idea was presented to the Chicago & Northwestern Railway, which was looking for a route into Milwaukee for its new "Air Line" from Fond du lac. The two roads teamed up, met at Lakeshore Junction (just south of Capital Drive) and from there ran on joint tracks to the depot on the lake front.

In 1887, the MLS&W purchased a considerable tract near what is now Fairmount Avenue in Whitefish Bay. Rumors spread that car shops and freight yards would be built. An enterprising real estate firm platted in the vicinity one of the first subdivisions north of North Avenue and set off a boom which resulted in platting of much of what is now the village of Whitefish Bay before the bubble burst in the panic of 1895. Even officials of the railroad were financially interested in some of the subdivisions and the road ran special suburban service to encourage prospective home owners to buy lots. The collapse of the boom brought an end to this service but before long trains were again stopping at Whitefish Bay.

An official of Whitefish Bay heard that the C&NW (which had purchased the MLS&W in 1895) had given up any intention of using its Whitefish Bay property for car shops and might be receptive to the idea of selling. He confirmed this at the Chicago offices and also found that the railroad would consider the abandonment of the line between Lakeshore Junction and what is now Fox Point, provided the villages of Shorewood and Whitefish Bay would jointly buy the old right of way. Because of the intense rivalry between the two villages, the Whitefish Bay official foresaw the trouble if Shorewood thought that the idea originated in Whitefish Bay. Accordingly this official and the railroad concocted a plot whereby the Shorewood officials were "tipped off" that the C&NW might remove its tracks. The Shorewood group eagerly went to Chicago to present the proposal. The railroad officials, as the story goes, were properly reluctant, but finally permitted themselves to be sold and the project was assured. Work started in 1927 and the last of the rails removed by 1929.

But there was still another steam railroad in the history of the North Shore-The Milwaukee & Whitefish Bay railroad, better known as the "dummy line." Actuated by the same motives which prompted Andrews to build his toll road, Guido Pfister and associates opened the new path in 1888. The tracks began at Farwell and North avenues, ran north on what is now Downer Avenue, then by twists and turns eventually reached the terminus at Henry Clay Street in Whitefish Bay at the front door of The Whitefish Bay Resort. In its short life span of 10 years the Dummy Line had a happy history. Limited service was maintained during the winter for the growing population of the North Shore but in summer a 20 minute schedule was provided for the crowds flocking to the numerous resorts and picnic grounds along the shores of both river and lake.

The socialites bound for the exclusive Milwaukee Country Club rubbed elbows with the holiday crowds headed for such places as Mineral Spring park, Welcome Park, Jefferson Park, and the one and only Whitefish Bay Resort. Here at the end of the line the chugging locomotives came to rest and the merry-makers entered the spacious pavillion overlooking the sparkling bay named for those succulent planked whitefish served in the spacious dining room. Here one could drink Milwaukee's Pabst Brewing Co. beer at the little round, white tables along the walk, enjoy band music by the Joseph Clauder Brass Band outside, and Clauder's quintette inside under the direction of violinist Herman Kelbe. Kelbe also conducted the orchestra in the Davidson Theater in winter. The Dummy Line passed out of existence when the Oakland Avenue street car line was extended to Silver Spring Drive in 1898.