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More than 30 traction companies have served the Rose City during the last 128 years. For this listing of important dates in Portland streetcar history I am indebted to the Oregon Historical Society, and the collections of my friends John Labbe (author of Fares Please: Those Portland Trolley Years) and Bill Hayes, as well as the “125 Years of Portland Transit History” chronology that appears on Tri-Met’s webpage.
1872
Ben Holladay's Portland Street Railway Co. began operating the first streetcar line in the Northwest, with horse or mule-drawn cars running on First Avenue from Glisan to Caruthers. The cars were shipped from San Francisco by steamer. 
1882-3
Multnomah Street Railway Co. and the optimistically named Transcontinental Street Railway Co. provided competition with new horsecar lines extending west and northwestward from downtown.
1888
The Willamette Bridge Railway Co. built the first streetcar line on the east side of the river, running horsecars across the old Morrison Bridge to the separate city of East Portland.  On the same side of the river Willamette Bridge also inaugurated the first steam dummy service in town, the Mt. Tabor Steam Line.  Horsecars continued to provide most street railway service, but horses couldn't provide longer suburban service.
1889
Willamette Bridge Ry. launched the state's first electric streetcars (and 3rd in the country) with service crossing the old Steel Bridge on the Albina Line.  Fare was five cents.  The trolleys were 4-wheelers built by the Pullman Co. of Chicago.
1890
The first cable cars in town were imported from San Francisco (built by the Stockton Combine, Harvester & Agricultural Works) by the Portland Cable Railway Co.  They were soon running from downtown to City (later Washington) Park and Portland Heights (later Council Crest).  At nearly the same time Willamette Bridge lost its uniqueness as a flurry of other electric streetcars appeared.   The Metropolitan Railway Co. began the first trolley service in downtown Portland on 2nd St., Multnomah Street Ry. started converting its horsecar lines to electric opertation and the Waverly-Woodstock Electric Railway began operation in Southeast Portland using trolleys ordered from the pioneering Sprague Co.
1891
A period of mergers began as City & Suburban Railway Co. acquired financially struggling smaller companies including, Willamette Bridge Ry., Transcontinental St. Ry. and Waverly-Woodstock Electric Ry. to form the largest street railway company west of the Mississippi River.  For the first time it was possible to cross from one side of town to the other (approximately 16 miles) on a single fare. 
1892
Consolidations continued as the Portland Consolidated Street Railway Co. absorbed the remaining small lines, including Metropolitan Ry. and Portland & Vancouver Ry (a steam line).
1893
The East Side Railway Co., incorporated in 1891, competed the first interurban railway line in the United States between Oregon City and Portland.  It utilized the first long-distance transmission of electric power.
1896
The Portland Consolidated Street Railway Company went bankrupt and its lines were purchased by the Portland Railway Company (the first of two companies with this name), which converted the last cable lines to trolley. 
1901
Although it managed to survive a depression, The East Side Railway Company was sold in foreclosure, resulting in the formation of the Portland City & Oregon Railway, which, in turn, became the Oregon Water Power & Railway Co. a year later. 
1904
Portland Railway had built the first electric streetcar line up to Portland Heights running powerful new trolleys over the Ford Street Viaduct when Portland Railway and City & Suburban merged and united remaining city streetcar operations in one company. The new entity was briefly known as the Portland & Suburban Railway (until it was learned that there was already a freight railroad using that name) but became Portland Consolidated Railway in time to host tourists from Oregon’s one and only world’s fair, The Lewis and Clark Centennial Exposition.
1905
Portland Consolidated Ry. was sold to the Clark and Seligman interests of Philadelphia and New York for $6 million and within months its name was changed to the (second) Portland Railway Co.
1906
The Portland Railway consolidated with the Oregon Water Power & Railway to become the city's one remaining streetcar company, the Portland Railway, Light and Power Company.  PRL&P presided over a system of 28 streetcar and interurban lines that reached their zenith in the years just prior to World War I.  PRL&P's standard vehicles were long-vestibuled "Pay-As-You-Enter" (PAYE) cars built by the American Car Company.
1911
After years of franchise battles the Mount Hood Railway & Power Co. completed laying tracks for an interurban line from east Portland to Bull Run.  Dreams of connecting Portland with Mount Hood died soon after the line became part of PRL&P the following year, however, and even though beautiful interurban cars arrived from the Kuhlman Car Co. of Cleveland the line was never electrified.
1918
PRL&P ordered 25 new BirneySafety Cars to maintain more efficient operation on marginal stub lines.  With the Birneys came the first one-man operation.  They were the last new cars ordered for many years.
1924
PRL&P changed its name to Portland Electric Power Company (PEPCO), but lines remained essentially the same.  Although PEPCO was operating the 3rd largest narrow gauge streetcar system in the US, growth slowed during the 1920s as cutbacks in service and labor, such as remodeling equipment to facilitate one-man car operation, became the norm.
1930s
PEPCO became Pacific Northwest Public Service Co. in 1930, but the name proved unpopular and was changed back to PEPCO in 1933.  The city division was now called Portland Traction Company in an effort to separate unprofitable interuban lines for possible sale.  The Great Depression brought financial troubles and gasoline or electric buses (trolley coaches) began to replace streetcars.  The last new Portland streetcars, 15 streamlined Brill "Master Units," went into service in 1932. 
1940s
PEPCO was made into a holding company in 1940, retaining operation of the interurban lines, with Portland Traction Co. city lines becoming more autonomous.  The advent of World War II brought a reprieve for trolley lines as the nation turned to fuel and rubber rationing.  The process of converting trolley lines to buses stopped.  In fact, the Bridge Transfer line wa brought back after its tracks were chipped out of the pavement.  However, “progress” returned after the war.  In 1946 the interurban lines were turned over to a new company called the Portland Railroad & Terminal Division which launched a modernization plan, bringing in several used streetcars from other cities for their suburban service.  By 1949 the Portland Traction Company retained only three narrow gauge city streetcar lines, Council Crest, Willamette Heights, and 23rd Avenue.
1950
The last city streetcars ceased operation and fans and reporters showed up for the last run, a Willamette Heights owl.  Only two trolleys, beloved “Council Crest” cars 503 & 506, were earmarked for preservation. 
1958
Though both passenger and freight service had become profitable, PR&T Division's San Francisco owners did not encourage ridership and, in spite of a last minute citizen’s effort called “Save Our Streetcars” (SOS), all trolleys disappeared from the Rose City with ceasation of interurban passenger service between Oregon City and Portland.  The writing had been on the wall when the Hawthorne Bridge was remodeled in 1956 without replacing its rails.  Diesel freight operation took over on the former interurban division.  In this same fateful year the Oregon Electric Railway Historical Society was formed to preserve traction heritage. Within a few years former Portland streetcars including "Council Crests" 503 & 506,  PAYE car 615, “Broadway” car 813, “Hollywood” car 4015, interurban 1056 and snow sweeper 1455 would find their way to the OERHS' Trolley Park in Glenwood, OR. 
1970s
Portland civic leader Bill Naito joined light rail advocate, and past OERHS President, Dr. Lawrence Griffith, radio station owner Bill Failing and others, to begin an effort to bring back trolleys to Portland’s historic districts.  Yet, talk of restoring local cars, or importing old trams from Portugal, made little headway. 
1986
MAX Light Rail service began to Gresham, renewing electric rail passenger service in Portland after a hiatus of nearly 30 years.
1987
Vintage Trolley Inc. was formed to assure operation of a vintage streetcar system in Portland. Four reproduction “Council Crest” style streetcars were ordered from GOMACO.  Patient civic leader Bill Naito spearheaded formation of a Local Improvement District to finance the local share of a two-million-dollar Urban Mass Transit Administration grant.  In this same year Oregon Electric Railway Historical Society began a six month trial operation of historic streetcars along the Southern Pacific R.R.'s abandoned Jefferson Street Line from Portland to Lake Oswego using a "tag along" (towed) generator.  This new tourist service was dubbed the Willamette Shore Trolley
1990
After two years of non operation Gales Creek Enterprises obtained the franchise for operating the Willamette Shore Trolley.  OERHS' cars were replaced by a historic trolley leased from San Antonio, TX (later to operate in Astoria, OR) and a former parade car from England, the ship-shaped "Blackpool Belle."
1991
Four Vintage Trolley replicas arrived in Portland during the spring and summer and service between Lloyd Center and downtown Portland began November 29 running over existing MAX track.  The new cars were numbered 511-514 in sequence after their Brill-built Council Crest ancestors.
1995
In October the Glenwood Electric Railway ceased operation at the OERHS' Trolley Park after 34 years and removal of the rolling stock to Brooks, OR, where a lease has been signed with Western Antique Powerland (WAPI), got under way.  In this same year OERHS once again took over operation of the Willamette Shore Trolley.
1998
Westside MAX light rail service began operation between Portland and Hillsboro. 
1999
First electric operation began under overhead at the OERHS' new Oregon Electric Railway Museum in Brooks, OR near Salem.

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