© 2026, Christian Cassidy
Happyland was a 30-acre, seasonal amusement park and recreational ground located on the south side of Portage Avenue between modern-day Aubrey and Dominion streets. It stretched from Portage Avenue down to the Assiniboine River.
It may seem an odd place to put an amusement park, but at the time this was beyond the edge of the city's residential development on the south side or Portage Avenue. Up until 1906, what is now Vimy Ridge Park was a cricket ground, a nine-hole golf course became part of the Happyland site, and the huge Jubilee Nursery farm was west of that.
Even in 1910, when the above map was published, streets around the park such as Lipton, Aubrey and Dominion, had very few houses on them. It was not until around 1912 that development began on a large scale.
Happyland was established by the Ingersoll Company of Pittsburgh, Pennsylvania, which operated parks in cities like Pittsburgh, Cleveland, Washington, D.C., and Coney Island. (See a list here.)
Officials from Ingersoll Co., including its chief designer Alfred Robinson, were in Winnipeg during the first week of May for a site visit. W. O. Edmunds, vice president, said the company was happy to invest in fast-growing Winnipeg, and the large site allowed the park to expand along with the city's population.
A local company called the American Park Company, made up of officials from Ingersoll and other local and American investors, was created to own and operate the venue. It appears that real estate man William M. Fisher, along with some smaller investors, owned the land on which the park sat.
Local carpenter S. B. Ritchie was the main contractor for the site. His work included Dalnavert, the J. H. Ashdown Co. Warehouse, plus several schools and fire halls. His main legacy is likely as the designer of the residential section of Winnipeg Beach, from laying out the streets to building hundreds of cottages and other buildings.
Ritchie soon received his first batch of Happyland building permits from the city. They included a 100 x 250 foot auditorium, administration building, cafe, 'house of illusions', main entrance structure, old mill building, bandstand, grandstand, 3,000 feet of fencing, and a circus ring.
Ritchie's men worked so quickly that the opening date was moved from June 1 to May 21, but a week of rain postponed it again to Thursday, May 24, just before the start of the Victoria Day Weekend.
Happyland's inaugural weekend was a great success. Some newspaper accounts, no doubt publishing figures provided by the park's publicist, claimed that 44,000 people came out for its first couple of days. This is unlikely as the park was only serviced by a single streetcar line along Portage Avenue.
An estimate in the Winnipeg Free Press put the number at 27,000, with 9,000 of those attending a pair of baseball games between the Winnipeg Maroons and Duluth of the Northern League.
Still, there is no doubt that thousands of people came to see the spectacle, causing huge lineups at times.
Admission to Happyland cost ten cents and it offered patrons a wide variety of activities to take part in.
There was, of course, the amusement park with its boardwalk, rides, booths, and other attractions. Most noticeable was the large Ferris wheel, the figure 8 roller coaster, and slip slide that was billed as the largest ever built in Canada. (Ingersoll was in the amusement ride construction business before it branched out into developing parks.)
The auditorium and a small theatre meant the site could host plays, concerts, vaudeville shows, dances, and roller skating. The huge grounds and grandstand allowed travelling rodeos and circuses to set up shop. The picnic pavilion and grounds welcomed large groups, such as church congregations and annual employee get-togethers. The recreation grounds had a running track and a baseball diamond that was home to the Winnipeg Maroons of the Northern League.
Thanks to a robust lighting system, events could take place late into the night.
A team of security staff, park guides, and an on-duty nurse helped keep people safe.
By all accounts, Happyland was a welcome addition to the city's entertainment scene with its fixed amenities and acts that rotated through each week to keep things fresh. It tried hard to appeal to people of all ages.
The park, of course, was seasonal. It usually opened for Victoria Day and closed after Labour Day. The baseball team kept its own schedule, and spectators could access the diamond in whatever month the team was playing.
August 6, 1908, Winnipeg Tribune
On the surface, things may have looked rosy, but behind the scenes, the park was in financial trouble. Not enough people came through the gates to pay the bills, including the $8,500 in rent it paid to Fisher, plus electricity, staff, entertainers, groundskeeping, and maintenance.
It was particularly cool and wet in the summer of 1906, though the novelty of the park meant it had decent attendance numbers. With the same, or fewer, people expected in 1907, none of the year two investments were made to the park to expand its attractions or grounds.
It opened as usual in 1908, with no new venues or big shows. On August 6, the directors announced that the park would close immediately due to financial reasons. the property It defaulted to landowner William M. Fisher.
What went wrong with Happyland?
The American investors may not have counted on the fact that Winnipeg's amusement season was likely shorter compared to some of its U.S. parks. There was also lots of existing summer competition from sporting events, smaller private recreation parks like River Park and Elm Park, and trips to the beach or cottage by train.
The Winnipeg Tribune noted that the lack of new investment after opening day made the park stale. That investment, it said, was paid to the American owners as dividends, and "A good many of the local men suffered heavy losses through the closure. The Americans who formulated the company have come out with the long end of the stick."
Fisher immediately put the park's contents up for auction to try to recover the value of some of the unpaid bills and, more likely, to clear the land to sell it off as individual suburban lots. Instead, a new group of investors called the Winnipeg Park Company stepped in and wanted to make another go of Happyland.
The new ownership group was a little mysterious. A list of investors was not released, and they left it to their lawyer to make the announcement of the purchase. The two names listed as officers of the company, P. H. Anderson, president, and O. C. S. Lavelle, secretary, do not appear in the Winnipeg street directory that year. Fisher continued to be the landlord.
The company appointed Frank Miller, who had been an assistant manager at Happyland, as its new manager. His first act was to allow the Maroons to continue to use the baseball diamond as their home field, but the park itself did not reopen in 1908.
As for future plans, the company lawyer said that the group was planning to make big investments in new amenities and other improvements to the site.
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