AUGUST 29, 1919

Ted Gilbert became the first motorcyclist to pilot a machine to the top of the rocky butte near Portland, Oregon. His machine of choice was a Harley-Davidson Sport Twin. 4,045 feet above sea level, Larch Mountain is 11,000 feet of narrow, brushlined trail. Rugged and heavily timbered, with huge boulders, sharp stones, and logs lining its sides, it had previously withstood all attempts to reach its summit on a motor vehicle. The three-mile climb took 2 hours and 20 minutes and needed neither chains nor a tractor band to help the Sport Model along. A big sign measuring 4 feet by 6 feet nailed to the side of a mighty fir tree marks the time, the name "Harley-Davidson Sport Model," and the name of its rider, so that when Mazamas and various other organizations of mountain climbers would later reach the top, they would be able to see that other things besides goats and nags could climb the hazardous cliffs of Larch Mountain.

Harley’s Sport Model can also be credited with other endurance feats.  H.C. “Hap” Scherer rode a Sport Model to break the Three Flag Record in 1920, riding from Canada to Mexico in 64 hours, 58 minutes, breaking the previous record by more than 5 hours. He also smashed the Denver-Chicago record that same year, riding more than 1,260 hilly miles for nearly 48 continuous hours. Throughout its life, 20,000 miles were accumulated on Scherer’s Sport Model, a testament to its agility and endurance.  

Harley-Davidson Vintage Off-Road Photograph

Oregon Rocky Butte Topped by a Motorcycle.

AUGUST 27, 1949

Jimmy Chann set his record time of 11 minutes and 18 seconds at the 15-Mile Championship in Milwaukee on August 27, 1949. This was the second year in a row that he won the Championship. It was also a week after he won his third 25-Mile Championship in Springfield, Illinois. Chann was a very successful rider to race for Harley-Davidson.  He raced for Harley-Davidson in the 1940s and early 1950s. During that time, he won several national championships and set numerous records. In 1953, he was seriously injured during the Daytona 200 and his career ended shortly thereafter. 

Jimmy Chann Holding a Trophy

Harley-Davidson racer Jimmy Chann sets an AMA record on a 15-mile track with a time of 11 minutes and 18 seconds.

AUGUST 24, 1958

Harley-Davidson swept the 1958 racing Grand National competition held in Du Quoin, IL, marking the fifth straight year that Harley was first in the nation. Leading the pack was Carroll Resweber with 36 points. One point behind was Joe Leonard in second place. Three new AMA records were set: Joe Leonard won the 200-mile Beach-Road Course in 1 hour, 59 minutes, 11.3 seconds and the 50-mile, 1-mile dirt track in 34 min, 33 sec; and Carroll Resweber led the 20-mile, 1-mile dirt track race in 14 min, 5.12 sec. Harley had an additional seven outstanding victories throughout the year. 

Harley-Davidson 1958 racing Grand National competition Poster

Carroll Resweber claims the 20-mile national title.

AUGUST 21, 1926

On the 1¼ mile board track in Rockingham, NH, Curly Fredericks set the record for fastest lap on a board track, registering 120.3 mph. That speed was never to be bested. Board Track racing was a teens and twenties’ form that involved speeding around a banked, wooden track. It was outlawed because of the high death rate of racers and spectators alike. Harley-Davidson’s Eight-Valve Racer was so successful in board track racing, that it was outlawed by the racing federation at the time. 

Curly Fredericks on A vintage Harley-Davidson

Record set for fastest lap on a board track.

AUGUST 15, 1939

The first National Gypsy Tour was held in 1917, as shown in this photo from that year. Gypsy Tours were large rallies organized by local motorcycle clubs. In 1939, the tours kicked off on August 15th. The events usually included a motorcycle tour that ended at a park where games and competitions were held. Participants were awarded watch fobs and trophies were handed out for various categories at a national level. These categories included best dressed, highest percentage of military participation, highest percentage of female participation, most riders, and fastest times for racing events. 

Gypsy Tours were open to all and were social events that attracted thousands of participants. They were billed as a way to show the public the fun times that could be had on a motorcycle. Although the American Motorcycle Association set the official date for when Gypsy Tours would take place, individual motorcycle clubs were free to hold them anytime during the summer. Gypsy Tours attracted large crowds, but their popularity began to fade in the late 1950s.The tradition of events like the Gypsy Tours were never lost, though, as motorcycle clubs around the country still hold annual rallies and tours. 

Vintage photo of the National Gypsy Tour

The official start date of the 1939 Gypsy Tours.

AUGUST 14, 1915

On August 14, 1915, over 150 Harley-Davidson employees and their families gathered at Army Lake for the first company picnic. The picnic featured games, prizes, and music and was, by all accounts, a great success. L. C. Rosenkrans, Harley-Davidson’s staff photographer, took several photos at the event in 1915. These images were among those recently re-discovered in 2012.  

Harley-Davidson First Picnic at the Park

The first Harley-Davidson company picnic is held at Army Lake.

AUGUST 6, 1939

More than 2,000 motorcycle enthusiasts gathered in New York to celebrate Motorcycle Day at the 1939 World’s Fair. Members of 30 motorcycle clubs from a dozen states converged upon the Fair Grounds in the early morning hours. Many were visiting New York for the first time, which was then the largest city in the world. The event was hosted by the Empire Motorcycle Club of NYC and corresponded with their tenth anniversary. Special shows for motorcyclists were held in the House of Magic, such as demonstrations of stroboscope light on a Harley-Davidson wheel. In the afternoon, Clubs and Auxiliaries assembled for a cyclists’ parade and competitions.  Trophies were presented for Best Uniformed Club, Highest Group Mileage (9,030 miles), Best Uniformed Auxiliary, and the cyclist who rode the Longest Distance. 

Motorcycle Day at the New York Worlds Fair

Motorcycle Day at the New York World’s Fair.

AUGUST 1, 1954

After WWII, the company was facing stiff competition from European manufacturers. Motorcycles produced by Europeans were smaller, lighter, and very powerful.  As they gained popularity, the company began to develop a new motorcycle in response. In 1952, Harley-Davidson introduced the K model. The K models were 750cc side-valve, V-twin driven motorcycles that retained plenty of power. They did well in competition and dominated with racers like Charles Carey. Harley-Davidson racers would go on to win several championships throughout the fifties, including seven straight victories at the Dakota 200. In 1957, the K model was replaced by the Sportster. 

Harley-Davidson introduced the K model

Charles Carey wins the 8-Mile National Championship on a Harley-Davidson K model.