Olympic silver medallist Armitstead raced with the men in the main race, which was watched by bumper crowds.
It is hoped that the evening will become an annual event.
There were four separate races, including one for youths, and several of the riders and spectators had come from overseas, with the Tour de France's Grand Depart taking place in Leeds on Saturday.
In total more than 150 cyclists took part.
The evening also boosted Ilkley's economy, with Ilkley Brewery's pop-up bar, Lishman's barbecue and crepe stall augmenting the bars around the circuit, which started and finished on The Grove.
Riders then turned right along Riddings Road before another right turn onto Albany Walk, which merges into Parish Ghyll Drive before further turns onto Wilton Road and Grove Road took the riders back to the start-finish straight.
The action at Ilkley was a precursor to the entertainment tonight when the focus switches to Otley for their town centre races.
The main events are the Pinsent Mason Otley Women's Grand Prix (6.10), the Chevin Cycles Classic Race (7.30) and the Property Development Grand Prix (8.30).
Home-town heroineArmitstead will compete in both the women's race and the Chevin Cycles race, the latter against her brother Nick.
Results: MAS Design U14s: 1 Euan Cameron – East Bradford CC, 2 Alistair Leivers – Blackpool Youth Cycling Association, 3 William Draper – Team RL360 Isle of Man, 1 Ella Lazonby – Clifton CC; MAS Design U16s: 1 Thomas Pidcock – Aire Valley RT, 2 Robert Gray – Clifton CC, 3 Harry Hardcastle – Kirklees Cycling Academy, 1 Sophie Thackery – Paul Milnes Cycles/Bradford Olympic RC; Avantigas Women’s: 1 Melissa Lowther – Matrix Fitness Vulpine, 2 Elizabeth Holden – RST Racing Team, 3 Rebecca Rimmington – Merlin Cycles; Lister Horsfall – Men’s: 1 Alex Dalton – Squadra RT, 2 Nathan Draper – RST Racing Team, 3 Jacob Trotter – Squadra RT.