Pickering Town are an old established football club, formed in 1888, making them older than many top professional clubs. Happy to compete in local leagues for almost 80 years, the club made the bold step up to senior non-league football in 1972, when an invitation to join the Yorkshire League was taken up. Those who made the momentous decision to leave local football back in 1972 could never surely have imagined the progress the club would make over the following years. The ground has developed beyond all recognition in this time, with the erection of floodlights, two smart seated stands and a covered enclosure, making it an impressive small football stadium.

On the field, there have been plenty of ups and downs along the way, as the club sought to become established in the highly competitive world of non-league football. The Pikes enjoyed many successful seasons in local football winning many trophies but the decision to join the Yorkshire League came after they had been relegated to the York League Second Division. Pikes had been unsuccessful in an application for membership of the Yorkshire League twelve months earlier, but after the terrible 1971/72 campaign, with the relegation, the club received an invitation to take up a vacant place in the Yorkshire League Third Division, and so the journey in senior non-league football began.

The team became champions of the third division in 1973/74 gaining promotion to the Second Division, then next season 1974/75 after another successful campaign, The Pikes achieved promotion to the Yorkshire League Division One. After maintaining their status in Division One the following season, the club ended being relegated at the end of 1976/77 to Division Two and suffered a similar fate the following season. Over the next four seasons The Pikes continued to play in Division Three of the Yorkshire League with mixed fortunes.

Then in season 1982/83 with the merger of the Yorkshire League and Midland Counties League, The Pikes were placed in Division Two (North) of the newly created Northern Counties East Football League. After re-organisation in the NCEL the team were placed in Division 1 (North) 1984/85, and again in 1985/86 after another reorganisation the Pikes found themselves competing in the Second Division. In the season 1987/88 the Pikes won the Second Division league title to gain promotion to Division One of the NCEL, where they finished a creditable 5th.

In 1990/91 the Pikes claimed their first major cup success since stepping up to senior football by winning the North Riding County Cup, defeating Marske Utd 3-2 at Whitby Town’s Turnbull Ground. Season 1991/92 saw Pickering gain promotion to the Premier Division of the NCEL by finishing runners-up in Division One to champions Stocksbridge Park Steels. The following season their first in the Premier Division saw a thrilling campaign with The Pikes finishing runners-up to Spennymoor United on goal difference, with the final result only being decided on the last day of the season. Season 1993/94 saw the Pikes finish 5th in the league and reach the Final of the North Riding Senior Cup for the first time losing 2-0 to Guisborough Town, this season also saw the club play their ever FA Cup tie, beating Penrith 5-2. The following season 1994/95 again saw the club again reach the Final of the North Riding Senior, suffering defeat again, losing 5-2 to Marske Utd.

The team continued to compete in NCEL Premier division, until suffering relegation to Division One at the end of the 1998/99 season. Two seasons later 2000/01 the club regained their Premier Division status by finishing runners-up in Division One to Borrowash Victoria.

The next few seasons saw the team have fluctuating fortunes, with the best campaigns being 2003/04 when finishing 5th, having been amongst the front runners for a large part of the season and third in 2008/09. The club also reached the last 16 of the FA Vase on three occasions before achieving their best run in the competition in reaching the Quarter Finals in 2005/06 losing out to eventual winners Nantwich Town.

Season 2012/13 saw The Pikes winning the North Riding Senior Cup, defeating Marske Utd 3-0 in the Final, the club again reached the Final in 2016/17, but on this occasion losing 3-1 to Whitby Town, the league campaign this season was also one of success with the club finishing runners up in the NCEL to Cleethorpes Town, unfortunately just missing out on promotion.

The following season 2016/17, saw The Pikes repeat the feat, this time finishing runners-up to Pontefract Collieries, but with two teams been promoted on this occasion The Pikes achieved their highest ever level in Senior non-league football.

Season 2018/19 was one of consolidation, but the club have continued to improve their facilities, with the extension of the players changing rooms and the building of an extension to create two new changing rooms for officials during this close season.