Earliest meeting: Friday 17th January 1840
Final meeting: Thursday 11th December 1851
Middletown is a small village in County Armagh just 2 miles from Tynan. Mt Thomas Bond and Mr James Stronge Babington were the initial driving forces behind organising steeplechases in the vicinity of the village as early as January 1840. By 13th January 1840 they had advertised the meeting, with the inaugural event held on Friday 17th January 1840.  The principal event was the prestigious Middletown Cup which, it was suggested, would be held in perpetuity for any horse winning it in consecutive years. In the end this proved not to be possible, for after the 1840 meeting, no further meeting was recorded until 1845, and there was then a further break until a two-day meeting in 1848. Once again racing lapsed until revived in 1851. On Wednesday 19th February 1851 the village organised a race meeting yet again over a course specially selected to ensure safe fences and a run-in over a long stretch of level grassland intersected by stiff jumps in order to test the fencing powers of the horses. The Middletown Purse was won by Mr E W Bond's Bob, while the feature Middletown Cup went to Drone for Mr Evatt, over-hauling long-time leader Baronet close home. Surprisingly, a further meeting was staged later that year on Thursday 11th December 1851, although this proved to be the last, as no further records exist of any races in the village.

Friday 17th January 1840
On 13th January 1840 an advert in the local paper broadcast that the Middletown Cup would be raced for towards the end of the week, a two-mile race open to Gentlemen riders with a 2 sovereign entrance fee. Entries had to be made with Mr John McGlone on, or before, Thursday 16th January, although an entry could be made at post time if double the fee was paid. This made betting prior to the race particularly challenging, given that punters were not aware of the entire field. On the day the Stewards were Mr James Stronge Babington and Mr Thomas Bond. A large crowd attended the inaugural meeting on Friday 17th January 1840, the course being described as one of the most desperate ever witnessed in Irish steeplechasing, with 38 fences, some of which were purposely designed to stop even the best of chasers. There was a two-race card, the first of which was the main event, the Middletown Cup over 2 miles, run in two heats, while the Two Sovereign Open Sweepstakes followed.
Middletown Cup over 2 miles and 28 fences
1. DICE, owned and ridden by Mr A Bond
2. CURLEW, owned by Mr C Conroy and ridden by H Bond
3. SPONGEROD, owned by Mr Dowling and ridden by Cassidy
Middletown Two Sovereigns Open Sweepstake
1. LANCER, owned and ridden by Mr Veitch
2. BILLY-THE-BEAN, owned by Mr E Bond and ridden by McBride
3. YOUNG DUNROE, owned by Mr Johnston and ridden by Cassidy
4. TRUE BLUE, owned and ridden by Mr Reynolds

Wednesday 19th February 1845
Despite the undoubted success of the inaugural meeting, racing appears to have lapsed for 5 years until a meeting took place on Wednesday 19th February 1845. The course, lit by bright sunlight, was described as romantic, bounded by a beautiful stream on one side, with undulating hills proving ample viewing points for the vast crowd, thought to be in excess of 20,000, to view all aspects of the races. Many of the aristocracy and gentry of the village and surrounding towns were attracted to attend, reinforced by a fair proportion of military gentlemen. An ambulatory Thespian group delighted enraptured audiences with Shakespeare between races, and there was an air of respectability and high fashion in the crowd. Unfortunately, the main race of the day, the Middletown Cup, resulted in a walk-over for Mr Lavery's Suspicion, a bay gelding who had such spirit that even though it was only walking over the course, his jockey had difficulty holding him, and it is doubtful whether he would have won had he been challenged.
Middletown Two Sovereigns Open Sweepstake over 2 miles
1. COURIER (2/1), a bay gelding carrying 10st 4lbs owned by Mr Shaw and ridden by Synnot
2. EVERGREEN (6/4 fav), a bay horse carrying 11st owned by Mr Twig and ridden by McLory
3. MISS EMILY, a bay mare carrying 10st 4lbs owned and ridden by Mr Armstrong
Middletown £5 Purse
1. LANCER owned by Mr A Bond and ridden by McLory
2. TOMTIT owned by Mr Lillyman
3. FANNY HILL owned by Mr Hayse
4. MISS EMILY owned by Mr Armstrong
5. UNNAMED bay gelding owned by Mr Johnston
6. SLIDEAWAY owned by Mr McCardle
7. LUCY LONG owned by Master Leslie
After this race the crowd dispersed without any bother, while a large number of sporting gentlemen were entertained at Leslie Hill by Dr Leslie, his generosity knowing no bounds. During the entertainment a match was got up for the next day between Mr Lavery's Suspicion and Mr Leslie's Bounty.

Thursday 20th February 1845
At 3pm precisely the two horses reached the post, the crowd having been very active in their betting. There were many takers of the 6/4 and 2/1 offered on Suspicion, with almost no one prepared to lay the odds on the mare Bounty, and in the end, Suspicion won the first heat hard held. With the second heat imminent, the large odds offered about the beaten mare were quickly taken, and it was clear that something of a coup was going off. The Mare won the second and third heats, and therefore the contest, with incredible ease, the ones in the know pocketing a large sum. So ended 2 enjoyable, successful days at Middletown, with all seeming set for a repeat the following year, although no record exists of racing taking place in 1846.
Match
1. BOUNTY owned by Mr Leslie and ridden by Slant
2. SUSPICION owned by Mr Lavery

Wednesday 22nd March 1848
It was to be 3 further years before Middletown races were widely publicised again.  They were disrupted by appalling weather, with the Stewards forced to take the hard decision to abandon the meeting after the main event. The meeting was scheduled for Wednesday 22nd March 1848, but a torrent of rain from morning until night drenched the crowd of thousands, yet despite this the Stewards were reluctant to disappoint the vast crowd, allowing the Challenge Cup to be run.
Middletown Challenge Cup for 25 sovereigns over 2 miles
1. ZOZIMUS, 6-year-old owned by Mr Hutchinson
2. NAPOLEON, 3-year-old owned by Mr Leslie
3. ADA, 4-year-old owned by Mr A Bond
4. SUSPICIOUS, aged horse owned by Dr Lavery
5. UNNAMED gelding owned by Captain Rogers
Although the ground was uncommonly heavy from the vast downpour, the race was run at a fast pace and the contest was close, with Napoleon challenging Zozimus throughout both heats. After the conclusion of the race the meeting was abandoned and the Stewards decided to reconvene the next day to complete the card.
Thursday 23rd March 1848
After the unclement weather of the previous day, on Thursday it was milder, although the course remained wretched, one half of it being trodden into mortar making galloping particularly challenging. Nevertheless, a two-race card was held, with 4 heats required to settle the Scurry Stakes, especially as there was no distance post (final furlong), meaning no horse was knocked out of any heat.
Middletown Scurry Stakes
1. UNNAMED mare owned by Mr Kidd
2. UNNAMED Mare owned by Mr Monaghan
3. TRAVELLER owned by Mr Cassidy
4. UNNAMED black horse owned by Mr Young
5. UNNAMED bay horse owned by Mr Sinnot
Second Scurry Race
1. NAPOLEON owned by Mr Leslie
2. SUSPICION owned by Dr Lavery
Thus ended two unusual days of racing, and it was to be a further 3 years before horse racing returned to Middletown.

In early January 1851 a newspaper reported that active efforts were being made towards reviving the old Middletown Cup race, a handicap steeplechase over 2 miles. Sums of money were invited to sponsor the race, with the meeting scheduled to take place on Wednesday 19th February 1851. Entries were to be made with Mr Hughes at his Hughes Hotel in Middletown, with 2 main races set to make up the card. The principal race was the Middletown Challengeable Cup over 2 miles, valued at 25 sovereigns, while the Middletown Handicap was also over 2 miles. After racing an Ordinary was planned to be held at Hughes Hotel for sporting gentlemen. The driving force of the meeting were the 3 Stewards, Mt T Tennison, Mr J Harris and Mr E Boyd.

Wednesday 19th February 1851
This event came off on Wednesday and offered lovers of the sport of horse racing a fair day's enjoyment over a well selected course, with safe fences, good viewing areas and a home run over a long stretch of lush grass intersected by stiff jumps which tested the fencing powers of even the best of horses.
Middletown Cup over 2 miles
1. DRONE owned and ridden by Mr Evatt
2. BARONET owned by Mr H Bond and ridden by Greer
3. WHALEBONE owned by Mr Winder and ridden by MrCrory
Middletown Handicap over 2 miles
1. BOB owned by Mr E W Bond and ridden by Greer
2. SIR ARTHUR owned by Mr Harrison and ridden by Piers
3. PADDY owned by Mr Boyle and ridden by McClory
Scurry Stakes over a mile
1. DRONE owned and ridden by Mr Evatt
2. PADDY owned by Mr W A Hutchinson and ridden by Kidd
3. BOB owned by Mr E W Bond and ridden by Greer
4. MISS ANNE owned by Mr Gray and ridden by Monaghan
5. NANCY owned and ridden by Mr Williams

After the undoubted success of the February meeting, it came as no surprise that a further meeting was held later in the year on Thursday 11th December 1851, although it was the last to be widely broadcast in the newspapers. The course lay along the side of a hill for a distance of about a mile and a quarter, then turned to the valley and finished with an excellent run-in seen by all, making the course 2 miles and 31 leaps.
Thursday 11th December 1851
Middletown Challenge Cup of 25 sovereigns, 2 miles and 31 fences
1. REGULATOR (5/3), grey gelding owned by Mr A H Bond and ridden by McClory
2. MAD-CAP (4/5 fav), bay mare owned by Mr McKeown and ridden by Cusack
3. MISS STEPHENS (5/1), bay mare owned and ridden by Mr McDaniel
4. WATER-HEN, black mare owned and ridden by Mr Doyle
100 Sovereigns Match
1. SPIDER (1/2 fav), bay gelding owned by Mr Smyth
2. WHITE-NOSE, bay gelding owned by Mr Montgomery and ridden by Martin
Middletown Sweepstakes over the Cup course
1. MISS STEPHENS (1/5 fav), bay mare owned and ridden by Mr McDaniel
2. LINNET (3/1), bay mare owned by Mr Dudgeon and ridden by Martin
3. MAD-CAP, bay mare owned by Mr McKeown and ridden by Cusack
Doogary Stakes over 2 miles of the Cup course
1. MISS STEPHENS, bay mare owned by Mr McDaniel and ridden by McClory
2. LINNET, bay mare owned by Mr Dudgeon and ridden by Martin
3. WATER-HEN, black mare owned by Mr Doyle and ridden by Horan
4. NORAH CREINA, chestnut mare owned by Mr Johnston and ridden by Callaghan
The course was the same as earlier in the year, although the number of spectators was much less than in former years, but all passed without incident and very few skirmishes, and those that did take place were caused by too much mountain dew.

Much of the information about this course has been found using internet research and is in the public domain. However, useful research sources have been:-

London Illustrated News

Racing Illustrated 1895-1899

The Sporting & Dramatic Illustrated

Northern Turf History Volumes 1-4 by J.Fairfax-Blakeborough

The Sporting Magazine

A Long Time Gone by Chris Pitt first published in 1996 ISBN 0 900599 89 8

Racing Calendars which were first published in 1727

ISBN 978-0-9957632-0-3

652 pages

774 former courses

ISBN 978-0-9957632-1-0

352 pages

400 former courses

ISBN 978-0-9957632-2-7

180 pages

140 former courses

ISBN 978-0-9957632-3-4

264 pages

235 former courses