This is the earliest newspaper notice for horse racing at Stokesley that I have been able to find. You can see that it was a good financial investment for the subscribers to the Plate, as they were the only people entitled to supply the race patrons with food and drink.
The racecourse at Stokesley was just south of Seamer Moor and more or less north of Brawith (which lies between Tame Bridge and Skutterskelfe); I think the name of Oneholmes Farm in the 19th century was Race Course Farm.
The Toll Booth in Stokesley stood on the site of the present Town Hall, which replaced it in 1853.
Newcastle Courant, 13 May 1727
On Trinity-Monday, the 29th Day of May, will be run for in a Field near Stokesley, in Cleaveland, a Subscription Plate, given by Stokesley Inhabitants, 3l. Value, by Galloways, 14 Handshigh or under, three Heats, each Heat 4 Miles, carrying 9 Stone, including Bridle and Saddle, each Horse, &c. to make the usual Allowance as in Galloway Plates, and paying 5s. Entrance, and to be enter'd the same Day betwixt 8 and 11-o'Clock in the forenoon at the Toll Booth in Stokesley; four or more to run or no Plate.
On Tuesday, the 30th Day of May, will be run for, in the same Field another Subscription Plate, given also by the Inhabitants of Stokesley, 10l. Value, by any Horse, Mare, or Gelding, carrying 10 Stone, including Bridle and Saddle, three Heats, each Heat 4 Miles, each Horse, &c. paying 15s Entrance, and to be enter'd in Stokesley-Toll-Booth, betwixt the Hours of 8 and 11 in the Forenoon of the 29th of May, four or more to run or no Plate, and none to run that has won above 20 l. Prize at one Time, and both the said Races to be govern'd by Articles that will be produced at the Day of Entrance.
This is to give Notice, that none but Subscribers will be allowed to set up any Tent, Hutt, or retail any Liquor in the Field, where the said Races are to be run.
For a full description of the Galloway pony, I refer the reader to Wikipedia. It was a breed that is now extinct, but its influence can be seen across the Pennines in the Fell Pony and it was said to have "good looks, a wide, deep chest and a tendency to pace rather than trot." In the 18th century Galloways were bred in Swaledale to haul lead ore.
Younger readers might need to know that 3l. = £3, 10l. = £10, and 5s. and 15s. means five shillings and fifteen shillings respectively. (12 pence made 1 shilling; 20 shillings made £1).
This website gives the results of later race meetings held in 1752 and 1782. I can't find the results of the 1727 races, I'm afraid.