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Late summer and early fall heat combined with persistent dry weather led to increasing drought intensity across eastern Kentucky. Jackson recorded it's hottest September ever while September 2019 ended up being the driest single month in Jackson's relatively short climatological history (records date back to 1981). In fact, Jackson only saw a trace of precipitation for the entire month. London also experienced its warmest and driest September in history, while seeing September 2019 rank as its third driest overall month (records date back to 1954). An astounding 10 maximum temperature records were set at Jackson for the month of September while London tied or broke 9 maximum temperature records. Additionally, this dry period contributed to a 7 day stretch of temperatures in the 90s from September 27th through October 3rd. This was the first time temperatures ever climbed into the 90s in the month of October since records began at Jackson. This heat and large rainfall deficits created high evapotranspiration rates and soil moisture losses, resulting in escalated drought impacts throughout the month. Level 1 and 2 drought declarations were issued on October 3rd for much of eastern Kentucky.

After a 37 day streak without measurable rain at the Jackson, Kentucky NWS office, a heavy rain event that occurred primarily on October 7th brought significant amounts of precipitation to many locations across eastern Kentucky. However, there was a sharp cutoff to this heavy rainfall, with much of the far southeast portion of the state only seeing around a half of an inch of total accumulation as opposed to 2 inches or more toward the Bluegrass region. This led to the expansion of Extreme Drought (D3) across a majority of southeast Kentucky, especially closer to the Virginia border. This rainfall that fell across eastern Kentucky was quickly absorbed by the dry soils, not offering much relief to the top soils or streams and rivers.

At the beginning of the month, extreme drought (D3) extended roughly from areas east of the Daniel Boone National Forest, along Mountain Parkway and southward to the Letcher County line. Severe drought (D2) generally remained south of the Interstate 64 corridor, while shrinking with extent through the month due to sufficient enough rainfall.

Burn bans were in effect for most counties in eastern Kentucky at the beginning of the month, with many of these being lifted into the second week of October. According to the United States Forest Service, wildfire danger was very high throughout the drought region. The United States Forest Service also implemented fire restrictions in the Daniel Boone National Forest.

Soil moisture remained very low compared to normal. In addition, crop moisture was excessively dry with yield prospects reduced. Pasture and hay conditions were also poor. Many farmers were supplementing feed for livestock well in advance of the winter months. This all led to 15 counties across eastern Kentucky being declared as primary disaster areas by the U.S. Department of Agriculture. Forage specialists said that at this time of year, regrowth would only be minimal, but the Agricultural Weather Center at the University of Kentucky reported that the widespread early-mid month rains likely promoted pasture growth and at least somewhat replenished ponds.

Streams across eastern Kentucky ran near to below normal in early October, before running near normal by mid month.

In Harlan County, the community of Benham experienced a water shortage as the mountain streams that normally provide the town's water had seen substantially lower flows. After dry conditions resulted in this low flow of water into the town, the town got approval to begin pumping water from the nearby Cumberland River. However, upon hooking up to the river, pressures within the pipe lines increased to a level that they could not handle, resulting in multiple line breaks and loss of water to the city once again. Several closures, including a local elementary school, resulted because of the lack of water. This appeared to the be the only water shortage impact in the region from the drought.

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