Winchester is a hub for exciting live entertainment. We've analyzed our sales data to bring you the most popular races so you can easily plan your next outing.

Top Races in Winchester This Weekend

Planning your weekend? There are 1 races happening around Winchester this weekend! Here are the most popular races happening in Winchester from Thursday to Sunday. Don't miss out on the action!

Event Name	Date	Venue	Lowest Price
Monster Truck Bash	May 30	Rockingham County Fair	$68

Top 2026 Summer Races in Winchester

Summer is the perfect time for live events in Winchester! Check out this list of the top races happening from May through September.

Event Name	Date	Venue	Lowest Price
Monster Truck Bash	May 30	Rockingham County Fair	$68
Renegade Monster Trucks	Jun 5	The Grandstand At The Great Frederick Fair - Frederick	$68
Renegade Monster Trucks	Jun 6	The Grandstand At The Great Frederick Fair - Frederick	$60
Renegade Monster Trucks	Jun 6	The Grandstand At The Great Frederick Fair - Frederick	$69
Renegade Monster Trucks	Aug 18	Montgomery County Agricultural Fair	$68
Renegade Monster Trucks	Aug 19	Montgomery County Agricultural Fair	$68
Truck Drags	Sep 3	Shenandoah County Fairgrounds	$52
Monster Trucks	Sep 5	Shenandoah County Fairgrounds	$69

Cheap Things to Do in Winchester This Weekend (Under $100)

Looking for fun in Winchester that won't break the bank? You've come to the right place. This list features the best-selling races this weekend with tickets under $100.