Winchester Events

Winchester is a hub for exciting live entertainment. We've analyzed our sales data to bring you the most popular events so you can easily plan your next outing. Whether you're searching for the top concerts, must-see sporting events, or unique things to do in Winchester, you'll find it all right here.

Top Events in Winchester This Weekend

Planning your weekend? There are 28 events happening around Winchester this weekend! Here are the most popular events happening in Winchester from Thursday to Sunday. Don't miss out on the action!

Event Name	Date	Venue	Lowest Price
Frederick Keys vs. Asheville Tourists	Aug 27	Nymeo Field at Harry Grove Stadium	$22
National Symphony Orchestra: Steven Reineke - Harry Potter and The Sorcerer's Stone In Concert	Aug 27	Wolf Trap National Park for the Performing Arts	$128
Tedeschi Trucks Band & Lukas Nelson	Aug 28	Wolf Trap National Park for the Performing Arts	$92
Crowder	Aug 28	Shenandoah County Fairgrounds	$108
Frederick Keys vs. Asheville Tourists	Aug 29	Nymeo Field at Harry Grove Stadium	$40
Tedeschi Trucks Band & Lukas Nelson	Aug 29	Wolf Trap National Park for the Performing Arts	$108
Travis Tritt	Aug 29	Shenandoah County Fairgrounds	$165
Frederick Keys vs. Asheville Tourists	Aug 30	Nymeo Field at Harry Grove Stadium	$35
Modified Truck and Tractor Pull	Aug 30	Shenandoah County Fairgrounds	$40
James Taylor	Aug 30	Wolf Trap National Park for the Performing Arts	$83

Event Name

Date

Venue

Lowest Price

Frederick Keys vs. Asheville Tourists

Aug 27

Nymeo Field at Harry Grove Stadium

$22

National Symphony Orchestra: Steven Reineke - Harry Potter and The Sorcerer's Stone In Concert

Aug 27

Wolf Trap National Park for the Performing Arts

$128

Tedeschi Trucks Band & Lukas Nelson

Aug 28

Wolf Trap National Park for the Performing Arts

$92

Crowder

Aug 28

Shenandoah County Fairgrounds

$108

Frederick Keys vs. Asheville Tourists

Aug 29

Nymeo Field at Harry Grove Stadium

$40

Tedeschi Trucks Band & Lukas Nelson

Aug 29

Wolf Trap National Park for the Performing Arts

$108

Travis Tritt

Aug 29

Shenandoah County Fairgrounds

$165

Frederick Keys vs. Asheville Tourists

Aug 30

Nymeo Field at Harry Grove Stadium

$35

Modified Truck and Tractor Pull

Aug 30

Shenandoah County Fairgrounds

$40

James Taylor

Aug 30

Wolf Trap National Park for the Performing Arts

$83

Top 2026 Summer Events in Winchester

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

Event Name	Date	Venue	Lowest Price
Gregory Alan Isakov	Aug 26	Wolf Trap National Park for the Performing Arts	$86
Tedeschi Trucks Band & Lukas Nelson	Aug 28	Wolf Trap National Park for the Performing Arts	$92
Crowder	Aug 28	Shenandoah County Fairgrounds	$108
Travis Tritt	Aug 29	Shenandoah County Fairgrounds	$165
James Taylor	Aug 30	Wolf Trap National Park for the Performing Arts	$83
Iron Maiden & Megadeth	Sep 11	Jiffy Lube Live	$58
TLC, Salt-N-Pepa & En Vogue	Sep 16	Jiffy Lube Live	$33
Daughtry	Sep 18	The Grandstand At The Great Frederick Fair - Frederick	$105
Treaty Oak Revival & Wade Forster	Sep 18	Jiffy Lube Live	$114
Erykah Badu	Sep 20	Wolf Trap National Park for the Performing Arts	$154

Event Name

Date

Venue

Lowest Price

Gregory Alan Isakov

Aug 26

Wolf Trap National Park for the Performing Arts

$86

Tedeschi Trucks Band & Lukas Nelson

Aug 28

Wolf Trap National Park for the Performing Arts

$92

Crowder

Aug 28

Shenandoah County Fairgrounds

$108

Travis Tritt

Aug 29

Shenandoah County Fairgrounds

$165

James Taylor

Aug 30

Wolf Trap National Park for the Performing Arts

$83

Iron Maiden & Megadeth

Sep 11

Jiffy Lube Live

$58

TLC, Salt-N-Pepa & En Vogue

Sep 16

Jiffy Lube Live

$33

Daughtry

Sep 18

The Grandstand At The Great Frederick Fair - Frederick

$105

Treaty Oak Revival & Wade Forster

Sep 18

Jiffy Lube Live

$114

Erykah Badu

Sep 20

Wolf Trap National Park for the Performing Arts

$154

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 events this weekend with tickets under $100.

Event Name	Date	Venue	Lowest Price
Frederick Keys vs. Asheville Tourists	Aug 27	Nymeo Field at Harry Grove Stadium	$22
Circus Vazquez	Aug 27	Under The Big Top - Lerner Town Square at Tysons II	$35
Tedeschi Trucks Band & Lukas Nelson	Aug 28	Wolf Trap National Park for the Performing Arts	$92
Frederick Keys vs. Asheville Tourists	Aug 28	Nymeo Field at Harry Grove Stadium	$26
Circus Vazquez	Aug 28	Under The Big Top - Lerner Town Square at Tysons II	$38
Frederick Keys vs. Asheville Tourists	Aug 29	Nymeo Field at Harry Grove Stadium	$40
A Thousand Horses	Aug 29	Jammin Java	$70
Frederick Keys vs. Asheville Tourists	Aug 30	Nymeo Field at Harry Grove Stadium	$35
Modified Truck and Tractor Pull	Aug 30	Shenandoah County Fairgrounds	$40
James Taylor	Aug 30	Wolf Trap National Park for the Performing Arts	$83

Event Name

Date

Venue

Lowest Price

Frederick Keys vs. Asheville Tourists

Aug 27

Nymeo Field at Harry Grove Stadium

$22

Circus Vazquez

Aug 27

Under The Big Top - Lerner Town Square at Tysons II

$35

Tedeschi Trucks Band & Lukas Nelson

Aug 28

Wolf Trap National Park for the Performing Arts

$92

Frederick Keys vs. Asheville Tourists

Aug 28

Nymeo Field at Harry Grove Stadium

$26

Circus Vazquez

Aug 28

Under The Big Top - Lerner Town Square at Tysons II

$38

Frederick Keys vs. Asheville Tourists

Aug 29

Nymeo Field at Harry Grove Stadium

$40

A Thousand Horses

Aug 29

Jammin Java

$70

Frederick Keys vs. Asheville Tourists

Aug 30

Nymeo Field at Harry Grove Stadium

$35

Modified Truck and Tractor Pull

Aug 30

Shenandoah County Fairgrounds

$40

James Taylor

Aug 30

Wolf Trap National Park for the Performing Arts

$83

Most Popular Family-Friendly Events in Winchester This Weekend

Looking for something fun for the whole family? Check out this list of top family events happening this weekend in Winchester. From children's concerts and theater to magic and circus shows, there's something for everyone!

Event Name	Date	Venue	Lowest Price
Circus Vazquez	Aug 27	Under The Big Top - Lerner Town Square at Tysons II	$35
Circus Vazquez	Aug 28	Under The Big Top - Lerner Town Square at Tysons II	$38
Circus Vazquez	Aug 29	Under The Big Top - Lerner Town Square at Tysons II	$35
Circus Vazquez	Aug 29	Under The Big Top - Lerner Town Square at Tysons II	$35
Circus Vazquez	Aug 29	Under The Big Top - Lerner Town Square at Tysons II	$35
Circus Vazquez	Aug 30	Under The Big Top - Lerner Town Square at Tysons II	$116
Circus Vazquez	Aug 30	Under The Big Top - Lerner Town Square at Tysons II	$38
Circus Vazquez	Aug 30	Under The Big Top - Lerner Town Square at Tysons II	$38

Event Name

Date

Venue

Lowest Price

Circus Vazquez

Aug 27

Under The Big Top - Lerner Town Square at Tysons II

$35

Circus Vazquez

Aug 28

Under The Big Top - Lerner Town Square at Tysons II

$38

Circus Vazquez

Aug 29

Under The Big Top - Lerner Town Square at Tysons II

$35

Circus Vazquez

Aug 29

Under The Big Top - Lerner Town Square at Tysons II

$35

Circus Vazquez

Aug 29

Under The Big Top - Lerner Town Square at Tysons II

$35

Circus Vazquez

Aug 30

Under The Big Top - Lerner Town Square at Tysons II

$116

Circus Vazquez

Aug 30

Under The Big Top - Lerner Town Square at Tysons II

$38

Circus Vazquez

Aug 30

Under The Big Top - Lerner Town Square at Tysons II

$38

Atlantic Union Bank Center	Merchant Hall At Hylton Performing Arts Center
Backseat Events	Meritus Park
Bobcat Stadium - Frostburg State	Nymeo Field at Harry Grove Stadium
Bridgeforth Stadium	Prince William County Fairgrounds
Bright Box Theater - VA	Ram Stadium
Capital One Hall	Riverside Center for the Performing Arts
Congressional Country Club	Segra Field
Dulles Expo Center	Shenandoah County Fairgrounds
EagleBank Arena	State Theatre - VA
Fredericksburg Convention Center	Tally Ho Theater
George Mason Center For The Arts - Concert Hall	The Barns At Wolf Trap National Park for the Performing Arts
Gregory Family Theater At Hylton Performing Arts Center	The Grandstand At The Great Frederick Fair - Frederick
Hollywood Casino at Charles Town Races	The Maryland Theatre
Hub City Vinyl	The Vault at Capital One Hall
International Community Church - MD	The Weinberg Center For The Arts
Jammin Java	Under The Big Top - Lerner Town Square at Tysons II
Jiffy Lube Live	Virginia Credit Union Stadium
Luhrs Performing Arts Center	Wolf Trap National Park for the Performing Arts
Majestic Theatre - PA

Winchester Events

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

Most Popular Family-Friendly Events in Winchester This Weekend