Events in Winchester , Virginia

Sat, Sep 19Community

Blessing of the Harvest

James Charles Winery

Winchester, VA

Sat, Sep 19Film

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Sat, Sep 19Film

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Sat, Sep 19Music

Petty Thieves

Piccadilly's Public House and Restaurant

Winchester, VA

Sat, Sep 19Music

Petty Thieves

Piccadilly's Public House and Restaurant

Winchester, VA

Sat, Sep 19 · 8:00 PMMusic

Willy Blaze and the Bad News Crew

Backseat Events USA

Winchester, VA

Ticketmaster

Sat, Sep 19 · 8:00 PMMusic

Willy Blaze and the Bad News Crew

Backseat Events USA

Winchester, VA

Get Tickets →

Sat, Sep 19Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Sat, Sep 19Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Sun, Sep 20Community

Fort Loudoun Historic Site: Sunday with a Sentry

Fort Loudoun

Winchester, VA

Sun, Sep 20Community

Fort Loudoun Historic Site: Sunday with a Sentry

Fort Loudoun

Winchester, VA

Sun, Sep 20Film

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Sun, Sep 20Film

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Mon, Sep 21Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Mon, Sep 21Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Mon, Sep 21Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Sep 21Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Sep 21Film

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Mon, Sep 21Film

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Tue, Sep 22Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Tue, Sep 22Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Tue, Sep 22Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Sep 22Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Wed, Sep 23Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Wed, Sep 23Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Thu, Sep 24Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Thu, Sep 24Sports

Ernie & Emma

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Thu, Sep 24Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thu, Sep 24Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thu, Sep 24Film

Film Club's THE LOST WEEKEND

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Thu, Sep 24Film

Film Club's THE LOST WEEKEND

Alamo Drafthouse Cinema - Winchester

Winchester, VA

2026 Carolyn Perry Golf Outing

Fri, Sep 25Sports

2026 Carolyn Perry Golf Outing

Rock Harbor Grill

Winchester, VA

2026 Carolyn Perry Golf Outing

Fri, Sep 25Sports

2026 Carolyn Perry Golf Outing

Rock Harbor Grill

Winchester, VA

Fri, Sep 25Music

Robbie Limon

Piccadilly's Public House and Restaurant

Winchester, VA

Fri, Sep 25Music

Robbie Limon

Piccadilly's Public House and Restaurant

Winchester, VA

Sat, Sep 26Art

Book Signing with Civil War historian, Jonathan Noyalas

Winchester-Frederick County Visitors Center

Winchester, VA

Sat, Sep 26Art

Book Signing with Civil War historian, Jonathan Noyalas

Winchester-Frederick County Visitors Center

Winchester, VA

Registration Now Open for a Scottish Evening at Kernstown Battlefield!

Kernstown Battlefield

Winchester, VA

Registration Now Open for a Scottish Evening at Kernstown Battlefield!

Kernstown Battlefield

Winchester, VA

DJ Curfew

DJ Curfew

Piccadilly's Public House and Restaurant

Winchester, VA

DJ Curfew

DJ Curfew

Piccadilly's Public House and Restaurant

Winchester, VA

Sun, Sep 27Community

The Last Sunday Market

The Exchange on Loudoun

Winchester, VA

Sun, Sep 27Community

The Last Sunday Market

The Exchange on Loudoun

Winchester, VA

Mon, Sep 28Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Sep 28Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Tue, Sep 29Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Sep 29Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

September 30, 2026 Sand & Suds

Wed, Sep 30Community

September 30, 2026 Sand & Suds

Rock Harbor Grill

Winchester, VA

September 30, 2026 Sand & Suds

Wed, Sep 30Community

September 30, 2026 Sand & Suds

Rock Harbor Grill

Winchester, VA

Thu, Oct 1Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thu, Oct 1Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

2026 Watts Golf Outing

Fri, Oct 2Sports

2026 Watts Golf Outing

Rock Harbor Grill

Winchester, VA

2026 Watts Golf Outing

Fri, Oct 2Sports

2026 Watts Golf Outing

Rock Harbor Grill

Winchester, VA

First Friday with Friends of Old Town

Downtown Walking Mall

Winchester, VA

First Friday with Friends of Old Town

Downtown Walking Mall

Winchester, VA

Robbie Limon

Piccadilly's Public House and Restaurant

Winchester, VA

Robbie Limon

Piccadilly's Public House and Restaurant

Winchester, VA

Savannah Dexter: Damage Control Tour II

Backseat Events USA

Winchester, VA

Savannah Dexter: Damage Control Tour II

Backseat Events USA

Winchester, VA

Sat, Oct 3Sports

Judges Classic-John Handley High School Cross Country Meet

Kernstown Battlefield

Winchester, VA

Sat, Oct 3Sports

Judges Classic-John Handley High School Cross Country Meet

Kernstown Battlefield

Winchester, VA

Sat, Oct 3 · 7:00 PMFrom $39Music

A Night of Elvis: 50's through the 70's

Backseat Events USA

Winchester, VA

Eventbrite

Sat, Oct 3 · 7:00 PMFrom $39Music

A Night of Elvis: 50's through the 70's

Backseat Events USA

Winchester, VA

Sat, Oct 3Music

Amulet

Piccadilly's Public House and Restaurant

Winchester, VA

Sat, Oct 3Music

Amulet

Piccadilly's Public House and Restaurant

Winchester, VA

2026 End of Season Member Scramble

Sun, Oct 4Sports

2026 End of Season Member Scramble

Rock Harbor Grill

Winchester, VA

2026 End of Season Member Scramble

Sun, Oct 4Sports

2026 End of Season Member Scramble

Rock Harbor Grill

Winchester, VA

Sun, Oct 4Music

Witchita Falls Band

Piccadilly's Public House and Restaurant

Winchester, VA

Sun, Oct 4Music

Witchita Falls Band

Piccadilly's Public House and Restaurant

Winchester, VA

Mon, Oct 5Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Oct 5Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Tue, Oct 6Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Oct 6Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Thu, Oct 8Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thu, Oct 8Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

2026 Boo Kees Golf Outing

Fri, Oct 9Sports

2026 Boo Kees Golf Outing

Rock Harbor Grill

Winchester, VA

2026 Boo Kees Golf Outing

Fri, Oct 9Sports

2026 Boo Kees Golf Outing

Rock Harbor Grill

Winchester, VA

Fri, Oct 9Music

Mission Road

Piccadilly's Public House and Restaurant

Winchester, VA

Fri, Oct 9Music

Mission Road

Piccadilly's Public House and Restaurant

Winchester, VA

Pumpkin Picking & Fall Fun at Shawnee Springs Market

Shawnee Springs Market & Cannery

Winchester, VA

Pumpkin Picking & Fall Fun at Shawnee Springs Market

Shawnee Springs Market & Cannery

Winchester, VA

Sat, Oct 10Festival

Apple Butter Festival

Hill High Farm

Winchester, VA

Sat, Oct 10Festival

Apple Butter Festival

Hill High Farm

Winchester, VA

Annual Membership Meeting

Kernstown Battlefield

Winchester, VA

Annual Membership Meeting

Kernstown Battlefield

Winchester, VA

Jill Fulton Band

Piccadilly's Public House and Restaurant

Winchester, VA

Jill Fulton Band

Piccadilly's Public House and Restaurant

Winchester, VA

Pete Evick's Retro Rock Revival!!

Backseat Events USA

Winchester, VA

Pete Evick's Retro Rock Revival!!

Backseat Events USA

Winchester, VA

Sat, Oct 10 · 8:00 PMMusic

Retro Rock Revival

Backseat Events USA

Winchester, VA

Ticketmaster

Sat, Oct 10 · 8:00 PMMusic

Retro Rock Revival

Backseat Events USA

Winchester, VA

Get Tickets →

Mon, Oct 12Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Oct 12Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Tue, Oct 13Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Oct 13Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Thu, Oct 15Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thu, Oct 15Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Fri, Oct 16 · 9:00 AMFREESports

Laptop Event for Veterans 10/16/26

HIVE — Hub for Innovators, Veterans and Entrepreneurs

Winchester, VA

Eventbrite

Free · Eventbrite →

Fri, Oct 16 · 9:00 AMFREESports

Laptop Event for Veterans 10/16/26

HIVE — Hub for Innovators, Veterans and Entrepreneurs

Winchester, VA

Free · RSVP →

2026 Turkeys for Sharing Golf Outing

Fri, Oct 16Sports

2026 Turkeys for Sharing Golf Outing

Rock Harbor Grill

Winchester, VA

2026 Turkeys for Sharing Golf Outing

Fri, Oct 16Sports

2026 Turkeys for Sharing Golf Outing

Rock Harbor Grill

Winchester, VA

Sat, Oct 17Community

Pumpkin Picking & Fall Fun at Shawnee Springs Market

Shawnee Springs Market & Cannery

Winchester, VA

Sat, Oct 17Community

Pumpkin Picking & Fall Fun at Shawnee Springs Market

Shawnee Springs Market & Cannery

Winchester, VA

Sat, Oct 17Music

Sun Dogs: A Tribute to RUSH

Backseat Events USA

Winchester, VA

Sat, Oct 17Music

Sun Dogs: A Tribute to RUSH

Backseat Events USA

Winchester, VA

Sun, Oct 18Community

Fort Loudoun Historic Site: Sunday with a Sentry

Fort Loudoun

Winchester, VA

Sun, Oct 18Community

Fort Loudoun Historic Site: Sunday with a Sentry

Fort Loudoun

Winchester, VA

Mon, Oct 19Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Oct 19Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Tue, Oct 20Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Oct 20Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Thu, Oct 22Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thu, Oct 22Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

2026 Blue Ridge Post Golf Outing

Fri, Oct 23Sports

2026 Blue Ridge Post Golf Outing

Rock Harbor Grill

Winchester, VA

2026 Blue Ridge Post Golf Outing

Fri, Oct 23Sports

2026 Blue Ridge Post Golf Outing

Rock Harbor Grill

Winchester, VA

Fri, Oct 23 · 8:00 PMMusic

Saxsquatch

Backseat Events USA

Winchester, VA

Ticketmaster

Fri, Oct 23 · 8:00 PMMusic

Saxsquatch

Backseat Events USA

Winchester, VA

Get Tickets →

Sat, Oct 24Community

Pumpkin Picking & Fall Fun at Shawnee Springs Market

Shawnee Springs Market & Cannery

Winchester, VA

Sat, Oct 24Community

Pumpkin Picking & Fall Fun at Shawnee Springs Market

Shawnee Springs Market & Cannery

Winchester, VA