Events in Winchester , Virginia

Tue, Sep 1Film

Terminator 2: Judgment Day 35th Anniversary

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Wed, Sep 2Film

Terminator 2: Judgement Day 35th Anniversary

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Wed, Sep 2Film

Terminator 2: Judgement Day 35th Anniversary

Alamo Drafthouse Cinema - Winchester

Winchester, VA

GenreBlast Film Festival

Alamo Drafthouse Cinema - Winchester

Winchester, VA

GenreBlast Film Festival

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Thu, Sep 3Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thu, Sep 3Music

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Butthole Surfers: The Hole Truth and Nothing Butt

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Butthole Surfers: The Hole Truth and Nothing Butt

Alamo Drafthouse Cinema - Winchester

Winchester, VA

By Any Means

Alamo Drafthouse Cinema - Winchester

Winchester, VA

By Any Means

Alamo Drafthouse Cinema - Winchester

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

Fri, Sep 4Film

By Any Means

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Fri, Sep 4Film

By Any Means

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Shane Click

Shane Click

Piccadilly's Public House and Restaurant

Winchester, VA

Shane Click

Shane Click

Piccadilly's Public House and Restaurant

Winchester, VA

Honeycrisp Festival

Marker-Miller Orchards

Winchester, VA

Honeycrisp Festival

Marker-Miller Orchards

Winchester, VA

Sat, Sep 5Film

By Any Means

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Sat, Sep 5Film

By Any Means

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Cazhmiere

Piccadilly's Public House and Restaurant

Winchester, VA

Cazhmiere

Piccadilly's Public House and Restaurant

Winchester, VA

Sat, Sep 5Comedy

BUSSI - Comedy, Music, Rock n Roll

Bright Box Theater

Winchester, VA

Sat, Sep 5Comedy

BUSSI - Comedy, Music, Rock n Roll

Bright Box Theater

Winchester, VA

Sun, Sep 6Art

Colonial Costume and Dance event

Winchester-Frederick County Visitors Center

Winchester, VA

Sun, Sep 6Art

Colonial Costume and Dance event

Winchester-Frederick County Visitors Center

Winchester, VA

Sun, Sep 6Music

Lil John

Piccadilly's Public House and Restaurant

Winchester, VA

Sun, Sep 6Music

Lil John

Piccadilly's Public House and Restaurant

Winchester, VA

Sun, Sep 6Film

By Any Means

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Sun, Sep 6Film

By Any Means

Alamo Drafthouse Cinema - Winchester

Winchester, VA

2026 Labor Day Scramble

Mon, Sep 7Sports

2026 Labor Day Scramble

Rock Harbor Grill

Winchester, VA

2026 Labor Day Scramble

Mon, Sep 7Sports

2026 Labor Day Scramble

Rock Harbor Grill

Winchester, VA

Mon, Sep 7Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Sep 7Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Tue, Sep 8Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Sep 8Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Sep 8Film

Psycho Cinema Presents: Mystery Meat

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Tue, Sep 8Film

Psycho Cinema Presents: Mystery Meat

Alamo Drafthouse Cinema - Winchester

Winchester, VA

2026 Ladies Invitational Golf Outing

Wed, Sep 9Sports

2026 Ladies Invitational Golf Outing

Rock Harbor Grill

Winchester, VA

2026 Ladies Invitational Golf Outing

Wed, Sep 9Sports

2026 Ladies Invitational Golf Outing

Rock Harbor Grill

Winchester, VA

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Practical Magic 2

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Practical Magic 2

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Raised on Truth: Struggle Jennings Live

Backseat Events USA

Winchester, VA

Raised on Truth: Struggle Jennings Live

Backseat Events USA

Winchester, VA

Thu, Sep 10 · 8:00 PMMusic

Struggle Jennings

Backseat Events USA

Winchester, VA

Ticketmaster

Thu, Sep 10 · 8:00 PMMusic

Struggle Jennings

Backseat Events USA

Winchester, VA

Get Tickets →

Fri, Sep 11Sports

Shenandoah University Twilight Cross Country Race

Kernstown Battlefield

Winchester, VA

Fri, Sep 11Sports

Shenandoah University Twilight Cross Country Race

Kernstown Battlefield

Winchester, VA

Live Music with Lindsay Beth Harper

James Charles Winery

Winchester, VA

Live Music with Lindsay Beth Harper

James Charles Winery

Winchester, VA

Franklin's Smokin Barnyard Food Truck

James Charles Winery

Winchester, VA

Franklin's Smokin Barnyard Food Truck

James Charles Winery

Winchester, VA

Yappy Hour: Tail-gate

James Charles Winery

Winchester, VA

Yappy Hour: Tail-gate

James Charles Winery

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Practical Magic 2

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Practical Magic 2

Alamo Drafthouse Cinema - Winchester

Winchester, VA

James Austin

Piccadilly's Public House and Restaurant

Winchester, VA

James Austin

Piccadilly's Public House and Restaurant

Winchester, VA

Country. Patriotism. ALL the Hits. - Aaron Tippin LIVE

Backseat Events USA

Winchester, VA

Country. Patriotism. ALL the Hits. - Aaron Tippin LIVE

Backseat Events USA

Winchester, VA

Fri, Sep 11 · 8:00 PM$12.51Comedy

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

Escutcheon Brewing Co.

Winchester, VA

Eventbrite

Fri, Sep 11 · 8:00 PM$12.51Comedy

Standup Comedy at Escutcheon Brewing! (Winchester, Va)

Escutcheon Brewing Co.

Winchester, VA

Fri, Sep 11 · 8:00 PMMusic

Aaron Tippin - Ages 16+

Backseat Events USA

Winchester, VA

Ticketmaster

Fri, Sep 11 · 8:00 PMMusic

Aaron Tippin - Ages 16+

Backseat Events USA

Winchester, VA

Get Tickets →

Sunflower Festival

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Sunflower Festival

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Sat, Sep 12Food & Drink

NAACP Fish Fry Fundraiser

Museum of the Shenandoah Valley

Winchester, VA

Sat, Sep 12Food & Drink

NAACP Fish Fry Fundraiser

Museum of the Shenandoah Valley

Winchester, VA

Dancing with the Goats at Peaceful Fields Sanctuary!

Peaceful Fields Animal Sanctuary

Winchester, VA

Dancing with the Goats at Peaceful Fields Sanctuary!

Peaceful Fields Animal Sanctuary

Winchester, VA

Twilight (2008)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Twilight (2008)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

National Park Service Star Gazing Party

Thoburn Property

Winchester, VA

National Park Service Star Gazing Party

Thoburn Property

Winchester, VA

Chris Darlington

Piccadilly's Public House and Restaurant

Winchester, VA

Chris Darlington

Piccadilly's Public House and Restaurant

Winchester, VA

Sun, Sep 13Food & Drink

Lebanese Wine Pairing Dinner & Dancing

Byblos Lebanese Restaurant

Winchester, VA

Sun, Sep 13Food & Drink

Lebanese Wine Pairing Dinner & Dancing

Byblos Lebanese Restaurant

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Practical Magic 2

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Practical Magic 2

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Mon, Sep 14Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Sep 14Community

Winchester Music Bingo

Vibrissa Beer

Winchester, VA

Mon, Sep 14Film

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Mon, Sep 14Film

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Tue, Sep 15Film

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Tue, Sep 15Film

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Tue, Sep 15Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Tue, Sep 15Trivia & Games

Trivia Tuesday @ Winchester

Vibrissa Beer

Winchester, VA

Wed, Sep 16Film

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Wed, Sep 16Film

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

Thursday On The Farm

The Homestead Farm at Fruit Hill Orchard

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Passion of the Christ (2026)

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Maybe It Was Winchester: An Evening with Pam Tillis

Backseat Events USA

Winchester, VA

Maybe It Was Winchester: An Evening with Pam Tillis

Backseat Events USA

Winchester, VA

Thu, Sep 17 · 8:00 PMMusic

Pam Tillis

Backseat Events USA

Winchester, VA

Ticketmaster

Thu, Sep 17 · 8:00 PMMusic

Pam Tillis

Backseat Events USA

Winchester, VA

Get Tickets →

2026 Harbor Cup Championship

Fri, Sep 18Sports

2026 Harbor Cup Championship

Rock Harbor Grill

Winchester, VA

2026 Harbor Cup Championship

Fri, Sep 18Sports

2026 Harbor Cup Championship

Rock Harbor Grill

Winchester, VA

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Transformers: The Movie

Alamo Drafthouse Cinema - Winchester

Winchester, VA

Fri, Sep 18Music

Derrick Tea

Piccadilly's Public House and Restaurant

Winchester, VA

Fri, Sep 18Music

Derrick Tea

Piccadilly's Public House and Restaurant

Winchester, VA

The Twilight Saga: New Moon

Alamo Drafthouse Cinema - Winchester

Winchester, VA

The Twilight Saga: New Moon

Alamo Drafthouse Cinema - Winchester

Winchester, VA