Events and Things to do in Winchester, VA

Search for something you love or check out popular events in your area.

Sleepy Creek Spring Fling Fest
Wed, May 6, 12:00 PM
Berkeley Springs · Joshua Lane
Sleepy Creek Spring Fling Fest
Wed, May 6, 12:00 PM
Berkeley Springs · Joshua Lane
Quad State Wine & Music Fest 2026 Sponsor Registration
Sat, Jun 20, 12:00 PM
Boonsboro · Washington County Agricultural Education Center
Quad State Wine & Music Fest 2026 Sponsor Registration
Sat, Jun 20, 12:00 PM
Boonsboro · Washington County Agricultural Education Center
Selling fast
Yoga & Sound Healing: a community event
Sunday at 10:00 AM
Aldie · 39070 Little River Tpke
Selling fast
Yoga & Sound Healing: a community event
Sunday at 10:00 AM
Aldie · 39070 Little River Tpke
Quad State Holiday Pickle Fest on National Pickle Day
Sat, Nov 14, 11:00 AM
Boonsboro · Washington County Agricultural Education Center
Quad State Holiday Pickle Fest on National Pickle Day
Sat, Nov 14, 11:00 AM
Boonsboro · Washington County Agricultural Education Center
The Kingdom Collective at MOVE
Fri, Apr 24, 10:30 AM + 5 more
Leesburg · MOVE Leesburg
The Kingdom Collective at MOVE
Fri, Apr 24, 10:30 AM + 5 more
Leesburg · MOVE Leesburg
Almost full
2026 Virginia Gold Cup
Sat, May 2, 9:00 AM
The Plains · Great Meadows
Almost full
2026 Virginia Gold Cup
Sat, May 2, 9:00 AM
The Plains · Great Meadows
Leesburg Daybreak Rotary
Sat, Jun 6, 11:00 AM
Leesburg · 17558 Dry Mill Rd
Leesburg Daybreak Rotary
Sat, Jun 6, 11:00 AM
Leesburg · 17558 Dry Mill Rd
Almost full
Help Your Board Thrive: Board Roles, Responsibilities & Fundraising 101
Wed, May 13, 8:30 AM
Leesburg · Claude Moore Nonprofit Training Center
Almost full
Help Your Board Thrive: Board Roles, Responsibilities & Fundraising 101
Wed, May 13, 8:30 AM
Leesburg · Claude Moore Nonprofit Training Center
Sales end soon
Berkeley Springs Shuffle Scavenger Hunt
Tomorrow at 11:00 AM + 387 more
Berkeley Springs · Fairfax Coffee House
Sales end soon
Berkeley Springs Shuffle Scavenger Hunt
Tomorrow at 11:00 AM + 387 more
Berkeley Springs · Fairfax Coffee House
Bee Squash x Wakefield School
Fri, Jun 19, 9:30 AM + 7 more
The Plains · Wakefield School
Bee Squash x Wakefield School
Fri, Jun 19, 9:30 AM + 7 more
The Plains · Wakefield School
Botanical Watercolor - Peonies
Sun, May 24, 2:00 PM
Leesburg · Sterling Hills Farm
Botanical Watercolor - Peonies
Sun, May 24, 2:00 PM
Leesburg · Sterling Hills Farm
Contemporary Play Reading Club (18+)
Thu, Apr 16, 7:00 PM
Leesburg · Simply Yoga
Contemporary Play Reading Club (18+)
Thu, Apr 16, 7:00 PM
Leesburg · Simply Yoga
Sales end soon
Composting: Beginner to Advance - Master Gardener Workshop Series
Sat, Apr 18, 9:00 AM
Boonsboro · Washington County Agricultural Education Center
Sales end soon
Composting: Beginner to Advance - Master Gardener Workshop Series
Sat, Apr 18, 9:00 AM
Boonsboro · Washington County Agricultural Education Center
Black Hoof Drag Bingo with Crimsyn
Tue, Apr 21, 7:00 PM
Leesburg · Black Hoof Brewing Company
Black Hoof Drag Bingo with Crimsyn
Tue, Apr 21, 7:00 PM
Leesburg · Black Hoof Brewing Company
A Workshop: The Art of Garden-Based, Sustainable Floral Design
Sat, Apr 18, 9:30 AM
Leesburg · Hotel Burg
A Workshop: The Art of Garden-Based, Sustainable Floral Design
Sat, Apr 18, 9:30 AM
Leesburg · Hotel Burg
Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!
Thu, Apr 16, 8:00 PM + 1 more
Leesburg · Leesburg
Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!
Thu, Apr 16, 8:00 PM + 1 more
Leesburg · Leesburg
Just added
Jumptown Concert at Creek's Edge Winery
Fri, May 15, 7:00 PM
Lovettsville · 41255 Annas Ln
Just added
Jumptown Concert at Creek's Edge Winery
Fri, May 15, 7:00 PM
Lovettsville · 41255 Annas Ln
The Wellness Way Approach to Inflammation
Thu, Apr 23, 6:30 PM
Leesburg · The Wellness Way - Leesburg
The Wellness Way Approach to Inflammation
Thu, Apr 23, 6:30 PM
Leesburg · The Wellness Way - Leesburg

Trends in Winchester

Explore more trends

Frequently asked questions about Winchester

What are the best events to attend?

According to Eventbrite, the best events are:

Sleepy Creek Spring Fling Fest

Quad State Wine & Music Fest 2026 Sponsor Registration

Quad State Holiday Pickle Fest on National Pickle Day

The Kingdom Collective at MOVE

Which events are currently trending in Winchester?

The trending searches this month in Winchester are:

easter

events happening today near me

craft fairs

kids events

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Berkeley Springs Shuffle Scavenger Hunt

Yoga & Sound Healing: a community event

Contemporary Play Reading Club (18+)

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

Sleepy Creek Spring Fling Fest

Sleepy Creek Spring Fling Fest

Quad State Wine & Music Fest 2026 Sponsor Registration

Quad State Wine & Music Fest 2026 Sponsor Registration

Yoga & Sound Healing: a community event

Yoga & Sound Healing: a community event

Quad State Holiday Pickle Fest on National Pickle Day

Quad State Holiday Pickle Fest on National Pickle Day

The Kingdom Collective at MOVE

The Kingdom Collective at MOVE

2026 Virginia Gold Cup

2026 Virginia Gold Cup

Leesburg Daybreak Rotary

Leesburg Daybreak Rotary

Help Your Board Thrive: Board Roles, Responsibilities & Fundraising 101

Help Your Board Thrive: Board Roles, Responsibilities & Fundraising 101

Berkeley Springs Shuffle Scavenger Hunt

Berkeley Springs Shuffle Scavenger Hunt

Bee Squash x Wakefield School

Bee Squash x Wakefield School

Botanical Watercolor - Peonies

Botanical Watercolor - Peonies

Contemporary Play Reading Club (18+)

Contemporary Play Reading Club (18+)

Composting: Beginner to Advance - Master Gardener Workshop Series

Composting: Beginner to Advance - Master Gardener Workshop Series

Black Hoof Drag Bingo with Crimsyn

Black Hoof Drag Bingo with Crimsyn

A Workshop: The Art of Garden-Based, Sustainable Floral Design

A Workshop: The Art of Garden-Based, Sustainable Floral Design

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

Jumptown Concert at Creek's Edge Winery

Jumptown Concert at Creek's Edge Winery

The Wellness Way Approach to Inflammation

The Wellness Way Approach to Inflammation

Things to do around Winchester

Trends in Winchester

1. Easter

2. Events happening today near me

3. Craft fairs

4. Kids events

5. Monster trucks

6. Easter brunch

7. Car show

8. Dating

9. Adult easter egg

10. Comedy show

11. Speed dating

12. Sip and paint

What are the best events to attend?

Which events are currently trending in Winchester?

Which events are coming up?