Free Events and Things to do in Winchester, VA

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

August 16th Posing Seminar Hosted by Team Smith Coaching
Sun, Aug 16, 10:00 AM
Ashburn · The Shop Gym
August 16th Posing Seminar Hosted by Team Smith Coaching
Sun, Aug 16, 10:00 AM
Ashburn · The Shop Gym
Hagerstown Back To School Craft & Vendor Market
Fri, Aug 7, 11:00 AM
Hagerstown · Valley Mall
Hagerstown Back To School Craft & Vendor Market
Fri, Aug 7, 11:00 AM
Hagerstown · Valley Mall
Sales end soon
Lost Rhino's 15 Year Anniversary Festival!
Saturday at 11:30 AM
Ashburn · Lost Rhino Brewing Company
Sales end soon
Lost Rhino's 15 Year Anniversary Festival!
Saturday at 11:30 AM
Ashburn · Lost Rhino Brewing Company
Sales end soon
Boom! Debuts at Thick N Thin Brewing
Saturday at 7:00 PM
Hagerstown · 18330 Spark Dr
Sales end soon
Boom! Debuts at Thick N Thin Brewing
Saturday at 7:00 PM
Hagerstown · 18330 Spark Dr
Sales end soon
Members Only Wine Club Pick Up Party
Sunday at 3:00 PM + 7 more
Ashburn · Ashburn Wine Shop, Wine Bar & Bistro
Sales end soon
Members Only Wine Club Pick Up Party
Sunday at 3:00 PM + 7 more
Ashburn · Ashburn Wine Shop, Wine Bar & Bistro
Going fast
lululemon Outdoor Yoga
Sun, Jun 21, 9:00 AM
Ashburn · 20233 Exchange St
Going fast
lululemon Outdoor Yoga
Sun, Jun 21, 9:00 AM
Ashburn · 20233 Exchange St
Sales end soon
Music on the Patio - Reggae Night with Adwela & the Uprising
Tomorrow at 6:00 PM
Warrenton · Claire's at the Depot
Sales end soon
Music on the Patio - Reggae Night with Adwela & the Uprising
Tomorrow at 6:00 PM
Warrenton · Claire's at the Depot
Free Vendor Event @ Silver Mane Stables
Sat, Jun 27, 8:00 AM
Jefferson · 4240 Jefferson Pike
Free Vendor Event @ Silver Mane Stables
Sat, Jun 27, 8:00 AM
Jefferson · 4240 Jefferson Pike
Sept 13th Posing Seminar Hosted by Team Smith Coaching
Sun, Sep 13, 10:00 AM
Ashburn · The Shop Gym
Sept 13th Posing Seminar Hosted by Team Smith Coaching
Sun, Sep 13, 10:00 AM
Ashburn · The Shop Gym
Sales end soon
KAGW Eid Milan 2026
Saturday at 11:00 AM
Ashburn · Stone Hill Middle School
Sales end soon
KAGW Eid Milan 2026
Saturday at 11:00 AM
Ashburn · Stone Hill Middle School
Sales end soon
Mastering Furnished Rentals, STR, MTR, Corporate! - Loudoun Gateway
Monday at 11:30 AM
Ashburn · 20116 Ashbrook Pl suite 200
Sales end soon
Mastering Furnished Rentals, STR, MTR, Corporate! - Loudoun Gateway
Monday at 11:30 AM
Ashburn · 20116 Ashbrook Pl suite 200
Summer Kick Off Party at The Learning Experience – Ashburn
Thu, Jun 18, 3:00 PM
Ashburn · The Learning Experience - Ashburn
Summer Kick Off Party at The Learning Experience – Ashburn
Thu, Jun 18, 3:00 PM
Ashburn · The Learning Experience - Ashburn
✨ The BTL Aesthetics Bus Tour is Coming to Simply Smiles! ✨
Fri, Jun 12, 4:00 PM
Ashburn · 44031 Ashburn Shopping Plz
✨ The BTL Aesthetics Bus Tour is Coming to Simply Smiles! ✨
Fri, Jun 12, 4:00 PM
Ashburn · 44031 Ashburn Shopping Plz
November 1st Posing Seminar Hosted by Team Smith Coaching
Sun, Nov 1, 10:00 AM
Ashburn · The Shop Gym
November 1st Posing Seminar Hosted by Team Smith Coaching
Sun, Nov 1, 10:00 AM
Ashburn · The Shop Gym
Triumph Demo Days (Roadster): Triumph Dulles
Fri, Jun 19, 10:00 AM
Dulles · Motorcycles Of Dulles
Triumph Demo Days (Roadster): Triumph Dulles
Fri, Jun 19, 10:00 AM
Dulles · Motorcycles Of Dulles
December 6th Posing Seminar Hosted by Team Smith Coaching
Sun, Dec 6, 10:00 AM
Ashburn · The Shop Gym
December 6th Posing Seminar Hosted by Team Smith Coaching
Sun, Dec 6, 10:00 AM
Ashburn · The Shop Gym
Triumph Demo Days (Roadster): Twigg Triumph
Fri, Jun 19, 10:00 AM
Hagerstown · Twigg Triumph Motorcycle
Triumph Demo Days (Roadster): Twigg Triumph
Fri, Jun 19, 10:00 AM
Hagerstown · Twigg Triumph Motorcycle
Ask the Appraiser
Mon, Jun 15, 11:30 AM
Warrenton · 1000 Clubhouse Wy
Ask the Appraiser
Mon, Jun 15, 11:30 AM
Warrenton · 1000 Clubhouse Wy
**FREE SHOW** Leroy Burks & The Voodoo Whiskey Band **Country**
Sat, Jun 13, 8:00 PM
Hagerstown · Live At Hub City Vinyl
**FREE SHOW** Leroy Burks & The Voodoo Whiskey Band **Country**
Sat, Jun 13, 8:00 PM
Hagerstown · Live At Hub City Vinyl
Going fast
Loudoun Job Fair: Unlock New Opportunities
Wed, Jun 10, 12:00 PM + 3 more
South Riding · Dulles South Recreation and Community Center
Going fast
Loudoun Job Fair: Unlock New Opportunities
Wed, Jun 10, 12:00 PM + 3 more
South Riding · Dulles South Recreation and Community Center

Trends in Winchester

Explore more trends

Frequently asked questions about Winchester

What are the best free events to attend?

According to Eventbrite, the best free events are:

August 16th Posing Seminar Hosted by Team Smith Coaching

Hagerstown Back To School Craft & Vendor Market

Members Only Wine Club Pick Up Party

lululemon Outdoor Yoga

Which events are currently trending in Winchester?

The trending searches this month in Winchester are:

memorial weekend

mothers day

mothers day brunch

events happening today near me

Which free events are coming up?

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

Music on the Patio - Reggae Night with Adwela & the Uprising

KAGW Eid Milan 2026

Lost Rhino's 15 Year Anniversary Festival!

Boom! Debuts at Thick N Thin Brewing

August 16th Posing Seminar Hosted by Team Smith Coaching

August 16th Posing Seminar Hosted by Team Smith Coaching

Hagerstown Back To School Craft & Vendor Market

Hagerstown Back To School Craft & Vendor Market

Lost Rhino's 15 Year Anniversary Festival!

Lost Rhino's 15 Year Anniversary Festival!

Boom! Debuts at Thick N Thin Brewing

Boom! Debuts at Thick N Thin Brewing

Members Only Wine Club Pick Up Party

Members Only Wine Club Pick Up Party

lululemon Outdoor Yoga

lululemon Outdoor Yoga

Music on the Patio - Reggae Night with Adwela & the Uprising

Music on the Patio - Reggae Night with Adwela & the Uprising

Free Vendor Event @ Silver Mane Stables

Free Vendor Event @ Silver Mane Stables

Sept 13th Posing Seminar Hosted by Team Smith Coaching

Sept 13th Posing Seminar Hosted by Team Smith Coaching

KAGW Eid Milan 2026

KAGW Eid Milan 2026

Mastering Furnished Rentals, STR, MTR, Corporate! - Loudoun Gateway

Mastering Furnished Rentals, STR, MTR, Corporate! - Loudoun Gateway

Summer Kick Off Party at The Learning Experience – Ashburn

Summer Kick Off Party at The Learning Experience – Ashburn

✨ The BTL Aesthetics Bus Tour is Coming to Simply Smiles! ✨

✨ The BTL Aesthetics Bus Tour is Coming to Simply Smiles! ✨

November 1st Posing Seminar Hosted by Team Smith Coaching

November 1st Posing Seminar Hosted by Team Smith Coaching

Triumph Demo Days (Roadster): Triumph Dulles

Triumph Demo Days (Roadster): Triumph Dulles

December 6th Posing Seminar Hosted by Team Smith Coaching

December 6th Posing Seminar Hosted by Team Smith Coaching

Triumph Demo Days (Roadster): Twigg Triumph

Triumph Demo Days (Roadster): Twigg Triumph

Ask the Appraiser

Ask the Appraiser

**FREE SHOW** Leroy Burks & The Voodoo Whiskey Band **Country**

**FREE SHOW** Leroy Burks & The Voodoo Whiskey Band **Country**

Loudoun Job Fair: Unlock New Opportunities

Loudoun Job Fair: Unlock New Opportunities

Things to do around Winchester

Trends in Winchester

1. Memorial weekend

2. Mothers day

3. Mothers day brunch

4. Events happening today near me

5. Car show

6. Craft fairs

7. Cinco de mayo

8. Job fairs

9. Speed dating

10. Comedy show

11. Sip and paint

12. Line dancing

What are the best free events to attend?

Which events are currently trending in Winchester?

Which free events are coming up?

FREE SHOW Leroy Burks & The Voodoo Whiskey Band Country

FREE SHOW Leroy Burks & The Voodoo Whiskey Band Country