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Free Events and Things to do in Winchester, VA

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Winter Tree-mendous Hike
Sat, Dec 5, 10:00 AM
Delaplane · Sky Meadows State Park
Winter Tree-mendous Hike
Sat, Dec 5, 10:00 AM
Delaplane · Sky Meadows State Park
Sales end soon
Trivia Night at Chilly Hollow Brewing Company
Monday at 6:00 PM + 45 more
Berryville · Chilly Hollow Brewing Company
Sales end soon
Trivia Night at Chilly Hollow Brewing Company
Monday at 6:00 PM + 45 more
Berryville · Chilly Hollow Brewing Company
Sales end soon
Music Bingo at Gus’s Bar & BBQ (Inwood, WV)
Wednesday at 6:30 PM + 30 more
Inwood · Gus's Bar & BBQ, LLC
Sales end soon
Music Bingo at Gus’s Bar & BBQ (Inwood, WV)
Wednesday at 6:30 PM + 30 more
Inwood · Gus's Bar & BBQ, LLC
Sales end soon
Music Bingo at Applemen Sports Bar (Muzingo)
Tuesday at 6:30 PM + 30 more
Inwood · Applemen Sports Bar
Sales end soon
Music Bingo at Applemen Sports Bar (Muzingo)
Tuesday at 6:30 PM + 30 more
Inwood · Applemen Sports Bar
First Saturdays at Sky Meadows
Sat, Jun 6, 11:00 AM + 5 more
Delaplane · Sky Meadows State Park
First Saturdays at Sky Meadows
Sat, Jun 6, 11:00 AM + 5 more
Delaplane · Sky Meadows State Park
Juneteenth Jeep Rideout
Sat, Jun 20, 12:00 PM
Purcellville · Breaux Vineyards
Juneteenth Jeep Rideout
Sat, Jun 20, 12:00 PM
Purcellville · Breaux Vineyards
Tartan Terrors - Levitt AMP Shenandoah Junction Music Series
Fri, Jun 12, 6:00 PM
Shenandoah Junction · The AMP at Sam Michaels Park
Tartan Terrors - Levitt AMP Shenandoah Junction Music Series
Fri, Jun 12, 6:00 PM
Shenandoah Junction · The AMP at Sam Michaels Park
ABLAZE 2026
Sun, Jul 26, 3:00 PM
Martinsburg · War Memorial Park Martinsburg
ABLAZE 2026
Sun, Jul 26, 3:00 PM
Martinsburg · War Memorial Park Martinsburg
Pride in the Park 2026
Sat, Oct 3, 1:00 PM
Martinsburg · War Memorial Park Martinsburg
Pride in the Park 2026
Sat, Oct 3, 1:00 PM
Martinsburg · War Memorial Park Martinsburg
Just added
Wine & Wisdom
Thu, Jun 18, 4:30 PM
Bluemont · 18755 Foggy Bottom Rd
Just added
Wine & Wisdom
Thu, Jun 18, 4:30 PM
Bluemont · 18755 Foggy Bottom Rd
DREAMWAVE WV Disability ACCESS Expo & Conference
Fri, Sep 18, 9:00 AM
Martinsburg · Holiday Inn Martinsburg by IHG
DREAMWAVE WV Disability ACCESS Expo & Conference
Fri, Sep 18, 9:00 AM
Martinsburg · Holiday Inn Martinsburg by IHG
Birding Walk
Mon, Jun 8, 8:00 AM
Harpers Ferry · Appalachian Trail Conservancy
Birding Walk
Mon, Jun 8, 8:00 AM
Harpers Ferry · Appalachian Trail Conservancy
Live Music with Wayne Snow
Sun, Jun 7, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Wayne Snow
Sun, Jun 7, 2:00 PM
Purcellville · Breaux Vineyards
Sales end soon
Live Music with Ben Fisher
Tomorrow at 2:00 PM
Purcellville · Breaux Vineyards
Sales end soon
Live Music with Ben Fisher
Tomorrow at 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Laura Farrell
Sat, Jun 6, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Laura Farrell
Sat, Jun 6, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Chris Compton
Sun, Jun 14, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Chris Compton
Sun, Jun 14, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Brian Harris
Sat, Jun 20, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Brian Harris
Sat, Jun 20, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Shane Gamble
Sat, Jun 27, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Shane Gamble
Sat, Jun 27, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Jason Teach
Sun, Jun 28, 2:00 PM
Purcellville · Breaux Vineyards
Live Music with Jason Teach
Sun, Jun 28, 2:00 PM
Purcellville · Breaux Vineyards
Parlour Philosophy
Thursday at 5:00 PM
Middleburg · Middleburg Community Center
Parlour Philosophy
Thursday at 5:00 PM
Middleburg · Middleburg Community Center

Trends in Winchester

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Frequently asked questions about Winchester

What are the best free events to attend?

According to Eventbrite, the best free events are:

Winter Tree-mendous Hike

First Saturdays at Sky Meadows

Juneteenth Jeep Rideout

Tartan Terrors - Levitt AMP Shenandoah Junction Music Series

Which events are currently trending in Winchester?

The trending searches this month in Winchester are:

memorial weekend

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:

Live Music with Ben Fisher

Trivia Night at Chilly Hollow Brewing Company

Music Bingo at Applemen Sports Bar (Muzingo)

Music Bingo at Gus’s Bar & BBQ (Inwood, WV)