September Events and Things to do in Winchester, VA

Virgos meet Customers Appreciation's
Saturday at 12:00 PM
Countryside · Ivy By The Lake
Virgos meet Customers Appreciation's
Saturday at 12:00 PM
Countryside · Ivy By The Lake
Trivia Night at Chilly Hollow Brewing Company
Mon, Sep 14, 6:00 PM + 2 more
Virginia · Chilly Hollow Brewing Company
Trivia Night at Chilly Hollow Brewing Company
Mon, Sep 14, 6:00 PM + 2 more
Virginia · Chilly Hollow Brewing Company
Mahjong & Merlot: Mahjong 101 at Aroma II Tasting Room in Haymarket
Thu, Sep 24, 6:30 PM
Haymarket · Aroma II Tasting Room
Mahjong & Merlot: Mahjong 101 at Aroma II Tasting Room in Haymarket
Thu, Sep 24, 6:30 PM
Haymarket · Aroma II Tasting Room
Shawna Karrasch Equine Clinic + Show Maryland September 18-20
Fri, Sep 18, 9:00 AM
Maryland · Misty Step Stables!
Shawna Karrasch Equine Clinic + Show Maryland September 18-20
Fri, Sep 18, 9:00 AM
Maryland · Misty Step Stables!
Berkeley Springs Shuffle Scavenger Hunt
Today at 11:00 AM + 45 more
Bath (Berkeley Springs) · Fairfax Coffee House
Berkeley Springs Shuffle Scavenger Hunt
Today at 11:00 AM + 45 more
Bath (Berkeley Springs) · Fairfax Coffee House
Music Bingo at Gus’s Bar & BBQ (Inwood, WV)
Tomorrow at 6:30 PM + 3 more
West Virginia · Gus's Bar & BBQ, LLC
Music Bingo at Gus’s Bar & BBQ (Inwood, WV)
Tomorrow at 6:30 PM + 3 more
West Virginia · Gus's Bar & BBQ, LLC
Inner Peace Summit: A Day to Recharge. Reconnect. Renew with Sister Jenna
Sun, Sep 20, 12:00 PM
Chantilly · Brahma Kumaris Meditation Museum - Virginia
Inner Peace Summit: A Day to Recharge. Reconnect. Renew with Sister Jenna
Sun, Sep 20, 12:00 PM
Chantilly · Brahma Kumaris Meditation Museum - Virginia
Silent Book Club Leesburg @ Firefly Cellars
Thu, Sep 24, 6:00 PM
Virginia · Firefly Cellars
Silent Book Club Leesburg @ Firefly Cellars
Thu, Sep 24, 6:00 PM
Virginia · Firefly Cellars
Music Bingo at Applemen Sports Bar (Muzingo)
Today at 6:30 PM + 3 more
Inwood · Applemen Sports Bar
Music Bingo at Applemen Sports Bar (Muzingo)
Today at 6:30 PM + 3 more
Inwood · Applemen Sports Bar
LOCKIN LIVE FREDERICK - Fitness Event & Competition
Sun, Sep 20, 12:00 PM
Rosedale · Baker Park Bandshell
LOCKIN LIVE FREDERICK - Fitness Event & Competition
Sun, Sep 20, 12:00 PM
Rosedale · Baker Park Bandshell
Pub Poll Game Nights at Lost Barrel Brewing - Middleburg
Thursday at 6:00 PM + 2 more
Virginia · Lost Barrel Brewing
Pub Poll Game Nights at Lost Barrel Brewing - Middleburg
Thursday at 6:00 PM + 2 more
Virginia · Lost Barrel Brewing
Guided Hike with the Walker's Club
Sat, Sep 26, 2:00 PM
Virginia · Seven Bends State Park
Guided Hike with the Walker's Club
Sat, Sep 26, 2:00 PM
Virginia · Seven Bends State Park
Guided Hike with Camp Lupton Alumni
Sat, Sep 26, 12:00 PM
Virginia · Seven Bends State Park
Guided Hike with Camp Lupton Alumni
Sat, Sep 26, 12:00 PM
Virginia · Seven Bends State Park
2026 Family Free Shopping Spree
Saturday at 9:00 AM
Leesburg · Douglass Community Center
2026 Family Free Shopping Spree
Saturday at 9:00 AM
Leesburg · Douglass Community Center
Frederick MD: MBX Local Networking Luncheon
Tue, Sep 15, 11:30 AM
Linden Hills · Il Forno Pizzeria
Frederick MD: MBX Local Networking Luncheon
Tue, Sep 15, 11:30 AM
Linden Hills · Il Forno Pizzeria
ALL IN - Raising the Stakes for Affordable Housing
Fri, Sep 25, 5:00 PM
Potomac Heights · Cortland Mansion
ALL IN - Raising the Stakes for Affordable Housing
Fri, Sep 25, 5:00 PM
Potomac Heights · Cortland Mansion
Wild and Rooted- A Day Retreat in Shenandoah
Saturday at 9:00 AM
Virginia · 1774 Hollow Run Rd
Wild and Rooted- A Day Retreat in Shenandoah
Saturday at 9:00 AM
Virginia · 1774 Hollow Run Rd
Maryland Psychic Fair
Sunday at 9:00 AM
Field Pointe · Frederick Event Center
Maryland Psychic Fair
Sunday at 9:00 AM
Field Pointe · Frederick Event Center

Trends in Winchester

Explore more trends

Virgos meet Customers Appreciation's

Virgos meet Customers Appreciation's

Trivia Night at Chilly Hollow Brewing Company

Trivia Night at Chilly Hollow Brewing Company

Mahjong & Merlot: Mahjong 101 at Aroma II Tasting Room in Haymarket

Mahjong & Merlot: Mahjong 101 at Aroma II Tasting Room in Haymarket

Shawna Karrasch Equine Clinic + Show Maryland September 18-20

Shawna Karrasch Equine Clinic + Show Maryland September 18-20

Berkeley Springs Shuffle Scavenger Hunt

Berkeley Springs Shuffle Scavenger Hunt

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

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

Inner Peace Summit: A Day to Recharge. Reconnect. Renew with Sister Jenna

Inner Peace Summit: A Day to Recharge. Reconnect. Renew with Sister Jenna

Silent Book Club Leesburg @ Firefly Cellars

Silent Book Club Leesburg @ Firefly Cellars

Music Bingo at Applemen Sports Bar (Muzingo)

Music Bingo at Applemen Sports Bar (Muzingo)

LOCKIN LIVE FREDERICK - Fitness Event & Competition

LOCKIN LIVE FREDERICK - Fitness Event & Competition

Pub Poll Game Nights at Lost Barrel Brewing - Middleburg

Pub Poll Game Nights at Lost Barrel Brewing - Middleburg

Guided Hike with the Walker's Club

Guided Hike with the Walker's Club

Guided Hike with Camp Lupton Alumni

Guided Hike with Camp Lupton Alumni

2026 Family Free Shopping Spree

2026 Family Free Shopping Spree

Frederick MD: MBX Local Networking Luncheon

Frederick MD: MBX Local Networking Luncheon

ALL IN - Raising the Stakes for Affordable Housing

ALL IN - Raising the Stakes for Affordable Housing

Wild and Rooted- A Day Retreat in Shenandoah

Wild and Rooted- A Day Retreat in Shenandoah

Maryland Psychic Fair

Maryland Psychic Fair

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