# Events & Things To Do in Winchester, VA in May 2026 | AllEvents

- **Subtitle**: Find events and things to do in May 2026 in Winchester, Virginia. Discover parties, concerts, meets, shows, sports, club, reunion, Performance happening in May 2026 in Winchester, Virginia.
- **Category**: May
- **Display Name**: Events in May
- **Type**: time_filter

## Audience

- **Followers**: 1.1k+
- **Recent Followers**: 
  - **Avatar 1**: https://cdn2.allevents.in/thumbs/attendeethumb689b208d2a182.png
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## Featured Events

- **Event Name**: Calendar Girls at Winchester Little Theatre Inc.
  - **Description**: 🎉 Welcome to Calendar Girls at Winchester Little Theatre Inc., where dreams come alive and possibilities are endless! 🏛️ Join us at Winchester Little Theatre Inc. in the heart of Winchester, VA
  - **Date**: Sat, 23 May at 08:00 pm – Sat, 30 May at 08:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winchester/calendar-girls-at-winchester-little-theatre-inc/2400029850856636
  - **Venue**: Winchester Little Theatre Inc.
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9kMGYzOWMyMC0zMWFmLTExZjEtODc5NS05ZDFjNWQxMGJmNTYtcmltZy13MTIwMC1oNjc1LWRjMDEyZDg5LWdtaXIuanBnP3Y9MTc3NTQ3NjY2Mg.avif
  - **Categories**: art, calendar, trips-adventures
- **Event Name**: Chris Cagle at Backseat Events
  - **Description**: 🌟 Be part of history at Chris Cagle at Backseat Events, an extraordinary gathering that will captivate your imagination! 🏛️ The prestigious Backseat Events in Winchester, VA sets the sta
  - **Date**: Fri, 29 May at 08:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winchester/chris-cagle-at-backseat-events/2400029995580234
  - **Venue**: Backseat Events
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9iNjEyYjg2MC00ZDNkLTExZjEtOGE2Ni0yZGM3MTQwZDMwYjYtcmltZy13MTIwMC1oNjc0LWRjMDQwNDAzLWdtaXIud2VicD92PTE3Nzg1MDYyODc.avif

## About

Wondering what to do on the weekend or on a not-so-fun night? We have all you need, discover all the happening events in May [YEAR] in [CITY] and find the best picks of yourself. Be it a theatre workshop, meditation class or an entertaining concert, there are a bunch of curated events in [CITY] in May [YEAR] for you.

## May Events in Winchester

- **Event Name**: Red, White, & Lights! Drone Show
  - **Description**: Conclude a day of summer fun with a dazzling drone show that blends innovation, patriotism, and Winchester pride. Featuring vibrant aerial visuals, this one-of-a-kind experience will celebrate 250 years of American history while highlighting the unique he
  - **Interested Audience**:
    - Count: 130
  - **Date**: Sat May 30 2026 at 09:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/red-white-and-lights-drone-show/200030022147705
  - **Venue**: 1001 E Cork St, Winchester, VA, United States, Virginia 22601
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy82ZjFjYzFjM2QzM2Y3NWIzZmVjYzk2MTY2ZTJlMTMxZDQyMGM2NTg1MDQxNDY1MmZkZjE4NGIzMDRhOGFkZDE1LXJpbWctdzEyMDAtaDY3NS1kYzFhMmU0YS1nbWlyP3Y9MTc3ODYwNjc4Ng.avif
  - **Categories**: Festivals
- **Event Name**: Bryan Martin in Winchester
  - **Description**: 🎤 Join Bryan Martin LIVE at Backseat Events on Thursday, May 28, 2026! 🎤  
Here is the moment you've been waiting for! Bryan Martin is coming to Backseat Events on Thursday, May 28, 2026
  - **Date**: Thu May 28 2026 at 08:00 pm – Thu May 28 2026 at 10:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/bryan-martin-in-winchester/3300029961751306
  - **Venue**: Backseat Events
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9iMWM0MDhmMC0zYWNjLTExZjEtOWFlOC0zMTlkOWVlZWI4YTUtcmltZy13MTIwMC1oNjc1LWRjN2Q3MTVlLWdtaXIud2VicD92PTE3NzY0Nzg2MjY.avif
- **Event Name**: Strawberry Festival
  - **Description**: Sweet, juicy, and oh-so-fun — it’s our annual Strawberry Festival! 🍓
Enjoy a day of strawberry picking, milkshakes, treats, live music, and local beer, wine, and cider. Bring the family and make it a berry special day at the farm!
📅 Saturday, May 23rd, 20
  - **Interested Audience**:
    - Count: 12652
    - Avatar: https://lh3.googleusercontent.com/a/ACg8ocLOk6WQJecGWkPkmnwYg1V3R7AeoFSmwBR893sErw1j2Jq1HkQk=s96-c?sz=200
    - Avatar: https://www.gravatar.com/avatar/6ea041c5adc58fde75679f33ec812bb7?s=100&d=identicon&r=g
    - Avatar: https://cdn-az.allevents.in/events9/banners/b069a7eda31c09c097f283e8d29ddde1044734a0602177e08a86b111d0d986c4-rimg-w200-h200-dceef0f3-gmir?v=1737738605
  - **Date**: Sat May 23 2026 at 11:00 am (-04:00)
  - **Event URL**: https://allevents.in/winchester/strawberry-festival/200029259145852
  - **Venue**: 4305 Middle Road, Winchester, VA, United States, Virginia 22602
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy85MTkyMWRkYTlmNDA1YjM4ODUyZDkwMTg3MDVkYWZiNTlmZTlhNjJmODlhMTgyYjNhN2MxYzk0YmMzOWZmZjc2LXJpbWctdzEyMDAtaDE1NTMtZGNmZmZmZmYtZ21pcj92PTE3NzgzOTM2OTQ.avif
  - **Categories**: festivals, music, live-music, entertainment
- **Event Name**: Chris Cagle at Backseat Events
  - **Description**: 🌟 Be part of history at Chris Cagle at Backseat Events, an extraordinary gathering that will captivate your imagination! 🏛️ The prestigious Backseat Events in Winchester, VA sets the sta
  - **Date**: Fri May 29 2026 at 08:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winchester/chris-cagle-at-backseat-events/2400029995580234
  - **Venue**: Backseat Events
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy9iNjEyYjg2MC00ZDNkLTExZjEtOGE2Ni0yZGM3MTQwZDMwYjYtcmltZy13MTIwMC1oNjc0LWRjMDQwNDAzLWdtaXIud2VicD92PTE3Nzg1MDYyODc.avif
- **Event Name**: Taste of Community Food Truck Festival
  - **Description**: Join us for a fun-filled day of food, music, and community! The Taste of Community Food Truck Festival brings together some of the area’s favorite food trucks, local vendors, and family-friendly activities—all for a great cause.

✨ What to expect:
• 7+ lo
  - **Interested Audience**:
    - Count: 733
  - **Date**: Sat May 16 2026 at 11:00 am – Sat May 16 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/taste-of-community-food-truck-festival/200029879678431
  - **Venue**: 1460 University Dr, Winchester, VA 22601, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy9kMGRkNjE2N2Y5OTgxM2Q2OGVkMDg0NjE3NGQ1NDA2YWFkYjFhNzAzNDY2ZjAxOWNiZjY3ZGY0MTkzZWViMmM0LXJpbWctdzEyMDAtaDYyOC1kY2YxZWJiNy1nbWlyP3Y9MTc3ODg0NzUxNw.avif
  - **Categories**: food-drinks, festivals, food-truck-festivals, kids, health-wellness, nonprofit, mental-health
- **Event Name**: The Amazing Castle Exhibit Opens!
  - **Description**: Get ready to travel back in time to a magical place where medieval storybook characters come to life. The popular special exhibit “The Amazing Castle™” opens at Shenandoah Valley Discovery Museum on May 19th in Winchester, Virginia! The exhibit will be at
  - **Interested Audience**:
    - Count: 81
  - **Date**: Tue May 19 2026 at 09:00 am – Tue May 19 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/the-amazing-castle-exhibit-opens/200030030413321
  - **Venue**: 19 W Cork St, Winchester, VA, United States, Virginia 22601
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy84MWI3NjFjM2QzZGE5OTYzOThjYmI5OTdlNWQ1M2Q5ZWExNjQ5ZDEzYjFiOWY0MmY2Y2U3ZTQ4ZjMxNzI0OWY0LXJpbWctdzEyMDAtaDY3NS1kY2ZlZGU1Zi1nbWlyP3Y9MTc3ODg0MTQxOA.avif
  - **Categories**: Workshops, Art, Theatre, Kids
- **Event Name**: 39th Loudoun Street Mile
  - **Description**: Mark your calendars for 2026 and join us as we race through the brick-lined streets of Old Town Winchester in a tradition 39 years strong! Whether you’re chasing a personal best, competing as a collegiate athlete, or enjoying a fun Memorial Day outing wit
  - **Interested Audience**:
    - Count: 50
  - **Date**: Mon May 25 2026 at 08:00 am (-04:00)
  - **Event URL**: https://allevents.in/winchester/39th-loudoun-street-mile/200029381198758
  - **Venue**: 1512 S Loudoun St, Winchester, VA 22601-4422, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9hNmQ1NTk5ZjkyMmQxZTc2MDc1MDI3MDZiMGVlZWJiMDIwN2U2OWZlZjBjMTAyMmJmN2Q0MWNjNThjMDhiMzlkLXJpbWctdzEyMDAtaDYyOC1kY2ZmZmZmZi1nbWlyP3Y9MTc3ODkyMjQxNQ.avif
  - **Categories**: sports, trips-adventures, memorial-day, calendar
- **Event Name**: Joshua Quimby & Matt Pless
  - **Description**: SATURDAY, MAY 16TH

DOORS, BAR, & KITCHEN OPEN at 7PM

SHOW at 8PM

TICKETS

GENERAL ADMISSION: $15

DAY OF SHOW: $20

Advance ticket sales end at 11:30PM the day before the show. If tickets are not sold out by this time they will be available for pur
  - **Interested Audience**:
    - Count: 12
  - **Date**: Sat May 16 2026 at 07:30 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/joshua-quimby-and-matt-pless/200029988416540
  - **Venue**: Bright Box Theater
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9iNWYyOWJmNGI5NTg0NDhiZWRlOWY1Y2QwMTdkNzQ0ZDViNTQ5ZTc0ZjdiMjQ4MzRjODViYzg0MWViZDBiYTI1LXJpbWctdzEwODAtaDEzNTAtZGNkOGQ4ZGEtZ21pcj92PTE3Nzg4NDE0Mzg.avif
  - **Categories**: Music, Entertainment, performances, Art, literary-art
- **Event Name**: 80s Prom Rescue Fundraiser
  - **Description**: 💃🐾 TICKETS ARE LIVE, BABY!! 🐾🕺

🙌 The moment we’ve been screaming into our scrunchies about is FINALLY HERE…

💥 80’s PROM: UNLEASHED is OFFICIALLY ON SALE!! 💥

We’re talking…

🪩 Neon lights + BIG hair energy
🎤 live music by The Reflex 
🎧 DJ Tracy Popkins,
  - **Interested Audience**:
    - Count: 528
  - **Date**: Sat May 30 2026 at 07:00 pm – Sat May 30 2026 at 11:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/80s-prom-rescue-fundraiser/200029856032842
  - **Venue**: Backseat Events
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy9jOTg5MTg5OTMzM2QzMzA5NWE5NjI4NzJmOGQ0ZWJlZDg5OGMxN2NkOTBhMTg0YjZjZjRhMzAzY2YwYmY1YjljLXJpbWctdzEwODAtaDE1MTItZGMxNjAyMzEtZ21pcj92PTE3Nzg5MjI0MTI.avif
  - **Categories**: dog, entertainment, nonprofit, parties, music, live-music
- **Event Name**: Winchester Police Dept. 5th Annual Auto Show
  - **Description**: Mark your calendars for the 5th Anniversary Winchester Police Dept Auto Show Downtown Historic Winchester, VA. Josh's Eats & Sweets along with Blessing Ridge Farm Creamery Ice Cream will be on hand serving delicious food and Ice cream, along with many
  - **Interested Audience**:
    - Count: 239
  - **Date**: Sat May 23 2026 at 09:00 am – Sat May 23 2026 at 04:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/winchester-police-dept-5th-annual-auto-show/200029735216231
  - **Venue**: 100 W Piccadilly St, Winchester, VA 22601-3916, United States
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9kNTAzODFiOTQ0ZWE0YjU3Y2E1NDgyN2Y0Nzk3MWFjNTAyYWFiODIxYjE0MWI5M2JiOGYyOWU4MmVlODQxYzFlLXJpbWctdzEyMDAtaDE1NTItZGNhZGQzZDktZ21pcj92PTE3Nzg3NTc4ODM.avif
  - **Categories**: car-shows, calendar
- **Event Name**: 12th Annual Splash Bash
  - **Description**: Join us for this exciting summer kick-off! Celebrate the start of the season with an evening full of fun for all ages. Enjoy music, delicious food, bounce around and slide on inflatables, and take a shot at dunking one of our city staff in the dunk tank.
  - **Interested Audience**:
    - Count: 101
  - **Date**: Sat May 30 2026 at 12:00 pm – Sat May 30 2026 at 08:30 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/12th-annual-splash-bash/200030022246548
  - **Venue**: 1001 E Cork St, Winchester, VA, United States, Virginia 22601
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9lMGM3NDhmYWZlYzIzODg1MDMwZjhmYTQzYzgzN2RiNDUxM2M4ZWM4ODk0ZmNkY2Y0NmJlNWRmZGM3MjU3M2NiLXJpbWctdzEyMDAtaDY3NS1kYzFiYmJkNS1nbWlyP3Y9MTc3ODg0MzMxOQ.avif
  - **Categories**: calendar
- **Event Name**: Queer Prom - May 30th TICKETS ON SALE NOW!
  - **Description**: SAVE THE DATE: Queer Prom May 30th 7-10pm @ MSV

Queer Prom is a space for connection and joy!  Come as you are. Dress up, dress down, or dress somewhere in between.  You belong here!

Hosted by Rainbow Ridge Social Club and ARE's R.I.S.E Center. 7-10pm a
  - **Interested Audience**:
    - Count: 164
  - **Date**: Sat May 30 2026 at 07:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/queer-prom-may-30th-tickets-on-sale-now/200029556279131
  - **Venue**: Museum of the Shenandoah Valley
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy81NDk4NTkxNjM0ZWY4MWZlZjI0NTliMzVhZWRlMDJhODA4ZDhkY2Q4MjUwOGJhMTRjMThkMjg5MzRmZjg4NGFmLXJpbWctdzEyMDAtaDE2MDAtZGMwMTAxMDEtZ21pcj92PTE3Nzg3MjcwMTI.avif
- **Event Name**: Mindfulness Meet-Up at Please Boutique
  - **Description**: Practice mindfulness as a community in a guided 30 min meditation practice - FOR ALL LEVELSAbout this EventPlease Boutique will be hosting Third Space Synchrony to bring you a beautiful, grounding experience centered on m
  - **Date**: Sat May 23 2026 at 12:00 pm – Sat May 23 2026 at 01:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/mindfulness-meet-up-at-please-boutique/100001989318343717
  - **Venue**: 16 S Loudoun St
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czUvYmFubmVycy82NjJmZjYwZWM1NGJmMDdmZGZlNmNlZTdmNzMxOGFjNGY0Y2MwMDkwMWVkNDgzMGViYjRlYTEyY2I5MjZhYzM3LXJpbWctdzEyMDAtaDE1NTMtZGNmZGZhZjEtZ21pci5qcGc_dj0xNzc4NzMyOTcw.avif
  - **Price**: Free
  - **Categories**: health-wellness, meditation
- **Event Name**: Charlie Collins & Matthew Goodnough w/ Your Friend Death
  - **Description**: SATURDAY, MAY 23RD

DOORS, BAR, & KITCHEN OPEN at 7PM

SHOW at 8PM

TICKETS

GENERAL ADMISSION: $15

DAY OF SHOW: $20

DOOR: $20

Advance ticket sales end at 11:30PM the day before the show. If tickets are not sold out by this time they will be availa
  - **Date**: Sat May 23 2026 at 08:00 pm (-04:00)
  - **Event URL**: https://allevents.in/winchester/charlie-collins-and-matthew-goodnough-w-your-friend-death/200030056003207
  - **Venue**: Bright Box Theater
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9mZmQ1OWYxYmY3YzU4ZWExZGE2MGVkMjQ5NjYyZjY4NWU3ZDAxYzAwOWFkZDhlNzIyY2Q3ZWNlYjhmZTc1OTU3LXJpbWctdzc5Mi1oMTIyNC1kYzJmMzAyYS1nbWlyP3Y9MTc3ODg0MTQyNw.avif
- **Event Name**: Calendar Girls at Winchester Little Theatre Inc.
  - **Description**: 🎉 Welcome to Calendar Girls at Winchester Little Theatre Inc., where dreams come alive and possibilities are endless! 🏛️ Join us at Winchester Little Theatre Inc. in the heart of Winchester, VA
  - **Interested Audience**:
    - Count: 1
  - **Date**: Sat May 23 2026 at 08:00 pm (-05:00)
  - **Event URL**: https://allevents.in/winchester/calendar-girls-at-winchester-little-theatre-inc/2400029850856636
  - **Venue**: Winchester Little Theatre Inc.
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9kMGYzOWMyMC0zMWFmLTExZjEtODc5NS05ZDFjNWQxMGJmNTYtcmltZy13MTIwMC1oNjc1LWRjMDEyZDg5LWdtaXIuanBnP3Y9MTc3NTQ3NjY2Mg.avif
  - **Categories**: art, calendar, trips-adventures

## Trending Events in Winchester

- **Event Name**: David Guetta in Las Vegas
  - **Description**: 🎶 Don't Miss this Out! David Guetta is Live at LIV Beach on Saturday, April 18, 2026! 🎶
This is your moment. David Guetta is hitting LIV Beach on Saturday, April 18, 2026, and with chart-topping hit
  - **Venue**: LIV Beach
  - **Banner**: https://cdn-az.allevents.in/events6/banners/600224f0-d11f-11f0-949e-c77059e80991-rimg-w1200-h675-dc120515-gmir.webp?v=1764859313
- **Event Name**: BTS in Las Vegas
  - **Description**: 🎤 Join BTS LIVE at Allegiant Stadium on Wednesday, May 27, 2026! 🎤  
Here is the moment you've been waiting for! BTS is coming to Allegiant Stadium on Wednesday, May 27, 2026, bring
  - **Venue**: Allegiant Stadium
  - **Banner**: https://cdn-az.allevents.in/events1/banners/a833cba0-f269-11f0-b438-d75247fd2adc-rimg-w1200-h675-dc030318-gmir.webp?v=1768519605
- **Event Name**: No Doubt in Las Vegas
  - **Description**: 🎤 Catch No Doubt Live at Sphere on Friday, May 29, 2026! 🎤
Ready to experience the night of your life? No Doubt is bringing their infectious energy and hit songs like Don't Speak, Just A Girl and It's My Lif
  - **Venue**: Sphere
  - **Banner**: https://cdn-az.allevents.in/events7/banners/ca153350-d1dd-11f0-996b-d59fe40bb918-rimg-w1200-h675-dcfcf0df-gmir.webp?v=1764941095
- **Event Name**: Ed Sheeran, Myles Smith, Sigrid, Aaron Rowe in Las Vegas
  - **Description**: 🎤 Experience Ed Sheeran Live at Allegiant Stadium on Saturday, July 18, 2026! 🎤
The countdown has begun! Ed Sheeran is taking over Allegiant Stadium on Saturday, July 18, 2026, and with hits like
  - **Venue**: Allegiant Stadium
  - **Banner**: https://cdn-az.allevents.in/events2/banners/3e0a5fc0-bc9d-11f0-a21c-5f84b628c251-rimg-w1200-h675-dc6191c0-gmir.webp?v=1762604398
- **Event Name**: Carín León in Las Vegas
  - **Description**: 🎶 Get Ready for Carin Leon Live at Sphere on Sunday, September 6, 2026! 🎶
This is not just a concert—it's a moment you'll talk about for years. Carin Leon is set to light up Sphere with their unforgettable sound on
  - **Venue**: Sphere
  - **Banner**: https://cdn-az.allevents.in/events8/banners/624ac4e0-d1ad-11f0-8e6b-3d758292774f-rimg-w1200-h675-dc1b1416-gmir.webp?v=1764920306
- **Event Name**: Guns N' Roses in Las Vegas
  - **Description**: 🎶 Don't Miss Guns N' Roses Live in Winchester on Saturday, August 22, 2026! 🎶
Are you ready to experience Guns N' Roses like never before? With chart-topping hits like Sweet Child O' Mine, Welcome To The Jungle and Paradise
  - **Venue**: Allegiant Stadium
  - **Banner**: https://cdn-az.allevents.in/events5/banners/d7fb3b90-d115-11f0-949e-c77059e80991-rimg-w1159-h652-dc000000-gmir.webp?v=1764855219
- **Event Name**: Romeo Santos, Prince Royce in Las Vegas
  - **Description**: 🎶 Don't Miss this Out! Romeo Santos is Live at T-Mobile Arena on Sunday, May 17, 2026! 🎶
This is your moment. Romeo Santos is hitting T-Mobile Arena on Sunday, May 17, 2026, and with chart-topping h
  - **Venue**: T-Mobile Arena
  - **Banner**: https://cdn-az.allevents.in/events2/banners/674ec850-df41-11f0-91ad-252c3bcf1605-rimg-w1200-h675-dcb9c8d5-gmir.webp?v=1766413250
- **Event Name**: Marc Anthony in Las Vegas
  - **Description**: 🎤 Join Marc Anthony LIVE at Fontainebleau Las Vegas on Wednesday, July 29, 2026! 🎤  
Here is the moment you've been waiting for! Marc Anthony is coming to Fontainebleau Las Vegas on Wednesda
  - **Venue**: Fontainebleau Las Vegas
  - **Banner**: https://cdn-az.allevents.in/events10/banners/195940c0-d1b9-11f0-8e6b-3d758292774f-rimg-w1200-h675-dc0160ad-gmir.webp?v=1764925337
- **Event Name**: Kenny Chesney in Las Vegas
  - **Description**: 🎤 Join Kenny Chesney LIVE at Sphere on Saturday, June 27, 2026! 🎤  
Here is the moment you've been waiting for! Kenny Chesney is coming to Sphere on Saturday, June 27, 2026, bringin
  - **Venue**: Sphere
  - **Banner**: https://cdn-az.allevents.in/events2/banners/ba416b10-d1c4-11f0-996b-d59fe40bb918-rimg-w1200-h675-dc76a5c0-gmir.webp?v=1764930331

## Browse May Events by Date

- [May Events Today in Winchester](https://allevents.in/winchester/may--today)
- [May Events This Weekend in Winchester](https://allevents.in/winchester/may--this-weekend)
- [May Events in May in Winchester](https://allevents.in/winchester/may--may)
- [May Events in June in Winchester](https://allevents.in/winchester/may--june)

## FAQs

- **Q**: What are the top May events in Winchester?
  - **A:** Red, White, & Lights! Drone Show (Sat May 30 2026 at 09:00 pm at 1001 E Cork St, Winchester, VA, United States, Virginia 22601), Bryan Martin in Winchester (Thu May 28 2026 at 08:00 pm at Backseat Events), Strawberry Festival (Sat May 23 2026 at 11:00 am at 4305 Middle Road, Winchester, VA, United States, Virginia 22602), Chris Cagle at Backseat Events (Fri May 29 2026 at 08:00 pm at Backseat Events), Taste of Community Food Truck Festival (Sat May 16 2026 at 11:00 am at 1460 University Dr, Winchester, VA 22601, United States).
- **Q**: What are the top free May events in Winchester?
  - **A:** Mindfulness Meet-Up at Please Boutique (Sat May 23 2026 at 12:00 pm at 16 S Loudoun St).
- **Q**: What May events are happening in Winchester today May 16, 2026?
  - **A:** Taste of Community Food Truck Festival (Sat May 16 2026 at 11:00 am at 1460 University Dr, Winchester, VA 22601, United States), Joshua Quimby & Matt Pless (Sat May 16 2026 at 07:30 pm at Bright Box Theater).
- **Q**: What May events are happening in Winchester this weekend May 15–17, 2026?
  - **A:** Taste of Community Food Truck Festival (Sat May 16 2026 at 11:00 am at 1460 University Dr, Winchester, VA 22601, United States), Joshua Quimby & Matt Pless (Sat May 16 2026 at 07:30 pm at Bright Box Theater).
- **Q**: What May events are happening in Winchester in May 2026?
  - **A:** Red, White, & Lights! Drone Show (Sat May 30 2026 at 09:00 pm at 1001 E Cork St, Winchester, VA, United States, Virginia 22601), Bryan Martin in Winchester (Thu May 28 2026 at 08:00 pm at Backseat Events), Strawberry Festival (Sat May 23 2026 at 11:00 am at 4305 Middle Road, Winchester, VA, United States, Virginia 22602), Chris Cagle at Backseat Events (Fri May 29 2026 at 08:00 pm at Backseat Events), Taste of Community Food Truck Festival (Sat May 16 2026 at 11:00 am at 1460 University Dr, Winchester, VA 22601, United States).
- **Q**: How can I find May events in Winchester?
  - **A:** You can discover upcoming May events in Winchester on AllEvents.in. Browse by date, venue, or price to find events that match your interests.
- **Q**: How do I buy tickets for May events in Winchester?
  - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets.
- **Q**: What are the popular venues for May events in Winchester?
  - **A:** Some popular venues hosting May events in Winchester include 1001 E Cork St, Winchester, VA, United States, Virginia 22601, Backseat Events, 4305 Middle Road, Winchester, VA, United States, Virginia 22602.
- **Q**: Who are the top organizers for May events in Winchester?
  - **A:** Popular organizers hosting May events in Winchester include Winchester VA Parks and Recreation, Sound Curator, West Oaks Farm Market.
- **Q**: Are there any online May events available?
  - **A:** Yes, many May events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere.
- **Q**: How can I get notified about new May events in Winchester?
  - **A:** Follow the May category on AllEvents.in to get notified when new May events are listed in Winchester.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/76/446ab5b8894647afc5dbe2e4aac27e/may.webp
- **Mobile Banner**: https://cdn2.allevents.in/transup/90/8647e35ea145e785f95cbfaed96658/may.webp

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