← Sweet Caroline's Old Town Winchester · VA

Halloween · Saturday · October 31 · 2026

The Old Town Monster Mash

presented by Friends of Old Town · live with Souled Out

Doors 5 PM · Party till 11 PM

Sweet Caroline's at The Newberry Building · 145 N. Loudoun Street

Buy Tickets on Eventbrite
Costumes encouraged

The Old Town Monster Mash is a Halloween costume dance party at Sweet Caroline's, 145 N. Loudoun Street in Old Town Winchester, Virginia, on . Souled Out plays live, the best costumes win $250, $150 and $100, and tickets are $17.85 on Eventbrite.

Monster Mash at Sweet's, Oct. 31! Friends of Old Town is throwing Old Town Winchester's Halloween party — and the dance floor is ours.

Souled Out, the area's favorite dance band, takes the stage on Halloween night. Doors open at 5 p.m. Dig out your best costume: $250, $150 and $100 go to the top three.

What
The Old Town Monster Mash, presented by Friends of Old Town
When
· Doors · 5–11 PM
Where
Sweet Caroline's at The Newberry Building, 145 N. Loudoun Street, Winchester, VA 22601
Music
Souled Out, live
Costumes
$250 · $150 · $100 prizes for the top three
Tickets
$17.85 — on Eventbrite
Dress to scare

Costume contest

$150

2nd Place

Top costume
$250

1st Place

$100

3rd Place

Come in costume, dance with Souled Out, and you might go home with cash.

Get in the door

Monster Mash tickets

$17.85

General Admission

Sat, Oct 31 · 5:00–11:00 PM

Admission to the Old Town Monster Mash, including Souled Out live and entry into the costume contest.

Buy Tickets on Eventbrite

Online sales close 5 PM Oct 31 · No refunds

Good to know

Monster Mash FAQ

When is the Old Town Monster Mash?

Halloween night, Saturday, October 31, 2026, from 5:00 to 11:00 PM. Doors open at 5 PM.

Where is the Monster Mash held?

At Sweet Caroline's in The Newberry Building, 145 N. Loudoun Street, Winchester, VA 22601, on the Loudoun Street pedestrian mall in Old Town Winchester.

Who is playing at the Monster Mash?

Souled Out, the area's favorite dance band.

Is there a costume contest?

Yes. Come in costume and compete for $250 (1st place), $150 (2nd place) and $100 (3rd place) prizes.

How do I get tickets to the Monster Mash?

Tickets are $17.85 on Eventbrite. Online sales close at 5 PM on October 31. All sales are final; no refunds.

What is there to do on Halloween in Winchester, VA?

The Old Town Monster Mash at Sweet Caroline's is a Halloween costume dance party in Old Town Winchester on Saturday, October 31, 2026, from 5 to 11 PM, with Souled Out playing live and $250, $150 and $100 costume prizes. Tickets are $17.85 on Eventbrite.

Do I have to wear a costume?

Costumes are encouraged, and you need one to compete for the $250, $150 and $100 costume prizes.

Who is presenting the Old Town Monster Mash?

The Old Town Monster Mash is presented by Friends of Old Town and hosted at Sweet Caroline's in Old Town Winchester.

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