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Woodlawn’s 1920 Halloween Mystery Gala

April 15, 2025 by Clara Everhart Leave a Comment

In November 2019, Woodlawn (National Trust for Historic Preservation) came alive with a one-of-a-kind 1920s Halloween gala. That evening, guests stepped back in time for an unforgettable night of intrigue and entertainment. Inspired by speakeasy glamour and whodunit suspense, the vintage Halloween celebration blended history with theatrical flair.

Woodlawn Whodunit: A Site-Specific Suspense

Creator Clara Everhart wrote the evening’s mystery game with guidance from site director Amanda Phillips. Together, they crafted an immersive murder mystery spotlighting one of Woodlawn’s real Jazz Age owners, Elizabeth Montgomery Sharpe.1 A fantastic cast of docents and volunteers brought the mystery to life with flair and energy.

To begin the evening, ticketholders gathered under the lawn tent in Woodlawn’s side garden. There, they sipped refreshments as a swing band set the mood. Soon, the cast of characters appeared to reveal the mystery of Miss Sharpe’s disappearance. Guests stepped inside the historic house by table number, searching the rooms for five puzzles and the hidden speakeasy. The night closed with a final set from the swing band. At last, the hosts revealed the answer to the mystery puzzle with a flourish. Finally, every winning table claimed a bottle of giggle water — champagne, of course — raising a toast to a night of hidden clues and high spirits.

Six Puzzles Straight from the Jazz Age

  • Mayhem in the Music Room
    Someone hit more than a sour note…
  • Betrayal in the Boudoir
    The heiress’ hideaway is hiding more than high society hush-hush.
  • Bills & Blackmail in the Banker’s Bedroom
    Debts, deceptions, and some very creative accounting… was the price of admission murder?
  • Gossip in the Guest’s Getaway
    Gloves, gossip, and a guilty conscience — the perfect place for a peek behind closed doors.
  • Safecracking in the Supply Storage
    What lies behind lock and key could crack the whole case.
  • The Secret Speakeasy
    If you know the password, the drinks are strong, the alibis stronger, and the truth harder to swallow.
You are cordially invited to the Smoke and Mirrors Mystery Soiree - an evening of sleuthing, spirits, and sustenance at Woodlawn Mansion.
The year is a rowdy 1924, and you are invited to the rather enchanting post-All-Hallow’s Eve Soiree thrown by the mysterious Miss Elizabeth Montgomery Sharpe, heir to an eerily-substantial fortune, who has established herself as a hostess of great parties at her home estate, Woodlawn. The 1805 Mansion is rumored to be haunted, and despite Prohibition, spirits of all kinds will flow, along with savory and sweet treats.
We have some tricks up our sleeves, so expect to be surprised and, while you are at it, hone your sleuthing skills, because there could be a rather unexpected puzzle to be solved in our candlelit halls. Era-specific costumes and cocktail attire are optional, but are very much encouraged. It is going to be the best fright, ooops we mean, night, of the year and you are going to want to be there!
If you dare to come, your invitation to this most important fundraiser (we have to protect those ghosts after all) includes our Mansion mystery “game,” as well as tasty bites and signature cocktails, wine and beer in the Speakeasy tent. Invite holders will receive more instructions post-purchase. Scared to have such a good time? Good. An evening like no other awaits!
An invitation in the style of the 1920s.
Party goer "AmbitiouslyCierra" shared about the evening on Instagram.
The side lawn of Woodlawn, decorated for an evening party with a smoke machine and large mirror.
The Smoke and Mirrors Mystery Soiree was featured in the Holiday 2019 edition of VIP Alexandria.

VIP Alexandria Magazine – Story & Photography by JD Davis

The Smoke and Mirrors Mystery Soiree kept everyone on their toes recently at Woodlawn Mansion. The evening focused on discovering and assimilating clues scattered throughout the mansion and its property to solve a mystery; the mansion was rumored to be haunted and featured 1920s decor that added to the atmosphere of the evening. Participants dressed accordingly for the theme, and 1920s music by live performers accompanied the night. Participants also used the game night as a networking event as it is a popular pastime for Alexandria professionals. The night ended with a final performance by the band, food and drinks, and the answer to the night’s mystery puzzle.

  1. Miss Sharpe took up residence at Woodlawn in 1924. ↩︎

Filed Under: Museums, Theater

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About the Artist

Clara Everhart is an emerging photographer, capturing the work of individual historians, reenactment units, and historic sites during the US 250th and beyond.

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