- “Speakeasy Password Challenge”
Materials:
- Blank cards or scrolls with fake “passwords”
- A doorman or greeter at the entrance
Rules:
- As guests arrive, each is given a card with a different secret password.
- During the party, they must find the matching guest with the same password (no showing cards).
- Once matched, they turn in their cards for entry into a prize drawing.
Prize:
- Vintage-style cocktail set
- Art Deco candle or mini champagne bottle
- “Charleston Dance-Off”
Materials:
- Jazz or Charleston playlist
- Clear dance space
- Optional: judges or a crowd clap-off
Rules:
- Guests pair up or dance solo.
- A few at a time show off their best Charleston or swing-era moves.
- Finalists are picked by audience applause or judges.
Prize:
- “Golden Gams” ribbon (custom award)
- Gift card to a jazz lounge or dance studio
- “Prohibition Trivia”
Materials:
- Trivia cards or a printed quiz
- Topics: Gatsby quotes, 1920s slang, jazz, Prohibition, flappers
Rules:
- Teams or individuals answer themed trivia questions.
- Correct answers earn chips or tickets for a final drawing or prize selection.
Prize:
- Copy of The Great Gatsby in vintage edition
- Art Deco barware
- “Guess the Flapper or Mobster” (Who Am I?)
Materials:
- Sticky notes or cards with famous 1920s figures (real or fictional)
- Headbands or tape
Rules:
- Each guest wears a card on their forehead without seeing who they are.
- They ask yes/no questions to guess their identity.
- Limit to 10 questions per player.
Prize:
- Vintage-inspired headband or fedora
- Small bottle of “giggle water”
- “Bootlegger’s Blackjack or Poker”
Materials:
- Card tables and chairs
- Vintage-looking playing cards
- Chips or play money
Rules:
- Run a mini casino with one or two card games.
- Chips can be exchanged for raffle tickets or “auction” items later in the night.
Prize:
- High roller gift box: mini bourbon bottle, poker chips, engraved flask
- “Flapper Fashion Walk”
Materials:
- Red carpet (or imitation)
- Judges or scorecards
- Jazz music background
Rules:
- Guests strut their outfits down a mini runway.
- Prizes given for categories like Most Glamorous, Best Mobster Look, Best Accessories.
Prize:
- “Best Dressed of the Jazz Age” sash or trophy
- Gift card to a vintage clothing shop
- “The Gatsby Heist Mystery Game”
Materials:
- Pre-scripted mystery game (DIY or printable kits available online)
- Character cards, clue envelopes
Rules:
- Guests are assigned roles for a mystery involving a stolen item at Gatsby’s mansion.
- Throughout the night, they mingle and collect clues to uncover the thief.
Prize:
- “Top Detective” trophy
- Gold magnifying glass paperweight
- “Jazz Bingo”
Materials:
- Custom bingo cards with 1920s slang, famous songs, movie quotes
- Markers or chips
Rules:
- Call out bingo items in themed order (with jazz trivia or clips)
- First to get a row or pattern wins
Prize:
- 1920s jazz vinyl or download code
- Roaring ’20s cocktail recipe book