Loading Events

On January 17, 1920, the United States went dry. The 18th Amendment ushered in a new era in American history, one characterized by booming business, new fashions, and immense cultural upheaval. And in the nation’s capital, politicians, bootleggers, activists, and everyone else in between all lived side by side, helping texture the stories from the past we tell today. They lived in an America of dynamic change. The march of progress that dominated this new modern era resulted in the banning of alcohol, with personal freedom sacrificed to preserve a perceived sense of collective morality. Washingtonians grappled with this paradox of prohibition in different ways, shaping events, influencing popular culture, and transforming American society. We invite you to join us for a one night only, one-of-a-kind immersive experience. Discover, detect, and deduce at Gentleman’s Gambit: A Prohibition Era Mystery.

Gentleman’s Gambit is an interactive, immersive, outdoor theater experience and fundraiser where visitors are invited to journey back to the Prohibition Era. Featuring live music, thematic cocktails, a costume contest, period dancing lessons, costumed actors, and an interactive history hunt, Gentleman’s Gambit is the perfect way to delve into DC’s past.

Legendary DC Bootlegger William Frank Dement, long put to rest at our historic burial ground, has returned for one night only and he has brought the dark secrets of his own past for a final reckoning with the circumstances of his untimely death. Team up with others or take up the challenge yourself to solve the mystery, win a prize, and complete the Gentleman’s Gambit!

Your Contribution:

While our immersive experiences and live theater events are tons of fun, they are also important fundraisers that benefit the preservation, maintenance, and repair of over 25,000 memorial stones, tombstones, and graves at Historic Congressional Cemetery This work is ongoing and remains a critical component of our non-profit mission. In order to safeguard our National Historic Landmark and to continue to bring history to life for our community, we are relying on your help.

All ticket prices for Gentleman’s Gambit include an automatically included, tax deductible, contribution to our non-profit mission. These amounts are clearly denoted below and are also included on the ticketing checkout page. We appreciate your generous support as we work to preserve Congressional Cemetery for future generations.


Gentleman’s Gambit is a one night only exclusive event held on June 29, 4:30 PM- 8:30 PM.

Both general admission and VIP tickets are offered for the event. The amounts in parathesis next to the total denotes the amount that is a tax-deductible charitable contribution (see above)

You may purchase tickets by scrolling down the page

OR, you may purchase tickets by clicking HERE.

General admission: $50 ($25 charitable contribution)

Includes: Admission to the event at anytime between 4:30 PM- 8:00 PM, A “Bootlegger’s Adviser” History Hunt, a period dance tutorial, and entry to the costume contest

VIP admission: $85 ($35 charitable contribution)

Includes: All General admission ticket benefits, a VIP swag bag (including a premium whiskey glass), a complimentary drink ticket, and exclusive access for a polaroid photo at the Public Vault (DeMent’s bootlegger stash).

Table Upgrade: $250 ($150 charitable contribution)

Includes: All VIP and General Admission ticket holders may purchase a table for use during the event. All tables are tent covered, includes 4 chairs, and are located at a premium location near the dance floor and band.

History Hunt:

William Frank DeMent was one of the many bootleggers who plied his elicit trade in the nation’s capital. Using this new revenue stream, DeMent grew wealthier, but ultimately his reach escaped his grasp as his trade led to his untimely end. At Gentleman’s Gambit, DeMent is returning, along with some other lost souls, and they need your help to solve a mystery.

What circumstances led to DeMent’s death? How did he die? Where? Who killed him? All of these questions and more will be answered when you solve the mystery at Gentleman’s Gambit…so long as you are up to the challenge.

Gentleman’s Gambit attendees will be tasked with solving an interactive history hunt where they will solve riddles to locate clues to unravel the mystery of DeMent’s death. Some clues may just be a simple gravestone. Others, are a bit more lively, as the lost spirits of those buried here wander the grounds. Perhaps, if asked the right questions, they will be kind enough to help you solve the mystery to win a prize?

All attendees at Gentleman’s Gambit will receive a Bootlegger’s Adviser History Hunt and instructions on how to participate upon arrival. The History Hunt may be completed at any time throughout the event and your prize may be redeemed at DeMent’s Speakeasy once you have solved the mystery.

Rain and Weather Policy:

This an outside event that will be held rain or shine. Guests should keep an eye on the forecast and prepare for the elements accordingly. A message will be sent to all ticketed attendees prior to the event with a weather advisory.

In the event that severe weather makes the event too dangerous to proceed, the event will be canceled. In this case, tickets will be refunded with the exception of the charitable contribution portion, which will be retained to cover event costs. Thank you for your understanding.

Live Music and Dance Demonstrations:

We love period music and dance and we hope you do too! We are excited to share that the Foggy Bottom Whomp Stompers will be playing multiple sets during the event. An area of the event will be opened up to act as a dance floor to truly transport you bac to the Roaring 20s.

In addition, dance instructors will offer two period dancing demonstrations from New Columbia Swing that will invite audience participants to learn how to dance like the country has just gone dry! See the programming schedule below for those times.

Costume Contest:

Were you born in the wrong time? Do you have a period costume you are proud of that you need an occasion to show it off? Perhaps you regularly dress like you lived during the Prohibition Era and you want to win a prize for it?

Well, at Gentleman’s Gambit, we have you covered! We encourage you to dress up for this event and all attendees are welcome to register for the costume contest. Registration is free and is done entirely on site at the event. All you need to do to be entered is to fill out a small form and present yourself to the judges. They will be judging the (2) winners based on three areas: quality, period appropriateness, and creativity/originality.

Thematic Cocktails:

We are happy to offer a selection of some of our favorite cocktails from Republic Restoratives and are proud to continue our partnership with DC Brau to provide high quality, brewed in DC beer for our live theater events.

Programming Schedule:

There will be a schedule of programming near the dance floor and bar which will include: dance demonstrations, the reveal of the costume contest winners, and remarks. Perhaps even a few lost souls will make their way to our secret speakeasy concert, drawn in by the music and excitement…


We are incredibly grateful for the support of the following sponsors 

As a non-profit organization, we rely on events like Gentleman’s Gambit to help fundraise in pursuit of our mission. We are extremely grateful for the support of the following sponsors. We encourage all attendees to learn more about these amazing organizations!

Fulcrum Residential: Keynote Sponsor

Eastern Memorials

Eastern Memorials is a full-service monument company, specializing in creating personalized memorials in both granite and bronze since 1992. We believe each family has a unique story to tell, and we understand the importance of capturing that story in stone for the benefit of future generations. Our caring staff will work with you in designing a lasting and unique tribute for your loved one. Eastern Memorials artisans use a combination of old-world knowledge and state-of-the-art equipment to design and make our memorials and headstones for graves. Covering regions of Maryland, Washington D.C. & Northern Virginia, we are the premier and most technologically modern monument company, located in Manassas, VA. Visit our website to view our wide array of work. Contact us with any questions that you may have at (703) 393-0999 or info@easternmemorials.com.

Learn more about them here!

DC Brau

Not too long ago, our nation’s capital was a world-class beer town without a brewery to call its own. Since Christian Heurich had closed the doors to his brewery in the 1950s, Washington DC had no brewery whose products were available in local stores and on tap outside its site of production. In 2011, DC Brau Brewing Company officially tapped its first keg of beer entirely brewed, packaged and sold within the District of Columbia. Since then, the brewery has crafted award-winning beer — utilizing a delicious and uniquely American blend of North American and European techniques and ingredients — with distribution throughout the greater National Capital Region, Maryland, Pennsylvania, Massachusetts and beyond

Learn more about them here!

You may purchase tickets below!