This is one of those spaces

From the moment you ascend the winding wood staircase, you get the sense that this is a space with character, history and charm. At the top of the stairs, you’ll discover a cozy area complete with a vintage stone, wood-burning fireplace. But the real “wow factor” occurs when you step into the heart of the room. Original dark wood-beamed ceilings soar above, punctuated with swirling amber chandeliers that cast a glow of light over the space. Diamond-paned windows encircle the room and an overall vibe of classic elegance surrounds.

The details all come together beautifully to create a truly special private event space. Whether you’re planning a wedding celebration or a corporate gathering, Upstairs at The Cheshire is a unique setting. The room’s shape provides flexibility in accommodating groups both large and small.

The space is just the beginning of a memorable event. Our experienced culinary and event planning team will ensure that no detail is overlooked.





Seated without
Dance Floor


Seated with
Dance Floor


The layout of the Upstairs space and the sophisticated décor make it an excellent choice for a wide range of events.

From a board room set up for corporate presentations and events, to a cocktail reception with room for entertainment, to a full sit-down dinner, the room lends itself to numerous unique configurations. Our fireplace room featuring an original stone wood-burning fireplace is perfect for pre-dinner cocktails or even a dance floor!

We provide full-service event planning for all of our clients. As needed, we can provide linens, full AV capabilities, special floral arrangements, custom menu cards, even arrange entertainment. Our facility features valet parking and can even arrange overnight accommodations for your guests in our adjacent boutique hotel, The Cheshire.

events_img events_img
events_imgtwo events_img
events_img events_img



Every bride has a vision for her special day. Our team welcomes the opportunity to work with you to make that dream a reality!

If you are looking for a signature St. Louis venue for your wedding, rehearsal dinner or other nuptial event, Upstairs at The Cheshire is perfect! For over 80 years, this very building hosted hundreds of bridal events. Today, it offers a traditional setting with a decidedly modern touch. Vintage details mingle with contemporary accents, and the largely neutral décor allows you to add your custom touches to personalize your event. Our grand staircase opens into the stunning room, giving the bride and groom the chance to make their dramatic entrance. We even have a small bridal “escape” room, where the bride can sneak away to touch-up her hair, take a breather or even change into a going away outfit.

The History


It is impossible to capture the uniqueness of Upstairs at The Cheshire without sharing a bit of its history. Our building dates back to the 1920’s, when it was established as one of the great meeting and dining spots of its day, Medart’s Olde Cheshire. Over the years, Medart’s welcomed thousands of guests to its tables for both intimate dinners and lavish galas.



In 1960, the property was acquired by the Apted family, who renamed it The Cheshire Inn. They added their own unique traditions and touches including authentic British art, antiques, furnishings and even themed dinners. For decades, the restaurant was a hot spot in town, known for its unique décor and tasty food.



In 2012, The Cheshire underwent a massive renovation under the new ownership. In the process, walls were chipped away revealing stunning architectural details long covered up. Wood work was delicately restored, leaded glass windows repaired, and of course, all the modern conveniences added.


Your Unique History

Today we welcome the opportunity to host your unique event, blending your special occasion with our rich history.


Rex Hale

Chef Rex Hale brings over 25 years of culinary experience and acclaim to his position as the executive chef at The Restaurant and Upstairs. His extensive resume includes positions at a number of notable restaurants around the world, from South Africa to California and Antigua to the British Virgin Islands, including Baby Ruth in Dallas and The Ojai Inn in Ojai, CA. He also currently serves as Executive Chef at St. Louis hot spot, Three Sixty.

Hale has been closely involved with Restaurant from its inception and his passion for ingredient-driven food, locally sourced whenever possible, is reflected in the menu. Chef Hale is passionate about creating event menus that demonstrate creativity and exceed clients’ expectations.

Please contact our Sales Manager for more information:

  • footer_cheshire
  • footer_boundary
  • footer_basso