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CROSSROADS

The Wise Guy, Then the Cloven Hoof at Tom's Town

Pizza and a martini at the Wise Guy, then Tom's Town's Halloween-themed basement speakeasy down the street.

About $75–$160 for two2 hrs 35 minEstimated fit
Plan this date
Map of the stops for The Wise Guy, Then the Cloven Hoof at Tom's TownA map of a few blocks, not to scale, north at the top, with straight lines between stops. Stop 1, The Wise Guy, the start. Stop 2, Tom’s Town Distilling Co., 0.3 miles from stop 1, 5 min walk. The route is about 0.3 miles end to end. Neighborhoods shown: Crossroads. Landmarks shown: Union Station.CROSSROADSGRAND BLVDMCGEE ST18TH STOAK STSW BLVD5 min walkUNION STATIONSTART The Wise GuyTom’s Town Distilling Co.12N0.1 miThe Wise Guy, Then the Cloven HoofFoodDrinksWalkStreetcar lineStraight lines between stops, not driving directions.Not to scale, north up. Map data © OpenStreetMap contributors
The route is about 0.3 miles end to end. © OpenStreetMap

Whole route inGoogle Maps Apple Maps

Also close by
  • Extra Virgin, food, 1 min walk from stop 1
  • Affäre, food, 1 min walk from stop 1
  • Kon Tiki Room, drinks, 1 min walk from stop 1
  • Up-Down KC, games, 1 min walk from stop 1
  • Messenger Coffee + Ibis Bakery, coffee, 2 min walk from stop 2
  • Café Corazón (Crossroads), coffee, 2 min walk from stop 1

The stops

  1. The Wise GuyOrder pizza and a martini.about 75 min · 1924 Main St, Kansas City, MO 64108 · hours checked recently · then 5 min walkWebsite Google Maps Apple Maps
  2. Tom’s Town Distilling Co.Themed cocktails in the seasonal Halloween basement bar; no cover, priced per drink (about $12 to $17 each, per the owner's own visit, not independently verified).about 75 min · 1701 Main St, Kansas City, MO 64108Website Google Maps Apple Maps

How the night flows

The Cloven Hoof is a seasonal Halloween takeover of Tom's Town's basement bar, running a limited stretch each fall; it was open as of late September 2026. No cover, but it is reservation-only and priced per drink, not by admission. Book through Tom's Town's own site and confirm it is still running before you go.

Good to know

Reservations
Required
Parking
Confirm current Crossroads street parking or a nearby lot.
Getting around
Driving
Setting
Indoors
Alcohol
A big part of the night
What to wear
Weather layers and shoes you don't mind getting a little dusty.

Before you go

Hours not confirmed for Tom’s Town Distilling Co.. Check their pages or call before you go.

Hours, prices and reservations change. Anything we haven't recently source-checked is marked “Confirm today” in the planner rather than presented as fact. Check the venue's own page before you head out.

We last looked over this date on September 28, 2026. That is a review of the plan, not a promise that every detail is current.

Spot something closed, moved or wrong? Tell us so it can be fixed.

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