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Explore the KC Streetcar Stop: Westport, 39th + Main

Welcome to the second half of our series about the history, food, and fun found just around the corner from the streetcar’s eight new stops.

KCtoday_Westport Streetcar

Test runs are already underway for the Main Street Extension.

Photo by KCtoday

We’re getting “Ready to Ride in 2025" with the fifth installment of our series, where we’ll be walking you through what riders can find — food, fun, a little history — just steps from the eight soon-to-debut streetcar stops. Up next: Westport, 39th + Main.

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It’s not quite the “dummy” line, but long before electrified lines we had mule-drawn carriages.

Photo via MVSC

Travel back in time

We’ve dissected our modern version’s connection to the Country Club streetcar line, but what about the track before the track before the track? Amid the growth and tumult of the late 1800s, Westport had the clunky-yet-charming Dodson “dummy” line — a steam-powered train muffled + disguised as a streetcar to keep, in part, from spooking horses. It rebranded as the Westport and Waldo Railroad in 1894, and the rest is smoggy, soot-covered history.

Tailleur KCtoday

Feast your eyes and your stomachs.

Photo by Heather White

Grab a bite

If you’ve made the long journey south, or you’re looking for a mid-trip pick-me-up, there are more than a few options for hungry travelers nearby.

  • Tailleur
  • Haha’s Pizza Hub
  • Island Spice
  • Sama Zama
  • Holy Brunch KC Brunch Bar
  • Pinches Tacos
  • Laney’s Get Down
  • Char Bar
Outside the building of Kelly's Westport Inn

Kelly’s recently celebrated 75 years in Westport.

Photo by KCtoday

Have a drink (or two)

There’s nothing wrong with a little liquid courage (or caffeinated courage) for your commute into the city.

  • Soli Deo Coffee & Bakery
  • Sk8bar
  • Kelly’s Westport Inn
  • Tin Roof
  • Offkey Karaoke Lounge & Suites
  • Q Kansas City
  • Chambre Coffee
  • Mainstreet Tavern
  • Side Kicks Saloon
Mills record company

Because everything sounds better on vinyl, right?

Photo by KCtoday

Things to do

While a walk around the neighborhood is always recommended, we know some prefer a full itinerary of can’t-miss experiences.

  • Nerd out over collectibles at Bubble Wrapp + Clint’s Comics or shop your next vintage grail at Gilded Chaos.
  • Admire the sleepy shop dog at Mills Record Company while you browse new and used vinyls, music equipment + books.
  • Take in a show tickling the ivories at Hammers Dueling Piano Bar or Upcycle Piano Craft.
  • Browse kitchen supplies at Pryde’s Old Westport before sampling hand-crafted pies at Ashleigh’s Bake House in the back.
  • See Santa Fe Trail history up close at the Harris-Kearney Historical House Museum, listed on the National Register of Historic Places.

Got a favorite Wesport gem we should add to our map? Your hot tip might just make it into the next ride-along.

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