This story was first published in KCUR's Adventure newsletter. You can sign up to receive stories like this in your inbox every Tuesday.
After years of construction, the KC Streetcar is finally opening its southward expansion, making this the perfect time to explore the areas around Midtown and Westport. The new route will include stops at 31st, 35th, 39th Street, 43rd, and 45th Streets — before going all the way to the Plaza and UMKC.
Westport was founded in 1833 by John Calvin McCoy, who set up a trading post on Westport Road and Pennsylvania Avenue — serving travelers on their way west on the California, Santa Fe and Oregon Trails. This was almost two decades before Kansas City was founded and incorporated as the Town of Kansas, and why Westport bills itself as “The Original Kansas City.”
As time went on, McCoy bought the surrounding farmland, which would eventually become the start of Kansas City. The southern parts of the city became known as Midtown, and then in 1898, Westport merged with Kansas City proper.
Westport and Midtown have grown to become one of the most invigorating parts of the city. Stock full of history, excellent restaurants, and a unique nightlife, these stops on the streetcar will have you adventuring for weeks.
Explore the history
For history buffs, Westport will keep you busy. You can find signs marking its connection to those westward trails as you walk around.
Then head to Pioneer Park right in the heart of Westport at 4509 Broadway. There you will find a statue of Alexander Majors (founder of the Pony Express), famed frontiersman James Bridger, and John McCoy, who on Chiefs gamedays is decked out in red.
Next up is the Harris-Kearney House (4000 Baltimore Ave.) and the location of the Battle of Westport. As the oldest brick home in Kansas City, it’s named for Colonel John Harris, who traded along the trails.
The Battle of Westport, fought in 1864, was the largest Civil War battle west of the Mississippi River, pitting Union Major General Samuel R. Curtis against Confederate Major General Sterling Price. There, 22,000 Union soldiers defeated a 8,500-man Confederate Army, marking the end of the Confederacy in Missouri.
Around the neighborhood, you can also find the Vietnam Veterans Memorial Fountain, which is worth a visit at 4181 Broadway Blvd. Then make your way into Midtown and visit the Thomas Hart Benton Home and Studio located at 3616 Belleview Ave.
Restaurants in Midtown and Westport
Buckle up, because there is a lot to explore — and we’re not even going to touch some other vital midtown neighborhoods, such as West 39th Street or Hospital Hill. And you can find our guide to Union Hill and Martini Corner here.
Let’s start in the heart of Westport. Char Bar is one of the most popular BBQ joints in the city, offering piled-high burnt end and brisket sandwiches as well as smoked jackfruit.
Holy Brunch is good for any time of day with their waffle sliders, and AR’s Breakfast and Brunch hits with a Hispanic twist. Their chorizo bowl will get your day started. For a bagel, there’s nothing more classically Kansas City than Meshuggah Bagels — especially their Chiefs and rainbow-colored bagels.
Providence Pizza is the place for New York-style slices or Detroit-style pies, which are square and made with a double-stretched dough, cheese first, and then the sauce.
For those brave few who want a challenge, check out the Five-Patty Burger at the Westport Flea Market. And across the street, you’ll find the James Beard-nominated Chewology for Taiwanese street food — their gua bao are a meal in and of themselves.
Jerusalem Cafe serves fantastic Middle Eastern food. You can read about it and more Mediterranean spots in our previous Adventure!
On the more upscale side, Westport Cafe is a necessary stop for French favorites like mussels and fries, not to mention their popular Tuesday steak nights and late-night happy hour. Around the corner, new contender Le Champion does it all with coffee, small plates and cocktails.
Now we can move on to the new streetcar route down Main Street, and explore more of Midtown.
Stay in the mood for French food and head to the extraordinarily decorated Tailleur. Ragazza, a cozy Italian restaurant with a limoncello made in-house, can’t be missed.
Gates BBQ, one of the original Kansas City barbecue powerhouses, has a streetcar stop of its own just south of 31st street. Next door is The Russell, a lunch and catering favorite. Move south and you’ll hit Swift’s Cajun Cuisine.
HaHa’s Pizza Hub is up next, with some exciting fusions of flavors. Make sure to check out their shawarma pizza or the gyro pie. Further expand your palette and visit Nour’s, a Lebanese restaurant with kebabs, dips and fun signature drinks, or get carryout from the Caribbean hidden gem Island Spice (don’t skip the oxtail).
Over on Broadway, you’ll find the famed Hamburger Mary’s. Eat one of the best burgers in Kansas City, and catch one of their drag shows like Dining With The Diva’s which is held every Saturday night at 7 p.m.
Nearby, you can’t miss Black Garlic, a unique restaurant specializing in Caribbean and Ethiopian food with an extensive rum menu. Pho Tower next door is one of the city’s best Vietnamese spots.
On Southwest Trafficway, you’ll want to stop off for Teetasty Foods for excellent African dining. Start with their beef samosas and see where the night takes you.
Midtown and Westport are such restaurant-packed neighborhoods that we can’t possibly list all of the best in one place. To get even more recommendations, KCUR’s Up To Date compiled Midtown food favorites from listeners and local food writers (note: some spots may have closed or changed names since the episode aired).
Grab a drink
Whether you need a shot of caffeine to get your morning going, or a shot of something else to get your night going, you’ll find both in Westport and Midtown.
In Westport, you can hit up Broadway Cafe — a community gathering place since 1992 – and get your own beans to brew. Janssen’s House Coffee, a new addition to the area, is another great source for farm-to-cup beans.
On the north end of Old Westport, you’ll find Chambre Coffee, which has a wide selection that includes coffee, tea, and matcha. At the edge of the neighborhood is Soli Deo, with a wide array of baked goods.
Heading into Midtown, you have Post Coffee Company on Broadway, and on Southwest Trafficway, you can stop by Whiskers Cat Cafe & Coffeehouse for some playtime and caffeine.
Kelly’s Westport Inn is a hallmark of our city, as one of the oldest buildings in the city. Built in 1851, it’s served as a variety of businesses, such as a grocery, and now is an Irish pub famous for meet-cutes.
Hit up Clandestino in the back of the Brix Cantina, which serves amazing Mexican food. The asada tacos with the onion and cilantro are about perfect. Gambal’s Social Club, Harpo’s, and Harry’s Bar & Tables all offer their own signature late-night environments.
See live music at Laney’s Get Down, eat weekend brunch, or come out for Thursday night karaoke (just down the block, book your own private karaoke room at OffKey). Next door is the Tin Roof, which also offers live music plus Chiefs watch parties.
For nighttime cocktails, Midtown has a lot of choices. Right on the streetcar’s path, you can hit up the Uptown Lounge, Mainstreet Tavern, and the Blanc Champagne Bar. Head up to their sun club to get one of the best views of the city and our sunsets.
Hammers Dueling Piano Bar is close by, along with the classy Cheval, or you can hop over to Broadway to discover dive bar extraordinaire Chez Charlie.
Let's go shopping
If thrifted and vintage clothing is your quest, Westport is your destination.
Warehouse Vintage, Gilded Chaos, Wonderland, Retro Vixen, and Clothz Minded all have you covered, literally. And for our sneaker enthusiasts, you have to check out DVA Percent. They sell vintage sneakers, and each pair is shrink-wrapped to keep them in mint condition.
Continuing with fashion and gifts, Bunker and It’s a Beautiful Day are definitely worth a stop. Bubble Wrapp, which specializes in Japanese blind boxes, is one of the city’s best toy stores. Then check out Mills Record Company and Gigantic Records (formerly Records With Merritt) for those wanting to expand your vinyl collections.
Pryde’s Kitchen & Necessities has everything to turn you into a top-notch chef except for the skill — that’s on you. Or hit up Fidel’s Cigar Shop, which has been around for 15 years and has 300 premium cigar varieties. Finally, make it a spa day at Spa On Penn.
Have some fun
There is always something going on in Westport. Their annual St. Patrick’s Day Parade is a must-see, and the annual art festival (held in September) includes over 100 local artists showing off their skills.
Check out the Westport event page to keep on top of what’s coming.
The Westport Center for the Arts believes that “when the community creates art, the arts create community.” Their Brown Bag Concerts bring lunch hour music to you at the Westport Presbyterian Church (201 Westport Road). They have a lot of programs throughout the year, so visit their calendar to stay up to date.
Enjoy a live concert at the historic Madrid Theater, a beautiful space that needs to be explored. The Unicorn Theatre has been a Kansas City staple since 1974, specializing in new, independent and boundary-pushing plays. Check out their 2025-26 season and grab your tickets.
And finally, the historic Uptown Theater has been entertaining Kansas Citians since 1928 and is still going strong with big-name concerts, stand-up comics and parties.
There are plenty more to see, including Warehouse on Broadway and the Metropolitan Ensemble based at the newly-reopened Warwick Theater. Have a night of laughs at The KC Improv Company, or take one of their classes and bring the humor to the stage yourself.
Head over to Midtown and catch a show at the unique miniBar, or do karaoke or open mics at the Uptown Arts Bar. Feel like dancing? June’s Night Club and Aura have you covered.
If you want something a bit more lively, Lotus may be for you. The Westport Latin club runs Friday and Saturday from 10 p.m. until 3 a.m.
Missie B’s is one of the main destinations for drag shows in Kansas City, and at Woody’s KC you’ll find an inclusive nightclub and bar with dedicated nights for the city’s different queer communities.
There is never a dull moment in Westport and Midtown. Take the expanded streetcar route and explore everything that it has to offer.
