Hop on, KC — we’re pulling into Southmoreland, the fourth stop on the Main Street Extension tour, for fine art, funky bars, and more good eats than you can fit in a to-go box (plus, it’s walkable to Westport — so, yes, you can make it a twofer).

Travel back in time

If you've been riding with us since the beginning, you already how the original Kansas City streetcar got its start (and it's end), so we figured it was time to catch a connection...

In 1965, Kansas Citians could sip cocktails in a decommissioned TWA airplane turned bar — Flight 42 Cocktail Lounge — parked right off 42nd + Main. Complete with aviation memorabilia, it was a high-flying happy hour before jet lag was trendy. Today? It's an H&R Block parking lot, but the legend lives on.

Without its wings, Flight 42 made its way to Southmoreland on four wheels. | Photo via Jackson County Historical Society

Grab a bite

Worked up an appetite en route? These nearby bites will have you cruising past your final stop:

Ragazza Food & Wine
Levee Bar & Grill
Snooze, an A.M. Eatery
Atomic Cowboy
Taco Bell Cantina
TACO NACO KC
Brix Modern Mexican Cuisine
Providence by the Slice
Gaia Masala & Burger
Jerusalem Cafe
Westport Cafe
Chingu
Chick-In Waffle
Beer Kitchen
Chewology
Westport Flea

Don't hit snooze on your brunch plans — use this guide to start planning. | Photo via Snooze A.M. Eatery

Have a drink (or two)

Need a pre-ride perk or post-ride pour? Take your pick:

The Roasterie
Broadway Café
Westport Bar & Rec
Harry's Bar & Tables
Gambal's Social Club
FireFly Lounge
Buzzard Beach
Clandestino
Jungalow
Harpo's
Lotus

We can smell Bar Rec's nostalgia from here. | Photo by Bar Rec KC

Things to do

While a walk around the neighborhood is always recommended, we have a few more ideas to stretch your legs:

Get inspired at The Artspace at KCAI, then stock up on supplies at Blick Art Materials
Hunt for retro treasures at Hula Hoop Vintage and Clothz Minded
Wander Mill Creek Park or head to Gillham Park to scope out “the Slabs”
Pop into Trapp and Company for fresh florals and home goods
Don’t forget to look up — Westport’s streets are sprinkled with murals, installations, and even a mysteriously placed phone booth

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