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Westport date ideas

There are 29 connected dates in Westport on Explore KC Together. They run from about $7 to $220 for two, and most cost $100 or less.

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The moods that come up most are playful, creative and relaxed. 9 are alcohol-free. Places that show up in more than one date here: Prospero’s Books, Chewology and Harry's Bar & Tables.

Plan a date in Westport
Map of places in WestportA map of a neighborhood or two, not to scale, north at the top, with 39 places in Westport drawn as small icons for what they are. 1 more place is not shown on the map. WESTPORTVALENTINE39TH STSTATE LINE RDMissie B’sChambre CoffeeThe KC Improv CompanyWestport Bar & RecChar Bar WestportWarehouse on BroadwayWhiskers Cat Cafe & CoffeehouseOffKey Karaoke Lounge & SuitesQ Kansas CityKelly’s Westport InnJerusalem CafeJanssen's House CoffeeWestport public-art loopHarry's Bar & TablesMills Record CompanyWestport CafeTiffany BakeryUncle Jim's Pool HallBroadway CaféChewologyGilded Chaos and Vintage RowWestport Flea MarketBistro 303Frost Frozen BarCreative CulturePryde's Kitchen & NecessitiesHarris-Kearney House MuseumUptown TheaterHistoric Westport loopRebel CoffeeBubble WrappThe Madrid TheatreUnicorn TheatreBlack Garlic Restaurant & Rum BarTwo SugarsProspero’s BooksGigantic RecordsRagazza Food & WineCafé Corazón (Westport)N¼ miWestportEat 9Drink 6Coffee 7Art and fun 15Not to scale, north up. Map data © OpenStreetMap contributors
1 more place is outside this view. © OpenStreetMap
All 40 places, as a list

Eat

Westport Cafe, Char Bar Westport, Westport Flea Market, Bistro 303, Chewology, Ragazza Food & Wine, Jerusalem Cafe, Black Garlic Restaurant & Rum Bar, Tiffany Bakery

Drink

OffKey Karaoke Lounge & Suites, Kelly’s Westport Inn, Missie B’s, Harry's Bar & Tables, Q Kansas City, Frost Frozen Bar

Coffee

Café Corazón (Westport), Two Sugars, Broadway Café, Rebel Coffee, Janssen's House Coffee, Chambre Coffee, Whiskers Cat Cafe & Coffeehouse

Art and fun

Harris-Kearney House Museum, Westport Bar & Rec, Mills Record Company, Prospero’s Books, Bubble Wrapp, Gigantic Records, Gilded Chaos and Vintage Row, Pryde's Kitchen & Necessities, The Madrid Theatre, Unicorn Theatre, The KC Improv Company, Uptown Theater, RoKC Underground, Creative Culture, Uncle Jim's Pool Hall, Warehouse on Broadway

Outdoors

Historic Westport loop, Westport public-art loop

The $10 Album Cover Challenge

Judge records only by their covers, swap picks, and reveal the winner over a casual Westport meal.

About $20–$113 for two2 hrs 55 min3 stops

Westport, 1855 to Last Call

Start inside Westport’s trading-post story, move into a modern French dinner, then decide whether one historic bar deserves an encore.

About $85–$190 for two3 hrs 37 min3 stops

Westport Coffee Walk

Two Westport Road coffee shops a few minutes apart: bright and cozy-chic first, then Latin American espresso and mate.

About $17–$48 for two1 hr 33 min2 stops

Books & Coffee on 39th Street

Coffee at Rebel, then browse three floors of used and rare books at Prospero’s a couple of blocks away.

About $7–$11 for two2 hrs 1 min2 stops

Westport Night Out, Your Way

A Westport dinner, then a night out: games, karaoke, a historic pub or a drag show. Both picks rotate with the night.

About $44–$124 for two2 hrs 46 min2 stops

Westport Dinner & a Nightcap

Taiwanese street food or house-limoncello Italian, then a nightcap. Both stops rotate by night.

About $60–$150 for two2 hrs 18 min2 stops

Vintage Row & a Kitchen Shop Stroll

Coffee, then a browse through Westport's vintage shops and a triangle-shaped kitchen store. The coffee stop rotates by date.

About $20–$90 for two2 hrs 21 min3 stops

Blind Boxes, Records & a Drink

Pick a mystery toy, flip through vinyl, then a cocktail. The last stop rotates by date and hours.

About $30–$100 for two2 hrs 47 min3 stops

Cat Cafe Visit & Dinner

Book a visit to a cat lounge over coffee, then dinner in Westport. The dinner rotates by date.

About $76–$88 for two2 hrs 43 min2 stops

A Painter's Home & Westport Dinner

A guided tour of Thomas Hart Benton's home and studio, then dinner nearby. The dinner rotates by date.

About $48–$92 for two2 hrs 26 min2 stops

Dinner, Then a Play or Improv

Dinner, then a small-stage play or a night of improv. The show rotates by what is on.

About $126–$138 for two3 hrs 23 min2 stops

Drinks Before a Madrid Concert

A drink or a coffee in Westport, then a concert in a theatre that opened in 1926. The first stop rotates by date.

About $50–$150 for two3 hrs 38 min2 stops

Vinyl & Coffee Afternoon

Coffee and crate digging at a record shop, then more vinyl in Westport.

About $15–$90 for two1 hr 53 min2 stops

Drag Brunch & Midtown Vintage

A drag brunch show at Hamburger Mary's, then a slow browse of vintage racks down the street.

About $40–$120 for two2 hrs 38 min2 stops

Bistro 303, Then a Drag Show at Missie B's

Drinks and bites at Bistro 303, then Missie B's for one of its weekly drag shows.

About $30–$100 for two3 hrs 53 min2 stops

Dinner, Then Dancing & Drag at Q

A Westport dinner, then Q Kansas City for dancing and its 10 PM drag show.

About $60–$150 for two4 hrs 8 min2 stops

Boulder at RoKC Underground, Then Char Bar

Climb side by side at RoKC Underground, then barbecue and yard games at Char Bar in Westport.

About $68–$130 for two2 hrs 51 min2 stops

Pho on Broadway, Then a Show at the Uptown

A bowl of pho at Pho Tower, then a short walk up Broadway to a concert or comedy show in the 1928 Uptown Theater.

About $70–$220 for two3 hrs 34 min2 stops

Prospero's Books, Then a Burger at the Flea

An hour lost in Prospero's shelves of used books, then a burger at the Westport Flea Market.

About $20–$44 for two1 hr 49 min2 stops

Paint Your Own Pottery, Then Cake in Westport

Walk in and paint a piece of pottery or pour a candle together at Creative Culture, then share a slice of cake or tiramisu at Tiffany Bakery.

About $54–$115 for two1 hr 49 min2 stops

Westport Dinner, Then Free Pool

Dinner in Westport, then a few games on the free pool tables and dartboards at Uncle Jim's.

About $20–$54 for two2 hrs 36 min2 stops

Dinner on Broadway, Then a Show at the Warehouse

Dinner a few blocks up Broadway, then a concert at Warehouse on Broadway.

About $50–$160 for two3 hrs 34 min2 stops

Crepes on 39th, Then a Bookstore

Share a crepe at La Fresca on 39th Street, then browse three floors of used and rare books at Prospero's a few minutes away.

About $26–$52 for two1 hr 19 min2 stops

Coffee, Then a Blind Box Each

Farm-to-cup coffee at Janssen's on Broadway, then a short walk to Kansas City's blind box shop, where each of you picks a mystery box for the other.

About $15–$50 for two1 hr 6 min2 stops

Chambre Coffee, Then Mills Records

A pandan matcha or a coffee at Chambre, then a few doors up to browse records at Mills Record Company.

About $10–$84 for two2 hrs 55 min3 stops

Bao & a Nightcap at Harry's

Dumplings and bao at Chewology, then a cocktail on the patio at Harry's Bar & Tables, open every night.

About $56–$96 for two2 hrs 23 min2 stops

Used Books, Then Pho on Broadway

Browse the stacks and vinyl at Prospero's Books, then a bowl of pho at Pho Tower.

About $26–$34 for two1 hr 56 min2 stops

Make Something Together, Then Pasta on Westport Road

A hands-on DIY studio session at Creative Culture, then a cozy Italian dinner at Ragazza.

About $72–$180 for two2 hrs 59 min2 stops

Dueling Pianos, Then Free Pool at Uncle Jim's

Catch Hammer's Dueling Pianos, then shoot free pool and darts at Uncle Jim's Pool Hall, open until 3 AM.

About $20–$50 for two2 hrs 46 min2 stops
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