The Westport Saloon District

The Westport Saloon District is the bar-and-nightlife concentration in the midtown Kansas City neighborhood of westport — an entertainment district built atop one of the oldest commercial sites in the region. Westport began in 1833 as a frontier outfitting town for the Santa Fe, Oregon, and California trails, predating Kansas City itself; the trade in provisions, taverns, and inns that served westbound emigrants seeded a drinking-and-lodging culture that, after a long decline, was revived as a dense bar district in the 1970s and 1980s. The district centers on Westport Road and the surrounding blocks, anchored by Kelly’s Westport Inn in a circa-1850 trading-post building, and remains one of Kansas City’s principal nightlife areas — drawing both a large weekend crowd and, since 2017, public debate over privatized sidewalks and weekend security screening.

Summary

The Westport Saloon District is the bar-and-nightlife concentration in the midtown Kansas City neighborhood of westport. The district:

• Centers on Westport Road and the surrounding blocks
• Is roughly bounded by Westport Road (north), Broadway (east), 39th Street (south), and Pennsylvania Avenue (west)
• Grew out of Westport’s 1833 origins as a frontier outfitting town for the Santa Fe, Oregon, and California trails¹²
• Is anchored by Kelly’s Westport Inn, housed in a trading-post building dating to about 1850 — among the oldest standing commercial buildings in Kansas City³
• Took its modern form as a bar-and-restaurant district during a 1970s-1980s revival⁴
• Operates today as a multi-block nightlife district and is the subject of an ongoing public debate over privatized sidewalks and overnight security screening adopted from 2017-2018⁵

History

Frontier outfitting origins (1830s-1850s)

In 1833, John Calvin McCoy built a two-story log store at the corner of Westport Road and Pennsylvania Avenue, selling supplies to travelers bound west on the Santa Fe Trail and the Oregon and California trails.¹² McCoy platted the town in 1834 and named it Westport because it was the last settlement before the open prairie of Indian Territory. The founding of Westport thus predates Kansas City, which McCoy and other investors organized at the river landing below the bluffs in 1838 (see downtown-kc).¹

Westport’s early economy was built on outfitting: stores stocked provisions, wagons, and livestock, and taverns and inns served the emigrants and traders passing through. By 1858 the town held roughly 2,000 residents, making it a commercial center in its own right before Kansas City overtook it.² This concentration of trade, lodging, and drink along Westport Road is the historical root of the later saloon district.

Kelly’s Westport Inn and the Boone store building

The clearest physical link to that frontier period is the building now occupied by Kelly’s Westport Inn at 500-504 Westport Road. The brick structure was built around 1850 as a store selling provisions to westbound travelers; it was operated for several years by Albert Gallatin Boone, a grandson of Daniel Boone, who ran it as a provisioning and outfitting business in the 1850s.³ (Some accounts attribute the building to traders George and William Ewing; the name “Albert Sausser building” is sometimes applied to the structure but is ****.)

The building and the adjoining Chouteau store are described as among the oldest still standing in Kansas City, though Mabry Hall on Pennsylvania Avenue is reportedly older.³ The structure was placed on the National Register of Historic Places in 1969-1972 (NRHP reference No. 72000718).³ It became a bar in the postwar years — operating as a saloon after the repeal of Prohibition and taking the Kelly’s name after Irish immigrant Randal Kelly tended bar there and became a partner — and is commonly cited as Kansas City’s longest-running tavern.³

Civil War and the Battle of Westport (1860s)

During the Bleeding Kansas / Border War period (1854-1861) and the Civil War, Westport sat on the volatile Missouri-Kansas line. The Battle of Westport (October 21-23, 1864) — sometimes called the “Gettysburg of the West” — was fought across Westport and the surrounding country and was the largest Civil War engagement west of the Mississippi.⁶ Markers around the neighborhood commemorate the action (see battle-of-westport-markers). The battle and the war disrupted Westport’s trade-based economy.

Annexation and decline (1897-1960s)

Westport was annexed by Kansas City in 1897, a result confirmed by the Missouri Supreme Court in 1899, and ceased to exist as an independent municipality.² Over the first half of the 20th century the area’s commercial prominence faded as Kansas City’s retail and nightlife shifted toward Downtown, the Country Club Plaza, and the suburbs. By mid-century Westport Road was a worn older commercial strip rather than a destination.

Bar-district revival (1970s-1980s)

Beginning in the late 1960s and accelerating through the 1970s, Westport’s older storefronts filled with head shops, coffee houses, boutiques, and bars catering to a younger crowd, and the neighborhood’s drinking culture re-established it as a nightlife destination.⁴ Long-running venues such as Dave’s Stagecoach Inn (opened 1952, relocated within Westport in the 1970s) and Kelly’s anchored the scene as restaurants, music rooms, and bars multiplied along Westport Road, Pennsylvania, and Broadway.⁴ By the 1980s “Westport” was again shorthand in Kansas City for going out.

Modern character and controversies

Today the Westport Saloon District operates as a multi-block concentration of bars, restaurants, music venues, and clubs, drawing a regional weekend crowd that includes a large young-adult and college contingent.⁴ Frequently cited operators include Kelly’s Westport Inn, Harpo’s, and Tin Roof, alongside dining and music venues; the long-running dive Dave’s Stagecoach Inn closed in 2024 after roughly seven decades, a loss widely noted in local coverage.⁴

The district’s most-debated modern issue is security. In December 2017 the Kansas City Council approved a plan to privatize portions of the public sidewalks in the core of the district — along Westport Road and Pennsylvania Avenue — so that operators could screen patrons with metal detectors during late-night hours (roughly 11 p.m. to 4 a.m.) beginning in 2018, a measure framed as a response to gun violence.⁵ The plan drew opposition, including from the local NAACP, over concerns about access to public space and about who is subjected to screening; the debate over privatized sidewalks and overnight security remains a defining feature of the district’s recent history.⁵

Long-term significance

Westport is among the oldest continuously settled commercial places in the Kansas City metro, and the saloon district preserves that lineage in built form. The Kelly’s building physically ties the present-day nightlife strip to the 1830s-1850s outfitting trade that gave Westport its reason to exist, making the district a rare case where a frontier trading site and a modern entertainment district occupy the same ground.

Within the KS.City Wiki, the Westport Saloon District is one of several Kansas City nightlife concentrations alongside the Crossroads Arts District, the Power & Light District, and 18th & Vine, and it is a likely source of Registry-eligible independent bars and restaurants for future heritage-recognition passes.

Sites in the Westport Saloon District

• Kelly’s Westport Inn (circa-1850 trading-post building, 500-504 Westport Road) — the district’s historical anchor and a long-running tavern³
• The Westport Road / Pennsylvania Avenue corner — site of John Calvin McCoy’s original 1833 store and the historic center of the district¹
• Dave’s Stagecoach Inn — longtime dive bar (1952-2024), an icon of the modern district until its closure⁴
• Harpo’s, Tin Roof, and other contemporary bars, restaurants, and music venues along Westport Road, Pennsylvania, and Broadway⁴

Sources

Footnotes

1. “John C. McCoy” and “Westport, Missouri” — Legends of America. https://www.legendsofamerica.com/john-c-mccoy/; https://www.legendsofamerica.com/westport-missouri/ (accessed 2026-06-12). 1833 store at Westport Road and Pennsylvania, outfitting trade, naming of Westport, 1838 Town of Kansas organization. ↩ ↩² ↩³ ↩⁴

2. “History of Westport” — Westport Historical Society. https://westporthistoricalkc.org/westport-history/ (accessed 2026-06-12). 1833 log building, 1834 platting, outfitting role for Oregon/California/Santa Fe routes, ~2,000 residents by 1858, 1897 annexation confirmed by Missouri Supreme Court 1899. ↩ ↩² ↩³ ↩⁴

3. “Kelly’s Westport Inn” — Wikipedia. https://en.wikipedia.org/wiki/Kelly%27s_Westport_Inn (accessed 2026-06-12). Circa-1850 construction, Albert Gallatin Boone (grandson of Daniel Boone), 500-504 Westport Road, adjoining Chouteau store, oldest-building claim, NRHP No. 72000718, postwar conversion to a saloon and the Randal Kelly partnership. See also “What is the Oldest Building in Kansas City?” — KC History / Missouri Valley Special Collections, kchistory.org. ↩ ↩² ↩³ ↩⁴ ↩⁵ ↩⁶

4. “Dave’s Stagecoach Inn… has closed after 70 years” — KCUR, 2024-02-17; “Westport” — Visit KC; “Complete Guide to Kansas City’s Westport” and “Guide to Bars & Nightlife in Westport KC” — Kansas City Locals Guide (accessed 2026-06-12). Late-1960s/1970s shift to a younger bar district, Dave’s Stagecoach Inn dates and 2024 closure, present-day venues. ↩ ↩² ↩³ ↩⁴ ↩⁵ ↩⁶ ↩⁷

5. “Privatizing Westport Sidewalks Is About Protecting Lives” — Flatland KC; “Safety” — westportkcmo.com (accessed 2026-06-12). December 2017 City Council vote to privatize core sidewalks, late-night metal-detector screening beginning 2018, NAACP opposition. ↩ ↩² ↩³

6. “Battle of Westport” — see battle-of-westport and battle-of-westport-markers; standard accounts date the battle October 21-23, 1864 and describe it as the largest Civil War engagement west of the Mississippi. ↩