Fiesta KC – Cinco de Mayo Celebration
Date & Time: May 1–3, 2026 | Fri 4–9 PM, Sat 12–9 PM, Sun 12–6 PM
Location: KC Wine Co
Celebrate Cinco de Mayo weekend at one of Johnson County’s most popular wineries. Fiesta KC brings live Latin music, margarita wine slushes, street tacos, contests and dancing to the vineyard. The lively outdoor atmosphere and scenic setting make it a perfect spring outing with friends.
Website: https://www.kcwineco.com/festivals/fiesta
Tacos & Margs Crawl
Date & Time: Saturday, May 2, 2026 | Afternoon & Evening
Location: Westport District, Kansas City
This festive bar crawl takes over the Westport neighborhood with margarita specials, taco tastings and DJ sets across participating venues. Guests hop between bars with an all-access wristband, making it a social, high-energy way to celebrate Cinco de Mayo weekend.
Website: https://www.barcrawlnation.com/events/kansas-city-tacos-margs-2026
Kansas City Corporate Challenge Half Marathon & 10K
Date & Time: May 9, 2026 | 7:00 AM (Half), 7:30 AM (10K)
Location: Heritage Park Marina, Olathe
Part of the region’s popular Corporate Challenge series, this race welcomes runners of all levels for scenic routes around Heritage Park. The event encourages workplace wellness and camaraderie with hundreds of participants representing companies across the metro.
Website: https://kccorporatechallenge.com
5. 80s Music Bingo at the Winery
Date & Time: May 9, 2026 | 2–5 PM
Location: KC Wine Co
Dust off your leg warmers for an afternoon of nostalgic fun. Guests sip wine while playing bingo inspired by classic ‘80s hits—from Journey to Madonna—making it a relaxed social afternoon among the vines.
Website: https://www.kcwineco.com/events
Hospital Hill Run
Date & Time: May 16, 2026 | 7:00 AM
Location: Crown Center Square, Kansas City
Known as the “Grandfather of Kansas City road races,” this iconic event features half-marathon, 10K and 5K distances through downtown’s famously hilly streets. Thousands of runners gather for the challenge and the lively finish-line festival.
Website: https://www.hospitalhillrun.org
Turkey Creek Festival
Date & Time: May 16, 2026 | All Day
Location: Antioch Park, Merriam
One of Johnson County’s most charming spring festivals, Turkey Creek features a pancake breakfast, 5K race, live music, artisan vendors and a kid zone. The setting at scenic Antioch Park makes it a perfect family day outdoors.
Website: https://www.visitkc.com
Country Line Dancing Night
Date & Time: May 16, 2026 | 6–8 PM
Location: KC Wine Co
Kick up your boots with guided line-dancing lessons and wine tastings. Whether you’re a seasoned dancer or a beginner, this lively evening blends country music, community and vineyard charm.
Website: https://www.kcwineco.com/events
Celebration at the Station
Date & Time: May 24, 2026 | Evening
Location: Union Station Kansas City
The Midwest’s largest free Memorial Day weekend event features a performance by the Kansas City Symphony followed by a spectacular fireworks show. Thousands gather on the lawn for picnics and patriotic music.
Website: https://www.visitkc.com
Stems: A Garden Soirée
Date & Time: May 16, 2026 | 7–10 PM (VIP entry at 6 PM)
Location: Overland Park Arboretum & Botanical Gardens
This elegant outdoor garden party is one of the Arboretum’s most anticipated spring events. Guests enjoy tastings from top local restaurants, craft drinks, live music, art installations and entertainment while strolling through the gardens in peak bloom. The event supports public art initiatives and beloved Overland Park destinations.
Website: https://artsandrec-op.org/stems
Wine Tasting on the Terrace
Date & Time: May 15, 2026 | 6–8 PM
Location: Overland Park Arboretum & Botanical Gardens
Sip and savor curated wines paired with small bites while overlooking the Arboretum’s beautiful landscapes. This relaxed tasting event offers a perfect evening for couples or friends to enjoy spring blooms and scenic views in a tranquil garden setting.
Website: https://www.visitoverlandpark.com
Second Saturday for Kids
Date & Time: May 9, 2026 | 9–11 AM
Location: Park Place
Families gather in Barkley Square for this free monthly event filled with kid-friendly entertainment, music, games and themed activities. The lively fountains and open lawn make it an ideal spot for kids to play while parents explore nearby shops and restaurants.
Website: https://parkplaceleawood.com
Spring Shopping & Patio Season Kickoff
Date & Time: May Weekends | Various Times
Location: Town Center Plaza
With warmer weather arriving, Town Center Plaza comes alive with patio dining, seasonal promotions and weekend pop-up events. Stroll the outdoor shopping district, enjoy brunch or happy hour and browse spring collections at local boutiques.
Website: https://www.towncenterplaza.com
Spring Garden Inspiration Weekend
Date & Time: May Weekends | 9 AM – 6 PM
Location: Family Tree Nursery
This beloved local nursery is a destination for spring gardening inspiration. Throughout May, visitors can explore blooming displays, get landscaping advice from plant experts and discover new flowers, shrubs and patio décor for their gardens.
Website: https://www.familytreenursery.com
HABITAT: House Music Night at the Zoo
Date & Time: May 9, 2026 | 7 PM – Midnight
Location: Kansas City Zoo & Aquarium
This adults-only after-hours event transforms the zoo into a nightlife destination. Guests dance to DJs, explore the aquarium, ride the carousel and train, and enjoy food trucks and drinks throughout the evening.
Website: https://kansascityzoo.org/events