April 25: The Brothers Bourbon Bash
- What: The Brothers Beer & Bourbon House hosts its fifth annual Bourbon Bash, an outdoor tasting featuring samples from a wide range of distilleries. Guests can enjoy whiskey pours, live music, and a relaxed park setting, with food trucks, draft beer, and cigars available. Each ticket includes tastings and a commemorative whiskey glass.
- Where: Kirkwood Park, 111 South Geyer, Kirkwood.
- When: Noon-3 p.m.
- Price: $49.08.
April 25-26: St. Charles Taco King Taco Fest
- What: Experience the Midwest’s largest taco festival as Taco King Taco Fest comes to St. Charles. This free, family-friendly event features the region’s best taco vendors, live music, and a high-stakes taco-eating contest. Don’t miss the Hot Sauce Showdown and the Best Taco Spot Battle while celebrating local culture and community at this vibrant, flavor-filled outdoor celebration.
- Where: St. Charles Riverfront, 1050 South Riverside, St. Charles.
- When: April 25, 11 a.m.-8 p.m.; April 26, 11 a.m.-5 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
April 29: Chartreuse Master Class & Cocktail Party With National Educator Matt Lofink
- What: Join The Gin Room for an intimate class and cocktail party exploring the legendary French spirit, Chartreuse. Guided by National Educator Matt Lofink, guests will taste through a curated lineup of the spirit’s different expressions while learning about the Carthusian Monks’ centuries-old craftsmanship. Conclude the evening with a refined cocktail celebration dedicated to the botanical complexity and heritage of this esteemed elixir.
- Where: The Gin Room, 3200 South Grand.
- When: 6-9 p.m.
- Price: $37.13.
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May 1: The Indomitable Spirit of America- 250th Birthday Bourbon
- What: On the first Friday of every month, St. Louis based Still 630 is issuing a rare, single-barrel release to commemorate the 250th birthday of the United States. Dubbed “The Indomitable Spirit of America 250th Birthday Bourbon,” each release commemorates a milestone in American history, including the signing of the Declaration of Independence, the Wright brothers’ first flight, and the March on Washington. Head down to May’’s release party for a toast and other bourbon-infused festivities.
- Where: Still 630 Distillery, 1000 South 4th.
- When: 5-9 p.m.
- Price: Admission is free. Beverages and subscriptions will be available for purchase.
May 2-3: Foodies Eat First
- What: St. Louis food influencer BradENSTL is back for a second Foodies Eat First food festival celebrating the best of St. Louis eats. Sample food and drinks from some of the area’s top restaurants and chefs and enjoy live music throughout the day.
- Where: Trust, 401 Pine.
- When: Daytime session 11 a.m.-2 p.m.; Afternoon session 3:30-6:30 p.m. (VIP tickets have 30 minute early access).
- Price: $39.49 (General Admission); $182.50 (VIP).
May 2: Manchester Craft Beer Festival
- What: Manchester Parks and Circle 7 Ranch bring the 2026 Craft Beer Festival to Schroeder Park, pouring samples from more than 30 breweries alongside live music from Cahill & Company. Sweet tooths can hit up Lily’s Cafe Dessert Truck between sips. Admission includes unlimited tastings and a souvenir glass, so come thirsty.
- Where: Paul Schroeder Park, 359 Old Meramec Station.
- When: 3-6 p.m.
- Price: $33.85 (advance); $40 day of event.
May 2: 21st Annual Royale Kentucky Derby Party
- What: The Royale’s beloved Derby party turns 20 this year, and they’re going all out to celebrate. Dust off the seersucker and go big on the hat for an afternoon of live music from Dawn Weber’s Boogaloo, a hat contest, and the race itself in St. Louis’s premier courtyard.
- Where: The Royale, Food & Spirits, 3132 South Kingshighway.
- When: 2-7 p.m.
- Price: From $19.58.
May 2: Derby Day at Peacemaker Lobster & Crab Co. Kirkwood
- What: Saddle up for Derby Day at 4 Hands + Peacemaker Kirkwood! Don your best hat for a chance at prizes while enjoying live music and fresh oysters. Sip on 1220 Spirits and Withered Oak derby classics alongside Peacemaker’s signature food specials. This all-ages bash is first-come, first-served, so grab your crew and get ready to cheer on your favorite steed.
- Where: Peacemaker Lobster & Crab Co. Kirkwood, 150 West Argonne, Kirkwood.
- When: Noon-6 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
May 2: Kentucky Derby Skyline Stakes Soiree
- What: The Skyline Stakes Soirée brings the Derby Day glamour with DJ Peezy on the decks, a Derby-themed photo booth, and giveaways for the best-dressed guests. Sip, snack, socialize and say hello to Coco the mini horse. General admission and VIP packages available, the latter including a whiskey and chocolate tasting.
- Where: 360 Westport, 111 Westport Plaza, Maryland Heights.
- When: 1-6 p.m.
- Price: $105.40 (General Admission); $132.99 (VIP).
May 3: Barko de Mayo
- What: HavaHeart Rescue and Yadi’s Yummies team up for Barko de Mayo at Frankie Martin’s Garden, Cottleville’s beloved food truck venue. It’s a Cinco de Mayo celebration with a twist: Sip and snack while meeting adoptable dogs who are ready to find their forever homes.
- Where: Frankie Martin’s Garden, 5372 St. Charles, Cottleville.
- When: 10 a.m.-3 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
May 3: BRUNCH, PLEASE! Rooftop Review Drag Brunch
- What: BRUNCH, PLEASE! takes over Form Skybar atop Hotel Saint Louis for a rooftop drag brunch with serious wow factor. Tabbi Katt headlines alongside Tiffany T Hunter, Krystal F Dupree and Penelope Booze, delivering performances as stunning as the 16th-floor skyline views. Craft cocktails, delicious food and a welcome mimosa round out this one-of-a-kind Saturday experience.
- Where: Hotel Saint Louis, Autograph Collection, 705 Olive.
- When: 11 a.m.-2 p.m.
- Price: From $49.42.
May 3: WorldFest
- What: Maryland Heights’ internationally-focused festival is a celebration of global culture featuring performances, food, crafts and more. Two stages showcase an impressive international lineup, from Bollywood and Samba to Irish dance, Flamenco, Wushu and German brass. Kids can collect passport stamps at country stations throughout the day. No passport required for the rest of us.
- Where: Saint Louis Music Park, 750 Casino Center, Maryland Heights.
- When: Noon-5 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
May 5: The Joy of Tinned Fish
- What: Tinned fish is having a moment, yet for many, it remains unfamiliar. Join this casual, tasty deep dive into the world of canned seafood — sardines and beyond — inside St. Louis’ premier chocolate shop, where you can sample unique flavors and learn simple recipes that make the most of these underrated, nutrition-packed tins.
- Where: Kakao Chocolate, 7272 Manchester.
- When: 6:30-8:30 p.m.
- Price: $60.54.
May 8: Grapes in the Garden
- What: The Missouri Botanical Garden provides a stunning backdrop for this annual wine festival, where more than 250 domestic and international wines await. Schnucks wine specialists are on hand to guide your sampling, live music sets the mood, and special case pricing lets you take home your favorites. A souvenir tasting glass and festival program are included.
- Where: Missouri Botanical Garden, 4344 Shaw.
- When: 5:30-8:30 p.m.
- Price: $55 (Garden members); $60 (non-members).
May 8: A Beer with Bach
- What: The Bach Society of Saint Louis and Beer Choir STL return for their monthly gathering at Das Bevo for this free night of singing, laughter and good music. No experience necessary, just a willingness to raise your voice and your glass.
- Where: Das Bevo, 4749 Gravois.
- When: 7 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
May 9: The Hill Wine Walk
- What: The only thing better than a stroll through St. Louis’ beloved Italian neighborhood is doing so with a glass of wine in hand. Walk at your pace, duck into the area’s shops and restaurants for a little taste of the Old Country right here in the Midwest.
- Where: Participating locations throughout the Hill neighborhood.
- When: Noon-4 p.m.
- Price: $55.20 (General Admission); $135.23 (VIP). *Tickets are currently sold out. Check the event website for additional availability.
May 9: Clancy’s Spring Market Day
- What: Clancy’s Spring Market Day transforms the Ellisville pub’s parking lot into a bustling outdoor market featuring local coffee, baked goods, fresh produce, honey, flowers, handmade goods, vintage finds and more. Clancy’s Irish Pub will also be open with a special spring menu; it’s a great excuse to shop local and stay for lunch.
- Where: Clancy’s Irish Pub, 40 Old State, Ellisville.
- When: 11 a.m.-3 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
May 9: Uncorked: STL
- What: The St. Louis Science Center transforms into an after-hours wine wonderland for the 6th annual Uncorked: STL. Sip and savor 100-plus wines and bubbles from around the world while exploring interactive exhibits, catching live science demos, planetarium shows and dancing to a live DJ. VIP, early admission and general admission ticket options available.
- Where: Saint Louis Science Center, 5050 Oakland.
- When: 7-11 p.m.
- Price: From $80.55.
May 10: See also: A guide to Mother’s Day dining at St. Louis restaurants
May 10: Bubbles & Blooms
- What: Bubbles & Blooms Afternoon Tea brings a springtime experience to the Ritz-Carlton St. Louis’ Solarium Rooftop Terrace. Guests can enjoy a selection of seasonal and classic tea sandwiches, homemade pastries, premium teas, and sparkling beverages. The experience also includes a bouquet bar, where attendees can create their own petite floral arrangement to complement the afternoon.
- Where: The Ritz-Carlton St. Louis, Solarium Rooftop Terrace, 100 Carondelet Plaza, Clayton.
- When: Noon.
- Price: $129.
May 13: Spring Fling Tea In Cocktails Party with St. George Spirits
- What: The Gin Room welcomes St. George Spirits National Educator Mike Losselyoung for an immersive tea-in-cocktails tasting experience, presented in collaboration with Garden District STL and South City Gin Club. Explore how tea aromatics and infusion techniques elevate gin and spirits, sample St. George’s celebrated lineup, and sip seasonal cocktails where botanicals meet the glass beautifully.
- Where: The Gin Room, 3200 South Grand Boulevard.
- When: 5:30-8:30 p.m.
- Price: Tickets are free; food and beverages will be available for purchase.
May 15-16: Taste of Maplewood
- What: Now in its 18th year, the Taste of Maplewood Street Festival showcases the best of Maplewood and Richmond Heights: beloved restaurants, boutiques and specialty shops all in one place. The fun kicks off Friday evening with a preview party before the full festival takes over the street on Saturday, with signature bites, libations, live entertainment and more.
- Where: Sutton Boulevard south of Manchester.
- When: Friday, 6-10 p.m.; Saturday, 11 a.m.-8 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
May 17: Picnic at Bellefontaine
- What: Experience a serene afternoon at Bellefontaine Cemetery and Arboretum with Lunch Under the Osage. Guests are invited to bring a blanket and meal to the Wild Wood Valley Gardens for an outdoor dining experience beneath a majestic Osage Orange tree. Hosted by staff and volunteers, this program offers light conversation and unique insights into the cemetery’s happenings, providing a tranquil opportunity to reconnect with local history and nature.
- Where: Bellefontaine Cemetery and Arboretum, 4947 West Florissant.
- When: 11 a.m.-1 p.m.
- Price: Admission is free; donations are accepted.
May 22-25: St. Louis County Greek Festival
- What: Presented by Assumption Greek Orthodox Church, the St. Louis County Greek Festival returns for Memorial Day weekend with authentic Greek food, live music and dancing. Load up on lamb shank, souvlaki, pastitsio, spanakopita, gyros and more, washed down with a cold Greek beer. Opa!
- Where: Assumption Greek Orthodox Church, 1755 Des Peres, Town and Country.
- When: Friday-Sunday, 11 a.m.-8 p.m.; Monday, 11 a.m.-3 p.m.
- Price: Admission is free; food and beverages will be available for purchase.
May 23: Hello Kitty Cafe Truck Central – St. Louis Appearance
- What: The Hello Kitty Cafe Truck makes a stop at West County Center, bringing super-cute treats and merch for fans of all ages. Swing by while supplies last.
- Where: West County Center.
- When: 10 a.m.-7 p.m.
- Price: Menu prices vary.
May 30: Missouri Spirits Festival
- What: The Missouri Spirit Festival brings distilleries, breweries and wineries together in scenic Augusta for a celebration of craft spirits, food and community. Meet the makers, discover new favorites, browse artisan vendors and enjoy live music, all in one of Missouri’s most charming settings. The event is family-friendly and open to all.
- Where: The Barrel Room, 5521 Water, Augusta.
- When: 3-7 p.m.
- Price: From $35.