Once Upon a Valentine at St. Charles Main Street
- When: Saturday, February 7, 2026, 12:00 pm - 3:00 pm
- Location: Main St., St. Charles, MO 63301
- Cost: Free
Each February in Saint Charles, love takes center stage on Historic Main Street as our Valentine's Celebration, Once Upon a Valentine® Stories for the Loved & Loveless, unfolds. This micro festival blends history, fun, and spirited entertainment for locals and visitors alike. Join us for an array of activities embracing both the adoration and the playful disdain for Valentine's Day traditions.
This festival caters to a diverse audience, ensuring an inclusive experience for families, friends, and those seeking unconventional V-Day activities. With a combination of pro and anti-Valentine's Day programming, Once Upon a Valentine® promises something for everyone, whether you're a hopeless romantic or you roll your eyes when the heart-shaped candy boxes hit store shelves.
"Pro"-Valentine's Day Activities:
Kisses with the Queen of Hearts head to our Candy "KISS"-ing booth to visit with the Queen and receive a token of her affection
Harlequin Novel Hunk takes a photo with our Fabio-inspired hunk at this fun photo-op
Roses are Red Poets Society stop by the Tourism Center at 230 South Main to get your very own spontaneous poem - typed on-site and in person by our Parisian Poet.
Card Making with Casanova and Femme Fatale. Craft your own old-fashioned Valentine's cards with the infamous king of romance, Casanova and our very own Femme Fatale
Romeo & Juliet - Shakespearean Love Sonnets Spin the “Wheel-O-Sonnets” to hear the star-crossed lovers recite some of the Bard’s most iconic words of affection.
Love is universal. Celebrate international love traditions as a trio of French tango dancers inspires you to bust a move
Cupid's Archery Practice Test your bow & arrow skills as you take aim at heart-shaped targets during Cupid's archery challenge
Renew your vows during our vow renewal ceremony on Sunday at 3:00 PM at the Gazebo in Kister Park
"Anti"-Valentine's Day Activities:
Six Wives of Henry VIII Commiserate with the Tudor Queens as they share their ill-fated experiences with ex-husband, Henry VIII, and join them for a candy-filled heart-shaped piñata smashing at 1:00 PM and again at 2:00 PM
St. Valentine's Day Massacre Gangsters Get your mugshot taken with some quirky 1920s gangsters, as they remind you that February 14th has been a historical day of infamy
HeartBURN with Miss Havisham Release frustrations through fire therapy under the guidance of famed jilted bride Miss Havisham, channeling a Great Expectations vibe
Heartbreak Hymnal Sing-a-long, join us for an anti-love anthem sing-a-long at the Gazebo in Kister Park on Saturday at 3:00 PM
Musical Entertainment:
Two a cappella singing groups, The Conversation Hearts and The Lonely Hearts Club, will provide the event’s soundtrack with a variety of love ballads and breakup anthems.
Head to the Gazebo in Kister Park on Saturday afternoon at 3PM to join the "Heartbreak Hymnal" sing-a-long.
- Website: www.discoverstcharles.com
- Category: Holiday Events
All repeats 
