Find the perfect Valentine’s Day gift for your better half by taking inspiration from your favorite characters from Once Upon a Valentine®: Stories for the Loved & Loveless. Step into a world where famous lovers, larger-than-life characters, and timeless romance inspire how you shop, dine, and celebrate. Hear from heartthrobs like the Harlequin Romance Novel Hunk, the famous winged arrow-slinger of love, Cupid, and more as you plan an unforgettable Valentine’s Day. This is just a sample of all of the great gifts you can find in St. Charles. Find more shops and restaurants with even more gifts on our website. For more inspiration, visit Main Street St. Charles for Once Upon a Valentine® on February 7 & 8 to meet these characters in person and participate in fun Valentine’s (or Anti-Valentine’s) activities.

FOR THE ROMANTIC VALENTINE…

Be mine, Valentine! Discover classic romantic Valentine’s gifts in St. Charles that will make your special someone’s heart swoon. From timeless Valentine’s Day clichés like pink, heart-adorned sweaters or Conversation Heart plushies and serving dishes from April’s on Main inspired by the cheerful, love song singing Once Upon a Valentine® group, to a stunning bouquet of roses from Lawrence Florist in Frenchtown, there’s no shortage of ways to show your love.

For star-crossed lovers like Romeo & Juliet, we suggest a dozen chocolate covered strawberries from Riverside Sweets or a box of decadent chocolate from Kilwins. If your Valentine spends the day wondering “Romeo, oh Romeo, where art thou?”, surprise them with Lydia’s and Sugar & Slice’s Coffee + Flowers Bundle, a thoughtful pre-order that pairs a small bouquet with your love’s favorite coffee that you can deliver to them as a wonderful surprise.

Take a cue from Casanova, the self-proclaimed expert of romance, and plan a special night out. Treat your Valentine to a romantic dinner at one of several charming restaurants along Main Street or at the Streets of St. Charles. For an extra touch of elegance, venture to Historic Missouri Wine Country and enjoy a candlelit, multi-course dinner at a local winery, where fine food and wine set the scene for a romantic evening. Find more things to do in our Valentine's events in Historic Missouri Wine Country blog.

FOR THE VALENTINE YOU REALLY WANT TO IMPRESS…

Cupid is visiting St. Charles (literally, you can do bow-and-arrow target practice with him at Once Upon a Valentine®!) and is striking his targets at Valentine’s events in Saint Charles. Take part in the St. Charles Main Street Cupid Crawl on February 7, where participating shops and restaurants offer sweet treats and special deals all day long.

Straight from the City of Love, the French Love Trio brings international romance to life with playful tango moves and fun facts about romantic traditions from around the world. Take your love international without ever leaving Saint Charles by planning at date at La Vie Vegan, a cozy Main Street café with French-inspired décor and menu items. Or, book an after tea date at the new La Patisserie Paris Tea Room and enjoy a date that feels like you’re strolling the sidewalks of Paris.

As for the Queen of Hearts, she thinks your Valentine deserves the royal treatment. Elevate her self-care routine with small-batch, handmade soaps and self-care essentials from Provenance Soapworks.

If you’re ready to make the ultimate grand gesture worthy of a Harlequin Romance Novel Hunk, plan a shopping spree at local boutiques like MOss, FR & Co, and Ju Ju B’s, where the latest trends await. Add on Pandora jewelry from First Capitol Trading Company and top it off with a day at aRa Spa at Ameristar Casino Resort Spa for a day of luxury and relaxation full of innovative spa experiences and VIP treatments.

Speaking of the Harlequin Romance Novel Hunk, why stop at one special day? Go all in with a weekend getaway to St. Charles. Book a stay at a charming guest house within walking distance of Main Street and spend the weekend exploring local shops, restaurants, and attractions.

FOR THE CAPTIVATING VALENTINE…

For the Valentine who leaves you completely awestruck, indulge them with items that will create an at-home spa experience like a handmade soy candles from 320 Sycamore Candles and handmade sugar scrubs from 2 Simple Sisters that will be a gift so indulgent it may even make the Femme Fatale jealous.

If your love leaves you speechless, follow in the Poetess’s footsteps and pick up a poetry book from Main Street Books or The Bookworm to help you express what’s in your heart.

Inspired by the Prohibition-era gangsters of the St. Valentine’s Day Massacre, elevate your date night with cocktail kits from the Cozy Shop. Pair the kit with cute cocktail glasses to mix up speakeasy-worthy drinks at home.

Let the 1970s Game Show Host take the lead on your St. Charles Valentine’s Day plans. The grand prize? A special gift, a surprise date, or an unforgettable experience in the City. Explore our Romantic Getaway Itinerary for inspiration to turn your Valentine’s into a true showstopper.

FOR YOUR GALENTINE…

There’s no need to fret if you’re flying solo this Valentine’s Day! Once Upon a Valentine® features anti-Valentine’s activities that make everyone feel included, regardless of relationship status. Inspired by Miss Havisham’s “Heart Burn” art therapy, channel your feelings into creativity by signing up for an art class at the Foundry Art Centre with a friend or get a watercolor book from Happy Camper.

As you listen to The Lonely Hearts Club belt out breakup anthems at Once Upon a Valentine®, soothe any lingering heartache with a scoop (or two) of ice cream from Sugarbot Creamery. After all, what can’t ice cream fix?

In the spirit of the Six Wives of Henry the VIII, gather your besties and celebrate friendship this Valentine’s Day. Attend a Galentine’s event in St. Charles, from festive pop-up bars to exciting brunches, and prove that you don’t need a date to have fun this Valentine’s Day.

Celebrate Valentine’s Day with the help of characters from Once Upon a Valentine® in St. Charles. Whether you’re channeling your inner Romeo & Juliet, Casanova, Queen of Hearts, or Miss Havisham, there’s a special Valentine’s experience waiting for you. Blending history, fun, and spirited entertainment, this St. Charles Valentine’s festival has an array of activities to help visitors embrace the adoration and playful disdain for Valentine’s traditions. Mark your calendars and step into the story at Once Upon a Valentine® on Main Street St. Charles, February 7 & 8, from noon to 3 PM.