Bike riding in Winter Garden

Downtown Winter Garden boasts all that is needed to make this Valentine’s Day special. With live music under the stars, unique dining and dessert options, fun things to do, charming twinkle-lit surroundings, Downtown Winter Garden has so much to fall in love with…and for you to share with your loved one. For those wanting some help planning their celebration, here are the top 10 things to do on Valentine’s Day:

  1. Be serenaded under the stars by Breezeway Trio on Thursday, February 14, 6-9 p.m., at Centennial Plaza Gazebo, 101 W. Plant St. Free, romantic jazz performance!
  2. Go on a bike ride together through quaint downtown and its adjoining 22-mile trail.
  3. Make your sweetheart…or yourself…something special for Valentine’s Day by signing up for a make-and-take jewelry class.
  4. Toast to your love at a couples pour at Crooked Can Brewing Company, or serenade your special someone at open mic night at Pilars Martini Bar!
  5. Stroll and Shop - take a stroll hand-in-hand along the charming, twinkle-lit, historic streets and pop in one-of-a-kind shops. A perfect time to buy your special someone that special something!
  6. Take a His and Hers Food Tour to experience romantic pairings.
  7. Have dinner at one of the many unique, award-winning restaurants in Downtown Winter Garden.
  8. Indulge on dessert – and don’t forget the chocolate! There is no shortage of dessert options with bakeries, chocolate shops, and coffee houses offering special sweets for your sweetheart.
  9. Take pictures…or selfies…to create lasting memories with downtown as the perfect backdrop to mark your holiday on social media. There is a reason that Winter Garden was named one of most photographed downtowns in Central Florida by the Orlando Film Commission!
  10. Dance and dine at a Masquerade. If you can’t make Thursday evening work, on Friday, February 15, the Winter Garden Art Association will be hosting their annual event, Splash of Masquerade starting at 6:30 pm.  Cocktails, dinner, and music provided by Nova Era. To purchase tickets, visit www.wgart.org.

Check out our list of Downtown Dining, Retail, Activities Specials.