10 Reasons to Spend Valentine's Day Weekend in Winter Garden

The most memorable Valentine’s Day gift to give this year is time spent together. Fortunately, historic downtown Winter Garden has a number of ways to celebrate the occasion to create a lasting impression. For those wanting some help planning their holiday celebration, here are 10 reasons to spend Valentine's Day weekend in Winter Garden with your favorite plus one.

Updated January 2024 by Meghan Roth

1. Horse-Drawn Carriage Tours

February, 14, 5:30-9:30 pm
20-minute tours depart at Downtown Pavilion, 104 S. Lakeview Ave.

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Ready to live out your fairy tale dreams? SOUL Haven Ranch is offering private horse-drawn carriage rides in a Cinderella coach throughout Valentine's Day weekend in Winter Garden. Cuddle up as you take in Winter Garden’s charming twinkling lights and sights all along Plant Street on the 20-minute tour.

The cost is $115 per tour and the carriage can accommodate up to four adults.

To make reservations, visit soulhavenranch.com/seasonalevents.

Image credit: SOUL Haven Ranch

2. Garden Theatre

Currently, we are not seeing any special Valentine's Day events at Garden Theatre for Valentine's Day 2024. However, All Shook Up is performing starting February 16.

3. Aphrodisiac Ale on Tap at Crooked Can

Make your way to Crooked Can to sample a selection of local brews, including a special aphrodisiac ale release Barrel Aged Cherry Cheeks (ooh la la!), and compare favorites. Relax to live music on the outdoor patio. Crooked Can Brewing Company is located at Plant Street Market (426 W. Plant St).

Note, this was offered in 2022. We have reached out to Crooked Can to confirm if something similar is being offered in 2024.

Valentine's Day weekend in Winter Garden - Crooked Can Brewing Company
Image credit: Whitney Bilodeau Photography


Saturday, February 24, 2024, 11:00 am – 10:00 pm, Historic Downtown

Enjoy the sights and sounds of Valentine’s Day the weekend after the big day. There will be 30 live music acts of a variety of genres across six stages plus strolling performers.

The performances are continuous and simultaneous from 11:00 am – 10:00 pm throughout Historic Downtown Winter Garden. Simultaneous and continuous performances will be held at various outdoor stages throughout historic downtown stretching from Central Avenue to Dillard Street.

5. “Blind Date with a Book”

Head over to the new local independent bookstore in town, Writer’s Block Bookstore, to pick up a wrapped mystery book with a clue to see if this blind date is a perfect match. Or play matchmaker for friends to gift a fun surprise!

Browsing a bookstore is also a fun date activity. Select a book to read together (perhaps a romance novel), and take turns reading each other passages.

While there, pick up a fun trivia or board game to play at home. Writer’s Block Bookstore is located at 32 W. Plant St.

Image credit: Writer's Block Bookstore

6. Bike Rides on the West Orange Trail

Winter Garden Wheel Works, 101 W. Plant St.

Perfect weather and the West Orange Trail, which runs through quaint downtown, are the perfect combo for a great date activity. Winter Garden Wheel Works has offered a special “Two-for-One Bike Rental” deal at the Winter Garden Trailhead in years past.

Or, visit the shop to consider the purchase of a tandem bike.

Image credit: City of Winter Garden

7. Romantic restaurants galore

Spend time reconnecting over dinner, enjoying your favorites, or trying something new. Downtown restaurant offerings run the gamut from multi-course prix fixe dinners and steak houses to pizza parlors, burger joints, and delis. Many of downtown's restaurants have expansive outdoor patios. Or take your romantic meal to-go to enjoy at home or on a picnic.

Find a complete list of dining options here.

8. Chocolate & Dessert Indulgences

It wouldn’t be Valentine’s Day without chocolate and sweets! Downtown’s chocolate shops, bakeries, coffee houses, and ice cream and custard parlors are the perfect places to indulge.

David Ramirez Chocolates inside Plant Street Market is one of our favorite Orlando Chocolate Shops for Valentine's Day.

Valentine's Day weekend in Winter Garden
Image credit: David Ramirez Chocolates

9. Toast over Drinks

Although this Valentine’s Day will look different from the last, take a moment to toast to having each other during trying times. Sip on custom-crafted cocktails, beer, wine, or your favorite beverage. Enjoy drinks indoors or on outdoor patios under the stars, or even take your beverages to-go for a private celebration at home.

Find a complete list of drink venue options here.

10. Local shops to get your special someone something special

Shop hand-in-hand along the charming historic streets and pop into the one-of-a-kind shops to find that perfect gift. Downtown Winter Garden's unique boutiques and stores sell everything from fine jewelry and chocolates to fresh flowers, apparel, home décor and so much more.

Here's a complete list of local shopping options.

The array of date night options all located within historic downtown Winter Garden make it easy to truly make this Valentine’s Day memorable. Since small businesses are the heart of downtown, visiting these shops and restaurants during Valentine’s Day weekend in Winter Garden supports local businesses.

Feature image credit: Cricket’s Photo & Cinema

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