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

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

SPONSORED — 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.

1. Horse-Drawn Carriage Tours all Weekend

February, 12, 13, and 14, 6:00-10:00 pm
20-minute tours depart at Downtown Pavilion, 104 S. Lakeview Ave.

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 $95 per tour and the carriage can accommodate up to four adults.

To make reservations, visit soulhavenranch.com/seasonalevents.

Image credit: SOUL Haven Ranch

2. Casablanca Movie Screening at Garden Theatre

Sunday, February 14, 6:30 pm
Garden Theatre, 160 W. Plant St.

Enjoy a special showing of rhe ultimate romance movie, Casablanca, on Valentine’s Day at Garden Theatre. We can’t think of a better way to watch the classic than snuggled up amidst the elegance of the historic single screen cinema. Tickets are just $15/person.

Limited tickets are available for advance purchase at gardentheatre.org/movies.

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 on February 12 at 6pm, February 13 at 1pm and 6pm, and on February 14 at 1pm. Take a Brewery Tour for a sneak peek at the fermenting process, offered hourly from 12-4pm on February 14 (advance reservations required). Crooked Can Brewing Company is located at Plant Street Market (426 W. Plant St).

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

4. Scenic sights and romantic tunes

February 12, 13, and 14
Winter Garden City Hall, 300 W. Plant St.
Downtown Interactive Fountain, 104 S. Lakeview Ave.

Enjoy the sights and sounds of Valentine’s Day while strolling through the twinkle-lit tree-lined tunnel of love path. Stop to marvel at the majestic City Hall, which will be lit up red, then stop by the Splash Pad lit up purple for the holiday. While you stroll, hum along to the romantic tunes broadcasted through the streets, perhaps even prompting a serenade. Downtown Winter Garden is the perfect spot for a romantic stroll hand in hand.

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

February 12-14, 2021
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 will be offering a special “Two-for-One Bike Rental” deal at the Winter Garden Trailhead. Or, visit the shop for a discount on the purchase of tandem bike. This offer is valid Valentine’s Day weekend (February 12 – 14, 2021).

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. Options are available for all dietary preferences, and you’ll even find treats for your furry friends.

Scout your sweet tour at downtownwg.com/winter-garden-locations/winter-garden-restaurants.

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 “Love Local,” a campaign initiated by the City of Winter Garden to help local businesses affected by the pandemic. For more information about Downtown Winter Garden, visit downtownwg.com.

Feature image credit: Cricket’s Photo & Cinema


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