Winter Garden is one of Central Florida’s fastest growing cities. It’s just 14 miles west of downtown Orlando and offers plenty of daytime and nighttime date options. Winter Garden was incorporated as a town in 1903 with a roaring train station and blossoming orange trees. Today, the beautiful architecture of Plant Street ─ the main drag ─ still exudes small town charm, but its hot-spots boast big time fun.
Here are five ways to date in Winter Garden:
For the Foodies…
The Saturday morning farmer’s market, held at the City Pavilion from 9am-2pm, bustles with acoustic music and a large assortment of food trucks, produce stands, plants & flowers, baked goods, fresh fish, local honey, artisan cheeses, fancy pickles, homemade soaps, eclectic accessories, artwork, and miscellaneous vendors. It’s truly one of the best farmer’s markets in the Orlando area.
If you didn’t get your fill of goods at the farmer’s market, the brick-lined street paves the way to a plethora of restaurants. Grab lunch at Market to Table, a seasonally-driven, modern American eatery run by former farmer’s market vendor Chef Ryan Freelove — recently spotlighted as one of the best new restaurants to try. Thirsty? Follow our DIY Plant Street Pub Crawl which includes a stop at Crooked Can Brewery located within the Plant Street Market. This industrial building is filled with eateries, shops, and occasional live acoustic music.
For the Cultured…
The Winter Garden Heritage Foundation preserves the history of West Orange County through the operation of the Heritage Museum, the Railroad Museum, and the History Research and Education Center. At the Heritage Museum, built inside the 1918 Atlantic Coast Line Depot, view a collection of citrus crate labels, Indian artifacts, vintage signage, items from local veterans, schools and officials, and more interesting pieces. Stroll toward the clock tower on historic Plant Street to find a charming fountain and flower-lined pagoda with porch-style swings. Venture on to the Railroad Museum, opened in 1913, for more vintage finds and throwback photos.
The Garden Theatre was originally built in 1935 as a single-screen cinema, and today hosts plays, concerts, ballets, movies and more. The theatre is gorgeous and adjacent to a martini bar that sets the stage for post-show beverages and piano entertainment.
Once a firehouse, the Winter Garden Art Association hosts monthly art exhibits and workshops, and serves as a studio space for artists. This community center is vibrant and offers colorful date night moments.
For the Adventurists…
Couples looking to make a splash with a new hobby can learn to waterski, wakeboard, and wakesurf together on Lake Gifford. Jodi’s Ski Skool, run by champion Jodi Fisher, caters to all levels — from learning to get up on two skis to performing tricks.
Escape Goat is one of many new entertainment experiences where each game is a real-life breakout challenge. Together, you’ll find clues, solve puzzles, use the elements of the room and unlock the story to conquer the escape room.
For the Outdoorsy…
The West Orange Trail is a 22-mile paved path perfect for biking, running, and skating dates. Currently under expansion, the stretch will eventually total 36 miles. Several stations rent various types of bikes, including bicycles built for two ─ a date day must! Along the way, you’ll pass orange groves, quaint cottage homes, preserved woodlands and more. You can venture off the trail to picnic at Newton Park on Lake Apopka.
The Oakland Nature Preserve usually gets lumped into Winter Garden as Oakland is merely 2.1 square miles. This park includes a 2/3-mile long boardwalk through mostly shaded wetlands, leading to a covered pavilion overlooking Lake Apopka. The Preserve hosts many educational events and also is home to four geocaches.
For the Sporty…
Winter Garden is home to two affordable golf courses. Orange County National has two championship 18-hole courses, a 9-hole (walking only) short course, a golf academy, and the largest driving range and practice facility in America. Stoneybrook West Golf Club is an 18-hole, par 72 course with the perfect blend of challenging shots and delightful scenery.
Grab a bite and beers at the club house grill or, better yet, head just around the corner from Stoneybrook West to find Hagan O’Reilly’s. From the golf green to the emerald island, this authentic Irish pub ─ with indoor and outdoor seating and bars ─ has a stellar beer selection, live Irish music, sports on big screens, darts/games, trivia tournaments, and yummy pub grub. Sláinte!