Thoughts on the best of Winter Garden from the campus’ own T Munroe. 

#1: The “small-town” feel and vintage charm

Although we are technically “The City of Winter Garden,” you can’t deny the small-town feel and vintage charm of our darling community. Maybe it is the enchanting trees that always light up downtown each night along Plant Street or being able to count on always running into someone you know when you are out and about. The amount of local love for Winter Garden is ever present and down right contagious.

#2: Plant Street Market

Open 7 days a week, Plant Street Market houses a number of vendors who can easily satisfy any craving. Brick oven pizza, BBQ, a mac and cheese stand, sushi, and the most beautiful acai bowls are just a sampling of the items found in the market. The renowned Crooked Can Brewery sits at the end of the market and usually hosts live music on the weekends for the entire family to enjoy.

#3: Plant Street (not the market, but actual street itself!)

For more dining options, continue down Plant Street and try out the Tasting Room or Market To Table (their Breads and Spreads appetizer is a must!) for a nicer dinner.  Sweet treat options are endless at Scoops Old Fashioned Ice Cream Store, Ms. Bees, and Kaebisch Chocolates. The coffee and atmosphere is relaxed at Axum and you support a good cause when buying any item there. If you really want a casual, trendy spot to impress your friends with – head to the Whole Enchilada Rooftop bar for eats and great views of downtown. Shop local at any of the boutiques along the way to dinner.

#4: Winter Garden’s Farmer’s Market (Saturdays only)

By far the biggest, weekly event hosted by Winter Garden. The Farmer’s Market has a ton of vendors for any product/produce that you can imagine. It is great fun for all ages with good eats, face painting for the kids, often live music, and even treats for friendly pets.

#5: Downtown Festivals (Seasonal)

Winter Garden seems to always be celebrating something. You can count on seasonal, if not almost monthly, festivals held downtown right along Plant Street. Whether it’s Halloweenfest, Christmas’ Light-up Winter Garden, Blues and BBQ, St. Patty’s Day Weekend, Spring Fever in the Garden, a car show, etc. – all the details can be found in an insert they send with your monthly water bill. Check there for details and try to get there early for parking (or better yet bike downtown and avoid all the traffic) and bring a fold out chair to sit and stay for awhile.

#6: West Orange Trail

The West Orange Trail stretches 22 miles across Orange County, and is perfectly paved for biking, walking, running, rollerblading and the occasional horseback riding. Much of the trail is shaded by beautiful over-arching trees making the trail popular for all seasons. Whether you have bikes or need to rent them at one of the stations along the way, get out on the trail.

#7: Neighborhood Playgrounds

I’m always impressed by the amount and upkeep of Winter Garden play areas. There is the Splash pad downtown that is always popular on hot days. Chapin Station and Speer Park (technically in our neighboring town of Oakland) are shaded by large oak trees and have a lot of playground equipment for the little ones to explore. Either are a perfect spot when hosting a playdate.

#8: Living So Close to Disney

Avoid the dreaded Interstate-4 and come to Winter Garden to have access to the all the back roads into Disney. It is no doubt one of the most magical places on earth, and you will have no problem finding someone to go with at Grace Winter Garden [a lot of church members enjoy annual passes]. From some Winter Garden neighborhoods, you can even watch the Disney fireworks every night from your own backyard.

#9: Golf

People say golfing is fun. If sweating while swinging metal and enduring other natural elements (often rain and lighting) for 4+ hours is your thing, then Winter Garden does not disappoint in the courses it has to offer. The beautiful Orange County National puts three pristine courses in one spot for you – 2 championship courses and a fun 9-hole walking course for all ages.

#10: DG Doughnuts

If you’re around Grace long enough, whether it be at the main campus or ours in Winter Garden, you can count on hearing about DG Doughnuts. (Most of us could either blame or owe our own obsession/weight gain to Pastor Rick Garrett.) Open Tuesday through Sunday from 7am until sold out, this small little sideshop in the Chevron off Tubb street is incredibly popular. They are known for their delicious donuts, cinnamon rolls and fritters. They don’t shy away from creating bold, FUN flavors and are some of the friendliest vendors you’ll meet.