Winter Garden - Orlando's Coolest Suburb

Submitted by mag on

Winter Garden West Orange Trail Head ParkWinter Garden makes the most of it's location - it's in the heart of the beautiful West Orange Bike Trail - and the Bike Trail is the heart of Winter Garden.  There are actually 2 terrific Trailhead parks -   one east of Winter Garden and one right in at the edge of town.  Both have a great rest building, an extensive playground and plenty of free parking.  

55 miles is a long ride for us and we were happy to reach Winter Garden. We checked immediately into our B&B hotel the historic renovated Edgewater right in the center of town.

The hotel has several restaurants, an ice cream parlor and a charming lobby with authentic fireplace on the ground floor and 29 rooms on the second floor that are reached by the original Otis Elevator - so old and cranky it has to be operated by an attendant. They provided a secure storage room for our bikes just off the lobby. There is also a lovely comfortable common area and breakfast room/kitchen on the second floor with self-serve cold drinks and snacks available all the time. And of course cyclists always appreciate being able to chill the water bottles for the next day.

Welcome to Winter GardenAfter a shower and rest we enjoyed exploring the charming historic town that makes the most of its location right on the trail. The wide main street has a lovely long park with fountains and gazebos - perfect for events like weddings and picnics. The town was bustling with activity and all the shops, bars and restaurants were full of people and there was a very active live theater. Everyone we spoke to in town attributed the revitalization of Winter Garden to the bike trail. According to Jeraden, the bar tender at The Chefs Table, "Over the last five years the trail has changed the whole character and economics of the town, giving it an 'outdoor lifestyle' flavor."

At breakfast in the morning we spoke to one of the owners of the Edgewater, Alicia Wilder. She said the bike trail brings thousands of customers every year. A number of cycling groups have standing reservations at the hotel, sometimes taking up every room. She said before the trail and town revitalization effort, which began in 1995, the town was known as "winter garbage". It required a major cooperative effort on the part of cycling and trail advocates, benefactors, entrepreneurs and merchants to bring about the change. Some wanted to demolish the historic buildings, including the Edgewater which had been derelict and in disrepair for years, but luckily people with the vision, power, pull and funding came together to completely renovate the town, turning the central space (originally the railroad tracks and then parking) into a minipark with fountains and places to sit. This slows the traffic and makes outdoor seating at along the entire main street pleasant, quiet shady places to enjoy.

Wining down and the Chef's TableThe Edgewater itself was saved from destruction and faithfully restored by a cooperative ministry over a period of about 8 years, and this group continues to own and operate the B&B portion. By working together, visionaries were able to revitalize the entire town and make it a destination that attracts cyclists and other tourists all year round.

Recently Winter Garden was named "Orlando's Coolest Suburb". It's a model community that can serve as inspiration to any small town that has access to a bicycle trail.  Listen up, Deland!

Winter Garden West Orange Trail Head Park
Winter Garden West Orange Trail Head Park
Welcome to Winter Garden
Welcome to Winter Garden
Checking in to the Edgewater
Checking in to the Edgewater
Historic room in the Edgewater
Historic room in the Edgewater
Historic train in Winter Garden
Historic train in Winter Garden
Wining down at the Chef's Table
Wining down at the Chef's Table