This sidewalk running down the middle of Plant Street in downtown Winter Garden is the West Orange Trail. During the day it’s filled with pedestrians, skaters and cyclists. At night it’s the median area running between shops, restaurants and bars that line both sides of the street. And it’s where OEN began Saturday night looking for music options.We began at Pilars.The bar was super busy but no live music; just a 90’s Hip Hop track being played in the background.Going out their back door and taking the elevator up one level brings you to Pilars Loft.This is a large room used for music events with bar service from downstairs.The Mike DiRubbo Group (USA) was on the small stage.The music, Jazz.Across the street is The Whole Enchilada.Despite the evening chill, their rooftop bar overlooking Plant Street was pretty jammed.We found DJ Chris (USA) over in the corner booth.The music, Top 40.Definitely a more upscale Winter Garden kind of crowd.We’ve seen live Rock bands in the past at Moon Cricket Grille but it was sadly already closed for the evening when we passed by. The most-famous spot in downtown Winter Garden is Crooked Can Brewing Company.The microbrew pub is highly acclaimed and draws a crowd every night.Part of the Plant Street Market complex, it is joined by a dozen or so other small restaurants, shops and kiosks but sadly no music anywhere. There’s typically more going on in DTWG on weekend nights but not last night. So it was time to move on out! To Orlando, but not downtown.Signed as Clearone Badminton outside, it’s hard to get more “underground” than a warehouse with a nightclub inside! Barbarella 2.0.Not to be outdone by the DJ Claude VanStroke (USA) open-to-close set on Friday night at Ace Cafe, we found DJ Indie John (USA) doing an open-to-close set last night!The music, 80’s New Wave and Alternative.It wasn’t super crowded last night but it was hardly empty either.And a good time was had by all.
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