Built in an Art Deco style, this is the City Hall building in beautiful downtown Winter Garden. As the sky darkened last night, they began throwing Halloween-themed projections up onto it. And it’s where we began our Friday evening right here in my hometown.The highly-acclaimed West Orange Trail passes directly through downtown Winter Garden. The multi-use trail runs from Killarney in the west to Apopka in the north. It follows the former Orange Belt Railway path. As we crossed the trail, we could hear singing coming from a gazebo further east so we followed the music.It was the Barbershop Dead Quartet (USA). Just in time for Halloween, we heard songs such as “Spooky” and “Monster Mash”.And Disney’s Haunted Mansion theme song, “Grim Grinning Ghosts”. Good stuff!Not far away, Crooked Can Brewing Company is holding its own.Lots of vats for lots of beer choices.We followed the music here too.Here we found Crooner Sam Johnston (USA) outside on the patio.He was singing Top 40 hits during our visit.Crooked Can is at one end of Plant Street Market, a food hall which is crammed with dining choices.Our next stop was Pilars located directly along Plant Street. While it seems that downtown Winter Park rolls-up its sidewalks after 10PM, downtown Winter Garden is just getting started.Pilars has a large bar and seating downstairs but you have to take an elevator up to the 2nd floor to find musical entertainment inside Pilars Loft.A live Jazz band was playing up here last night.There were five members in this quintet but we did not see a group name in the program listing.It featured Scott Dickerson (USA) on the vocals and trumpet.Time for some DJ entertainment! Next stop The Whole Enchilada. It’s a quick-serve Mexican restaurant downstairs with music taking place up on the rooftop.Here we found DJ Marc Thyssen (AUS/USA) playing Top 40 during our visit.Full-liquor rooftop bar plus you can order food from the restaurant too. Fun vibe up here.Marc told us he’s playing for three nights next month elsewhere in downtown Winter Garden but we had never heard of the venue, Harlow Grove.So we had to go check it out. It’s on Main Street a few blocks south of Plant Street and we learned we had never heard of Harlow Grove because it’s brand new!The booth is located in front of the venue and it was here we found DJ Ani (USA).He was playing a Chill House set during our visit. This is primarily a restaurant with the common sense to feature background music from DJ’s.A huge bar occupies about a third of the downstairs and every seat was taken.Everywhere we went last night, a good time was had by all.
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