{"id":38336,"date":"2026-10-31T07:00:00","date_gmt":"2026-10-31T11:00:00","guid":{"rendered":"https:\/\/www.orlandoentertainmentnews.com\/?p=38336"},"modified":"2026-10-30T23:14:06","modified_gmt":"2026-10-31T03:14:06","slug":"club-reports-crooked-can-brewery-pilars-loft-the-whole-enchalada-harlow-grove","status":"publish","type":"post","link":"https:\/\/www.orlandoentertainmentnews.com\/?p=38336","title":{"rendered":"Club Reports: Crooked Can Brewery, Pilars Loft, The Whole Enchalada, Harlow Grove (Winter Garden)"},"content":{"rendered":"\n
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Built in an Art Deco style, this is the City Hall building in beautiful downtown Winter Garden.<\/figcaption><\/figure>\n\n\n\n
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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.<\/figcaption><\/figure>\n\n\n\n
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The highly-acclaimed West Orange Trail<\/a><\/em> 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<\/em> path. <\/figcaption><\/figure>\n\n\n\n
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As we crossed the trail, we could hear singing coming from a gazebo further east so we followed the music.<\/figcaption><\/figure>\n\n\n\n
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It was the Barbershop Dead Quartet (USA). <\/figcaption><\/figure>\n\n\n\n
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Just in time for Halloween, we heard songs such as “Spooky” and “Monster Mash”.<\/figcaption><\/figure>\n\n\n\n
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And Disney’s Haunted Mansion<\/em> theme song, “Grim Grinning Ghosts”. Good stuff!<\/figcaption><\/figure>\n\n\n\n
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Not far away, Crooked Can Brewing Company <\/em>is holding its own.<\/figcaption><\/figure>\n\n\n\n
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Lots of vats for lots of beer choices.<\/figcaption><\/figure>\n\n\n\n
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We followed the music here too.<\/figcaption><\/figure>\n\n\n\n
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Here we found Crooner Sam Johnston (USA) outside on the patio.<\/figcaption><\/figure>\n\n\n\n
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He was singing Top 40 hits during our visit.<\/figcaption><\/figure>\n\n\n\n
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Crooked Can <\/em>is at one end of Plant Street Market<\/em>, a food hall which is crammed with dining choices.<\/figcaption><\/figure>\n\n\n\n
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Our next stop was Pilars <\/em>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.<\/figcaption><\/figure>\n\n\n\n
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Pilars <\/em>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<\/em>.<\/figcaption><\/figure>\n\n\n\n
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A live Jazz band was playing up here last night.<\/figcaption><\/figure>\n\n\n\n
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There were five members in this quintet but we did not see a group name in the program listing.<\/figcaption><\/figure>\n\n\n\n
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It featured Scott Dickerson (USA) on the vocals and trumpet.<\/figcaption><\/figure>\n\n\n\n
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Time for some DJ entertainment! Next stop The Whole Enchilada<\/em>. It’s a quick-serve Mexican restaurant downstairs with music taking place up on the rooftop.<\/figcaption><\/figure>\n\n\n\n
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Here we found DJ Marc Thyssen (AUS\/USA) playing Top 40 during our visit.<\/figcaption><\/figure>\n\n\n\n
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Full-liquor rooftop bar plus you can order food from the restaurant too. Fun vibe up here.<\/figcaption><\/figure>\n\n\n\n
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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<\/em>.<\/figcaption><\/figure>\n\n\n\n
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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<\/em> because it’s brand new!<\/figcaption><\/figure>\n\n\n\n
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The booth is located in front of the venue and it was here we found DJ Ani (USA).<\/figcaption><\/figure>\n\n\n\n
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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.<\/figcaption><\/figure>\n\n\n\n
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A huge bar occupies about a third of the downstairs and every seat was taken.<\/figcaption><\/figure>\n\n\n\n
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Everywhere we went last night, a good time was had by all.<\/figcaption><\/figure>\n\n\n\n

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