Top Places To Get Your Hipster On In Orlando

    Places that every self-respecting hipster in Orlando should frequent.


    By Kaleb Quast


    Over the past few months, I have been trying to to put together a collection of Orlando’s best hispter hangouts, and am proud to present my finalized list. Check it!


    Cocktail Bars—


    Lil’ Indies: If you’re a drinking hipster —which most of us are— then chances are you’ve wandered through Lil’ Indies. Located next door to Will’s Pub on Mills 50, they never have covers for their bar and they offer creative and delicious craft cocktails. They also have an “Industry Hour” happy hour from 11 P.M – 1 A.M. on Mondays and Tuesdays where they have a rotating selection of $5-7$ cocktails.


    Address: 1036 N. Mills Ave., Orlando FL, 32803. 
Phone: N/A. Hours: M-F | 7:30PM-2:00AM


    Matador: While their menu cocktails are a bit pricey (~$8-$10) they also offer slightly cheaper (~$6) beers on tap, and a High And Low, which is a shot of whiskey and a six oz. Miller High Life for $6. Spacious and decorated with a collection of mirrors, slightly vintage furniture and various Spanish matador themed items on the wall, this place manages to maintain a laid back environment. There is also a pool table, and a smaller back room with darts to keep oneself entertained.


    Address: 724 Virginia Dr., Orlando, FL, 32803
. Hours: M-F | 5:00PM-2:00AM


    The Woods: Walk up a small flight of stairs into this intimate space. The lighting is dim and the bar is beautiful, wooden, and intricate, so it’s ideal for impressing a date and hiding your overnight stress pimples. They are a bit pricey (~$8-$10) but they are in Downtown Orlando, so keep that in mind. They offer a vast selection of craft beers and their craft cocktails shift monthly so they can utilize fresh and seasonal ingredients. They also offer a mixing class where you can learn to make specialty drinks from one of the bartenders.


Address: 49 N. Orange Ave., Orlando, FL, 32801
. Phone: (407) 203-1114. 
Hours: 5:00PM-2:00AM


    Hanson’s Shoe Repair: For those who think secret bars are cool, Hanson’s Shoe Repair is an old-fashioned speakeasy where you have to call on the day of and request the password to get in. Dress well and be prepared to shell out a little bit extra for your drink – ($10+). But, hey, you’re paying for the cozy quarters (the bar can not promise to hold more than four customers at a time) and the novelty of being able to answer, “What’s the password?”


 Address: 27 E. Pine Street, Orlando, FL, 32801. 
Phone: (407) 476-9446
. Hours: 7:00PM-2:00AM


    Courtesy: The most intimate bar in Downtown Orlando. Most of us can’t afford to drink here all night (~$10) but if the plans are to go dancing down at I-Bar later then you’ll want to open your night of debauchery with some soft vibes and a finely tailored cocktail. I wouldn’t recommend going on a weekend though, the small space can get pretty tightly packed. They also offer a cocktail class on every other Saturday.


    Address: 114 N. Orange Ave., Orlando, FL, 32801
. Phone: (407) 450-2041
. Hours: M-F | 5:00PM-2:00AM || Sat | 7:00PM-2:00AM || Sun | 3:00PM-2:00AM


    St. Matthews Tavern: It’s a shitty, smoking, gay friendly, dive bar that also happens to host mass on Sundays. That’s not meant to be offensive, all the regulars will agree, and they love it. The drinks are strong and cheap (~$3), and can be extremely creative. They have a selection of beers on tap if liquor isn’t your style. They also host a selection of events including shows. This is the one bar on Mills where one can actually get pretty damn drunk without spending their lifesavings. Also, it’s now got windows so the second hand smoke isn’t palpable!


    Address: 1300 N. Mills Ave., Orlando, FL, 32803. 
Phone: N/A
Hours: M-F | 4:00PM-2:00AM || Sat&Sun | 1:00PM-2:00AM


    Beer and Wine Bars—


    The Falcon: This bar is relatively close to the Orange Ave strip, and only a couple of blocks away from Lake Eola, so it’s a great place to come if you’re tired of the usual Orlando hustle, but not the downtown scenery. They have rotating beers on tap, $2 PBR tall boys, and they routinely hosts art shows that showcase local artists. (Plus if you get too white-girl-wasted there are a handful of restaurants around the corner).


    Address: 819 E. Washington St., Orlando, FL. 
Phone: (407) 423-3060. 
Hours: M-S | 5:00PM-2:00AM || Sun | 12:00PM-12:00AM


    Thirsty Topher: If your parents want to know where you spend your time/money, or you want to have a nice impression on a first date, this is the place to take them. You can come here without your parents too (and we highly recommend doing that) but this bar is a subtle and classy gem. The interior is small and wood harvested from the Ocala forest (it smells so good and earthy inside). They’re visited by a rotating selection of food trucks, just like Will’s Pub, the Imperial, and BART. The menus are located in several places (you don’t have to crowd around the bar to figure out what you want, yay!), and the selection of brews is relatively diverse. They also host tasting events for special batches of beer, including the rare and seasonal brews of Cigar City.


Address: 1609 Alden Road, Orlando, FL, 32803. 
Phone: (407) 491-4342. 
Hours: M-TH | 4:00PM-12:00AM || F-Sat | 4:00PM-2:00AM || Sun | 2:00PM-12:00AM


    The Imperial: One would think that blending an antique store with a bar would be a messy move (drunks spill their drinks, let’s face it) but somehow that’s never a worry here. The furniture is all imported wooden pieces, all for sale, too. It smells like heaven (if you’re in here, and everywhere you look you can find another intricate detail, or hidden Buddha. The beer selection is moderately priced ($5+) and pulls from many locations around the world.


    Address: 1800 N. Orange Ave, Orlando, FL, 32804
. Phone: (407) 228-4992
. Hours: Sun-Th | 5:00PM-12:00AM || Fri-Sat | 5:00PM-1:00AM


 • BART: If you don’t like video games, this place might not be your cup of tea, but you don’t have to play games to enjoy the incredible selection of brews. If you happen to be a fan of pixels and puzzles, you wont be able to help falling in love with Bart’s rotating selection of arcade consoles. Small, dimly lit, and run by some of the nerdiest and bearded people. Bart contains an easy going atmosphere and an excellent selection of beers, ranging from ~$2-$11. On Tuesday’s Terrapin beers are $2 off (making them $3-$4) and there’s usually a food truck outside. Come for the beer, stay for the beards.


    Address: 1205 N. Mills Ave, Orlando, FL, 32803
. Phone: (407) 796-2522. 
Hours: Tue-Sun | 5:00PM-2:00AM 


    Milk District Strip (Sportstown, Milk Bar, Space Bar, Sandwich Bar): All of these bars have something different to them, and they’re all located on the same strip, so they tend to blend together after a couple of drinks. Sportstown: They have a slew of games (board games, card games and all the typical bar games) and they’re only 21+ Friday through Sunday, so if you’re trying to go out with that one underage kid, this is a place where they can at least amuse themselves. It’s also a great place to go if you just want to play pool, or other games with your friends. Warning: It can get very crowded on the weekends.


    Milk Bar: A really tight space, it’s easy to walk past. Inside the tight quarters create a sensation of closeness and intimacy, it almost feels like a hole in the wall diner. It’s usually pretty easy to talk to people here, too. They’ve got bottles and a few drafts that they rotate frequently. 
Space Bar: Feels like Milk Bar’s older and hotter sister. It’s slightly roomier than Milk Bar, but it’s still compact. Body Talk has been known to host here. There’s also comedy nights occasionally, and Tasty Tuesdays (you guessed it) every Tuesday. The coolest thing about them is that they’ve been known to allow people to bring in and play their records in exchange for a beer.




    Santiago’s Bodega: Located right next door to The Matador (if you forget about Flag World, like everyone else). Santiago’s Bodega is primarily a tapas, dinner, and Sunday brunch restaurant, but they contain a full liquor bar and the ability to concoct some of the most exquisite drinks. They also have a happy hour on workdays from 11 PM- 2AM where certain cocktails and tapas are discounted.


Address: 802 Virginia Dr, Orlando, FL, 32803. 
Phone: (407) 412-6979. 
Hours: 11:00AM-2:00AM


    Dandelion: Admittedly very expensive for their 100% vegan meals, Dandelion does host beautiful drum circles every full and new moon. The building is a restaurant created out of a house, so every room contains a comforting feel to it. Prices be damned, if you are able to, make it out for one of their drum circles. If you’re into the whole vibration aspect of existence, you won’t regret attending. Giddyup Mondays, all day their giddyup wraps are $5. Weekdays they have Dandy Hour from 5PM-7 where appetizers are $5.


Address: 618 N. Thorton Ave, Orlando, FL, 32803. 
Phone: (407) 362-1864
. Hours: M-Sat | 11:00AM-10:00PM || Sun | 11:00AM-5:00PM


    Yellow Dog Eats: Located around Gotha – which is kind of near Lake Buena Vista—this place is a little out of the way for most central Orlandoians, but it is a restaurant in a beautiful two-story house. Meals are on the pricey side (~$8~$12) but it’s a neat place just outside of Orlando. They host open mics there on occasion. It’s worth a visit just to explore the property and enjoy the reprieve from the city. If the trek is too far for you, the Courtesy has a weekly Sunday brunch catered by Yellow Dog.


    Address: 1236 Hempel Ave, Gotha, FL, 34734
. Phone: (407) 296-0609
. Hours: 11:00AM-9:00PM


    Tako Cheena: Open late on the weekends, and within walking distance of the bars on Mills, so they can be pretty life saving after a night of drinking. They serve a blend of Oriental and Latin flavors and techniques into something delicious, plus the burritos are the size of your entire stomach. They also have a rotating selection of art hanging up.


    Address: 932 N. Mills Ave, Orlando, FL, 32803
. Phone: (321) 236-7457. 
Hours: Closed Monday | Sun-Thur | 11:00AM-11:PM || Fri-Sat | 11:00AM-4:00AM




    Will’s Pub: If you’re over 18 and you’ve been in Orlando for more than two weeks, chances are you’ve heard about Wills Pub. This is where great shows go down, this is where your friends host successful events. If you are in any way interested in music, then you’ve been here, or planned on it anyway. Wills Pub is recently a full-liquor bar and they do not disappoint. Except, on some nights, there’s a cover.


    Address: 1042 N. Mills Ave, Orlando, FL, 32803
. Phone: (407) 748-8256. 
Hours: 4:00PM-2:00AM


    The Space: The Space is the best young person venue in Orlando. You can see some of the best punk shows and sweat through your shirt, experimental bands and eclectic art. There is no concrete definition for what The Space represents, only that “It is now. You are here.” Primarily donation based. If you don’t understand you need to check it out. 


    Address: 1206 E. Colonial Dr, Orlando, FL, 32803
. Phone: N/A. 
Hours: Depends on event


    Uncle Lou’s: If you can’t stand cigarettes, stay away, because as soon as you open the door, you’ve time traveled straight into the 1980’s New York. The bar is as dingy as you would expect, the pool table is hidden if there’s a show. The beers are pretty overpriced for being on Mills/50, but still, Uncle Lou’s LMGA is one of the key locations for broke touring bands, which means a lot of musical talent floats through those doors. But, seriously, if you can’t stand a cigarette, be prepared. 


    Address: 1015 N. Mills Ave, Orlando, FL, 32803
. Phone: (407) 898-0009
. Hours: 4:00PM-2:00AM


    Park Ave CD’s: Anyplace that sells physical manifestations of music is a worthwhile place to be, but Park Ave CD’s has this way of making one not feel so alienated about buying vinyl in the 21st century. They have a wide selection of CD’s and wax, and if they don’t have what you want in store, they can most certainly order it for you. In addition, they also sell concert tickets and host in store performances with some bands that float through the area. The in store performances are usually free, so if you’re as broke as us, you want to hop on their mailing list and keep up to date on who’s coming in.


    Address: 2916 Corrine Dr, Orlando, FL, 32803
. Phone: (407) 447-7275
. Hours: M-Sat | 10:00AM-10:00PM || Sun | 11:00AM-8:00PM




    Vespr: Located around Waterford lakes, this spacious coffee house is primarily occupied by a collegiate crowd (woooo, youth!) One can generally expect to see most of the customers with their faces buried in their laptops, using the place as an office. Craft coffee and fair trade as fuck. Relatively new addition to the coffee spectrum. It’s fresh and a welcome change of pace from the usual coffee house grind. Certainly worth a visit if you happen to be on the East side.


    Address: 626 N. Alafaya Trail, Suite 105, Orlando, FL, 32828
. Phone: (407) 476-3093
. Hours: 8:00AM-11:00PM


    Credo: Tucked away in College Park, Credo is a crisp and calming environment. It’s donation based, and non-profit. The baristas are all volunteers, so you know that their dedication to concocting coffee is deep and true. It’s the place to go if you only have a couple dollars, or if you want to splurge and know that the money is going to a worthwhile cause that *gasp* actually benefits the community.


    Address: 706 W. Smith Street, Orlando, FL, 32804
. Phone: (407) 371-2925


    Drunken Monkey: Right by Beefy King on Bumby is this quaint and art filled coffee shop. Good to sit in and accomplish work, but also has a drive through, which is totally sweet if you have a car. Stocked with local art on the walls and plenty of vegan options, this place is known for its weekly Friday comedy nights.


    Address: 444 N. Bumby Ave, Orlando, FL, 32803. Phone: (407) 893-4994. Hours: M-Thu | 7:00AM-10:00PM || Fri | 7:00AM-11PM || Sat | 8:00AM-11:00PM || Sun | 9:00AM-10:00PM


    Stardust: Anyone worth their salt in the expansive hipster world has been to Stardust at least once. Generally pretentious and expensive, their merit shows through with all the events that they host. From small literary events to the weekly Monday Market, and the community driven Grandma Party, Stardust is worth keeping on the radar.


    Address: 1842 E. Winter Park Road, Orlando, FL, 32803. Phone: (407) 623-3393. Hours: 8:00AM-12:00AM


    Body//Talk: Last but not least, (in fact, probably the best on this list) is Body Talk, which simply put is an indie dance party that changes venues. It’s created by locals with an emphasis on visual aesthetics and a growing sense of togetherness and breaking down of the barriers, labels, stigmas and categories that society lumps upon us. It’s an attempt at human connection in a large group. Sounds like some hippie manifesto, but it’s true! It’s basically the best house party you’ve ever been to. There’s usually face painting (or stickers) at the front. Sometimes there’s fortune telling. This event is constantly evolving, in the year or so it’s been around it’s gone from being at the Space and people’s houses to selling drinks and hosting nights at Back Booth. (~$5-$10 sometimes includes a drink.) –



    Kaleb is a senior in the Creative Writing & Journalism program at the University of Central Florida. Quast previously served as an editing intern and writer for the Orlando Weekly in 2014 before joining the East Orlando Post. Kaleb also serves as an editor for UCF’s literary magazine and worked as a staffer for the Florida Democratic Party in the 2014 election cycle. In his spare time, he makes black out astrology and is growing an avocado tree.