St. Matthew’s Tavern

Definitely what you would call a dive bar. If I hadn’t been going to see a friend play a show here, I probably would never have bothered to step a foot in the door. It’s grungy, poorly lit, and the wiring looks a bit like a fire hazard. I can see this place being good for an acoustic show, but the stone walls and hard floors make anything other than that sound terrible.
When I first got up to the bar to get a drink I was greeted with a «What the fuck do you want?» from the bartender, which is not really what I was expecting and it started the night off on a iffy footing for me. I will say they have a good selection on tap, but if you want food they’ve got a pretty limited bar menu and it’s cash only. On the upside, the beer was cheap and cold.
This is one of the few places that still allows smoking inside the building which was gross. Definitely one of the top reasons I would not come back. They’ve got a «beer garden» in the back, which I never made it out to, but that would probably be a better place to smoke than inside the bar itself. The tables are rickety and look like church pews. They have some board games, but they’re pretty beat up and I can imagine some of them don’t have all the pieces.
Overall, there are much better bars in that area and Orlando in general.

I posted a review and St. Matthew’s was sure to find a way to have it removed so that people could not see it claiming «privacy reasons» so I’ve removed the bartender’s name & reposted it, as all who is considering visiting this place has a right to it: Eek! Methinks not is RIGHT! This is literally my first review I’ve ever left for anything, and only because my first and last experience at St. Matthew’s was so unbelievably horrible, it’s actually to the point of being offensive. I ensure that I tell each person I know to never visit. Although I can’t speak for the entire establishment as a whole the female bartender that we had was awful, the fact that they would allow someone so incredibly rude to work for them, speaks volumes; I don’t care how seasoned of a bartender someone may be. there is no excuse for employing a condescending nightmare. My friends and I were in the Winter Park area on October 30^th looking for a fun spot to visit for the night. It being the night before Halloween, we were dressed in our costumes. St. Matthew’s Tavern was decorated festively, had live music & looked inviting. As we enter, the bar was decorated for Halloween, all of the patrons were dressed in costumes and we went to the bar to order a drink. The visitors at the bar were all super friendly; however, I cannot say the same about the two bartenders that were working that night. Bear in mind, the bar was not busy and we ended up standing there for a good 20 minutes without recognition whatsoever… which is to be expected if we were visiting a busy downtown Orlando bar on a weekend… but this bar, on that night was NOT busy enough to warrant the experience that we had. My boyfriend had gotten the attention from the male bartender on several occasions only to be ignored with an eyeroll. It got to the point that it was so obvious we were deliberately being ignored, that the man sitting next to us stated «this is ridiculous; let me call them over here.» My boyfriend was dressed as bane, with his shirt off, flak jacket on & bane mask. He had attempted to order a drink from her several times and although his mask made his voice sound different, he was understandable. Despite the fact that everyone in the bar was dressed in costume, the bartender FINALLY comes up to us and yells in front of everyone «THE MORE YOU DO THAT THE LESS YOULL GET SERVED» and I’m not exaggerating when I use the word YELL, because that is exactly what she did. We were all shocked, including the visitors to both sides of us. My mind was completely blown at that point, because to this day I have literally no idea what she was even referring too. Was it because he didn’t take his mask off? Was it because we didn’t fit in to the «punk» vibe of the bar (which sounds so ridiculous, but I can’t come up with anything else). We patiently waited for 20 minutes just to be acknowledged .and then were screamed at in front of everyone. We were not the least bit loud or rowdy and the people who witnessed this woman’s meltdown were just as shocked as we were. Maybe she was drunk, as I’ve read from some of the reviews… the bartenders here are known to drink on the job. We’ve gone over every possible reason or misunderstanding that could have taken place that may have prompted her outburst, but can’t come up with anything other than we didn’t fit in. It was just the strangest customer service experience I’ve ever encountered. I’ve worked in the bar scene myself, and can relate to wanting to go off on rude or obnoxious customers (but would know better than to actually ever do this for the sake of remaining professional), but there wasn’t even any of that; we did NOTHING wrong. I am still dumbfounded by her actions & outright pissed off at the embarrassing scene that she had made, as I’m sure you can tell from the length of this review. She reminds me of one of those bartenders who have been doing it for years, is on a never-​ending power trip and thinks that people will tolerate verbal abuse just to get a drink from her. To treat costumers this way (especially when undeserving) is NEVER acceptable on any level. From what I’ve seen this is a bar that takes pride in being unique and accepting all types of people, and ironically this was the first time I’ve felt discriminated against… at a BAR on Halloween of all places. According to these reviews, St. Matthew’s is a gay bar/​gay friendly. which we didn’t know at the time but wouldn’t have made a difference to us one way or the other… but they took one look at us and decided they weren’t serving us… I’m gay friendly, hes gay friendly, maybe this place just isn’t «straight friendly» …Don’t know. couldn’t tell ya .but Pretty pathetic whatever the reason. If you can’t handle working in a bar atmosphere on a half-​dead Friday night in Winter Park, why work in it at all?!

I intend to meet my future husband or wife here.

Thank goodness it’s secretly a gay bar. Come here for humble conversations and an unforgettable ambiance.

i like the outside seating. always pour good drinks.

I go here all the time. Super chill place, always poppin’. Good priced drinks, live music, board games, chill people. I only take away a star because of the smoking. I’m not a cigarette person– so I don’t really like that it has smoking inside.

this bar was great. the staff was friendly and helpful. it is a little bit of a dive but there has been a ton of work put into the place and they continue to make reinvention s. they have border games and live entertainment almost everynight. they have a food truck that parks out front that is pretty nice when drinking. also there are a few new restaurants about to open that look promissing.

In the world of rising craft cocktail bars, St. Matt’s holds strong to the classic dive bar stereotypes– dangerously cheap liquor specials, dim lighting and a plume of smoke that will stay with you for days. I always feel as if I’ve gone underground when I come in here, although they have recently added windows which bring in some light. It is a huge space with lots of bars, tables and booths around hidden corners. They host lots of local bands and the occasional trivia night. Be warned– going to the bathroom here is always an adventure :) they’ve been «gender neutral’ before it was the cool thing to do. Bartenders here are super friendly, they usually have about 6 decent beers on tap and there are lots of board games laying about. On my last trip we busted out jenga and found out someone took the liberty of adding dares to each block! St. Matt’s is the kind of place that has no problem if you want to demonstrate making passionate love to a bar stool or steal a sip of everyone’s drink at the bar.

I was really excited to check this place out and I have to say I was not disappointed! This place really has a lot for you to do and to spend the night here having a real good time. Between the bar, the jukebox/​photo booth, board games, app games, video games, dance floor, crane game, and what I believe was a DJ host, you have it all here. Must I also mention: Cards Against Humanity.
The feel of this place is really cool, it’s like a nice trendy dive. The atmosphere is really chill, which I liked. They’re gay friendly, and I know so because of their equality stickers on the wall, so that was also a really nice plus.
The drinks are good and inexpensive. They have a nice collection of drinks, so you can go ahead and try something new.
The bartenders are sweet and conversant. Whenever you go, have a conversation with the bartenders, they’re really nice and enjoy a really nice conversation!
Can’t wait to come back to this place.

No matter how you put it, St Matthews isn’t a good bar. From the cheesy cuts coming from the jukebox, to the rude staff, to the horrible beer selection, to the worst part of it all, having to inhale a thousand cigarettes a breath as, YES, SMOKING IS PERMITTED INDOOR where it makes it absolutely unenjoyable having to spend a single second without the cloud of nicotine instantly burning your eyes, it is totally disgusting and you will leave with your hair and clothes smelling like an ashtray. The staff seems to dread having to be there as it felt as though serving you a beer was the most painstakingly thing in the world. The crowd varies but it’s mostly people that haven’t fully come to terms with the age they currently are.

Very friendly staff, great drink specials nightly, nice atmosphere. There’s no more pool table though :(

Not 100% sure why I haven’t written a review for Matt’s since for a bit there I was here weekly. I haven’t been as much any more because my job changed and no more weeknight, late night, hangout experiences.
Matt’s has evolved significantly over the last year — starting off with more of a steampunk vibe as created by Matt himself, it got a bit more divey as time went on, and with the recent addition of the Joe’s New York bar décor, windows, and artwork — it’s taken on a new, quite fun feeling.
I took a friend last night and she said it felt like someone’s huge house party. I hadn’t ever thought of it like that before but it’s a perfect description of Matt’s. The patrons are an eclectic mix of 70 year old burned out druggies, hipsters, heavy metal band followers, gay men and lesbians, and some service industry folk. It’s pretty fabulous because you can fit in no matter your style.
The drinks are good — they have a pretty decent beer selection and I’ve had some damn good sangria here. The bartenders sometimes experiment with drinks but generally it’s pretty basic. This isn’t a craft drink bar and standards are going to be the way to go.
Speaking of the bartenders, they are all pretty awesome. If you’re lucky to go on a slow night and get into a convo with them, you’ll meet some great people. They also run the gamut of ‘types’ — there’s nothing cookie cutter about Matt’s.
If anything, Matt’s might be too eclectic. Sometimes I think it’s still trying to find an identity. But aren’t we all?!

Sundays are awesome. Karaōke is awesome. Di is awesome. Drinks are awesome. Love that the is only one bathroom. Love the games. Love the outside. So hipster and totally worth it. Feel like I’m at home whenever I’m here. Always welcoming and inviting even if it seems like a dive.

This place is a dive. Some people really love a good dive bar. I don’t love it but can appreciate it’s appeal. The outside of the building makes it look even more like a pit. There isn’t really a sign so describe it to your friends as that weird new bar on Mills with the spray paint and icicle lights. They’ll know what you mean.
I hate indoor smoking so I was bummed to see it lived on in this bar that fells almost like your grandpas tricked out basement. It is dark and a hodgepodge of church pews, virgin mary candles, tvs, with an outdoor area I wouldn’t call a garden. The whole thing smells like an ashtray.
Now and then there are acoustic nights here which are enjoyable. Everyone listens, chats, chain smokes, and drinks the night away.
Service was alright. Drinks were nothing special. But hey – maybe you just want a cheap beer you can drink in a church pew while you smoke.

My second favorite bar in Orlando! Always a good time.

This is a gay bar! Just to throw that out there. Draft beer was not cold, cool but not cold. Different crowd!

Probably my favorite bar in Orlando. Board games, live music on occasion, patio, outdoor seating, cheap beers. I think this is the only bar I have stayed at past 2am in the last 3 years.
Let me elaborate on their patio. It is perfect, and getting better with time. I really love the lighting back there.
They have Cards Against Humanity. VERY good choice.

Formally Paradise, St. Matthews had a change of décor but the same old vibe. This is a gay bar, now a Holy gay bar. Bartenders are great– very attentive and polite. This is a neighborhood gay bar, but a great casual place to hang. I’m a beer person and was impressed they had an IPA and Porter on draft… casual not a scene type bar, fun.