Headless Horseman

Bar$$$$
Union Square, New York
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7.2/10
513
ratings
  • Peter C.
    "Great selection of beers on tap including Mother's and Founder's."(9 Tips)
    Evan C.
    "Try the fried pickles!"(8 Tips)
    Lauralee K.
    "Order the kale caesar salad and roasted turkey leg sandwich...yum."(2 Tips)
    Mia M.
    "Happy hour any drafts, wells and house wines $5 make you holla!"(12 Tips)
99 Tips and reviews
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  • fried pickles
  • good for groups
  • grilled cheese sandwiches
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  • Tariq A.
    Tariq AhmadApril 30
    Good place near Union Square to meet friends and colleagues. Also, good wings and friendly staff.
  • Liam K.
    Liam K.March 31
    Rowdy crowd, so so music
  • David S.
    David SteinMarch 31
    Great hearty hungover breakfast
  • YN
    YNMarch 9
    Beer was great and bartender was cheerful, but music was way too loud for me.
  • Andrew C.
    Andrew CMarch 4
    Great playlist and nice ambiance. Be prepared to pay midtown prices for bottles.
  • Carleen
    CarleenFebruary 8
    If you're trying to decide between a Manhattan and a Boulevardier, get the Boulevardier. Get the fried pickles and shishito peppers.
  • Rebecca M.
    Rebecca MazzaDecember 10, 2016
    Always crowded and noisy
  • Roxanne P.
    Roxanne ParetsSeptember 30, 2016
    The brunch was great. They constantly refilled mimosa, our friend ordered a Bloody Mary and had to wait awhile between drinks. They food was good and fries come with a delicious aioli
  • Nitzan B.
    Nitzan BJune 3, 2016
    Nice place, liked the music and big screen tv
  • Jesse L.
    Jesse LaneMay 19, 2016
    Happy hour until 8pm, with a pretty wide selection
  • Justin L.
    Justin LukMay 12, 2016
    Been here 10+ times
    The fried oysters and fried chicken sandwich are too legit. I like fried things.
  • Ralph W.
    Ralph WeberApril 24, 2016
    They change there theme every year. Always have something going on even for kids & family. Before Christmas its Frosty Fest. If from Morris County your looking at over an hour drive. Worth the time
  • William S.
    William StudartApril 4, 2016
    Many options of beer and great cocktails! The tavern-like appearance makes this an one and only experience!
  • Claudia F.
    Claudia FilthFebruary 10, 2016
    So dark, I could barely see my date.
  • James C.
    James CFebruary 5, 2016
    Nice bar and good location
  • Stephen K.
    Stephen KnowlesDecember 11, 2015
    Decor, ambience, beer, bartenders good
  • Calvin M.
    Calvin MultanenNovember 25, 2015
    Nice bar. Shares the same kitchen as Ichabod's. Good beer selection. Very dark inside though
  • Jackie M.
    Jackie MucilliNovember 19, 2015
    Not many tables or much standing room. But if you're sitting down it's perfect for pre-show drinks.
  • Evan C.
    Evan ChangAugust 27, 2015
    Been here 5+ times
    Great happy hour selection. Try the fried pickles!
  • Jesse G.
    Jesse GillJuly 31, 2015
    Great cozy atmosphere. Lively attitude but many corners to hide in
  • Kimmie O.
    Kimmie OhhJuly 3, 2015
    Great beer selection! Come for the happy hour!
  • Ritika S.
    Ritika SinghJune 25, 2015
    Super dark but cozy vibe, great apps and beers
  • Ally V.
    Ally VinsJune 5, 2015
    Kolsch is amazingly smooth! If you're into light beers.
  • Kiran B.
    Kiran BankuJune 5, 2015
    Try crispy chickpeas. U won't b disappointed.
  • Taylor G.
    Taylor GerardApril 11, 2015
    Overpriced liquor, place is full of yuppies - hit crocodile lounge instead.
  • Catie S.
    Catie SiasonMarch 30, 2015
    Mehhh! Happy hour drink choices are ok. There are other better places. Mehhh! We got a whole table for 6 people and spent almost $400 just to be disrespected by management. I will never go back here!
  • Gabriel H.
    Gabriel HayesMarch 29, 2015
    Nice selection of draft beers.
  • Shawn C.
    Shawn C.February 27, 2015
    Great place for after work drinks.
  • Therran O.
    Therran OliphantFebruary 18, 2015
    The chicken is good. The after work crowd is young and semi-hip bit its a cool dunheonesque environment. I think they need a better hook though. Maybe live music? Maybe a pool table? Something!
  • Florence H.
    Florence HFebruary 14, 2015
    It's a strange blend of dive bar and wanna be sleepy hollow-esque bar (with mixed success, in terms of decor), but the atmosphere is fun and young.
  • Rebecca P.
    Rebecca PlaineFebruary 2, 2015
    Don't waste your time. Dark, crowded and impossible to get to the bar.
  • Finley B.
    Finley Bomer-LawsonJanuary 15, 2015
    Feels like you're in the bowels of an old ship
  • Chet M.
    Chet ManciniDecember 7, 2014
    You probably shouldn't be going to a bar next to Union Square, but if you must, Headless has a great vibe and draft menu.
  • Ka K.
    Ka KuehnNovember 22, 2014
    Free coat check!!
  • Clyde Kelly J.
    Clyde Kelly J.October 15, 2014
    Been here 5+ times
    It may look spooky on the outside, but the dark interior, low ceilings, and aged decor will only make it look spookier. But they have drinks.
  • Craig A.
    Craig AustinOctober 8, 2014
    Cask aged Manhattan, fried pickles, grilled cheese sandwich
  • Meg F.
    Meg FarmerOctober 6, 2014
    Cozy atmosphere, great for catching up with friends in a central location.
  • Victoria L.
    Victoria LambinoSeptember 30, 2014
    Happy hour lasts from 4-8 at $5/beer. I had 6 beers on my tab & 2 bar plates at $7/$6. Did she already include her tip in my bill? If so, I want my $10 back & the correct amount charged to my card.
  • Jeremy J.
    Jeremy JacobowitzSeptember 16, 2014
    Really cool, chill spot with a great selection of beers!
  • In NYC
    In NYCAugust 24, 2014
    Good beer selection. Good bar food.
  • Kristin D.
    Kristin DaltonAugust 20, 2014
    Fries and cider on tap!
  • Nicky K.
    Nicky K.August 19, 2014
    Been here 5+ times
    Sit outside order food and beer and hope you aren't dealing with obnoxious people nearby this bar sometimes attracts.
  • Michael F.
    Michael FabianAugust 16, 2014
    The French fries are amazing
  • Juwan M.
    Juwan MimesAugust 13, 2014
    Midnight's Sky is almost as delightful as the masterpiece it's named after.
  • Neetin
    NeetinAugust 12, 2014
    Good happy hour but gets loud as the night goes on.
  • Amadou C.
    Amadou CrookesAugust 12, 2014
    Beer is good. Server charged us more for multiple items so check the bill before paying.
  • Michael S.
    This is a really great cool spot. Warning: it gets bro-y as the night goes on.
  • James J.
    James JAugust 7, 2014
    Been here 5+ times
    Cool vibe. Good drinks. Beyond that just a standard bar. But good!
  • Amanda R.
    Amanda RodriguezAugust 2, 2014
    Grilled cheese is amazing
  • Adolfo R.
    Adolfo Rivera JrJune 23, 2014
    Didn't dig the vibe at all. It was trying to be way too upscale for what it was. Beers were too pricey. Also..a dress code? Yeah..NEXT!
  • Nicky K.
    Nicky K.April 30, 2014
    Been here 5+ times
    The fries are THE BEST...oh yeah they have good beer.
  • Peggy E.
    Peggy English-VladykaApril 26, 2014
    Forbidden fruit cocktail was delicious !
  • Compass
    CompassApril 25, 2014
    Duck into the unassuming arched stone door on 15th Street for a top-notch beer selection and to get away from Union Square tourists.
  • Will A.
    Will ArnoneApril 23, 2014
    Unreal grilled cheese with bacon and a very sweet flavor. A killer with fried pickles of course.
  • Julia S.
    Julia SeongMarch 30, 2014
    Been here 5+ times
    The bar manager, Holden, is my favorite!
  • Chris R.
    Chris RiccaFebruary 23, 2014
    Fries are heavily (perhaps overly) seasoned but thin and very tasty.
  • BIG D.
    BIG D'AFebruary 22, 2014
    Been here 10+ times
    Grilled Cheese with bacon and Strawberry Jam OH MY LAAAAAWWWWDDD
  • Joanne F.
    Joanne FulmerFebruary 2, 2014
    Great place to stop for a drink or three. Bartender was friendly & attentive even when they got busy. Hope to return
  • atomly l.
    atomly leeJanuary 4, 2014
    used to be my favorite dive, now they think they fancy... at least they have McClure's pickles
  • Charnette S.
    Charnette SotoDecember 17, 2013
    The low level of lighting gave a certain ambiance that was cool. What was even cooler was that this place is next door to Ichabod's and is bordered by Irving Plaza. Lots of FDNY when I was there
  • Paul G.
    Paul GriffinNovember 17, 2013
    Saturday nights are jumpin' like 21 Jump Street!
  • Kelsey
    KelseyNovember 1, 2013
    The patron is not patron!
  • Taylor H.
    Taylor HartSeptember 15, 2013
    Should be re named roofie palace. Party meat heads and fat barbies live here. Great party music. Though.
  • Skye L.
    Skye LawlerSeptember 6, 2013
    Shipyard Pumpkin Ale is incredible!
  • Cici Y.
    Cici YoungAugust 31, 2013
    Very cool place for happy hour! Get a couple of rounds of drinks and have fried pickles as sidedish!
  • ErrolJay
    ErrolJayAugust 19, 2013
    Very cool bar. Great cocktails and the food is decent.
  • Josh H.
    Josh HickmanAugust 11, 2013
    Grilled cheese. . .nuff said.
  • Mia A.
    Mia AlicataAugust 6, 2013
    Fried pickles forever!
  • Henry L.
    Henry LiJuly 27, 2013
    Nice chill place for after work beers. Down those ice cold pints of IPA with fried pickles and red cabbage cole slaw...quite the experience!
  • Mia M.
    Mia MillerJuly 22, 2013
    Happy hour any drafts, wells and house wines $5 make you holla!
  • Mia M.
    Mia MillerJuly 22, 2013
    Have the henry weinhard
  • Lexi M.
    Lexi MadisonJuly 14, 2013
    This place is great. The back room is perfect for dancing and incredibly spacious. Highly recommend it.
  • Kory G.
    Kory GrowJune 30, 2013
    Great place to spot 'douchebaggicus Maximus' in its native environs!
  • alison c.
    alison cunninghamJune 13, 2013
    Hands down the best fried chicken I have ever had.
  • James O.
    James OgleMay 25, 2013
    Cool vibe and the grilled cheese with bacon and strawberry jam is unreal.
  • Snooty Waiter
    Snooty WaiterMay 7, 2013
    50% off on crafts during happy hour and definitely get the turkey leg sandwich.
  • Tierney C.
    Tierney CookeApril 17, 2013
    Feels like a time trip with the decor & features. Make sure to go on a night where there isn't a show at Irving Plaza, the walls literally shake.
  • karen m.
    karen mApril 16, 2013
    Amazing beer selection!
  • Laurie H.
    Laurie HorsmanApril 14, 2013
    The grilled cheese with bacon and strawberries is delightful. Totally unexpected, but the salt with sweet is an amazing combination.
  • Sarah
    SarahApril 5, 2013
    Happy Hour is miraculous $5 for all but two of their beers. Ends sharply at 8 so get your Allagash Triple White orders in on time.
  • Jane A.
    Jane AldridgeApril 4, 2013
    Great vibe. $5 drafts and well drinks until 8
  • Ben B.
    Ben BearnotMarch 29, 2013
    Too crowded and too loud -- even on weekdays at unexpected hours.
  • JO S.
    JO SimonMarch 10, 2013
    Oh pretzels
  • E.Rod
    E.RodFebruary 26, 2013
    Love love love!
  • Jane R.
    Jane RFebruary 23, 2013
    Amazing fries and pretzel!
  • Joe n.
    Joe nevinsFebruary 20, 2013
    Great new bar on Irving with $5 happy hour drink specials on a diverse beer selection. It's dimly lit, cool and refreshing. Get here before everyone finds out about it!
  • Simi
    SimiFebruary 16, 2013
    Nice winter spot, it feels like you're in a cabin drinking with your buddies.
  • Sam J.
    Sam JFebruary 16, 2013
    Been here 5+ times
    Go back in time and come to this bar before it got terrible.
  • katharine r.
    katharine ricciFebruary 11, 2013
    Been here 5+ times
    Solid burger. $5 beers during happy hour. Great spot.
  • Lauralee K.
    Lauralee KellyFebruary 4, 2013
    This is my new favorite place in the neighborhood. Order the kale caesar salad and roasted turkey leg sandwich...yum.
  • Cindy
    CindyJanuary 30, 2013
    Come here for the bar and get service at the bar. Waitstaff is horrendous for food--not worth the incompetence.
  • Uranium T.
    Uranium TVJanuary 28, 2013
    Fried pickles are the bees knees!
  • Allison M.
    Allison M.January 26, 2013
    Gas lamps flickering inside and out
  • Peter C.
    Peter CrysdaleJanuary 25, 2013
    Great new bar with a medieval vibe. Great selection of beers on tap including Mother's and Founder's. Highly recommend!
  • Kerri L.
    Kerri LoudisJanuary 20, 2013
    Great bartenders and beer selection. New go-to.
  • Caitlin S.
    Caitlin StrandbergJanuary 17, 2013
    Best bar around Union Sq. - low key, good music, nice range of beer on tap and under the radar. Goodbye, Lillie's et al.
  • Daniela G.
    Daniela GyslerJanuary 6, 2013
    Music's great, coat check's free, comfortably busy and perfectly dark and cabin-like. Sold!
  • Laura B.
    Laura BedrossianJanuary 5, 2013
    Might be my new favorite bar. Awesome tunes, friendly staff and the bar looks like the basement of a pirate ship.
  • Alex
    AlexDecember 18, 2012
    Pass the intelligence test - PUSH the front door open!
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