Saturday, December 27, 2014

The ONLY Comprehensive Guide to Drinking in Downtown Crossing Boston

2015 Guide to Drinking Your Way Through Downtown Crossing Boston

This time of year is my personal favorite. Christmas season is finished, the fall is a distant memory and what have we to look forward to? The answer is, if you live in New England, not much really. It’s cold, wet and miserable. If you are independently wealthy I guess you can ski every day but most of us have jobs and responsibilities. I am lucky if I get to ski once a year these days and most people don't ski. Most people do not snowboard, snowshoe, or even build snowmen. Sorry I even brought it up. This time of year is a time for being indoors with friends or people who will be your friends for at least a few hours. This is a time of year I like to call:


We work and we play. That is the winter lifestyle. Let’s be honest. Even on the occasion when we are having a great time outside during the winter, it IS rare. Bars and restaurants that have bars are pretty much everywhere around here. Downtown Crossing may still have its issues but we have alcohol every few feet and as far as I’m concerned, that more than makes up for a few panhandlers and empty storefronts.

Below you will find the Ultimate Bar Crawl. Let me take that a step further. It is the Ultimate Bar Crawl if you are a superhuman mutant with three livers. It is too much for one bar crawl. Trust me I have tried it. I am about as close to a superhuman as you are going to meet and I couldn’t do it. You have to pace yourself. The thing is, some of these places have an amazing selection of beers and mixed drinks. There are some very talented people in this neighborhood mixing some pretty creative libations. I have to assume if you are reading this then you are not a 22 year old college child who feels every night out is a race to the finish line. Wanting to chug as many drinks as you can to see how quickly you can make a fool of yourself is stupid and if that is you please click away. I hate you anyway and you would not like me either. So as MJ would say, Beat it.
People I Hate

This guide is for the person who works for a living. You may not get out more than a few nights a month and DTX is a convenient place to grab a few and you may not be familiar or you may be new here. Either way, it’s a perfect guide for the adult who needs to blow off steam once in a while and appreciates the diverse selection of drinks, ambiance and munchies in our Hub of the Imbibers Universe of Boston.

People I Hate Slightly Less

I did not include every single place that has a bar in it. There are places I just do not go or places I just do not feel are bar oriented. There are plenty of nice restaurants that have drinks, Oceanaire and Avenue One to name a few. There are a few places I am not familiar enough with to point you to. For Example 49 Social and the new Bar at the Ames Hotel I have never walked into. If you have, feel free to report back. This is a list of CappyinBoston stamp of approval places where I personally have enjoyed myself with many other people. If a place truly sucks, I would never tell you to go there. You have my permission to agree or disagree in the comments section below. I love to know that I am being heard out there somewhere in the digital galaxy. If you feel I left any place out, please tell me. Also, these are what I consider to be Downtown Crossing bars. Although I love Shojo and Biddy Early’s, I don’t consider them to be in DTX. We can also debate the boundaries of this neighborhood as well if you like. I’m easy.

I will start at the border of Chinatown and work my way North. Once I get to State Street I will make a U-turn and head back.  

  1. The Avery Bar

10 Avery Street, Boston, MA 02111
Phone:(617) 574-7176

This little hidden diamond is located in the Ritz Carlton on Avery Street. You could call it their lobby bar. I wouldn’t though because that is selling it short. It is a beautiful little oasis right in the heart of Boston. I know you hear the Ritz and think, “Hoity Toity Expensive, No Way, I am not going in there and being made to feel as if I should be a Sheik or a movie star or I am just not good enough….”

Well stop thinking that. You sound ridiculous. This IS upscale but not overly expensive. The bartenders are very accessible and friendly. The free nut selection and munchies are delish and the drinks are professionally made. There are comfy couches and a nice fireplace. It kind of reminds me of what a ski lodge would look like if Trump bought Killington.

I enjoyed a Daquiri, Negroni and various Micro Brews at different times. Great first or last stop for drinks or to meet a date you’d like to impress before dinner.

2. Legal Crossing

558 Washington Street, Boston, MA 02111
Phone:(617) 692-8888

One of the newer places in the neighborhood, Legal Crossing is Roger Berkowitz’ take on DTX Legal Seafood style. In other words, it is a spin off concept based on Legal Seafoods but, completely different. Whatever. It has a great bar. 

One thing you should know. If you drive in for your night out and you park at the Hyatt next door you can get a validation worth a few dollars off from Legal Crossing and that will cover your first drink. Also, if you go late night it is 50% off everything from the raw bar. We usually go there after working all day on a Saturday. We get the validation then get oysters & Cherrystones and this awesome Bang Bang cauliflower app as well. 

My go-to drinks are a classic Martini or a tall beer. Once I was there and a certain over the hill news man chewed our ear off for about an hour so be on the lookout and avert your eyes. Great Ambiance.

3. The Back Deck

2 West Street, Boston, MA 02111
Phone:(617) 670-0320

The Back Deck has been around for a couple of years and is more of a restaurant than a bar with a theater crowd taking up all the tables when the Opera House has a good play there, but its proximity to the other bars makes it a good stop. If you get in the mood for some good meat dishes or their take on S’mores which is pretty yummy then it is a nice diversion.They have a small bar at the front which is a cool place to hang if you can get a seat. They also have a nice drink menu and a respectable beer selection.

4. Papagayo

15 West Street, Boston, MA 02111
Phone:(617) 423-3600

This used to be Max and Dylan's and is the same owners but now it has a Mexican flair. There are around three other Papagayo’s around. Personally I only had drinks here but when I ate at the one in Ft. Point the food was good. The somewhat little downstairs bar has a great Tequila selection so do a few shots then get the guacamole. They have another small bar upstairs too. All entrees are under $20.

5. Fajita’s & Rita’s

25 West Street, Boston, MA 02111
Phone:(617) 426-1222

This place has been here for a long time. You go here for nachos and fajitas. They have a nice bar in the back where you can grab some big Margaritas and they also have a decent tequila selection. I rarely go here now that I am a grownup (lots of college kids) but sitting at the bar, chomping on tortilla chips and salsa while drinking frozen mango ritas if the Sox are on isn’t really the worst thing that could happen.

Fajita's and Rita's

6. Stoddard’s Fine Food and Ale

48 Temple Place, Boston, MA 02111
Phone:(617) 426-0048

I used to go here for all my cutlery needs back in the day but now I go here for all my sudsy, hopsy type needs. 

They have a truly excellent beer selection. They have a football field sized row of beers on tap as well as some cask conditioned ales. The bartenders are “mixologist” types who can pour some very unique and interesting mixed drinks too. Check out the drink menu. Jamie Walsh, my buddy and yours is the bar manager and he knows beer, booze and a story or two. 

The food is also great. I usually grab a charcuterie plate and let Jamie choose the beers of which he can tell you plenty. Obviously I really like this place despite the corsets on the wall. There is also a nice space downstairs too. That’s the bar I would hang at if given the choice.


7. jm Curley

21 Temple Place, Boston, MA 02111
Phone - (617) 338-5333

Located a few feet up Temple Place from Stoddards this is another place where “real” bartenders dwell. They make some of the best cocktails in the city. The food is off the hook good. Millions have raved about the hamburger there. I love to munch on the burger and some fried pickles.

The drink menu is amazing. I usually get something with Bourbon and put myself in the hands of the bartenders and let them run with it. Now in the back is an upscale steakhouse called Bogie’s to go for a nice piece of beef. It is not cheap but it is so worth it. I love this bar. You need to go right after work or later in the evening because hipsters have recently discovered the place and take all the good seats. (eff them) But I still love Curley’s. 

PS. If anyone there is reading this please bring back the bacon peanut brittle.

Read the Law and Order Rules of the Bar:

8. The Merchant

60 Franklin Street, Boston, MA 02110
Phone:(617) 482-6060

Another of the newer entries in the DTX bar scene is the Merchant. Also an upscale place, it boasts a pretty good sized bar with plenty to choose from. They have a decent beer selection and a strong cocktail menu. The food is delicious, the ambiance is great and it should be part of your after work/weekend bar rotation for sure. The beet salad is a must try believe it or not. They also have a nice raw bar and things like pork belly, scallops and a killer burger on the menu. I would definitely plan on staying for a bite.

The Merchant

9. Sidebar

14 Bromfield Street, Boston, MA 02108
Phone:(617) 357-1899

Not too long ago I used to have a pretty rocking Karaoke night there called Cappyoke (what else). It was good times. Now it is under new ownership and I’ve heard good things. They still have the $7 pitchers and a good bar style menu. This place is cheap. You could have 5 drinks here for the price of 2 in some of the other places mentioned. Stick with pitchers and generics. Generics = Rum & Coke, Vodka & Tonic…

(I miss you Sidebar)

Sidebar's Web Site

10. Silvertone Bar & Grill


69 Bromfield Street, Boston, MA 02108
Phone:(617) 338-7887

My true go-to bar in DTX.

I have loved this place for many years. Giant delicious Manhattans, The Rochester wings are so so good, The steak tips are my favorites in the area, the Mac n Cheese is, as a woman I know says, TO DIE FOR… One of my friends says they put the Come in Comfort Food. I told him that was gross but you get what he means hopefully.

They have a great little bar where you may have to fight for a seat (maybe the back one is open too) but it really is worth it. Josh Childs may not be at the bar any more but the staff is good. Real good.  The selection of amazing drinks never ends. Cheap beer too. Good beer too. I always have a good meal there. Very reasonably priced as well.

Oh and if you like meatloaf and garlic mashed this is the place to get it.


11. Beantown Pub

100 Tremont Street, Boston, MA 02108
Phone:(617) 426-0111

This is the place to chug/sip a Sam Adams while staring across the street at 
Sam Adams actual grave.

I don’t care what anyone says it IS a tourist trap. They can’t help it. It is on the Freedom Trail and during the summer it is always packed. You know lots of kids also drink there because there is always a doorman proofing everyone. Grandmas, Santa Claus, George Burns mummified remains. 

That’s ok though. It is actually a decent place. I love all the sandwiches and the Barrister burger is my fav. The place has a bunch of Irish people working there and they are all consummate pro’s. It has nice long bar to grab a seat at even if it is crowded and also they have POOL. That is correct. There are pool tables in the back. This has become a rare thing since the Rack by F-hall became the Hard Rock (gag). Now that’s a tourist trap. 

The Beantown is a cool after work bar. Also very affordable.

The Beantown Pub's Web Site

12. The Barracuda Tavern

Don't sit in the boat

15 Bosworth Street, Boston, MA 02108
Phone:(617) 482-0301

Right around the corner from the Beantown is another great bar.

The Barracuda is the unsung hero of the bar scene I think. They have great prices, good food and are almost never over crowded. They do dollar oysters all the time. They have an excellent beer selection.

I love the fish tacos and conch fritters. Luka Stepinov who owns the place is also a great guy. Make sure to find the Barracuda. It should be  a place where you grab lunch (specials like every day) and grab drinks A LOT. 

Barracuda's Site/Menu

Marliave is next door too if you feel like doing the booze loop. I didn't include Marliave in the list frankly because I hardly ever go there. Nothing against them. It's just a fact Jack.


Sidebar - Silvertone- Beanton Pub- Barracuda- Marliave.

You could also include Highball Lounge in that loop too. It is right there.

13. Highball Lounge

Ladies looking psyched to Imbibe

90 Tremont Street, Boston, MA 02108
Phone:(617) 772-0202

Located in the Hotel Nine Zero on Tremont Street is another newbie to the Crossing imbibing scene.

The Highball is upstairs and is another mixology type bar. It is funky and fun. They have board games although I really would love to meet the person who goes out to play Sorry or Go Fish. Not I my friends, and certainly not anyone who can work out a way to have a conversation.

BUT having said that it is a pretty cool place to drink. They have an upscale cocktail menu and it is also fun. Did I already say that? They put floaty things in your drinks sometimes and plenty of alcohol too which excuses the floaty things. (rubber ducky) Tater Tot nachos are good too.

A Vintage Cocktail Bar

14. The Hub Pub

18 Province Street, Boston, MA 02108
Phone:(617) 227-8952

The Hub Pub is a real bar. Not that the others aren’t as well but this place has a few road miles on it. By the way, I like road miles. When you walk in the semi-circle bar is right in front of you and don’t be surprised if everyone stops what they are doing to look at you. It is fine. Go in and sit down.

I have been coming in here for many years. The hooch is cheap. The food is good. How about a lobster roll that I would put up against anyone else's in Boston for ten dollars and comes with chips and slaw? Right. Exactly. 

No pretentious crap here. It is a good solid Boston bar. You can eat upstairs and see the giant TV if the game is on. You can hang at the bar and start up convos with the people who work for a living. Very affordable too.

They have a web site too surprsingly

15. Scholars

25 School Street, Boston, MA 02108
Phone:(617) 248-0025

I was just told that the actual name is “Scholars American Bistro and Cocktail Bar”. Guys. Come on now. You forgot to add , “and we also have a men’s and women’s restroom if you need to pee while you are here”

Scholars is a restaurant by day and a nightclub by….er night. It has changed a lot since it first opened. The menu is totally different and the drink menu constantly changes. My feelings about Scholars changes depending when I go. Right after work I love it (around 7). If you go on a Saturday night late, it is young. It is too young for me, but I was there on a Friday night once and had a table which made for a great evening. It is overall a great place. It is also big and has pool tables too. I don’t get there as much as I should. 
It can also be classified as upscale.

Scholars Boston Bistro Dot Com

16. The Elephant & Castle

Ello Mate! (not really)

161 Devonshire Street, Boston, MA 02110
Phone:(617) 350-9977

It is a chain. They are in Canada and all over the US. This can also be classified as a hotel bar because it is wedged up next to the Club Quarters hotel over on Devonshire Street. 

It is an English Pub. Well, It is an English-ish Pub anyway. They have no locations in England. The Shepard’s pie is decent as well as the Bangers and Mash. The burger was pretty damn good too actually. They have beer and a nice bar. The game is on there and it isn’t too expensive. It isn’t cheap either.

It is centrally located so if you are walking from DTX towards Faneuil Hall and want a beer it is right on the way.

E&C web site

17. JJ Foley’s Bar & Grill

21 Kingston Street, Boston, MA 02111
Phone:(617) 695-2529

I have spent many a night over at the DTX location of Foley’s. I classify this as an Irish Pub. My first clue is the great big Guinness mural outside. They also pour a mean pint of the stuff.

It is a great bar and has a ton of history. The Foley’s have been running a bar since 1909 or something. They know what they are doing. They also have really surprisingly good food. It is also affordable as hell.

JJ Foley's

18. Kingston Station

Next Stop Kingston Station!

25 Kingston Street, Boston, MA 02111
(617) 482-6282

Don’t get confused. You aren’t in a train station. Yes I know. You thought you were.

 This upscale eatery has a nice bar too which is where you should head immediately. Order a Vesper Martini and catch a buzz. The place grows on you. It is a bit pricey.

 If you haven’t figured it out yet, when I use the word “upscale” I am not referring to the decor as much as I am saying they have the $8 beer and the over $10 cocktail. There is no judgement here at all. I pay that and more quite frequently, but you should be aware when you may need the Visa or to hit up a bank machine.

 Like I was saying - They make a kick-ass burger there and also validate at the Hyatt’s garage. Last time I was there I had a Moscow Mule which was done up right. The proximity to the other two bars makes it nice little mini bar crawl too. JJ Foley’s and the Good Life are steps away. (so is Chinatown)

Kingston Station's Site (click here) 

19. The Good Life

28 Kingston Street, Boston, MA 02111
(617) 451-2622

The Good Life was once a rat pack type hangout with soup bowl sized cocktails where darkness and red leather was the name of the game. NOW it is not.

Now, it is a pretty convincing club scene. They have hip hop nights and live DJ’s and …..

lots of other things I have no interest in but the upstairs bar after work is cool. The restaurant is also cool. I don’t do clubbing and hip hop nights but I’m sure they are cool too. They have a serious drink program. Try the Kitchen Sink and try to remember how you are getting home. They had Dale’s Pale Ale which is my go to boat beer in the can so they earned a place in my heart for that too. Again, they are right next to two other bars which makes for a variety of options.

20. Shojo Boston

9A Tyler Street, Boston MA 02111

I know I said I wasn’t going to include Shojo in this list because technically it is in Chinatown but as I was visualizing how close Shojo is to Good Life I just had to include it.

You should actually thank me. It is one of my favorites and would be yours as well if you had been there. First of all they have a great chef in Mr. Mark O’Leary (from jm Curley) Try the Tiger Style Ribs, the Tamarind Glazed Pork Belly, or the salt and Pepper Calamari. It is all delicious!

But not only is the food off the hook they also have a bar wizard named Markus Yao who truly knows his stuff. Try the Fulong Blood and Sand which is Kavalan Whiskey, Cherry Herring, Orange,& Sweet Vermouth or the Yakuza Old Fashioned.


There are a few places I did not include merely because I haven’t been there and have no knowledge of but just for the sake of being comprehensive I will mention them.

Mojito’s - 48 Winter Street, Boston, MA 02108

Phone:(617) 817-2533

49 Social - 49 Temple Place, Boston, MA 02111

Phone:(617) 338-9600

Salvatore’s - 545 Washington Street, Boston, MA 02111

Phone:(617) 542-5555

and more.......

Now before I leave you I will impart you with what I consider to be the perfect Downtown Crossing bar crawl.

Avery Bar - Stoddard’s - JM Curley - Silvertone - Barracuda - Highball Lounge - JJ Foley’s - Good Life

If you are still standing by the time you get to the Good Life I commend you and hope you have no intention of driving. Remember to always have a DD and to drink responsibly. Once you reach the point where everyone is attractive and interesting then it is probably time to switch to water and eat copious amounts of Chinese food.   (my guide to Chinatown is coming soon)

 Be careful out there. 

Sincerely Yours,



  1. I live in Boston and it’s really a cool place. All these Boston restaurants and bars you have listed here are awesome. I have been to almost all of them. The Barracuda Tavern is my favorite one. They serve really yummy food. I usually go there to grab excellent beer over there.

    1. ‘Ello Mate! What a great guide & a very ‘andy read. We are 3 English Couples in our maturing years (50 something’s’) and will touch-down in Boston for the very first time, this coming June. We are staying for a couple of nights at Club Quarters Hotel (Elephant & Castle), so your guide covers the Bars within staggering distance to our hotel.
      The gents of our group like to partake in a few Craft Beers of the local variety, and the ‘Ladies’ preferring a fruit based drink, tasting the local Wine.
      We have crossed-off some from your list as we don’t want to look like “the Oldest Swingers in Town” (in every sense of the word), and we ain’t really into the Cocktails. So, our selection from your list includes, Stoddard’s, Silvertone, JM Curley, The Hub Pub & The Merchant looks good too, for some grub.
      Our two nights are on a Monday & Tuesday, before we head off for a 3 week road trip around New England. Any further tips you may have around our choices or tastes, would be greatly appreciated. Cheers & bottoms up!