Another Boston Bar Crawl

In Boston it is sometimes difficult to distinguish which bar you have entered once inside. Standard sports décor and dingy pub accoutrements decorate more than one watering hole in the downtown area. Jillian’s is an exception to the sub-standard decorating patterns of other establishments. It is hard to confuse this bar/sports mega-plex with any other in Boston.

Jillian’s has positioned itself successfully as some sort of adult playground. On the first floor there is a standard bar and dance club. On the second and third floors are pool tables, dart boards, and some video games. The fourth floor houses a bowling alley and lounge. Occasionally a floor or two is rented out for private parties, but otherwise patrons are free to entertain themselves on the floor of their choosing.

Bowling is probably the most popular activity at Jillian’s followed by pool. If you want to participate in these games, it is wise to try to reserve a lane or table ahead-of-time. Typical wait-times for a bowling lane on a busy Friday night are from one to three hours!

Jillian’s is conveniently located next to Fenway Park on the famously historic Landsdowne Street. On more than one occasion, my friends and I have gone to there during a game to take in the scene. Jillian’s has a large (bigger than 10 feet across) TV screen on the fourth floor that is perfect for watching games. You might even feel like you’re at the game (minus the obstructed views and high ticket prices) since Jillian’s gets the echo of crowd noise from Fenway.

Food at Jillian’s isn’t the greatest, but is edible. Their menu includes standard pub foods like fries and chicken wings. Waitresses tend to not wait on people even if they’re seated at tables, so it might be best to place your food order at the bar. Prices on drinks and food are reasonable (between $10-$15), but not inexpensive. Mixed drinks are prepared with heavy-handed servings of alcohol.

Jillian’s is a Boston establishment that has been around for at least the past fifteen years, but still somehow feels fresh on the inside. Judging by the crowds that still frequent it, Jillian’s looks to be in business and capable of producing a good time for visitors for the foreseeable future

"The Greatest Bar" might not live up to its name, but it is a perfectly nice sports bar located conveniently within a block of the TD Banknorth Garden (current home to the Bruins and Celtics). Any bar with such a superlative name automatically draws my criticism, but my problems with The Greatest Bar pretty much stop at its moniker.

The Greatest Bar is an excellent sports bar. It’s proximity to the TD Banknorth Garden makes it the ideal pre-game meet-up place or post-game regroup place for when the Bruins or Celtics have home games. Local teams dominate the sports-bar décor, but fans from any team could feel comfortable here.

For those fans not lucky enough to get tickets to the game, the Greatest Bar has one of the biggest projection TVs that I have ever seen within a bar. This TV is visible from both the first and second levels and is surrounded with smaller TVs that are all playing different games. Typically the Bruins, Celtics, Red Sox, or Patriots are playing on the main TV; or whatever happens to be the most popular local draw. If you would like to see a particular game and are organizing a group event for its viewing, the Greatest Bar can accommodate such needs with advance notice.

After the games have ended for the evening, the Greatest Bar transforms itself into some sort of dance club complete with deejay and dancing crowd. I found this to be slightly annoying; having gone to the bar to see a sporting event, I like to stay within that frame- of-mind and didn’t enjoy the sudden transformation. The sports crowd tends to be of varied ages when the dance crowd tends to be of the earlier 20’s set making the contrast between the two groups of people obvious.

The food at the Greatest Bar is not the greatest, but will do in a hungry pinch. Typical pub food (nachos, burgers, pizza, fries, etc) dominate the menu. The items are reasonably priced (below $15), but come out tasting less inspired than the menu describes them as.

Drinks and service at the Greatest Bar are top notch. Tables are easy to come-by on low-key game days and the wait staff is quick to make sure that drinks and food are served quickly. The bar staff is great for days when you’re left standing to watch the game without a dedicated waitress.

Every neighborhood in Boston has it’s own bar where locals (and some brave tourists) can kick back and enjoy fairly-priced drinks and colorful conversation. The Sail Loft is such a watering hole for the North End neighborhood of Boston.

The North End is historically known for its many significant stops along the "Freedom Trail" and as Boston’s "Little Italy". However neither of these factors is represented at the Sail Loft; which is probably why it has escaped being turned into a tourist trap contrary to the fact that it is very favorably located on the waterfront of this neighborhood.

The local crowd that frequents the Sail Loft is mostly male in their early-30s. You won’t hear many people speaking with Italian accents in this bar, which is a characteristic of the crowd or workers at almost every other bar and restaurant in this part of town. I don’t know why this is, but the pretty much the only accent you’ll hear at the Sail Loft is a Bostonian one. The majority of the crowd grew up here or in nearby Boston suburbs.

The Sail Loft is a bare-bones dive bar. Beer and drinks are served in plastic cups and paid for with cash (they don’t take credit cards, but do have an ATM in the corner). The dark wooden interior makes patrons feel like they are in the underbelly of a ship instead of a waterfront bar. Stools and tables are plentiful, but if you sit down you should expect to be harassed by the locals. I found it was best to stand when at this bar so that when approached by a local who has had one-too-many who wants to know who the new face is in his bar, I could make a swift getaway.

My husband used to live in the North End and avoided the Sail Loft most evenings because of the likelihood that there would be some sort of fight there (the locals get rowdy by the end of the evenings). The cheap drinks and lack of dress code were usually not enough of a temptation to get him to stop by.

The Sail Loft is great for cheap drinks and very casual pub food. The clam chowder is said to be very good, though I have not tried it myself since I am vegetarian. The wait staff is very colorful and might (or might not) give you good service (it typically depends on whether they think they recognize you). If a non-pretentious scene is what you’re after and you think you won’t mind some attitude with your food and drink I would give the Sail Loft a try.

There is a group of "new-school" Irish bars in Boston that are very popular with the upper-20s to mid-30s crowd. These bars are owned by a common development group that transformed these once-dives into slick reinterpretations of the Boston Irish-bar experience. Lir is one of the bars owned by this group.
Lir is located at the end of Boylston Street, making it convenient to students of Northeastern and Boston Universities, several T stops on the Green Line and residents of the gentrified south end. It is also the usual location of the beginning of a Boylston Street bar crawl as perpetrated by my friends and I on several occasions. Most of the clientele at Lir tends to be in their mid to late 20’s. On my several occasions to visit this location, it seemed like males out-numbered females 2-to-1, but that might have just been because those were nights that big-games were playing on the bar’s TV screens.
Lir has several different levels, all with their own bar-tending areas. The large center-island bar on the first floor is where most patrons tend to gather. Large TV’s that surround the floor’s perimeter are typically showing the "game-du-jour". The dark wood interior and cozy seating nooks make this a nice place to gather for a casual night out.
Lir typically does not have a line to get in, but occasionally it can become overcrowded after 10pm and the bouncers must make would-be patrons wait outside. The menu at Lir is not really anything extraordinary beyond pub-grub, but it is reasonably priced and tends to be delivered in a timely manner once-ordered. Drinks are averagely priced for the reason with cocktails being about $10 and drafts being about $4.
I don’t really understand what defines an "Irish" bar in Boston other than the nationality of the ownership group and the fact that they keep Guinness on tap. You won’t run into many "Irish" patrons from the old country here, just typical Bostonians with Irish routes somewhere in their ancestries. I find this fact to be the most disappointing thing about the "new-school" Irish bars in Boston; those that come to this town looking for the pub experience will have a hard time finding it with the proliferation of establishments such as Lir marketing to the whims of the tourist crowd. Lir is a completely respectable place and makes for an enjoyable casual night out, but the marketing of it as an Irish pub has struck a pet peeve of mine that can not be ignored.

After numerous misadventures at the crowded Cask n’ Flagon (the bar across from Fenway park; the epitome of pre-game drinking), my friend and I decided that we would try something different. Right outside the Kenmore Square T stop and one block over from Yawkey Way; Eastern Standard Kitchen opened up about two years ago in a location that once housed a punk-rock club.
Eastern Standard Kitchen (or ESK as it is often abbreviated) is a far cry from your average sports watering-hole though its proximity to Fenway might indicate otherwise. Patrons are greeted by first a well-maintained outdoor seating area that is open during Boston’s seasonal months. An overhang shields this space from the frequent element changes that the area experiences and the patio is often packed with the "after-work" crowd lending to a more "buttoned-up" than "sports bar" ambiance.
Once inside ESK, it is hard not to be impressed with the awesome décor. Dark wood finishes and a marble-topped bar give this eatery a classic feel, but it is unlike other Boston joints that tend to feel like relics instead of classics. Modern touches like the plasma TV’s behind the bar, raised seating in the bar area, and crisply pressed linens on the dining tables keep this restaurant looking up-to-date.
On any given weekend (or before nearby sporting events), the bar at ESK is completely packed with patrons. A light menu is offered for those seated at the bar, but most people in this area are there to enjoy the atmosphere, cocktails, and perhaps a game if one is playing on the TVs. It is difficult to move from one end of the bar to the other due to the weekend crowds, but it is never difficult to get a bartenders attention to take your drink order. It also should be noted that I have never had to wait outside ESK to gain entrance into the bar area, no matter what the crowd was like inside (unlike other area bars).
Reservations are recommended for the evenings and weekends if you wish to dine at ESK or be guaranteed a table in the outdoor patio area. The menu here consists of mostly comfort food that is reminiscent of what my New England mom made us on cold days. The grilled cheese is excellent- made from 5 different cheeses and perfectly crusty bread. I know they have a variety of other salads and entrees on the menu to please almost everyone’s taste, but I have to be honest that I never have looked further than the grilled cheese- which I order upon every visit.
Prices at ESK are a bit high for what they offer ($12 for grilled cheese seems a bit steep), but the food is good and not completely out of the range that I would expect. Drinks are well-made and average-priced for the area.
Service at ESK in the dining area of ESK has been good and bad on occasions, but the bartenders here are always at the top of their game. If you’re looking for a little more than a sports bar to hang around before your trip to Fenway, I would recommend giving ESK a try.