Bootleg Special - Cajun Food and Cocktails in Boston
The pre-concert meal is a tricky endeavor. You need to fill up enough to make sure you survive the show, and ideally aren’t tempted to eat trash on the way home, but not so much that you’re dragging. Quality is important alongside quantity - too much grease, and you’re in trouble. At least when you’re in your thirties.
A few weeks back we ventured into the city for a country concert - Midland was playing at Royale - and we wanted to try a new place before the show. We’ve driven by Bootleg Special a bunch of times on our escape route out of the city but hadn’t had the chance to check it out yet.
The first thing you notice when you walk in is how big Bootleg Special is. From the street it’s fairly unassuming; it’s marked by a small-ish sign on a brick building on the corner of Tremont Street, But when you go inside and head down the staircase, you’re greeted with high ceilings, an assortment of swanky chandeliers, and unique local art covering the walls in a warehouse style atmosphere.
In some ways, Bootleg Special almost feels too cool for Boston. The industrial vibe with bright lights and old school music videos on the big projector would work for an after-work drink, a date, or gorging on a a couple pounds of crawfish.
In retrospect, we probably didn’t do our first trip to Bootleg Special well. One of the stated specialties of Bootleg Special is the seafood boils - that would have to wait another night for us; we went straight down the appetizer list for the pre-concert meal.
If you know me and Cait, you know we’re bar-sitters. Our preference is always to post up at the corner of a bar rather than go through the whole process of sitting at a table, having a waiter, yada yada yada - it’s a whole thing. The only problem is that sometimes this prevents us from appropriately handling a menu.
As for the stuff we probably should have tried - the signature seafood boils are designed for 2-3 people; the “Bootleg Special” is lobster, shrimp, crawfish, mussels and more. There’s another boil centered around crab. You can also build boils a la carte.
As for the cocktails, there are some great signature cocktails on the list - the Pina-Coco Mojito, the “You Can’t Sip With Us,” and the “Blue Bulls,” are all part of the “Bootylicious” section of the menu. It’s a collection of fruity, beachy drinks that fit the neon vibes perfectly.
Admittedly, we went relatively simple on all fronts here. A good old fashioned is usually a measure for me of how well a restaurant does drinks. Bootleg Special’s old fashioned was on point - the right balance of sweetness without being overwhelming and annoying.
All of that said, we’ll definitely be heading back, likely before winter is over, to have some tropical cocktails and seafood, and hopefully feel like we’re not stuck in the never-ending hellscape that is Boston winter.
I’m a sucker for a pun, and an even bigger sucker for food soaked in soda. True to form, we started out with the Ribs on Coke - baby back ribs with a cherry coke glaze. The ribs were perfectly sticky and sweet, and being that they were the first course we crushed them before we could remember to take a picture.
We also tried the Gumbo Poutine, because how do you not try the Gumbo Poutine, and stuffed our faces with the Braised Pork Mac & Cheese. We kept it simple, but it paid off. We probably could have done a better job leaning into the actual vibe of the menu, but everything we tried was really good. Most importantly, we didn’t get weighed down before the concert.
We’re monsters, but even while ordering the menu items most likely to derail our night by making us feel like we weighed 10,000 pounds, we felt great. This is a huge plus for a comfort food place! I want all of the delicious flavor without the requisite regret. And in this respect, Bootleg Special delivered for us.
PHAIT’S RATINGS: Bootleg Special
Food: 7/10 - Probably not fair for us to give a rating here - we’ll need a second visit to try the signature seafood dishes. That said, the food we did have was really well done. We had ribs, mac and cheese smothered in pork, and gumbo poutine, and somehow didn’t feel gross afterward. This is a huge win in itself!
Ambiance: 8/10 - The vibe at Bootleg special is unique for Boston. It’s not a sports bar, and it’s not the typical New American cocktail bar.
Value: 7/10 - The appetizers are super reasonably priced. The signature boils are a bit on the pricier side, but they’re also unique. Again, another good reason for a repeat visit.
Repeatability: 9/10 - I could see Bootleg Special becoming a regular part of the rotation.
Je ne sais quoi: 8/10: Great drinks, good conversation, friendly and attentive staff, nice people sitting with us at the bar - all in all, it was a fun place to spend a Friday night, and we’ll definitely be back.
OVERALL RATING: 78%
All in all, Bootleg Special came through for us for the pre-concert spot. We’ll be back to Bootleg Special for the full rundown of everything it has to offer. In the meantime, give it a go and let us know if you do a better job going all in than we did!
