Guest Feature: Top South End Spots to Beat the Tourist Crowd

This week, we are lucky to feature Kali Hawlk from Going Beyond Wealth. Her blog is Boston-based and extremely well-written. Head there to check out strategies for mindful living through intentional spending all kinds of interesting advice and stories. We asked Kali to explore some "off the beaten path" finds in a neighborhood she loves, the South End.
Boston south end view

South End Boston Food Tour

The first thing I do when traveling to a new place is some extensive Googling to find the best local blogs who profile the best restaurants their city has to offer — that the tourists don’t know about.

My name is Kali Hawlk, I run a personal finance lifestyle blog called Going Beyond Wealth, and I may or may not have some hipster tendencies that lead me to want to run away from crowds and into the little-known cafes and secret spots in every town I visit.

And since I rely so heavily on local bloggers to help me figure out how to get off the beaten path when it comes to great food, I figured I should start paying it forward and do my own quick recap of some of my favorite stops in my own neighborhood: Boston’s South End.

There is no shortage of fantastic places to grab a bite in the South End — and no shortage of food tours and Yelp reviews that will lead you to the same spots every time: The Buttery. Formaggio.

Don’t get me wrong: these spots are well-known and highly recommended for great reasons. The Buttery is the only place I know in New England that has legit biscuits — and I’m from Atlanta; I should know. You could entertain yourself for days just gazing upon the cheese case at Formaggio.

(It doesn’t hurt that both Formaggio and The Buttery are within 2 blocks of my house, either.)

But still, if you’re looking to get off the beaten path…you’re gonna want to know about these South End spots that will let you skip the tourist crowds every time.

Get Your Caffeine Fix at Render or Wholy Grain

When I want excellent coffee, I head to Render. They brew both Tandem and Gracenote coffees, and frankly, Gracenote is the absolute best you can get in the city (although on some days, George Howell gives them a run for their money).

When you’re there, order a drip coffee, or, if you’re feeling extra-fancy, go for the pour over. Either way, don’t sully the complex and incredible flavors by adding dairy; this is one coffee you’ll want to drink black.

The pastry case is always stacked with incredibly delicious treats, too, and the Columbus Avenue location serves up hearty quiches and bagels all day long.

As great as Render is, first love in the South End was The Wholy Grain. There’s a special place in my heart for it. When I moved to Boston, I was there every single day. Make sure to go early and get a Jordan Marsh blueberry muffin before they run out (and ask for it warmed up with a side of butter).

Forget About the North End for Italian: Cinquecento Is Where It’s At

There’s nothing certain except death, taxes — and recommendations to eat in the North End if out-of-towners ask where they should go for dinner when they’re in Boston.

And sure, the North End is an experience worth having. But if you want to feel like a local in the know rather than just one in a herd of tourists, you want the other End. Head south and try Cinquecento.

It’s the site of one of the best meals I’ve ever had in Boston and it’s brunch ain’t bad, either. Ask your server about the specials and if venison is ever on the menu, get it — along with a recommendation on a wine to pair it with (you’ll want to skip the cocktails here, but I’ll tell you where to go for those next).

Drink Up at Gallows or Masa

Gallows has a very simple but very strong drink list that anyone who appreciates a straightforward, booze-heavy cocktail will enjoy. The Wildfire is my favorite choice, but you really can’t go wrong here.

If you decide to do more than drink at Gallows, you must order the only dessert on the menu: Stoner’s Delight. It’s one of the best treats I’ve ever had (and no, you don’t need to munchies to crave this dish days after you try it for the first time).

If you’re a fan of tequila and/or mezcal, Masa will have you covered. They have arguably one of the top three mezcal inventories in the city. But don’t let that scare you off if you’re not into that deliciously smokey taste: their Naked and Famous cocktail will suit even tamer palettes.

And here’s a bonus spot for you: The Beehive. It shouldn’t really be on this list because it’s one of the best-known South End spots… but if we’re talking excellent drinks in cool places, it deserves a shoutout.

With live music every night and a solid cocktail list, you won’t regret hanging out at the very large, spacious basement bar for an hour or two.

Go for a Dive at Delux Cafe, or Feel Like a Regular at the Franklin Cafe

If a divey spot is more what you have in mind, check out the tiny Delux on Clarendon. Just be sure to bring cash with you, as they don’t accept anything else.

Less of a dive but very much a neighborhood joint is The Franklin Cafe — which happens to be nestled between Formaggio and The Buttery. Strike up a convo with the bartender or your fellow patrons and you’ll feel like you’re right at home.

Be the First in the Doors at Bootleg Special

Finally, if you’re one of those “I tried it before it was cool” people (it’s okay, I can relate), here’s one for you: Bootleg Special just opened up on the corner of Tremont and Herald Streets, and it seems like word hasn’t spread quite yet.

Fans seafood boils and NOLA style eats, need to go immediately and check it out. Bring a crowd and get a boil — or go with a smaller party and don’t miss the po’boys, which are as good as any I’ve had in Louisiana.

You won’t need to worry about too big of a crowd at any of these places, and even better, you’ll have some great new recommendations to share with your friends and family to make you look like a true South End regular.


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