Essential Boston: Southie and Back Bay

The first time I went to Boston was during college. It was with some friends who lived just outside of the city. We spend one night there, going to all the stereotypical terrible bars. Blacked out dudes, blasting techno, and a ‘cover your drink’ vibe. Cartoonish accents, sketchy streets, and preppy douchebags at Harvard (Yes, I know - #NotAllHarvards). To be fair, I wasn’t exactly Queen Elizabeth - but even then it was too much for me. It didn’t seem to offer anything that any college town didn’t also have. I was completely uninterested in ever going back.

Cut to 2016, and my youngest sister decides to make a move to Boston. South Boston, to be specific. Southie, thanks to all the movies and from what I gather much of history in the city, has a reputation for being dangerous and downtrodden. That is not the Southie of today. Some of the most exciting restaurants in Boston are there - one was just featured in Food & Wine Magazine as a best of 2019. My favorite little artisan grocery is there. There’s Castle Island - a beautiful beach right in the city where you can chill and watch sailboats bounce in the water. Since my sister lives in Southie, and works at Healthworks in Back Bay - this is where I’ve spent most of my time so far. Since I have done so much exploring in Boston, though - other areas of the city (North End, Shawmut, Financial District, Seaport, etc) will be coming soon with their own lists.

Boston. The city I thought I hated, has become one of my absolute favorite places to be over the last three years. I’ve done some solid recon on the food/drinks/coffee/fitness front - and I think it’s about time to share so that next time you go - you can fall in love, too.

FOOD

Let's start at the most important place - stuffing your face full of food.

These crispy garlic shrimp at Loco are gluten free. I get this taco every time.

These crispy garlic shrimp at Loco are gluten free. I get this taco every time.

  1. Loco Taqueria and Oyster Bar (South Boston)
    http://locosouthboston.com/
    Loco is my favorite place to go in Boston, and I dont’ think I’ve ever gone to Boston and not had Loco be my first stop. It’s tacos, oysters, and margaritas. Almost the entire menu is gluten-free, down tot the fried shrimp taco and the fried Oaxaca cheese. The team behind Loco is also the masterminds behind three other South Boston spots that are equally unique and well-done: Fat Baby Sushi, Capo Restaurant (Italian), and Lincoln Tavern (Gastropub-ish). I would hang my hat on a visit to ANY of these places.

  2. Buttermilk & Bourbon (Back Bay)
    https://www.buttermilkbourbon.com/
    New Orleans cooking meets small plates. I had the suckling pig fries: cheese curds, gravy, and tender pork over fried potatoes? Yes, please and thank you. We also got some of the Nashville Hot fried chicken. If you can tolerate some gluten - eat this. As good as our main meal was, the star of the show was the most unexpected. Dessert. My sister saw that there was a 'soft serve of the day'. It was raspberry white chocolate ice cream in a pretzel cone. My dad couldn't keep any level of attention to hold a conversation - that's how good it was.

  3. Local 149 (South Boston)
    https://local149.com/
    On one of my earlier trips to Boston, my sisters and I were looking for one more bar to grab a drink and some food. I started googling and found this place that was seemingly near my sisters new apartment so we figured we'd check it out and end the night there. Turns out, Local 149 is a pretty sweet spot. It's just solid. The draft line up is decent. You’ll find a few locals, some craft standards, and probably a cider or two. Solid standard food - I always appreciate good buffalo wings and they definitely have those.

  4. American Provisions (South Boston)
    https://www.americanprovisions.com
    This is possibly my favorite little grocery that I have ever been to. Aside from what I’m told are the best sandwiches in town, and what I KNOW is some of my favorite coffee and espresso drinks, they have got a gloriously curated selection of artisan and small-batch food stuffs. Salts, seasonings, coffees, sauces, salsas, chocolates, cheese, wine...the list goes on. If you're the kind of person that wanders around Whole Foods looking for cool new shit - you're going to obsess here. The beach at Old Harbor is right up the road - so head in and get yourself a latte and go for a walk down the water. Maybe get some meats and cheeses and have a picnic. Yeah. Do that.

  5. The Fox & The Knife (Southie)
    https://www.foxandtheknife.com/
    I have not been able to eat here yet, because I have not been able to get a table. This newly opened enoteca is the talk of the town. After a few short months open, they found themselves at number 7 on Food & Wine Magazines top 10 new restaurants of 2019. Since then (not to mention the fact that the Chef is 2018 James Beard Award Winner of Best Chef: Northeast), it’s been tough to get a res. It’s going to be one of those things I remember to plan for way ahead of time instead of a week or two. The menu boasts aperitivo cocktails, and food inspired by Modena, Italy. It’s one of the best restaurants in the country - and it’s right in South Boston. I told you - it’s not the Southie you think you know.

  6. Stephanie’s on Newbury (Back Bay)
    https://www.stephaniesonnewbury.com
    We came to Stephanie’s for brunch, but later found out that she’s got a bit of a cult following and is deeply beloved by the locals and tourists alike. Thanks to it’s coner location - it’s got a massive patio in a prime people watching spot. We went for brunch, and while I can’t remember what I got, I can remember being very happy about it.

Shown above, from left to right: Short Rib Poutine at Lincoln Tavern, the Jam/Honey/Nut Butter shelf at American Provisions, and a gluten-free strawberry tart from The Thinking Cup.

DRINKS

I love a good cocktail, a glass of wine, a tall cider, and an impressive beer lineup. I'm also particular about things like atmosphere, seating, and GLASSWARE. If you hand be the best wine in the world in a garbage, stubby, shit wine glass - I don't want it. I love what's happening in the world of cocktails and sprits right now. People are paying attention to the quality of what goes into their glass. Fresh juices, craft spirits, herbs, spices. And interesting cocktail list, thoughtful draft line up, and wine list beyond 'red and white', tells me that you care.

  1. Loco is where to go for margaritas in Southie. Capo has a great lineup of cocktails, and a solid wine list. Lincoln has an OK draft list, with a few locals and usually a cider option, some decent cocktails as well. I have to say, we don’t do a ton of just drinking in Southie or Back Bay - the alcohol specific stops will be coming later - when we look at Shawmut, Downtown Crossing, and Seaport/Waterfront. Honestly, just head to Newbury Street and walk around - it wont be hard to find something.

COFFEE

Essential. Especially if you're a remote-worker like myself. Finding a space with tables and good caffeine is critical.

Nothing quite like grabbing a latte at the Thinking Cup. They don’t have wifi, so I usually jump onto xfinity, or get a hot spot going with my phone if I have work to do.

Nothing quite like grabbing a latte at the Thinking Cup. They don’t have wifi, so I usually jump onto xfinity, or get a hot spot going with my phone if I have work to do.

  1. The Thinking Cup (multiple locations)
    My stand-by. Absolutely perfect lattes and cappuccinos. Tons of baked goods, including many gluten free options and my favorite pastry situation: the French Macaron (tiny sandwiches of cookie and filling - not to be confused the the coconut macaroon). They also have a hot food menu, which includes sandwiches AND gluten-free bread. I'm partial to the sausage, egg and cheese breakfast sand, myself. The only dilemma with The Thinking Cup is lack of wifi. While you can usually pick up a signal from Xfinity or Att or something similar (or a neighboring shop), it can be problematic if you're really looking for a long post-up with a strong signal. I've never had problems, myself, but I know others who have. If you're not looking to get on the laptop - it's definitely a must-visit.

  2. Barrington Coffee Roasters (Back Bay)
    https://barringtoncoffee.com/
    I found this sort of randomly one day, but it’s just a great little spot with quality coffee. I don’t know that I’d post up here for a day’s worth of work - but when you’re looking for a morning bev that was given some care - this is where to go.

  3. Flour Bakery (multiple locations)
    https://flourbakery.com/
    This bakery/cafe is pretty much always bustling. I’ve stopped here a few times to grab coffee while we waited for a table at The Friendly Toast. Lots of baked goods and snacks to be found here - and you might even find a place to sit.

  4. American Provisions
    As previously mentioned, definitely not for staying to do work, but definitely yes for coffee-getting.

FITNESS

To be honest, most of my time in Boston is spent eating and very little of it is spent fitnessing. Not NONE, but little. I haven’t done any CrossFit in the Southie or Back Bay areas. Back Bay does have a Reebok CrossFit One location (Reebok CrossFit Back Bay), but I’ve only Been to CrossFit Southie once.

  1. CrossFit Southie
    https://www.crossfitsouthie.com/
    CrossFit Southie marked my first experience ever with a ski erg. Those are hard. Anyway, CFS is comprised of two buildings, so you might feel a little disoriented upon arrival - but everyone I met there was super nice and very helpful in telling me where to go. It’s one of the first CF gyms to open in the Boston area, and holds one of the biggest annual competitions outside of (RIP) Regionals - The Southie Showdown (now in it’s 9th year).

  2. Healthworks Women's Fitness (Back Bay)
    https://healthworksfitness.com/
    OK so if you're in the mood for a non-CrossFit experience, you should drop by Healthworks in Back Bay and take a class with my sister, Katie Kaschak. She's a personal trainer and group instructor there and puts on really fun spin classes (plus Barre, a 45 min conditioning class called IGNITE, and a HIIT class as well). It's a nice change of pace to what we're used to at CrossFit, and don't fool yourself into thinking it's easy. Healthworks is a part of the clasps program BUT it is a women-only facility, so keep that in mind if you're traveling and looking to fitness with a mixed crowd. They also have the standard machines you’d expect to find, and I’ve done plenty of treadmill/rower workouts there when a class wasn’t an option.

When most of us think of Boston, particularly South Boston - we don’t think of this. This is Castle Island. It’s underrated, under the radar, and one of the best places to relax in town - for free.

When most of us think of Boston, particularly South Boston - we don’t think of this. This is Castle Island. It’s underrated, under the radar, and one of the best places to relax in town - for free.

There’s where you can start exploring Back Bay and Southie. Don’t let movies like The Town, The Departed, and Good Will Hunting make you think you should steer clear. Yes, there are definitely some tougher areas (as there are in any city) - but Southie is not what you think. It’s a unique little slice of city meets town that’s getting modernized without wiping out it’s character. So go, grab a latte and maybe a cider, sit on the beach and enjoy the view.







Kristin Kaschak