Boston, United States
Annie, 39
Cannabis industry and consummate wanderer
see her Boston city guide

ask Annie about

museums beaches viewpoints monuments cocktail bars music venues

What do you do and why do you do it?

After beginning my legal career in oil and gas, I moved to Boston to work in campaigns. I'm a consultant at a government relations and political consulting group and I do it because it's ever-changing, it keeps me on my toes, and it gives me the chance to move things forward while still staying below the radar.

What’s the worst job you’ve ever had and why was it so effing bad?

I've worked many different jobs in many different industries; two are tied for the worst. Although they were drastically different jobs - one in a bar and the other in an office - they were bad for the same reason: both times, I worked for desperate and grasping villains. They were both condescending and unkind, and each lacked in social grace. Neither was as smart as he thought he was and both were profoundly cheap. Both jobs lasted only a few months and ended with brief, fiery encounters. Both were thrown over for more interesting and pleasing positions.

Were you born and raised in Boston? If not, where did you grow up and what brought you to Boston?

I was born and raised in Oklahoma City, Oklahoma. I moved to Boston five years ago to volunteer for a campaign, a move that was initially supposed to be a detour leading to Washington, DC. An unexpected series of life changes happened and I ended up staying. The longer I live in Boston, the more I view it as a long-term option, and the more I love it.

What’s your current hood in Boston and what’s the best/worst thing about it?

The best thing about Cambridge, where I currently live, is the diversity and density. It's a tiny city that makes up a portion of the Greater Boston Metropolitan area, and though she be but little, she is fierce. Cambridge has great food, world class universities, culture, and is bright with life all year. I live in a quiet corner of the city that is under-developed and not very neighborhood-like, but it's coming up. All the good has a down-side, though, in that the density and concentration of young people can make for crowded commutes and make it hard to find a quiet bar for a cocktail with friends.

What kind of music do you listen to and what kind of music do you absolutely HATE?

My love of music is broad and varied. I'm a huge American Roots fan; I love hip hop, the symphony, electronic, and select catchy pop. There's no type of music that I absolutely hate because hate takes a lot of energy and I'm too lazy for that, though there are types - pop country, for instance - that I don't love as much as others.

You’re broken hearted - what tracks does your heartbreak playlist consist of?

Ken Booth: Anything I Own, Charlie Rich, Sitting and Thinking; Hepcat: Home; Merle Haggard and the Strangers: The Longer You Wait; Jackie Wilson: Lonely Teardrops; Bonnie Raitt: I Can't Make You Love Me; Jimmy Cliff: Many Rivers to Cross; Labrinth: Jealous; Michael Kiwanuka: I'll Never Love; John Moreland: Break My Heart Sweetly; Bill Withers: Hope She'll Be Happier; and Nothing Takes the Place of You, as covered by JD McPherson

Name the best TV shows of all time, and what makes them so good?

30 Rock is one of my all-time favorites; it's so smartly written and drenched in ridiculousness. The West Wing is an incredibly compelling and relatable show full of great characters.

Name some spots in Boston that are good for a Tinder date.

Dates can always benefit from an interesting setting; sometimes you need a little help breaking the ice. 1. The Lawn on D: local grown-up playground with art installations, music, lawn games, food trucks, and a bar. 2. The Delux Cafe: tiny dive with good food and drinks, and fun of decor to break the ice. 3. Night Shift: the taproom for this local brewery is spacious, has a handful of board games and occasional pub trivia, often has a food truck available - or you can have something delivered - and the beer is varied and tasty!

Which public figure would you want to see “roasted”? (every public figure is fair game).

I only love a roasting when the roastee can defend him or herself and be in on the laugh. I generally enjoy the roasting of comedians or public officials with more advanced senses of humor. All that is to say I have no idea.

Who’s your hero and where in Boston would you take them out for a serious hang?

Ruth Bader Ginsburg and I would hit the Boston Athenaeum and then the Lash Hurrah at the Omni Parker House for cocktails. She would impart her wisdom and I would try to keep up.

Where do you buy those fabulous clothes of yours?

Any place that strikes my fancy from designer to thrift.

What’s the area/ spot in town you’ll never be caught dead in?

The bars at Faneuil Hall. They're just not my style. Also, Cheers. I won't even go when I have friends in from out of town.

What’s the thing you LOVE to do in your city that you never get to do?

Boston is a great town for meandering. The city is very small and very walkable. I love to spend a pretty day wandering the city, finding new haunts and new places to shoot pictures.

Where do you go in Boston for a casual night out?

One of the best things about Boston is that it's a very casual city. There's great food and things to do available without having to be dressed up. A casual night out for me is dinner out - trying a new restaurant or popping into a favorite - then some live music or other show. In the alternative, we'll hit a taproom of one of the many local breweries, have dinner delivered, and spend an evening chatting and playing cards.

Where would you go in Boston to celebrate some freaking good news?

Probably Neptune Oyster - my favorite restaurant in the city. It has become my celebration spot and the spot I take my favorite people when they come to visit. It can be hard to get into, so you have to be committed, but if you fill that wait with a stop in at a bar or a stroll around the North End, it can enhance the evening.

What’s your choice of transportation in Boston and why?

Public Transit all the way! It's one of the cheapest transit systems in the US, goes almost anywhere you want to go, generally runs on time, and is almost always faster than driving. The T, as we call it, has good three-day and week-long pass options or you can just pay for a few rides at a time. Google Maps does a really good job with transit navigation and there are free apps available that will tell you in real time where the busses are. Boston also has a large and reasonably-priced bike share called Hubway.

What are the Boston spots a first-time visitor can’t miss?

Every city has must-see touristy things. Here, it's the Freedom Trail - a 2.5 mile trail of Boston and early American history. It really is interesting and encompasses a lot of the must-see stops - and a few must-skip. All in all, though, it's worth the time. Fenway is a must-see if you're into sports; check out the tour or catch a game at this storied park.

What are the Boston spots tourists should run from screaming?

1. Faneuil Hall Marketplace. It's a mall full of chain stores, carts selling generic crap, and a ridiculous food court inside a historic building. Instead of Faneuil Hall, hit SOWA or one of the many art markets that pop up during the warm seasons to find souvenirs. 2. Cheers - it's just not worth the time or money. 3. Duck tours - they're overpriced and don't provide a good tour of the city.

Tomorrow’s your last day in Boston. How do you spend it?

A sunrise run then coffee on the harbor, lunch at Neptune Oyster, laze about in the grass at the Public Gardens, dinner at Coppa or Gaslight, ballgame, then drinks out with friends.

What’s your favorite vacation city in the world and why?

Budapest was the last city I fell in love with.

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Michaela Menard