Notes From Off the Beaten Path: Boston

Traveling Local in Boston

I don’t like crowds. Massive groups of people make me uncomfortable. Times Square gives me the hives. I know I am not alone in this confession. Even in my home state’s capital, Boston, I specifically find the more peaceful, authentic places to wander.
Give me a beach, give me a beautiful hike, give me a small neighborhood that I can stroll through while I sip on my almond milk café au lait (The Thinking Cup of Boston, I’m looking at you). “Avoid the tourists” is one of my favorite games to play, and let’s just say, I’m on level nine and climbing.  I truly believe that one of the best ways to make the most unique memories is to explore authentically. These tips can be applied anywhere you travel–and have proven specifically useful here in Boston. The keys to achieving this clever style of exploring are to conduct proper research, think like a local, go off the beaten path, and always, always strategize.

Plan Accordingly

If you want to learn about a city in non-touristy fashion, a great place to begin planning your trip is with an outlet like Viral. Not only do we write about events and happenings, but also about neighborhoods, day trips, and cool areas to explore. Sift through the available information and put together a list of areas in your destination that interest you. Look into where locals grab drinks, get the best coffee in town, and enjoy the best eats. Then find neighborhoods and day trips that look fun, organize your plans, and hop to it. When it comes to Boston, the key is to explore by neighborhood. Areas like Somerville, Cambridge, Beacon Hill, the North End, and Brookline are all both residential and brimming with local favorites.

Think Like a Local

Eat local, go local, and wander. Talk to folks who live in the area you’re visiting and follow their lead. Locals often have the best knowledge of where to go, what to do, where to chill, and their advice can be priceless. So, two of the best things a traveler can do is either a.) ask a friend, family member, or connection who lives in the area where to go and what to do; or b.) ask the locals! Asking around can be an excellent source in figuring out where to explore a place you know next-to-nothing about. It can also turn out to be a super fun exercise. I found the best chocolate shop in all of Charleston, South Carolina, by asking a friendly woman who owned a store downtown for her recommendations. We talked for almost thirty minutes and I learned about her life in the area and where her favorite places to go were. Thanks to her, we had an amazing local seafood dinner later that day.
In Boston, you’ll find that people are usually pretty friendly and helpful. If you want to find a good place to go, don’t be afraid to ask a local. Just don’t be surprised if you hear them drop every “r” in their vocabulary.

Residential Areas

Stay away from ultra-commercialization whenever possible. Just say NO to commercial malls, plazas, movie theaters, and chains whenever possible. When visiting a new place, chain restaurants are sacrilegious. Sometimes the best finds are even hidden within the most “locals only” areas. Cue residential areas. Don’t balk so fast! You never know what could be hidden in little nooks far away from tourist traps. For example, the Beacon Hill area of Boston is incredibly residential, yet it harbors some of the best cafes, bistro, flower shops, and bars in all of Boston. Additionally, the North End, Cambridge, Brookline, and Somerville house some amazing little spots.


If you are indeed going to attend a major event–let’s be honest, it happens–then you must at least strategize. What would a local do? Get there early, get a good spot, get the scoop on the best place to go, find out the easiest travel route, and so forth. When I make an appearance at a huge event, I always plan out how to make the experience as easy and fun as possible. When I attended the Washington D.C. Memorial Day celebration on the West Lawn of the Capitol Building, I strategized using insight from locals. We packed fruit, cheese, and wine, brought chairs, and got there early through one of the lesser-known gates. We were able to secure a spot right on the steps with an incredible view of the stage. It was an amazing night, regardless of the massive crowds.
These same tricks work perfectly for Boston events at Fenway Park, or the Fourth of July celebration on the Esplanade. Get to your destination early for a good spot, brings snacks (when allowed), and relax. Strategize like a local, people!

A Boston Quick List

by viral