How to Experience Boston Like a Local

Boston is one of the oldest and most popular destinations in the United States. With a rich history and plenty of things to do, it's no wonder people from all over the world flock to this city every year. Whether you're moving to Boston, just moved to Boston, or simply want to explore the city, this blog is for you. Keep reading for expert tips on how to experience Boston like a local and get the most out of Beantown.

 

If you want to start your day like a true Bostonian, there's no better way to do so than with a “coffee regular” from Dunkin’ Donuts. A coffee regular in Boston is far from plain — it typically boasts two creams and two sugars for a medium coffee. This creamy, sweet treat is the perfect way to start your day, and Dunkin’ Donuts is the best place to get it. With locations all over the city, you're never far from experiencing a delicious coffee regular like a true Boston local.

Our next best tip for experiencing Boston like a local? Never rent a vehicle! Even locals who have lived in Boston their entire lives find it difficult to navigate the one-way streets without rhyme or reason. Boston is home to the oldest subway system in the country: the T. The T is easy to navigate and practical for traveling during rush hour or getting to a game. We advise starting with a roundtrip CharlieTicket from a subway vending machine. Regardless of where you get off, the fare remains the same. Of course, you can always add extra cash to cover additional trips.

Moreover, it can be easy to forget the simple pleasure of walking in a world that seems to be increasingly dominated by cars and other forms of motorized transport. Boston is pretty tightly-packed, with most destinations within a 30-minute walk from the city’s center. And thanks to Boston’s extensive public parks, it's easy to find a scenic route to suit your mood, whether you're looking for a stroll or a vigorous hike. So next time you're tempted to jump in a cab, remember that sometimes the best way to experience Boston like a local is on foot.

Once you've gotten your coffee fix and a roundtrip Charlie ticket, it's time to explore your city like a local. As one of the oldest cities in America, Boston offers its fair share of traditional tourist spots. If you've been a Boston resident for some time now, you may have already visited Faneuil Hall, posed for a photo in front of Cheers, beheld the Green Monster, and traversed the Freedom Trail. But have you ventured to Boston’s Seaport to see some of Boston's finest avant-garde artwork or searched under a highway overpass for the city’s best pizza? If you're looking for some great views, head to the top of the Prudential Center or take a walk along the Charles River Esplanade.

Suppose you're in the mood for some Boston shopping. In that case, Newbury Street is Boston's premier shopping destination with a variety of boutique shops, name-brand retailers, and cafés and restaurants. Start with some high-end shopping near Arlington Street; the further west you go, the less formal the designers. But no matter where you choose to shop on Newbury Street, you're sure to find something to fit your taste and budget. Whether looking for the latest fashion trends from international designers like Marc Jacobs, Chanel, and Ralph Lauren, or unique gifts, Newbury Street has something for everyone and is an excellent destination for shopping and relaxation when you need a break from the hustle and bustle of Boston.

When it comes to dining, Boston has an incredible array of options. From renowned Michelin-starred restaurants to cozy local cafes, there's something to suit every taste and mood. With such a wide variety of cuisines, there's always something new to try. Whether you're in the mood for seafood fresh from the docks, succulent steakhouse fare, or authentic Italian pasta, you'll find it all in Boston.

With art deco furnishings, dry-aged steaks, and a tastefully-chosen wine list, The Capital Grille offers a comfortable and luxurious dining experience. Each item on the menu boasts top-quality, seasonal ingredients to delight the palate. Steaks are dry-aged for 18 to 24 days to get the ideal texture and flavor and prepared to strict standards after being hand-carved in-house. What’s more, simple elegance permeates the surrounding architecture and atmosphere.

Union Oyster House is another local favorite that serves superb oysters and seafood prepared according to traditional techniques. Not only is it the oldest oyster house in Boston and a renowned favorite of John F. Kennedy, but this dining spot served as headquarters for Ebenezer Hancock of the Continental Army in 1775. Daniel Webster also frequented this pub in the 1800s. Even now, the interior decor harkens back to the founding era of our country, and sitting down will make you feel as though you're stepping into the past.

In a time of impersonal music venues, Paradise Rock Club (also known as “The Dise”) is a refreshing change of pace. Boston locals love its grungy feel, with a stage that’s so low it feels like the band is performing in your basement. This 900+ standing capacity theater is close to Boston University and primarily draws young adults looking to see emerging talent. Bands like Rage Against the Machine, Big Boi, Grimes, the Black Keys, and U2 performed here. Local tip: arrive early to get a seat on the balcony or close to the stage!


Although most people associate Boston's North End with Italian restaurants, it also plays host to Improv Asylum — one of the top comedy clubs in the city. Their Mainstage show blends improv and scripted sketches. They even offer classes for aspiring comics!

So there you have it — our tips on how to experience Boston like a local. Whether you're relocating to Boston or already call this city home, we hope you enjoy exploring all that Boston offers!

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