Travel Like A Local: A Guide To Boston, Massachusetts

by Emily Iris Degn
Travel Like a Local: A Guide to Boston, Massachusetts

Anyone who knows anything about Boston knows that it’s historic… think brick town homes, naval ports, and the Founding Fathers. How do you know where to go for activities to do in Boston? We’ve got the perfect guide for you. A friend of mine recently moved to Boston so I see myself as an expert on the city. She bought a lovely property from a company like Donnelly + Co. and I visit her whenever I can. Once you’ve visited Boston, you’ll fall in love with it just like my friend did – trust me!

Before you leave on your adventure, make sure to take out some cash and bring good walking shoes. Many shops only take cash due to the old-timey feel, but it does of course, depend on what neighbourhood you’re in. As for the shoes, they’re essential! Boston is a place that will require you to be on your feet for a while, so don’t forget this.

Getting into the city can be tricky and Boston traffic will always be crazy. The streets are small and crooked so make sure to be patient if you’re driving, and just try to have a good playlist (and some delicious car snacks) going. Enjoy the bridge views of the harbour. If you do choose to drive, try parking as close to the harbour as possible – it’s cheaper and far more convenient, location-wise. You can always take the train in from any major city nearby, a bus, or the T (their subway system). It might save you some time.

To start, there are some huge and beautiful ships in the harbour, so marvel at them from the shore, or pay for a tour of one. Touring the USS Constitution is especially exciting!

Run around on the deck, stand at the wheel, and take in the beautiful sights that every Boston Naval hero once did.

From there, you can walk up to Quincy Market for some killer food samples, local art, and of course, some classic Boston Cream Pie. Everything is fairly cheap, and the market itself is always bustling with exciting stalls and cuisines. If you want to grab some breakfast, they have some amazing bagels available at the market! We think the pizza bagels at Bagelville were especially scrumptious.

After you’re fully stuffed on pie and bagels, make your way up to the Freedom Trail. This is a walking path throughout Boston that lets you self guide through places like old bookstores, historic burying grounds and Paul Revere’s house. Make sure to take a tour through the actual house because between the original floors and tour guides inside, this is a definite must see. Enjoy the brick and vines that serve as accents to the lovely Beacon Hill neighbourhoods, and the cobblestone streets.

There are so many sights to take in and it can be so fun to go at your own pace, exploring the cafes and boutiques nestled in between historic markers. Make sure to pay a visit to Mike’s Pastry across the street from the Revere house, where Cannoli was invented! Many famous faces have passed through and the tile floor, decorated ceilings, and endless piles of goodies had us adoring this bakery. If you fancy doughnuts instead, walk a few minutes over to Union Square Donuts for the most Instagram worthy ones you can find (try their famous Maple Bacon doughnut!) When you’re ready for some lunch to go with your dessert (which we think should always come first), you can walk a few blocks over to North End – the famously Italian neighbourhood of Boston. If you want something quick and delicious, we love the traditional Regina Pizzeria for their fantastic slices. For espresso and sandwiches check out Tatte Bakery and Cafe for beautiful food and some gorgeous, rustic aesthetics.

Then, head over to Boston Common for a walk in the park and a taste of local life. Once you get there, you’re bound to feel like you have found a Boston-meets-Central Park sort of place. Boston Common serves as their city park and is home to festivals, gardens, and people watching.

Cross over the park into their Public Garden area and grab a ride on one of the swan boats – it feels like a fairytale!

Take the T over to the Public Library – this is something we highly recommend. The columns, the open space and the Hogwarts-esque studying hall are wonderful. Bring your camera along, because this stop is beyond pretty.

Heading back over to the harbour, you can choose from multiple museums and even an aquarium to visit if that piques your interest. The Institute of Contemporary Art is especially cool thanks to the surrounding ocean views, insane architecture and great deals for admission. Admission is free every Thursday from 5-9pm and they have lots of other free days throughout each month – you can check it out online before your visit.

The Irish pubs, the endless Italian food, the pizza… these are all highlights. But, there’s one thing that we feel every Boston traveler needs to try – Lobster Rolls. Whether you get a fancy lobster sandwich at a bistro or go for a low key roll, there’s no way to go wrong. Either are great choices. Lobster is famous in the region and to leave without sampling would be a shame. For the chill eaters out there, try the lobster sandwiches at Alive and Kicking Lobsters, and for those wanting something a little more sleek, grab the Lobster Rolls at Eventide for a beautifully crafted option. Another choice is to head down to the fish market at Yankee Lobster Company for a seaside taste of Boston.

To end the night, you can always hit up an Irish Pub or take part in some good, old fashioned candlepin bowling. We recommend Sacco’s Bowl Haven. This quirky twist on traditional bowling and pizza attracts locals from all over the city, so be prepared to brush shoulders with some true Bostonians. While Boston is definitely a historic city, it’s also a modern metropolitan area full of artists, unique cuisine and inventors of all sorts! There’s so much to see and do in good old Beantown, so take it all in and enjoy.

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