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Boston at sunset|©walknboston
Boston at sunset|©walknboston
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A Practical Guide To Boston From A Local's Perspective

Picture of Casey Campbell
Updated: 8 September 2016
Tourism in Boston is often neatly categorized under three topics: history, sports, and seafood. Of course Boston’s role in the Revolutionary War is a fascinating one, but you can only walk the Freedom Trail so many times. The same goes for Red Sox games and clam shacks. Also, it can be difficult to see all of Boston’s sights in one day due to pure logistics (Boston has terrible traffic, and a decades-old public transportation infrastructure that is far from perfect). Locals know that there’s so much more to Boston that tourists miss out on and travel books never advertise. Use this guide to spend a day in the city like a local.

One thing the travel guides are sorely lacking in is a robust examination of Boston’s food scene—and it is a delicious one. Start out your day at Flour Bakery + Cafe, the brainchild of Owner Joanne Chang, where you should order one of their famous sticky buns. There are many other confections to choose from, however, and all are delicious. With four locations in the city, we prefer their South End outpost as it’s usually less crowded by tourists.

Sticky Bun from Flour Bakery | ©Jules Morgan/Flickr
Sticky Bun from Flour Bakery | ©Jules Morgan/Flickr

Since you’re already in the South End, head on over to South Boston to explore hidden gems of the area. The Lawn on D is a fairly new installation that’s a favorite for Instagrammers, children, and college students alike. Here you can play lawn games, hang out on futuristic swings, and even grab a bite to eat. Also right in the area is the SoWa Market, a massive farmer’s market featuring local produce, artisans, and a good amount of food trucks every week. They expanded their space this year to bring in even more vendors, so be sure to spend a Sunday here.

From the South End, another local favorite is Castle Island. A quick eight minute drive from the Lawn on D, this state-protected park is the home of Fort Independence, historically used for harbor defense. Today, you can grab a quick lunch at Sullivan’s and tour the fort in the summer. The area is also located in Pleasure Bay, great for sunbathing and fishing, and it sits right across the harbor from Logan Airport, with planes flying overhead all day.

Castle Island | ©Robert Linsdell/Flickr
Castle Island | ©Robert Linsdell/Flickr

At dinnertime, you don’t have to go all the way back downtown for a delicious meal. If you’re ready for an international culinary experience, stay in the South End. Local favorites Jamie Bissonette and Ken Oringer have partnered to create two award-winning restaurants, Toro and Coppa, serving creative tapas and Italian small plates, respectively. For traditional American, stop into Franklin Café. Order one of their classic french fry plates. Looking for something out of the ordinary? Then Addis Red Sea Restaurant is for you, where diners sit on the floor and eat traditional Ethiopian food utensil-free. The list goes on, but the South End is a welcome respite from traditional New England cuisine.

A big part of getting the most out of Boston is often doing exactly the opposite of what a travel agent might tell you. This guide showed you the best parts of the South End—but explore all the neighborhoods of Boston. Instead of hanging out in Harvard Square—where you’ll only be annoyed by crowds of students—check out the lesser known Davis or Porter Squares. Don’t be afraid to venture to the city limits to catch a show at Brighton Music Hall or a movie at Coolidge Corner Theater. Hunt down the famous Keytar Bear or stand inside a giant map of the world. Locals know that the best parts of Boston are these hidden gems, and even in this small city, there’s always something new and interesting to do.

Flour Bakery & Cafe, 1595 Washington Street, Boston, USA +1 617 267 4300

Lawn on D, Boston, USA

SoWa Market, 460 Harrison Ave, Boston, USA +1 857 362 7692

Castle Island, Boston, USA

Torro, 1704 Washington St, Boston, USA +1 617 536 4300

Coppa, 253 Shawmut Ave, Boston, USA +1 617 391 0902

Franklin Cafe, 278 Shawmut Ave, Boston, USA +1 617 350 0010

Addis Red Sea Restaurant, 544 Tremont St, Boston, USA +1 617 426 8727

Davis Square, Somerville, USA

Porter Square, Cambridge, USA

Brighton Music Hall, 158 Brighton Avenue, Allston, USA +1 617 779 0140

Coolidge Corner Theater, 290 Harvard St, Brookline, MA +1 617 734 2501