5×5: Boston

All the best hangouts, in all the best cities, from the locals who know… 

As a relative newcomer to the East Coast, there is a decent number of cities I’ve yet to explore, Boston being one of them. Intersected by cobblestone streets, historic neighborhoods and fueled by learning, Boston is tops on the list. Today it is among the most forward-thinking cities in the nation and boasts some pretty stellar food, sports, art and music. We reached out to five Free People store employees to learn more about this event-filled city and shed a little insight on what makes this place home.

Katherine Harrison: FP Store Stylist


Beacon Hill — Beacon Hill, Boston, MA 02108

The quintessential Boston destination. On the weekends, I love to peruse its narrow cobblestone, tree-lined streets and pick out which of the brick walk-ups I’d love to call my own (spoiler: all of them). Hop off the “T” – Boston lingo for the metro – and take a stroll down Charles Street. The real magic, however, rests in all of the branching side streets. Be sure to check out the famed Acorn Street and the incredible display of blooms outside Rouvalis’ flower shop.

The Isabella Stewart Gardner Museum — 25 Evans Way, Boston, MA 02115

Decadent yet haplessly curated, the Gardner Museum is an absolute treat — part art exhibit, part home, part garden. The greenhouse and central atrium seem plucked straight from a fairytale or, in the least, a charming European town.

Juliet — 257 Washington St, Somerville, MA 02143

Juliet feels as though it belongs on a quiet street in Paris. Serving lovely café and brunch fare during the day, Juliet transitions into a phenomenal chef’s prix-fix dinner destination come nighttime. Snag reservations if you can. The quotation on its wall from Bon Appetit gets the point across pretty well: “One thing is guaranteed: This will be energetic, personal cooking that’s truly one of a kind.”

Loyal Nine – 660 Cambridge St, Cambridge, MA 02141

Another Cambridge locale worth making the cross-river jump for. Go for a morning coffee at the café and return for the incredible, locally-sourced dinner menu or the famed Sunday brunch. The colonial-inspired fare can’t be missed (and you’ll probably want to snag a few Instagram pics along the way).

Olives and Grace — 623 Tremont St, Boston, MA 02118

Shop local: Olives and Grace is the kind of store where you walk in for a small gift and end up having a glass of prosecco with the owner. It’s best described as a boutique tchotchke shop. Olives and Grace contains all the best in locally sourced, artisinal goods, from cards to perfumes to trinkets to food. So much thought goes into each and every item displayed. It’s the kind of place where you wish all of your housewarming or christmas gifts came from. Bonus: the owners love the area and will direct you to all of the best locally owned and operated stores and restaurants!

Sarah Casto: Store Manager of Chestnut Hill


The Charles River Esplanade — Along the Charles River

Hands down my favorite park in the city. This 3-mile stretch follows the south bank of the Charles River which separates the cities of Boston and Cambridge. It is always buzzing with people riding bikes, walking dogs or jogging, but it never feels busy unless it’s the Fourth of July. I most enjoy walking the length of the park, picking up somewhere around the Harvard Bridge and watching all the collegiate rowing teams gliding up and down the river. If you don’t feel like walking, just set up camp on one of the public docks and enjoy the sunshine.

Harvard Square, Cambridge — Intersection of Massachusetts Avenue, Brattle Street, and John F. Kennedy Street

Another Boston fav located in Cambridge that holds a special place in my heart. As I managed the Harvard Sq. Free People, this adorable area worked its way up to the top of my list of places to visit in the city. Summer in the square is an absolute dream. A hub of college students, corporate professionals, small businesses and stellar bars. Great food, great drinks, great shopping. Some of my top picks are Crema Café, The Beat Brasserie, Felipe’s, and Goorin’s Hat Shop.

Bagelsaurus — 1796 Massachusetts Ave, Cambridge, MA

Anyone who knows me knows that I live off of breakfast sandwiches and, after 25 years of searching, I have finally found that that this tiny bagel shop in Porter Square has the. Best. Bagel. Sandwiches. Ever. Their unique selection of bagels are freshly made every day — you can choose from several of their acclaimed sandwich menu options or just grab a simple bagel+spread combo. My order: the Eggspanola on a Seasalt bagel – over-medium egg, feta, pimenton aioli, parsley gremolata, avocado optional. These delectable bagels are available from 7am to whenever supplies last, and they do sell out. So bike there, Uber there, ride there, and don’t be surprised to see a line out the door. I’m not a fan of lines but this place is worth the wait.

Babbo Enoteca and Pizzeria –11 Fan Pier Boulevard, Boston, MA 02210

This wonderful Italian restaurant by Chef Mario Batali, The Chew personality, Iron Chef, and one of the creators of Eataly, is one of my top choices for any birthday, anniversary, or date night dinner. I am a HUGE fan of charcuterie and Babbo really brings it. The menu of anipasti, pizzas, small plates, pastas, and gelati paired with an even larger menu of wine truly make this restaurant an experience to remember. It’s a large space that boasts three separate bars for pizza, antipasti and cocktails, located in the ever-growing seaport district on Fan Pier. Go to the ICA (Institute of Contemporary Art) and then hit up Babbo for a spread that will blow your mind. The truffle honey accoutrement that they serve is to die for.

The Isabella Stewart Gardner Museum –25 Evans Way, Boston, MA 02115  (2 VOTES FOR THE GARDNER!!)

One of the most unique art museums in the city. It is located right near my alma mater, the Massachusetts College of Art and Design, so one can image how many hours I spent here while in school. It started as the private residence and collection of patron to the arts, Isabella Stewart Gardner, and has grown into a noteworthy assemblage of historical and contemporary art. Major points of interest are the famous Sargent paintings, the four-story courtyard in the center of the museum, and the empty frames left as reminders of the yet unsolved 1990 heist in which $500 million worth of art works were stolen from the museum including pieces by Vermeer, Rembrandt, Degas, and Manet.

 Madison Warchol: Assistant Visual Manager, Free People Burlington


Hauswitch Home and Healing — 144 Washington St, Salem, MA 01970

Magical, Whimsical, Girl Power…..Just a few things that come to mind when I think of Hauswitch! Along with tons of natural light and good energy, this shop holds everything you need to bring magic and healing into your everyday spaces. Just when I thought it couldn’t get any better, they now hold amazing in-store events, such as “New Moon Guided Meditation” and “Tarot And Tea.”

Mill No. 5 — 250 Jackson St #402, Lowell, MA 01852

Set inside the fourth floor of a 1873 textile mill, that’s where you will find Mill No. 5. The recently renovated space holds dozens of boutiques and attractions tucked away behind salvaged architectural storefronts. With a vintage movie theatre, yoga studio, record store and much more, this is the perfect spot for everyone.

Pressed Cafe — 200 District Ave, Burlington, MA 01803

If you’re looking for locally sourced, light and delicious food, Pressed Cafe is the spot!  With indoor and outdoor seating you can enjoy a wide variety of sandwiches, smoothies, fresh juice and…breakfast ALL DAY… say no more, right?

Bruce Freeman Rail Trail — Bruce Freeman Rail Trail, Chelmsford, MA 01824

It’s nice to get a small taste of nature without having to make a trip outside of the city proper. This fully paved trail is perfect for walkers, runners and bikers. It extends 7 miles through the woods, ending at Hearts Pond, the perfect spot to stop and watch the sunset. :)

Boston Rock Gym — 78 Olympia Ave, Woburn, MA 01801

I have always been afraid of heights, so rock climbing wasn’t something that generated much interest in me. But after a few visits to the Boston Rock Gym and meeting the amazing community of climbers that surround it, I was hooked! BRG is the oldest rock gym on the east coast and is open to climbers of all ages and climbing abilities. This is a perfect day or night trip to try something new with a group of friends.

Gabriella Zen: Free People Sales Associate


JUGOS — 145 Dartmouth St, Boston, MA 02116

As an LA transplant, I need my juice fix. Yes, my fresh cold pressed juice. And like all Angelenos, I was skeptical that anything could compare to my go-to juice place back home. But then I tried JUGOS. This tiny hole in the wall, right next to Back Bay Station, serves up unbelievably fresh and delicious treats. Whether you’re into juice cleanses, acai bowls, or something a little heartier (they have three kinds of avocado toast!), you cannot go wrong with JUGOS.

SoWa Open Market — 530 Harrison Ave, Boston, MA 02118

You know it’s summer once SoWa starts up. Touted as the largest outdoor market in Boston, SoWa promises to fulfill all your farmers’ market dreams. And trust me, it delivers. On top of the traditional farmers’ market, SoWa also includes an art market, food truck bazaar and beer garden. Running every weekend for six months, SoWa presents the opportunity to try fresh locally grown produce, eat from your choice of deliciously iconic food trucks, and purchase handmade art. I don’t know about you but I’m itching for SoWa season.

Blackbird Doughnuts — 492 Tremont St., Boston, MA 02116

I love doughnuts. My mom loves doughnuts. My grandpa loved doughnuts. As much as I try to resist it, doughnuts are in my blood. Thankfully, Boston’s donut scene does not disappoint. With several artisanal donut shops across the city, Blackbird Doughnuts hit the spot every time. As the only doughnut shop in Boston to bake on-site, Blackbird ensures freshness. They come out hot and ready. This South End bakery offers an array of both raised and cake doughnuts that are as gourmet as they get. Some of my favorites include the Rooftop Honey, Triple Chocolate, and the Everything Bagel Doughnut. Embrace your sweet tooth. The doughnuts are calling.

Tatte Bakery and Café — 1003 Beacon St, Brookline, MA 02446

First drawn here by their avocado toast, I fell in love with Tatte Bakery and Café’s unreal baked goods and brunch. I dream about their flaky croissants and mint lemonade, and don’t even get me started about their shakshuka. In the winter the cozy interior and their hot chocolate proves perfect refuge from frostbite. But as the days get longer and warmer, the outdoor seating area is a hot commodity. Bring a book, grab some grub, and soak in the sun.

Lookout Rooftop and Bar, Envoy Hotel — 70 Sleeper St, Boston, MA 02210

Sometimes when I feel like being an adult and the weather is just right, all I want is to get dressed up and go to a rooftop bar. The rooftop bar at the Envoy Hotel has the perfect combination of delicious cocktails and gorgeous views of the Boston skyline. You can sip and mingle while taking in the sights and sounds of other young Bostonians looking for a good time. Go during the day for a happy hour tan, or out late for a drink under the stars.

Falon Moran: Free People Store Stylist


The South End — 539 Tremont Street, Boston, MA 02116

Brick brownstones and adorable shops and restaurants, i.e. the ultimate New England vibe. The South End is that perfect package. Spend an afternoon strolling this neighborhood and take in the unique architecture, parks and all it has to offer. Stop by Follain for beauty needs, Store Ore for beautiful selections from local jeweler Sophie Hughes, Barcelona for an extensive wine list, and Gaslight for the best French meal. Boutique shops dot Washington, Columbus, and Tremont Streets and some of the best cuisine in the city.

Redbones BBQ — 55 Chester Street, Somerville, MA 02144

BBQ may not be your first thought when you think Boston but, as a girl with a strong affinity for smoked meats and mouthwatering sides, I’ve found the best the city has got to offer. Tucked away in Somerville’s trendy Davis Square, this dive makes you feel right at home with authentic pulled pork, brisket, ribs and all the fixings. Do yourself a favor and get the corn fritters, too.

Fenway Park — 4 Yawkey Way, Boston, MA 02215

Boston is definitely known for their sports culture and serves as home to the oldest ballparks in Major League Baseball. As a huge baseball fan, Fenway is by far one of the coolest stadiums I’ve ever visited and, even if you’re not in love with the game, there’s gorgeous views, lovely exposed brick, a strong history, and of course the ever-traditional Fenway Frank.

Bova’s Bakery — 134 Salem Street, Boston, MA 02113

This 24-hour North End spot is tucked away from the crowds of Hanover Street, but at any given time, you’ll find a crowd. Inside sits cases of traditional Italian pastries, breads, arancini, pizza, and just about any other type of sweet dessert you can imagine, from canolis to cookies to cupcakes and even cheesecake. Not only are the selections and portions large, but they are delicious. Stop by here, anytime! You won’t be disappointed.

The Esplanade — 47 David G. Mugar Way, Boston, MA 02108

Perhaps one of the most iconic places in Boston, the Esplanade runs between the Charles River and Storrow Drive (basically the length of the city). When the weather is nice, it’s worth taking a walk over to enjoy the river breeze and scenic vibes. Take a walk, go for a run, rent a bicycle, or even just sit on the grass amongst the trees or one of the many docks and enjoy the afternoon while taking in views of Cambridge.

+ Traveling? Check out more 5×5 features here

Follow April on Instagram.

0 0 vote
Article Rating
Notify of
Newest Most Voted
Inline Feedbacks
View all comments

The food all looks so good. I’d love to chow down at Loyal Nine!

Charmaine Ng | Architecture & Lifestyle Blog

Emily O'Neil
7 years ago

You left out Life Alive in Central Square in Cambridge! Highly recommend their Green Goddess Bowl!

7 years ago

This insight into Boston is incredible. I love cities with rich history and I’m dying over all the exposed brick.

7 years ago

Such a great post and photos! Absolutely love it!

7 years ago

My husband and I met and lived in Boston for 5 years – it’s the BEST city, and will always have a special place in our hearts <3

6 years ago

My mother and I went to Boston this past weekend and this list was SO helpful to us!. All of the recommendations we tried were great; we went to the ISG museum, the Charles river esplanade, Tatte, Harvard Square, Fenway, Lookout Bar, and Beacon Hill. I don’t know how we would have gotten by without this list!

Thanks so much for putting this together, and next time I am traveling somewhere I am looking here first to see if you guys have recommendations!

6 years ago

Wow, this is so awesome. Lots of great food photos but also amazingly photographed people/places in Boston. Seriously, I always recommend my friends come visit. (I’m originally from Alabama) Gotta hit up that cafe and try the food!

6 years ago

What a wonderful overview of things to do in Boston. I liked how you had different people share their favorite spots in Boston. I’ve tried to go to as many cities as possible, but Boston always calls me there. So much fun stuff there and so much history. I grew up reading about Boston from Robert Parker’s “Spenser” novels and Marvel Comics’ “Tomb of Dracula” series. When I finally went there, I was delighted by the city. My big goal right now is to attend the Independence Day concert featuring the philharmonic.

6 years ago

Beacon Hill looks gorgeous! I imagine it would be particularly nice in the spring or fall. I know I’d have a great time taking in the sights, particularly the rich history that is Boston. I love Boston’s quaint side streets and while I haven’t used it extensively, I’ve never experienced any problems using Boston’s transit system. BTW, do they have Uber in Boston?