The Inside Out Guide to Boston

The Inside Out Guide to Boston
Credit: Miguel Romero

Next to New York, Boston is the most bustling city in the Northeast (but with more reliable public transportation and fewer skyscrapers). If the past two Super Bowls and 2018 World Series are any indication, Beantown residents are best known for their raucous, diehard fandom. But outside of the Fenway neighborhood, Boston’s culture is rich and marked by rows of historic buildings where the likes of W. E. B. Du Bois, Susan B. Anthony, and Horace Mann worked for civil rights in the United States.

As well as being a monument to America’s political history, Boston is also home to some of the country’s most infamous criminals, from Lizzie Borden to Whitey Bulger and many a Scorsese character. It’s also produced comedians such as The Office‘s Steve Carell, Mindy Kaling, John Krasinski, and BJ Novak.

There’s no dearth of attractions in Boston and each neighborhood has its own style and vibe. It’s worth taking a long stroll down Newbury and Boylston streets for window shopping or mapping your own Freedom Trail meets Boston Tea Party meets Kennedys sightseeing tour. You could take in Boston’s culinary treasures, slug a pint at an Irish pub or, maybe, get a tattoo of Wally, the Red Sox furry, green mascot.

Where to get tattooed in Boston:

Brilliance Tattoo: If you’re looking for an intimate tattoo experience, Brilliance Tattoo prides itself on privacy and low-volume. Artist Dia Moeller creates muted, artful still-lifes and portraits where her shading looks like it was blended with her fingers and not a needle. Amanda Abbott recently returned to Brilliance, where the realism of her in-demand portraits match the romance and history of Boston. In stark contrast to both Moeller and Abbott is Jenpa Konchok, who specializes in expressive, bold linework.

3399 Washington St, Boston, MA 02130, 617-902-0957 (cancellations only)

Boston Tattoo Company: Boston Tattoo Company has three locations open seven days a week throughout the city, each with artists whose style and experience runs the gamut. Roz Thompson creates custom designs with delicate, intricate details — both in color and black ink — whereas Lucian Toro replicates your favorite Star Wars characters, superheroes, and movie villains that are mind blowingly realistic. So, maybe hit up Newbury Comics before your appointment with Toro for some inspiration.

260 Elm Street, #102, Somerville, MA 02144, 617-625-8282
567 Fellsway, Medford, MA 02155, 781-393-8282
36 Prospect St, Cambridge, MA 02139, 617-714-4515

Paola Pokes: A one-person stick and poke studio whose books close as fast as they open. If you follow Pao on Instagram, be ready to book as soon as they release new dates. Their designs are all black ink and often no bigger than the palm of your hand. But their small size doesn’t leave out any detail, like this junebug or peaches that give us serious Call Me By Your Name vibes.

Where to stay in Boston:

Hotel Commonwealth: The location of Hotel Commonwealth is ideal if this is your first time in Boston and you’re looking to hit all the major attractions like the Museum of Fine Arts and Fenway Park. Its proximity to Fenway is why the hotel is the official hotel of the Red Sox, though it’s not likely you’ll see an outfielder walking through the lobby. The rooms are spacious and more modern in aesthetic than the stately building would lead you to believe and it’s close to The Hawthorne. Their craft cocktails are thoughtful and varied and although there are bar snacks available, it’s better to hit this spot with a full(er) stomach. Less than a ten-minute walk from the hotel is the House of Blues, where you’ll find popular and more indie acts gracing the stage.

500 Commonwealth Avenue, Boston, MA 02215, 617-933-5000

Inn at St. Botolph: The Inn at St. Botolph feels more like your very wealthy second-cousin’s brownstone than a hotel. Its interior is as unassuming and elegant as the exterior, with four-post beds clad with plaid blankets and kitchenettes perfect for preparing morning coffee. While continental breakfast is available, there’s plenty of dining options in the area to try, like Flour Bakery & Cafe, where you can grab a pastry to eat in the nearby Copley Square. The Inn lacks the standard luxuries of bigger hotels, like an on-site bar or restaurant, but the room’s luxe products and lounge area complete with working fireplace offers a quiet reprieve from a day on Boston’s busy streets.

99 St. Botolph St., Boston, 617-236-8099

The Godfrey: The Godfrey falls in between Hotel Commonwealth and the Inn at St. Botolph with chic rooms and a few luxuries beyond continental breakfast. In the lobby you’ll find George Howell Coffee, the namesake brand of the pioneer of third-wave coffee. In addition to drip and espresso options you can geek out over coffee flights, public cuppings and, if you have some time, training clinics. Ruka is the hotel’s restaurant serving Peruvian-Japanese that’s standard fare in South America. So, if you’re craving a simpler option for room service, you may want to hit up Postmates. Your bill will show a $25 “urban fee” so be sure to take advantage of what that includes: bicycle and helmet rentals, guided tours, bottled water, an e-newspaper and more. For history buffs, the Downtown Crossing location is a perfect choice because of its proximity to Boston Commons and Public Garden, the Freedom Trail, the Old State House, and the John F. Kennedy Federal Building.

505 Washington St., Boston, MA 02111, 617-804-2000

Where to get inspired in Boston:

Newbury Comics: Founded by two MIT graduates in 1978, Newbury Comics began as a small comic book vendor on a street by the same name. Now there are two locations in Boston and two in Cambridge, as well as others across the country, selling new and used CDs, LPs, comics, posters, trading cards, action figures, and other novelty items that will bring out your inner-teen. Since the stores began selling music in the 1980s, now-famous musicians like Aimee Mann got their starts behind the counter at Newbury Comics. A few doors down from the Newbury Street location you’ll find Trident Booksellers to continue your cultural edification.

1 North Market Building, Boston, MA 02109, 617-248-9992
348 Newbury Street, Boston, MA 02115, 617-236-4930

Museum of Fine Arts: If you’re lucky enough to be in Boston when the Museum of Fine Arts is hosting MFA Late Nites you can fulfill your childhood dreams of exploring a museum after hours. The museum has one of the largest collections of Monet’s work in its permanent collection and recently acquired the Howard Greenberg Collection of Photographs, which will go on display in August 2019 and will feature photos from Alfred Stieglitz and Yousuf Karsh.

Avenue of the Arts, 465 Huntington Avenue, Boston, MA 02115, 617-267-9300

Institute of Contemporary Art: The Institute of Contemporary Art is worth visiting for the location alone. It’s built on a pier overlooking the harbor, with prime sunset views year round from the deck or through the translucent glass that encases the building. The gallery hosts large-scale, thematic exhibitions of varying mediums. From May through September the ICA Watershed is open in the Boston Harbor Shipyard and Marina. The 2019 exhibition is Purple, from artist and filmmaker John Akomfrah, who took hundreds of hours of archival footage and new shots to talk about climate change.

25 Harbor Shore Drive, Boston MA 02210, 617-478-3100

Gallery NAGA: Gallery NAGA is located in a gothic church and features mostly painters from the New England area in its exhibits, though you can also find photography, prints, and sculptures on occasion. There are usually two artists exhibiting at once, whose work does not necessarily follow the same theme so you may find yourself walking through opposing forces and styles. Visiting Gallery NAGA will make you think and challenge your view of beauty and art.

67 Newbury Street, Boston, MA 02116, 617-267-9060

What to do in Boston:

SoWa Open Market and Artists Guild: Every Sunday from May through October, Boston celebrates local food and makers at the SoWa Open Market. The market, which is open to all people and pets, is free to walk through but the fresh food, local art and beer garden will make it difficult to keep your wallet closed. At the beer garden you can enjoy live music from local musicians and you can purchase something to eat from the food truck bazaar. On the same street is the SoWa Artists Guild, a non-profit association of artists that hosts first Friday and second Sunday events where you can take in the local art. There are also opportunities throughout the year to visit the artists in their studios, so check the guild’s calendar.

530 Harrison Ave, Boston, MA 02118, 857-362-7692
450 Harrison Ave, Boston, MA 02118

Boston Harbor Whale Watching: You may not immediately connect Boston with whale watching — given that it’s bitterly cold for several months of the year — but mid to late March starts whale watching season that lasts through November. While there are a few tours you can do on foot, we recommend a whale watching cruise to increase your chances of seeing the humpbacks. Boston Harbor Cruises operates catamarans that leave from Boston Harbor and go out a few dozen miles to the Stellwagen Bank National Marine Sanctuary. While there’s no guarantee you’ll see whales during the tour, you’re sure to enjoy the beautiful views.

Rose Kennedy Greenway: The Rose Kennedy Greenway is a long stretch of parkland that wraps around Boston from the North End to the Leather District. The greenway, which has been nicknamed the People’s Park, has four distinct parks all connected through pedestrian and bike trails. Each park area offers something different, whether it’s fountains for children to splash through or food vendors and picnic tables for an afternoon meal outdoors. The greenway also connects to the Freedom Trail, Harbor Walk, and Walk to the Sea self-guided tours or you can join one of the free fitness classes offered — just check the calendar.

Boston Symphony Orchestra (BSO): You’ve probably heard rumors of the exceptional talent of the Boston Symphony and Boston Pops Orchestras, but now is your chance to listen for yourself. They gave their first concerts in 1881 and 1885 respectively and host over 200 concerts annually. From the BSO you’ll hear music by the likes of Strauss and Stravinsky, whereas the Pops are a bit more playful in their selections. They might play the score from Star Wars: A New Hope live while accompanying the movie and welcome guest artists like Bernadette Peters and Arlo Guthrie. No matter your taste, seeing the BSO and Pops live is a magical experience.

301 Massachusetts Avenue, Boston, MA 02115, 617-266-1492

Isabella Stewart Gardner Museum: A visit to the Isabella Stewart Gardner Museum is as much for the art hanging on the walls as it is for the art that’s missing. In March 1990, two thieves dressed as police officers pulled off one of the biggest art heists in history which still remains unsolved. They made off with pieces by Rembrandt, Degas, Vermeer, and Manet. Some of the work, such as Rembrandt’s Christ in the Storm of the Sea of Galilee, were the only one of their kind in the artist’s body of work. The museum was once home to Isabella Stewart Gardner, who filled the walls with art from her own collection and stipulated in her estate that none of the pieces be removed and nothing new acquired. As a result, you’ll notice empty frames hanging from where the stolen works were taken. There’s a $10 million reward for safe retrieval of the collection, in case you’re up for the adventure.

25 Evans Way, Boston, MA 02115, 617-566-1401

Where to eat and drink in Boston:

Haley Henry: Sure, Boston is home to Sam Adams’ catalog of beers, but there’s also great wine to be drunk in the city. Haley Henry opened in 2016 in Downtown Crossing with the goal of toasting to health and education over their extensive wine list. The food menu is as long and varied as the wine, taking advantage of fresh New England seafood in dishes like oyster toast with leeks and dill oil, and sea scallop crudo with brown butter, sunflower seeds and capers. On the lighter side are radishes and Calabrian chili butter, and richer dishes like roasted bone marrow served with onion jam and sourdough toast. They’re closed Sundays and only open before 3pm on Saturdays for the brunch crowd.

45 Province Street, Boston MA, 02108, 617-208-6000

Tiger Mama: Though Tiger Mama sits comfortably in Boston’s Fenway neighborhood, don’t expect to find typical Boston fare on the menu. Chef Tiffani Faison has created an outstanding menu of Southeast Asian dishes and flavors, supported by Brian Callahan’s tiki cocktails. Tables are topped with lazy Susans, so expect to share everything. The spicy and umami flavors of the food are balanced by the fresh, living wall of plants and herbs. If you’re going with a group, the Tiger Duck is a must, putting that lazy Susan to good use. But, if you want to try a bit of everything, the papaya salad is a classic always worth ordering, as are any dishes from the “veggies” section on the menu. The spring dan noodles swap pork for short rib and are lightened with the addition of shaved asparagus. Each of the tiki cocktails is special in its own way, so you can’t make a mistake when ordering.

1363 Boylston Street, Boston MA, 02215 617-425-MAMA

Saltie Girl: Nothing says New England like a menu overflowing with seafood. Saltie Girl has an enormous stash of artisanal tinned fish, but where they really stand out is with dishes like fried lobster and waffles, pan roasted Atlantic cod and anything from the raw bar. Don’t walk in expecting to make changes to your order — modifications are (kindly) unwelcome. Beer, wine, and cocktails are available, some of which are meant to be shared, so take note before ordering.

281 Dartmouth Street, Boston MA 02116, 617-267-0691

Chickadee: Though Chickadee is closest to the Atlantic and named for the Massachusetts state bird, its menu is inspired by the Mediterranean. Dishes are led by the seasons and made with locally sourced ingredients whenever possible. Open for brunch, lunch and dinner, each meal is truly special. While we’re inclined to fill up on pastries like jelly donuts with rhubarb and rose petals at brunch, the asparagus carbonara with speck, a slow-cooked egg and parmigiano-reggiano is a must. At dinner, the smoked trout dip offers a mellow start before diving headfirst into a bowl of harissa cavatelli with lamb merguez, chickpea, rapini, and parmigiano. Although the cocktails on the menu are tasty, we recommend sticking with beer and wine to not overpower the excellent flavors of the food.

21 Drydock Avenue, Boston, MA, 02210, 617-531-5591

The Tam: Every city needs its own roster of dive bars, where you can go to enjoy friends without feeling like you need to speak in hushed tones or slowly sip your bespoke cocktail. The Tam is a cash-only dive in Boston’s Theater District, making for the perfect addition to your high brow-low brow night out. Mixed drinks are made with a heavy hand, so if you’re not looking to stumble out of the bar after last call, stick with canned beer — preferably a Narragansett (you’re in New England afterall). This is the spot if you’re looking to unwind with zero frills. Don’t expect anything but raw Boston personalities behind the bar.

222 Tremont St, Boston, MA 02116, No phone

Related: The Inside Out Guide to New York City

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