12 Best Things to Do in Boston
- 1/12
Isabella Stewart Gardner Museum
Zoom out. What’s this place all about?
At once intimate and unparalleled in its grandeur, the Isabella Stewart Gardner museum draws on the art collection of its eponymous founder. Within a Venetian-style palazzo, surrounding an elegant courtyard decorated in verdant plants, masterpieces hang next to architectural elements Gardner purchased from Europe. The ambience of the museum itself is a treasure, and the wonders it holds offer a one-of-a-kind experience. If you’re lucky enough to be in Boston during the third week of the month, soak up the museum’s monthly Third Thursdays event, when neighbors come together to sip champagne, listen to lively music in the courtyard, and laugh together over gallery games.What will we find in the collection?
Gardner’s personal collection reflects her thirst for travel, a bohemian lifestyle, and the fine luxuries of ancient cultures. Stewart Gardner herself delicately arranged the collection of more than 7,500 fine and decorative art objects, 2,700 books and manuscripts, and over 8,000 historic objects from around the world, including sculptures, furniture, textiles, metalworks, and ceramics, that she collected over the course of her lifetime. (She provided an endowment to operate the museum, stipulating in her will that nothing in the galleries should be changed, and no items be acquired or sold from the collection.) During one of many tours abroad, Gardner set a world record for her purchase of Titian’s Rape of Europa, outbidding representatives from Paris' Musée du Louvre and London's National Gallery. In 1990, the largest property theft in the world left the museum without 13 works in its permanent collection, including pieces by Degas, Vermeer, Rembrandt, and Manet. A $10 million reward still stands for information on the stolen works, adding even more intrigue to this beloved museum.What about temporary exhibits?
Seasonal exhibits often pull from the Gardner’s extensive collection or feature the contemporary work of current or former artists-in-residence. Steve Locke’s 2018 exhibition, “Three Deliberate Grays for Freddie (A Memorial for Freddie Gray),” for example, challenged visitors to look at violence and racism in the United States.What did you make of the crowd?
The legacy of bohemian heiress Isabella Stewart Gardner attracts curious travelers and locals who adore this oasis in the city. It's not the best museum for kids, but it’s a thrill for artists who come here to sketch. And because of the almost spiritual experience of walking through the serene courtyard, this is a visit even museum-averse guests will enjoy.On the practical tip, how were the facilities?
The historic palazzo and modern wings are all accessible. Be aware, though, that the original galleries (as arranged by Gardner) often feature low lighting and use narrow hallways to connect different parts of the palazzo.Any guided tours worth trying?
During weekdays, the museum gives guests two types of free days tours that enliven a visit. Take an introductory guided tour for an overview of the museum or deepen your understanding with a collection conversation, both of which add tremendously to your connection to the marvels within these walls. On the weekend, sign up for a spotlight talk or an open studio art event.They’re not tours, but it’s also worth noting the museum’s music schedule: There are classical concerts practically every weekend, and more contemporary ones once a month on Thursday evenings.
Gift shop: obligatory, inspiring—or skip it?
Gift at the Gardner matches the whims of its namesake in its artsy, refined choices. This bright, modern shop curates the work of small-batch makers from around the world alongside art books and accessories. The best souvenir may be coffee mugs decorated with snappy quotations attributed to Gardner. “Shan’t you and I have fun with my museum?” one says.Is the café worth a stop, or should we just plan on going elsewhere?
The Gardner’s bistro, Café G, serves elegant dishes in a contemporary space framed by glass walls. It's part of the Renzo Piano-designed addition to the museum, which opened in 2012 and provides interdisciplinary, multipurpose space for contemporary artists, musicians and scholars. The café is an easy spot to savor a salad or light entrée for lunch (the café is only open for dinner on Thursday). Lucky for you, nearby Fenway is a culinary hotspot, so keep your options open for dinner.Any advice for the time- or attention-challenged?
Although two hours is ideal for a meaningful visit, you can walk through the museum in one hour if you keep a steady pace. The Spanish cloister features must-sees like El Jaleo, by John Singer Sargent, a portrait of Isabella Stewart Gardner by the same artist, and Titian’s Rape of Europa. - 2/12
Brattle Book Shop
What's the skinny?
In the heart of Boston’s downtown, carts and shelves of $1, $3, and $5 books fill an alley off of West Street. The seller: Brattle Bookshop, a store that encompasses three floors of used books, the top one filled with rare collectibles. Its purveyor, Ken Gloss, is a regular appraiser on the PBS’ Antiques Roadshow and has gained modest fame among antiquers and public-television addicts.What can we find here, or what should we look for?
The subtle thrill on the lower floors is the hunt. From cheap reads to remarkable copies of beloved classics, the inventory runs the gamut, in part because of the enormity of their incoming stock from estate sales. There’s no way to go wrong given the number of gems hidden among these stacks. While the outdoor carts are organized by price, indoor stock displays like a library, with books shelved by categories (e.g., music, world history, sports, world history, black studies, religion).If money’s no object, what goes in the cart?
Make a beeline for the third floor. Here, uncover rare books and collectibles with prices that top $100,000. Third floor sales have included Yellowstone National Park, illustrated in watercolors by Thomas Moran, 1876 ($165,000), the two-volume, first edition of Lolita c. 1955 by Vladimir Nabokov ($1,250) and a signed photograph of Abraham Lincoln ($75,000). If you came to Brattle Bookshop with a big wad of cash, speak to Ken or his wife, Joyce, about finding a first edition of the most meaningful book in your library. A future family heirloom is more than becoming of a trip to a college town.And … what if we’re on a strict budget?
If you’re counting change, buy something obscure and unknown from the $1 section outside. It may be marked down, but that doesn’t mean it’s any less worthy of a cover-to-cover read.Who else shops here?
Independent bookshops attract an eclectic mix of characters, and that’s as much a part of the experience as the books themselves. Curmudgeonly regulars, bespectacled students, and travelers who value a good read all make Brattle Bookshop an institution. Even J.D. Salinger stopped here once.What stands out the most?
You’ll remember the sheer volume of books, and if you’re a reader, the joyful struggle of committing to just one or two. After all, most people don’t bring an extra “book suitcase,” although now would be the time to do it. - 3/12
Seaport District
What makes this neighborhood worth a visit? Strolling around this high design neighborhood, expect manicured waterfront walkways, tiers of high-rise glass towers, green spaces aplenty, and art-strewn streets. Keep an eye out for Frank Stella’s mural reproduction of Damascus Gate (Stretch Variation I) and seven Boston-themed monumental sculptures lining Seaport Boulevard. Discover some unique retail therapy with Direct-to-Consumer brands that have set up shop, such as Everlane, Helly Hansen, and jewelry store Mejuri. Furthermore, don’t miss a visit to the Institute of Contemporary Art (ICA), even if it’s just to admire the eclectic museum for its architectural greatness. Also consider Legal Harborside (the flagship location of Legal Sea Foods), Wood Hills Pier 4 (farm-to-table dining), Flight Club (darts, beers, and bites), Committee (Greek-Med hotspot) and the Lookout Rooftop. Though Boston Seaport is only partially complete, it’s currently the hottest place to hang out, eat, drink, and live in Boston.
So what's the vibe throughout the neighborhood?
Positive and ready for the future.How easy is it to get around?
You can wander the neighborhood at your own pace, but given the size of the Seaport, you might find yourself Ubering to and from certain places.What's the crowd like?
Although we love old-school Boston, the Seaport's modern vibe feels like a breath of fresh air. The streets are filled well-dressed young professionals on lunch breaks and travelers admiring the neighborhood's growth.What will we come away from a visit with?
Given the many opportunities for retail therapy, expect to leave physically with several shopping bags in tow. In addition to the conversation-worthy long-term retail tenants, the Seaport houses ‘The Current,’ a pop-up village with an ever-changing collection of local Boston retailers, all worth getting to know.For those who thought they knew Boston, the Seaport is a harbinger of a more modern city. Finally, those who like to dig deeper than the superficial may leave with a heavy heart. Within the Seaport, Martin’s Park reveals a dark but important side of Boston’s recent history. The park honors Martin Richard, the youngest victim of the 2013 Boston Marathon bombings—he was only eight. The beautiful waterfront park is an eternal celebration of young Martin’s life.
Any parting words of advice before we plan a day here?
You don't need to spend an entire day here, but it's certainly worth coming to see what all the buzz is about. Feast on an amazing meal, sip libations at Boston’s best rooftop bar, and enjoy the people-watching. Yahoo News is better in the app
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- 4/12
Tatte Bakery & Café
What's the vibe?
It's easy to understand why Instagram influencers flock to Tatte, with its unmistakably Parisian aesthetic of black-and-white subway tile and antique apothecary table repurposed into a pastry counter. Often filled to the brim with guests, Tatte's original location in Brookline is more than a decade old and has since expanded to 16 cafés in the Boston area.Who's sitting around us?
Boston University students cluster together to indulge in pastries, while neighborhood families jockey for seats, and the occasional tourist from Fenway fights indecision at the counter. The energy here can border on joyful chaos, especially when winter weather confines guests to the indoor seating area.Give us some suggestions for drinks.
Stumptown coffee and local Mem teas serve as the backbone for Tatte's thoughtful drinks, all of which are poured behind elegant marble counters. If you're visiting on one of those blustery Boston days, curl up in a corner seat with a Belgian chocolate mocha.The moment we've all been waiting for—the food. What's there to eat?
Tatte's Parisian aesthetic underscores the French-Israeli menu that's enthralled the city. Owner Tzurit Or bakes in the French tradition with Middle Eastern ingredients, and she's turned Boston's dining obsessives on to the joys of halva, za'atar, and halloumi. Shakshuka is served three different ways—traditional, lamb meatball with labneh, or summer vegetable—and always draws an adoring crowd. Salads pair greens with rich accompaniments like seared halloumi cheese and creamy tahini vinaigrette.And the service?
The team at Tatte can be strapped for time, as is the nature of a café with more guests than tables. They keep things rolling, but you may find them somewhat harried during the lunch rush. If you catch them outside of peak hours, they're happy to chat about the menu in more detail.Well, we're sold—any other tips?
Tatte delivers on fancy food without the formalities of a reservation. Given the coffee-shop style seating, you either have to time your meal strategically or put up with a bit of mayhem. Keep your party small and nimble; bringing large groups can be precarious considering the near impossibility of securing a table that will fit everyone. - 5/12
Museum of Fine Arts, Boston
Zoom out. What’s this place all about?
The crown jewel of Boston’s art scene, the Museum of Fine Arts (MFA) houses more than 500,000 works of art in a striking neoclassical building abutting the Back Bay Fens park. Wholly historic and beautifully modernized, it enriches you with a deep sense of gratitude for the cultural heritage of the world.As the fifth-biggest museum in the United States, the MFA is a significant draw to this small city, and Bostonians are immensely proud of its collection, exhibitions, and dynamic programming, from film festivals to art courses. No matter your interests or disinterests, you can find something that resonates with you here.
What will we find in the permanent collection?
The MFA’s vast collection of art and artifacts is exceptional by any standard. The museum houses one of the best collections of Korean art outside the Korean peninsula, the only permanent exhibition space for ancient coins in the United States, one of the world’s largest holdings of ancient Egyptian treasures, and its most comprehensive collection of work by John Singer Sargent. The museum’s claims to fame are so varied in fact, you could spend weeks documenting its exceptionality.
The MFA collected the works of Claude Monet during his own lifetime, and you can see the museum’s impressive holdings of his art in a gallery devoted to his oeuvre. These hang in the European Wing, reinstalled in 2016 with one of the greatest caches of the Impressionist’s work outside of France.Today, the museum’s leaders continue to invest in contemporary art that draws this institution deeper into the 21st century and heightens the promise of the its continued legacy. And they’re always updating galleries to better display work from across the centuries. Check out the impressive Arts of Islamic Cultures Gallery, whose summer 2019 reinstallation was developed in collaboration with local Muslim groups.
What about rotating exhibits?
With over 10 seasonal exhibits on view at any given time, there are always world-class options to choose from at the MFA. An intentional range across mediums, experiences, artists, geography, and time periods cultivates surprise. Every time you walk into the museum, you can expect to see something new. For an absorbing visit, pick one exhibit that you think you would enjoy and one that challenges you rather than trying to jam in all 10.What did you make of the crowd?
This prestigious museum attracts visitors from all over the world, but it rarely feels packed. You’ll notice a 50/50 balance between art lovers and passerbys taking an obligatory walk through the galleries during a visit to the city. Devoted members of the MFA also weave through its halls, quietly bringing their attention to previously unexplored exhibits or beloved parts of the museum’s collection.Any guided tours worth trying?
Free daily programming makes it easy to crack through the novice perspective you may have brought to the MFA. A 60-minute guided tour of the museum, gallery talks, and weekly drawing sessions bring depth while also keeping things accessible. If you would rather immerse yourself in the museum solo, you can take one of eight different audio tours ($6).Gift shop: obligatory, inspiring—or skip it?
The three museum shops lure you in with the promise of beautiful objects inspired by the MFA’s noteworthy collection and rotating exhibits. Among the classics—art books, mugs, scarves—you’ll find a mix of delightful gifts that you may not need, but you definitely want.Is the café worth a stop, or should we just plan on going elsewhere?
The MFA gives guests a handful choices for a drink or a meal. Its Garden Cafeteria lacks the charm of the higher-end options but opens onto a leafy courtyard that’s perfect for an iced tea in summer. Of the other three options (escalating in fanciness)—Taste, New American Café, and 465 Bar and Restaurant—465 is the most expensive and likely to deliver, but none are home runs. Instead of indulging in a possibly not-so-great museum meal, take a break in the outdoor courtyard or the indoor Ruth and Carl J. Shapiro Family Courtyard overlooking the Chihuly installation.Any advice for the time- or attention-challenged?
A short visit to the MFA means you need to narrow your ambitions. The Art of the Americas Wing is a worthy focus, with 49 galleries that explore the art and artifacts of this continent with increasing emphasis on ancient American and Native American art. Galleries like “The Revolutionary Boston and New Nation” provide deeper understanding of Boston’s irreverent spirit and iconic role in American history. There you'll find John Singleton Copley’s “Paul Revere” and Thomas Sully’s expansive “Passage of the Delaware,” that hallmark image of George Washington on horseback. - 6/12
Public Garden
What's the big picture?
A manicured Victorian daydream, the Public Garden is a delight to behold. In 1837, George Meachem won a contest for the garden’s design and his vision of a tree-filled haven dotted with over 80 species of colorful plants is still impeccably managed by Boston’s Parks and Recreation Department. The Commonwealth Avenue entrance serves as the park’s most enchanting introduction, with a statue of George Washington surrounded by flowers greeting you at the gate. In this pleasurable moment, remember that Victorian Bostonians found this park to be offensively bright. Oh, how times have changed.Any fun features we should be sure to see?
The lagoon, which wanders almost the entire length of the garden, adds a swath of blue to this oasis of green. The Paget family has managed the lagoon’s Swan Boats for over a century, and the promise of a leisurely ride on their foot-peddled boats is an old-fashioned delight.The famed ducks are also worth snapping a picture of. Make Way for Ducklings, the iconic children’s book by Robert McCloskey, tells the story of a family of ducks that make a home in the garden’s lagoon. In 1987, the park installed sculptures by Nancy Schön of Mrs. Mallard along with her eight duck children. All of the ducks don festive attire during holidays and big New England sports events.
Was it easy to get around?
Given its rectangular shape, the Public Garden is easy to navigate along any set of its walking paths. A plethora of benches make the prospect of a pitstop a good idea.So, what should our plan of action be?
Bostonians breeze through the gardens as a shortcut from one side of town to the other. Follow their lead and take the paths en route from Back Bay to Beacon Hill. It also abuts the oldest park in the country, the Boston Commons, and it’s easy to walk both in one go. Yahoo News is better in the app
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- 7/12
The Freedom Trail
Tell me: What’s this place all about?
The Freedom Trail starts at the Boston Common, the oldest public park in the United States, following a red brick path lined with 16 storied landmarks, which paint a picture of Boston’s revolutionary history. The most appealing part of the 2.5-mile trail is that you can choose your adventure, hopping on and off to explore beyond a set route.What’s it like being there?
Although tourists flock the Freedom Trail, this pedestrian path coincides with the day-to-day rush of downtown Boston. You’ll see revolutionary sites in a modern setting and walk alongside commuters and kids after-school. The experience paints a fitting portrait of how Boston has evolved around these landmarks, which have become a part of everyday life.What's the deal if we want a guide?
The Freedom Trail Foundation offers 90-minute guided tours led by historical actors dressed in 18th-century garb. If you can get over the costumes, you’ll learn a lot from guides, who provide an in-depth primer on revolutionary history while in character, which is harder than it looks! If you would rather take an audio tour, download the foundation's snazzy new smartphone app and benefit from guided expertise on your own schedule. During Black History Month (February) and Women’s History Month (March), the foundation also leads specific tours with a narrow focus on the historic contributions of each group.Does it live up to the hype?
Boston’s Freedom Trail is essential part of any trip in this city that’s a walker's dream—as long as the weather holds. It's hard not to feel the history by walking this path, tread by people who honor the city’s lasting legacy as the birthplace of the revolution.So, what if we don't have time to do the whole thing?
If you’re short on time, prioritize the North End section of the trail, home to landmarks like the Paul Revere House (c. 1680), Old North Church (c. 1723), and Copp’s Hill Burial Ground (c. 1659), in a historic neighborhood that’s known as Boston’s “Little Italy.” In fact, this section of the trail is the perfect place to throw away the map (or turn off the Google Maps) and simply wander the cobblestone streets. You’ll ogle the mix of architecture from all periods of American history and stumble upon some fabulous hole-in-the-wall bakeries and restaurants serving up Italian classics for a nice respite from all the colonial history. - 8/12
Charles River Esplanade
Let’s start big picture. What’s the deal?
A narrow paradise along both sides of the Charles River, the Esplanade stretches for three miles from the Longfellow Bridge to the Boston University bridge. Over 1,500 trees, charming bridges, playgrounds, ponds, and gardens bring a lyrical quality to this meandering landscape, all of which has been cultivated over the last century to create a calming waterfront retreat. When the green trees brighten into sparkling reds and oranges in autumn, the Esplanade shows its true colors.What should we put on our must-see or must-do list?
The Hatch Shell is a half-shell performance space that serves as home base for all things at the Esplanade. Friends meet here to go for walks and enjoy countless free activities, from Zumba classes to concerts. (The venue is most famous for featuring Boston Pops on the Fourth of July.)Boston is fantastic when seen by the water, and the Community Boathouse (the first public boating program in the country) is the perfect jumping-off point for a river paddle. On a nice day, hop in a kayak and explore the inlets that curve through the Esplanade before floating down to the Massachusetts Avenue bridge. The less adventurous can settle on a dock with a sandwich, which is equally rewarding and doesn’t require a life preserver.
Anything tricky about getting here?
Divided from Back Bay by harrowing Storrow Drive, the Esplanade requires crossing over perpetual traffic on one of eight pedestrian footbridges. Be aware that only some of these bridges are handicapped-friendly; the Arthur Fiedler footbridge at Arlington Street is wheelchair accessible and an ideal starting point.All said and done, what's the best path to take?
If you’re exploring Boston for the day, take a walk up through Back Bay from Massachusetts Avenue and loop back down along the Esplanade. If at any point you need a break, you can pop back out to Beacon Street or relax along the water. If you’re feeling ambitious or want the best city views of Boston, cross the Harvard Bridge on Massachusetts Avenue and continue east along the Cambridge side of the Esplanade, crossing back to Boston at the Longfellow Bridge. - 9/12
Harvard Square
Tell me: What’s this place all about?
Home to the country’s oldest and most prestigious university, Harvard Square is where you'll find some of the world's most international and intellectual residents (fitting for a petite square that has had an outsized impact on the world). You don’t have to be a student to savor this neighborhood, which, interestingly enough, keeps expanding as businesses and buildings try to latch themselves onto the atmosphere and accessibility of its much-beloved epicenter.What’s the vibe?
Eccentric and enlivening, Harvard Square feels like the quintessential college town plopped into a city. Brick sidewalks and painted colonial homes share space with street performers, shops, and some of Boston’s best restaurants.How do we get more info when we're there?
Although there are tours of this neighborhood, helpful plaques and a plethora of reading material (check out Harvard Book Store) make its history accessible without a guide.What's the crowd like?
Harvard Square isn’t off the beaten path—tourists come in droves to walk the famous Harvard Yard. Far fewer tourists stay for a genuine wander, and that’s the best way to take in the campus and the neighborhood.Any favorite spots you can share?
Take an afternoon and evening to sink into this corner of Cambridge, and you’ll have discovered a city unto itself. You’ll find art and natural history museums on Harvard’s campus, quirky boutiques for souvenirs like Black Ink, Grolier Poetry Book Shop (the oldest in the country, opened in 1927), world-class restaurants like Alden & Harlow, Waypoint, and the legendary pizza joint that’s been feeding Harvard students for more than 30 years, Pinocchio’s Pizza. Plus, you’ll stumble upon histories like that of Christ Church, where George and Martha Washington once worshipped, Theodore Roosevelt taught Sunday school, and Rev. Dr. Martin Luther King, Jr. gave powerful sermons on Civil Rights and peace in Vietnam.Got it. So who should come here? Where should we go if we're stretched for time?
There's something for everyone in Harvard Square. At the least, plan for a dinner here and set aside time for a post-meal stroll on campus. Yahoo News is better in the app
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- 10/12
South End
Tell me: What’s this place all about? Boston's South End is a neighborhood with both spirt and soul. Picturesque streets here reveal the area's mid-to-late-19th century roots with vast collections of Victorian row houses and European-style square and circular parklands. The streets also unearth more recent endeavors in revitalization—the neighborhood was neglected for much of the 20th century until the LGBTQ community began investing in the late nineties. Nowadays, the South End continues to embrace diversity and houses some of the city’s best restaurants, markets, boutiques, and design showrooms plus the best dog parks.
Who comes here? The South End is far more residential than touristy and that's its charm. You'll dine at insider haunts, cross paths with the neighborhood's surfeit of dogs (and dog walkers) and admire the mix of refinished brownstones, reimagined warehouses, and new construction.
Did it meet expectations? This neighborhood has the kind of charm that'll make you want to move to Boston. There are so many historic plaques that pique your interest of the neighborhood's past and an abundance of small, hidden art galleries and design showrooms that will keep you searching for more.
So then what, or who, do you think it’s best for? Art and design aficionados should definitely come here on Sundays, when the South End's SoWa Art & Design District shows off its weekly best. This is when you can visit the treasure-filled SoWa Vintage Market, and browse the expansive, art-filled SoWa Open Market and the SoWa Farmer's Market. Beyond the markets, discover a number of art galleries, one-of-a-kind boutiques and design showrooms (which are typically open seven days per week). The South End is also a requisite Boston stop for foodies. Try, for example, Black Lamb, an elevated American brasserie that impresses with a sensational raw bar and sublime lobster rolls.
- 11/12
Arnold Arboretum of Harvard University
Let’s start big picture here. A gorgeous 281-acre green space within Boston, Arnold Arboretum of Harvard University is the oldest public arboretum in North America (c. 1872) and the highlight of Frederick Law Olmsted's famed Emerald Necklace. Prolific biking and walking trails zigzag past more than 16,000 accessioned plants, many meticulously marked with signs. The natural splendor is a feast for the eyes, which are able to spot the sheer diversity of trees and plants at every turn. QR-coded signs and the arboretum’s easy-to-use “Expeditions” app make it possible to dig deep into the environment.
Any standout features or must-sees? There's not a bad view to be had in the entire arboretum. But a good starting point is the quarter-mile long Explorers Garden Tour, which showcases dozens of exotic plants from Central China and Korea plus the much-photographed Franklin Tree, which once grew in Georgia but is now extinct in the wild.
Was it easy to get around? The arboretum is easy to navigate, but it's also easy to get lost (Don't worry, given the many well-marked intersections, you won't stay lost for long.) The best thing to do is to download the “Expeditions” app, which has a map feature that will help guide you along trails and keep you on track during audio tours. Since the terrain is hilly and not all paths are paved, touring the arboretum could prove difficult for those with mobility issues.
All said and done, what—and who—is this best for? Arnold Arboretum is free 365 days a year and open from sunrise to sunset. Tree huggers and budding botanists will find themselves in heaven, but anyone looking to immerse in nature and learn (a lot) in the process, will find a visit here time well spent. Grab one of Boston's blue rental bikes, breeze across the city, and enter through any of the eight entry gates. Note that bikers must stick to paved roads. Alternatively, explore by foot (and off-road), starting at the Forest Hills gate, accessed by taking the Orange Line to Forest Hills. This is the way to do it if you’re looking to learn anything or everything about this awesome collection of trees, which happens to be one of the world's most comprehensive and best documented collections of temperate woody plants.
- 12/12
Lookout Rooftop
What are your first impressions? Wow, this is one big rooftop bar! Unlike its contemporaries occupying slivers of rooftop real estate, The Lookout spans the entire length—and almost the entire width of its building. Located on the waterfront edge across from downtown, the views are tops—literally. There's a buzz to the place, with small groups of friends laughing, chatting, and dancing in their chairs to mash-ups of 80's pop and modern hip-hop, and drinking the night away. It almost feels like pre-pandemic times.
How’s the crowd? With a (deserved) reputation as Boston's premiere rooftop bar, Lookout often reaches capacity with the city's work-hard, play-hard young professional crowd (Reservations are required these days; no walk-ins). For most, Lookout isn't a novelty—it's a mainstay—though you may find the occasional bridge-and-tunnel-type folks later on weekends. The crowd definitely likes a solid cocktail but they're here for the views, vibe, and highly social atmosphere.
How are the drinks? The bar menu doesn't channel the apex of mixology, but there's a solid, creative cocktail selection. There is also a handful of beers on draft plus 15 by the bottle as well as an impressive selection of wines by the glass (almost two dozen!) One of the cocktail standouts is the Bee Line, a sweet mix of Aberfeldy Scotch, honey, lemon, passion Fruit, and ginger beer.
If there’s food, is it worth ordering something to eat? There are a trio of similar food menus, one for lunch, one for dinner, and one more for late-night, all with bar bites and hot sandwiches. Given current pandemic guidelines, patrons must order food in addition to drinks. The must-get on all menus is the tostones with guacamole. If you want something more substantial, try the beer battered fish sandwich with truffle fries or the lunch-only lobster roll.
Did the staff do you right? Servers are busy but they make regular rounds to their tables and booths. The turn-around time between ordering and drink/food delivery is remarkably fast.
Wrap it up: what are we coming here for? In a city that skews historic and can feel sometimes like a college town, The Lookout Rooftop provides big-city appeal with a cool crowd, awesome skyline views, and strong drinks.
Aspire to the Ivies, discover new neighborhoods, and feast like a local.
Originally Appeared on Condé Nast Traveler