40 Local Leaders Share Their Favorite Places in Boston
Everyone’s got one, after all. We asked 40 local leaders—people who know this city inside and out—to share their secret go-to spots. Here are the spaces, sanctuaries, and spectacular views that bring them joy and make us all proud to live here.
Edited by Andrea Timpano
Reporting by Spencer Buell, Colbi Edmonds, Catherine Elton, Erin Kayata, Ann Matica, John Spooner, John Terhune, and Lisa Weidenfeld
CEO of Moderna
Pre-pandemic, Toscano Restaurant had almost become my family’s Saturday lunch canteen. We know the menu so well that when we sit down, we don’t even look at it. The food is excellent, and everybody has a favorite. My youngest daughter, who is 17 now, always orders the four-cheese gnocchi. She will dream about it all week long. My wife is the only one who orders the specials. And I order the veal Milanese. Every time.
We also love the team at Toscano. They have a very strong loyalty to the restaurant, so the servers are always the same. It makes you feel almost like you are going to a place that you have known forever. Plus, we run into people from the community all the time there. Because it’s such an institution, it is rare that we go and don’t see somebody we know. That’s part of the Toscano ambience. It is super homey and, because it is in our neighborhood, it feels like part of our family and household.
Suffolk County District Attorney
Jamaica Pond is an absolutely gorgeous green space in the middle of our city. It’s also a community where you can see bikers, joggers, and walkers of all ages and backgrounds. I have a special appreciation for it because of my dad. Really, some of the most special memories I have about my childhood are the times I got to spend with him walking and talking at Jamaica Pond.
Now, I bring my own family there. Victoria can have her little scooter or bike. Meya can have her roller skates. And I can just pull my sweatshirt hood up and put a hat on so people don’t recognize me. It’s just an opportunity to move my body and think alone for a little bit. As a family, we can all enjoy it for our own reasons.
Fresh Pond Reservation
Fresh Pond Reservation in Cambridge is wonderful. It’s not only my favorite place, it’s my husband Bruce and dog Bailey’s favorite place. We walk Fresh Pond every morning and every evening that we possibly can. We’re out there when the first sprigs of green arrive in the spring and when the first touch of color hits in the fall. We’re there in gorgeous sunshine, mist, ice storms, and high winds. We always make jokes about going surfing there when the wind really whips up. Fresh Pond puts the rest of my world in perspective.
It also probably saved my sanity during the pandemic. When we couldn’t be out to do anything else, we could always go to Fresh Pond and make a loop. By the end of our walk, as we’d get back in the car, I always felt like I could handle whatever came next. When we lost my brother early during COVID, after I got the call, Bruce held me for a few minutes and said, “C’mon, let’s go out to Fresh Pond.” And that’s where we went. It’s our place.
Mayor of Boston
Ron’s Gourmet Ice Cream & Bowling
Ron’s Gourmet Ice Cream & Bowling in Hyde Park is our family go-to for a celebration, a pick-me-up, or just because. I’m a loyal caramel-fudge brownie fan, Conor goes for the frozen pudding, and the kids mix and match. This family business has brought joy and delight to our neighborhoods with friendly faces behind the counter, locally made ice cream that’s among the top-ranked in the world, and candlepin bowling that has drawn families for decades. And I’m proud to count my family among the generations who have made Ron’s a second home for so many delightful memories and moments.
Founder of Christopher Kimball’s Milk Street
You can tell a lot about a restaurant in the first five seconds. You can tell if it’s about passion. You can smell it, you can see it, you can hear it. For my wife, Melissa, and me, sitting at that little bar in the back of Oleana is our favorite place. We’ve spent a lot of evenings there over the years. You get a sense that nobody designed that restaurant as a business concept. Owner Ana Sortun went into it because she had just a tremendous passion for Turkish cuisine in all of its infinite variations, and I think that represents the very best of the restaurant industry. Like the best cooks, she hasn’t changed her formula; she stuck to what she loves, and does it in this intimate, highly personal setting.
President and CEO of Colette Phillips Communications
The ‘Quin House
The ‘Quin House is the hottest new club in Boston. I’m there at least once a week either for lunch, breakfast, or dinner. The food is off the charts, and the people are extremely friendly. You walk in and the personnel know exactly who you are. It’s a very friendly, inviting, inclusive environment. And it has many different levels. You can go formal, you can go casual. You can watch sports. If I have a lunch meeting at the ‘Quin, I will go up to the Reading Room after and have a private Zoom call and conversation without interrupting anyone else or being interrupted. I can take my laptop and work from there. It’s a great place.
CEO of Sportsmen’s Tennis & Enrichment Center
Harambee Park is in Dorchester. It used to be called Franklin Field years ago. When I was a kid I used to play soccer in the park, and there were some adults that were playing that would just let me fit in with them a little bit, which was a lot of fun. I like that the park is a gathering point for people from diverse backgrounds. It’s a place where you can go hang out for a day and see all these different sports taking place right up close. Dorchester itself has become more diverse since I was born here almost 60 years ago, so the sports that are being played there are more robust and vibrant. They draw people not only as players but as spectators. At Harambee, you see very traditional sports such as baseball, basketball, and football. But you also see cricket and lacrosse and, as a result, you get to learn about different sports and different cultures. You meet people that you might not otherwise have the chance to meet.
Conductor of the Boston Philharmonic
Acoustically, Symphony Hall is possibly the greatest concert hall in the world. It has an uncanny sound that you can’t quite believe. When I bring down my baton at the beginning of a piece, the sound that comes from the stage is of such beauty, clarity, and transparency, and yet such power. As it travels back into the hall, it becomes more and more beautiful and more and more rich. There are no bad seats in Symphony Hall, but the best seats in the house, generally speaking, are in the last row of the second balcony. With certain kinds of music—and I’m thinking particularly of Bruckner’s Eighth Symphony, which I did in my first concert with the Boston Philharmonic—the sound is probably as beautiful as you can find on the planet.
The hall is kind of a nirvana or mecca for musicians. Every time I bring a new musician in to play with the orchestra, they’re always amazed. The excitement levels shoot up literally from every player, whether they’re young and have never been there or they’ve been there 100 times. You never get over the excitement of playing, so I can’t think of any place in Boston that causes this amount of joy and satisfaction.
President of University of Massachusetts
The UMass Club
The UMass Club is a special place for me because it connects people who want to learn from each other and share ideas. A highlight for me was the time two champions of civil rights—my friend and former congressional colleague John Lewis and Supreme Judicial Court Chief Justice Margaret Marshall—visited along with other close friends and colleagues, and we talked about making “good trouble.”
Artistic Director of the American Repertory Theater
There is nothing better than spending time at the Arnold Arboretum of Harvard University. This 281-acre museum of trees is a stunning sanctuary that invites us to reflect on our relationship to nature. When asked what got me through the pandemic, I say “trees.” There was nothing more centering than taking in a tree’s beauty, energy, and history. The past year and a half has made me more aware than ever that our relationship with the natural world is inextricably connected to our health and wellness.
Co-author of Charlie Numbers and The Woolly Mammoth
Mandarin Oriental, Boston
We love staying at the Mandarin Oriental, Boston. They did this whole renovation, and the suites are designed with little kitchenettes in them. So it’s kind of catered more toward families and people who may not want to go out to restaurants while they’re traveling. We did my husband Ben’s book launch there and stayed in their presidential suite. It was basically like having an apartment in the city. You can just pop into the mall from the hotel, so when we were staying at the Mandarin, we loved to run over to Eataly and go to the bookstore with our kids. That was just awesome. The hotel is very dog-friendly, too, which is another thing I always enjoy. We love to travel with our little pug puppy, who felt so welcome there. Our puppy is like a part of our family. And there was another fun thing: The Mandarin has this robot that can deliver stuff like a toothbrush. The kids loved ordering toothbrushes and bottles of water from it.
Founder and CEO of Boston While Black
One thing that’s really cool about Boston is that you don’t have to go to the beach if you want to be near the water. Castle Island is off Morrissey Boulevard, so you’re still very much in the city. I’ve often gone there after work. Walking around and being able to witness the sun setting and the skyline of the city—it’s just a really great experience. The ability to have access to space and water even in a metro area is really important and unique. It’s part of what makes Boston a great place to live.
CEO and Owner of the Varano Group
There really is one place that’s truly my favorite, and it’s because I was born and raised there: our Little Italy in Boston’s North End. When my mom and dad came from Italy, my mom opened a beauty salon on Salem Street. My greatest memories are growing up around the Italian culture. There was something special in that neighborhood. One place, Galleria Umberto, was one of four or five places where I–you know, a chubby little kid–could go every day and buy pizza with no money. They would write it down, and my mother, after finishing her week at work at the beauty salon, would go there and pay them. It was like a credit account. Just being in that atmosphere around the people who made that neighborhood so amazing is something I’ll always cherish, and it’s still like that to this day. Some of those people are actually still there. It’s funny, I went into Umberto’s today and saw that the two brothers that were there back in the ’70s and ’80s are still there on Hanover Street, working the counter as though it was the 1970s. I got a slice of pizza—well, to be honest with you, I got three slices of pizza. If you want to experience Italian culture, you can make a day or two full days of just running around that neighborhood, seeing everything. It’s something special, and there’s nothing like it in the United States.
Ibram X. Kendi
Founder of the Center for Antiracist Research at Boston University
Nubian Square Public Art Initiative
One of the things that I look for in a city is whether it has murals. So naturally, I’ve been keeping an eye on the Nubian Square Public Art Initiative. When I came across the Reflection Eternal mural by ProBlak (Rob Gibbs) and Marka27 (Victor Quiñonez) in Roxbury late this summer, I had to stop and take a second look. This mural is beautiful. Powerful. Poignant. Eminent. Not only were the colors captivating, but the story behind the piece grabbed me. When I read up on it and saw that the mural celebrates the healing process of creating and receiving art, I sat in stillness. It left me in awe because it honors the legendary [Black artist] Paul Goodnight. Like Frugal Bookstore (the only Black-owned bookstore in Boston), the mural is evidence of the power and necessity of conserving Black art. We preserve and create art in the face of resistance. As Mr. Goodnight says, “We gotta get lost in what’s right.” Art helps us heal our nation. To honor our complexity and refute the denial that history exists solely in the past. We are living and marking history—and this is what ProBlak and Marka27 did when they started painting here.
Chef/Owner of Trade
Victory Road Park
A year ago, my husband and I got two rescue dogs, Anya and Miki. A couple of months after we got them, I discovered Victory Road Park, which is a peninsula near our house in Dorchester. It’s this amazing place where people go with their dogs. They can let them off the leash, and the dogs can just run. There’s a little hill, there are trees, there’s brush, there’s a beach. I go there every morning, and often I’m the only one there with my dogs. It’s a time to set the foundation for the day. My mind stops; all I’m paying attention to is what the dogs are doing. Or, if there’s somebody else there, I’ll interact with other people or dogs. There’s this funny social world of the few people that I do interact with when I’m there. We don’t really know anything about each other besides our dogs. So it’s just this slice of my day that’s sort of protected. It’s almost like the peninsula itself is a metaphor, because a peninsula is surrounded by water; I feel like that hour of my day has a moat around it that protects me from worrying about what’s next. I just pay attention to what’s in front of me, appreciate the skyline, the wildflowers, the changing of the trees. It’s just a beautiful little bit of paradise in Boston Harbor.
Massachusetts Attorney General
For me, it’s the Esplanade—either by Community Boating, sitting on the docks there, or down by the Hatch Shell. It’s just beautiful anytime of the year; the foliage, whether it’s in the fall or the spring, is a beautiful part of our city. You look out and you see people from all walks of life running along the Esplanade. It’s a place that I like to run anyway. And you’re right on the river. I actually have loved kayaking out there and seeing the sailboats.
Alberto Vasallo III
President and CEO of El Mundo Boston
Museum of Science
I’ve absolutely loved the Museum of Science ever since I was a little kid. It’s kind of like my local Disney World: It’s the happiest place in Boston for me. When I walk through those exhibit halls, it brings me back to fifth and sixth grade—a simpler time. It’s like that “Stand By Me” time, right? After you reach a certain age, not everything is as innocent. I go back to the museum and I’m back in school, and we don’t have all these problems. We don’t have the pandemic. It’s a time machine. I now have a business relationship with the museum, which is doing this huge outreach into the Latino community, but I still look at it as my iconic childhood place.
CEO and President of the Boston Foundation
One of my favorite places, where I go for sustenance and inspiration, is Franklin Park. It’s a shining jewel, connecting five of the most diverse neighborhoods in the city. It has such a rich history. I am grateful to encounter the great diversity there.
If I want a sense of what this city actually is, and could become, I will head right for the park. People talk to me as I walk the miles of trails. Some of them recognize me, and often I see people I’ve known for years, all seeking the refuge the park offers. It’s tough to believe that something so beautiful is smack-dab in the middle of the city.
African Meeting House
When we toured the African Meeting House at the Museum of African American History as a prospective venue for our 2014 wedding, Conan and I felt the immediate presence of our ancestors. It was important to us both that we be married in a church and in a Boston location rooted in rich, significant—and usually unknown—Black history. Built in 1806, the African Meeting House is the oldest Black church building in the country and the site where several prominent abolitionists came to speak, including Frederick Douglass and Maria Stewart. The African Meeting House represents Black resistance, excellence, faith, and joy. It was the heart of political, cultural, and educational gatherings for Boston’s free and thriving Black community in the 19th century. On our wedding day, in this sacred gathering place, we felt the embrace of our village and our ancestors, including my beloved mother, Sandy, who we lost to cancer several years prior. When our pastor asked, “Who gives this woman?” a dozen women, each holding an 8-by-10 black-and-white picture of my mother holding me as an infant at a tenants’ rights march, proudly declared, “We do!”
Founding Member and First President of the Friends of the Public Garden
Boston Public Garden
In the 1970s, the Boston Public Garden was almost totally neglected. The grass, the flower beds—pitiful. The women’s restroom had broken windows, and toilet paper rolls on a rope that had to be tossed over the stalls to reach anyone. The mayor in the 1970s, Kevin White, along with a real estate developer, wanted to build a 40-story building that would cast giant shadows on the park and cause winds to gust up to 60 miles an hour, potentially ruining this gem. I helped form a committee to fight this tooth and nail. At the time, I was also teaching the mayor’s son in school. He’d tell people, “In school, he’s a sweetheart. In Boston, he’s a son of a bitch.” The publicity we got through this battle brought in money and media support from everywhere. We won. The developer moved to New York. Now, the entire Garden is beautifully maintained.
Chairman of Mintz
We all come back, sooner or later, to roots. The magnet for me over the years is where I grew up in East Boston. My house on Sumner Street was the oldest house in the community. There was a huge grain elevator right there, about 20 stories high. It blocked all of our views. When it was time for high school, I took the old South Ferry to the North End. We called it the “penny ferry.” I went to Christopher Columbus High School and was taught by Franciscan priests. We still have high school reunions, and none of us can believe we’ve come so far from those days. When I go back to East Boston now, I particularly focus on something that didn’t exist until recently: Piers Park. It’s the most gorgeous space, done in an absolutely first-class way, with full access to the waterfront and the best views of downtown Boston. There are a bunch of pavilions that line long walkways. I wander the park, which seems to have everything for Eastie residents, and for tourists as well: an exercise facility, a playground area, and even a section for concerts or plays or anything you’d want to celebrate. Piers Park is my magnet.
Cochairman of Colliers
The University Club of Boston
I’ve been a member of the University Club of Boston for more than 50 years. We all need a refuge, and if we’re lucky as adults, we can find one. The University Club is it for me. And within the club, my special focus is the men’s locker room. That’s the icing on the cake. I’m not a barfly. I don’t hang out there. My place of restoration is that locker room. I played squash there for years. I never took to golf. Physically, golf was fine. But mentally, I was a wreck whenever I played. With squash, I always felt it was mentally great and physically tiring: perfect as a lead-in to a good night’s sleep. I now go to the cardio room and do about 45 to 50 minutes on the elliptical and the bike. And I love the diversity of this locker room. You’ll see restaurateurs, dentists, politicians, lawyers, stock brokers—a cross-section of all the professions in the city. I am proud to have been a president of the club. As a real estate person who’s very involved politically as well as in the philanthropic side of Boston, it’s key for me to be close to the pulse of the city. You can get the real gossip of this town from the University Club locker room.
Founder of Booty by Brabants
It’s definitely the Seaport. I live there, and it’s also where I taught one of my first-ever Booty by Brabants (BBB) workout classes and sold my first few pairs of BBB leggings. Everyone says it’s like my hub. I do everything there. I love grabbing my coffee at La Colombe Coffee Roasters. I love LoLa 42. I do a lot of girls’ nights at Ocean Prime and Nautilus Pier 4. I’m just inspired by the energy in the Seaport—how fresh and youthful it is. It has a city vibe, but still it’s not so busy that I feel like I’m in New York. It gives me the best of both worlds.
Father John Unni
Pastor at Saint Cecilia Parish
Engine 33, Ladder 15
I do a lot of bike riding. I walk all over the city as well. But one of my favorite destinations is the firehouse—Engine 33, Ladder 15—on Boylston Street, almost opposite the Prudential Center. I often walk there after mass. That’s the firehouse that lost two men in that horrific Back Bay conflagration several years ago. I love talking with people, and the gang at the house give me energy and laughter. They’re great cooks, and they also give me leftover stuff from their fridge: steak tips, pasta, grilled veggies, pieces of pie. “You’re just a mooch, Father,” they tell me. But it’s good banter. I think all of us feel good about my visits to the firehouse. It’s a good place to go during the day or night and touch base with them. And they’re always good for a lot of laughs and some deep conversations.
Chairman and CEO of Suffolk Construction
My favorite place is the community surrounding Suffolk Construction’s headquarters in Roxbury, where we moved the company approximately 30 years ago. I chose this location for our headquarters because the Newmarket District was traditionally underserved and hidden from the rest of the city, but still managed to punch above its weight because of the hard-working people living here. I wanted our building to serve as an anchor for this community and spark interest and future investment. Having our headquarters here allows us to be the eyes and ears for the community and serve as its advocate when necessary.
This community has been in the news recently because of the tragedy of Mass. and Cass. Every day on the way to work, we pass by people who are struggling with homelessness, drug addiction, and mental illness. We must remember these individuals are someone’s sons and daughters, brothers and sisters, and friends. They just need help. They all want to be loved by someone. Regardless of our address or standing in the community, we must always remember there are others, oftentimes in neighborhoods that are outside the beaten path, who need our support.
Owner of the Lyons Group
I go to this little coffee shop on Newbury Street to get my morning mocha. It’s called the Thinking Cup, a cozy and popular neighborhood joint. But it’s my kind of joint—lots of people and action, a place that makes us feel happy and welcomed. It’s really a little microcosm of the clubs and restaurants and venues I’ve always tried to specialize in. Their cups are also a delight, all made of recycled materials. The baristas even make little hearts floating in your coffee.
Then I take the New York Times and sit in my car as the people in the city move around me. I turn on the radio and listen to Howard Stern. The juxtaposition of the Times and Stern always triggers what I’m going to focus on that day. Then I mix in the Globe online and I’m prepared for almost anything.
We all have our rhythms. If you can find someplace that starts your day with a smile…go for it.
President of Kraft Family Philanthropies
My favorite place is Jordan Club in Chelsea, for the Boys & Girls Clubs of Boston. My first job after college was teaching history as an intern at Belmont Hill School. Then a friend happened to call me and told me about a job at a small teen center in Chelsea. It was in the basement of a housing development. I took the job, and that was the start of my love affair with Chelsea, a neglected but amazing immigrant community for people of all races, religions, and nationalities. Eventually that basement with a handful of kids turned into a brand-new clubhouse for the Boys & Girls Clubs of Boston. It’s not just the Jordan Club that inspires me. It’s Chelsea itself. I see the hardworking, resilient people, whether they’re working for a small business or leading community nonprofits. It’s so powerful to see how people there come together for those in need. There’s a lot of love in that little area north of Boston. Although I’ve been so lucky for the life I lead and the family I have, I will never forget the character and compassion of Chelsea and its residents. I drive over to visit quite often, even in my new role with the Kraft foundation, grateful for what Chelsea has taught me. And still does.
CEO of Boston Impact Initiative
SOWA Open Market
My favorite area is the South End, specifically the SoWa Open Market and all of its different components. I used to live right across the street from it and saw it grow from a tiny market to a place where people from all over Greater Boston come to enjoy the vendors and the different galleries. It became this experience that I watched unfold throughout the 10 years that I lived on Harrison Avenue. It was not the prettiest area when I first lived there, and the market actually helped transform it into this thriving destination for tourists.
Former Justice of the Massachusetts Supreme Judicial Court
One of my precious places is Mooo, the restaurant at the top of Beacon Hill inside of the XV Beacon Hotel. Mooo has been our celebratory go-to place since it opened. My husband, who was also a judge, and I tend to be particular about our likes and dislikes in restaurants. But the attractions of Mooo are several. It’s the only place where we can find real old-fashioned beef Wellington. It’s fabulous there. Also, they have one of our all-time favorite desserts, bananas foster. It’s a New Orleans specialty, and it’s difficult to find on local menus. Very often it’s the timeless things in life that are the best.
Top American Finisher at the 2021 Boston Marathon
Bear Cage Hill
I ran at least 10 different cross-country races at Franklin Park over the years, and there’s this one spot called Bear Cage Hill. It’s a windy hill that runs right past the old zoo’s bear cages. In middle school, I remember the older kids telling us scary stories about how a bear got loose from there and took off running after some kid in the race one time, so you should make sure you’re not in last place. Later it became a landmark: If you want to win, make sure you put your nose to the grindstone and run hard up those 400 meters. Once you can see into the bear cage, you know you’ve done the hard part and you can just let it rip after that. It’s similar to the idea of getting over Heartbreak Hill; once you get to the top, it’s downhill all the way through to the finish. It’s a little bit of a mind game. Our running coach Chris Fox always told us if you can crush the hill and get a bit of a lead, then maybe you can crush the other runners’ spirits. The lessons I learned running in the park with my teammates all throughout high school and college carried over and shaped the runner I am today.
Cofounder of General Catalyst
Deuxave and Uni
I have two favorite places: the yin and yang about what matters in life. The sense of taste is one of those things. My wife, Nina, and I moved into Boston several years ago. Not for the usual reasons, including being empty nesters. Downsize? Nope. We moved in to be next to the twin towers of our lives: two restaurants, one very French, one very Asian. Deuxave is on the corner of Mass. Ave. and Commonwealth Ave. French to the core. The other is directly across the street, Ken Oringer’s Uni. Chris Coombs is the chef at Deuxave. The greatest tasting food in Boston lives on the west side of Mass. Ave. Culinary excellence. My favorite dish at Deuxave is the lobster gnocchi. I know, I know, Italian creeps in a bit. But it’s too tasty not to mention. At Uni, it’s the spicy tuna roll and shishito peppers. Important to get contrast in life.
This might sound like a controversial or an unpopular opinion, but I love driving down Storrow Drive and seeing the foliage across the river in Cambridge. And then conversely, specifically at night, driving down Memorial Drive and seeing the Boston skyline lit up across the Charles. I used to do a lot of stand-up in Boston and Cambridge, and I got a lot of those views coming home from shows late at night. Being across the river always gives you that feeling of like, wow, it’s yonder. You know what I mean? It’s off in the distance and it feels more remote and imposing. I love seeing the city from the fringes. It’s the same kind of feeling as when you’re touching down in an airplane and you’re like, oh, there it is. It just feels really nice and peaceful.
CEO and Chairman of Intercontinental Real Estate Corporation
I grew up in nearby Belmont, and I always favored the independent movie houses in the area. One of my favorite places is the Capitol Theatre in Arlington. They have real butter that they put on the popcorn. I like that they also have ice cream at the stand, so you can drop a scoop of vanilla ice cream into your popcorn. They have good teas and snack foods, too. It’s not as nice as some of the modern cinemas with the luxury chairs and seating, but there’s a romance to going to that theater. It’s a beautiful building. I used to take my older children to the movies there. It just felt less like going to Disney World, you know? It’s more intimate—the waiting in line and waiting for your popcorn, the whole thing.
Cathedral High School
My favorite place evolves. I think the spirit of Boston kind of lives in me, so anywhere that is in Boston feels like home. Right now, my favorite spot is Cathedral High School in the South End, where I teach a music appreciation class. Some of the most amazing humans I’ve met in the past year exist there and are growing there. They are building relationships with each other and with me and the other staff there. My students are really special people. I think all the kids there either know they’re special, or they just happen to be special. And I happen to be lucky enough to witness it. All the students are just eager to learn and grow—to develop. And it’s kind of just like, if you’re excited about music and you believe in it and you believe in them, they open themselves to it, which is really cool.
Clarrissa Cropper Egerton
Co-Owner of Frugal Bookstore
Roxbury Heritage State Park
One of my favorite places is right here in Roxbury: Roxbury Heritage State Park. It’s not a huge area, but it’s packed with so much history. It’s the home of the Dillaway-Thomas House, [the headquarters of the Continental Army during the Siege of Boston in 1775]. There’s a map at the house of how it used to look, and it’s cool to see the before-and-after pictures of the area.
Because the park is really close to the bookstore, after a nice long day, you can go and walk up the hill off Malcolm X Boulevard and then stroll through the neighborhood. The First Church, which is across the street from the park, is like a time-traveling machine. Some churches you go in and can see some modern upgrades, but this church still has original history. You can see it, you can hear it—it’s kind of squeaky when you walk inside of there. This place had been occupied by ancestors, people who came before us, and it’s still standing. I think, like the park, it’s a true testament of the area, the neighborhood, preserving and making it a historical place so that more generations to come can experience it.
Cohost of Boston Public Radio
When I think about Boston, I think about the peeks into history. The whole city is an inspiration, but the real magnet for me has always been the Citgo sign in Kenmore Square. No matter where you drive, you can see it from almost anywhere. Storrow Drive. Memorial Drive. Its lights have been such an attraction for me. In college, I took a summer course at BU, and I lived right next to it. We made a 30-second documentary-type film about Kenmore Square. It was set to the song “Summer in the City” by Lovin’ Spoonful, and the film talked about the noises in the city—the traffic and the horns—and the sign’s lights. And as an adult, I used to take my kids there when they were little. I live exactly 2 miles away from the sign. It’s not the most gorgeous thing you’ll ever see in your life, but it looks even better now that some of the bulbs have been fixed.
Cohost of Zolak & Bertrand
Grill 23 & Bar
My family and I like to go to Grill 23 & Bar, especially around the holidays for birthdays—we’ve got a couple of birthdays in December. I usually get the porterhouse, which is cooked to perfection. They really char the outside of the steak. The inside of the steak is awesome, too; it’s always moist. That’s the best thing about going there. You know your food will be made the same way every single time.
Harvard professor and former assistant secretary for intergovernmental affairs
I think the most magical and somewhat inspiring place is on the Red Line, where it emerges from the tunnel between Kendall/MIT and Charles/MGH and goes over the Longfellow Bridge. The view gets me every time. It’s a beautiful part of Boston, and the Charles River never fails to disappoint. I’ve been doing that T ride into Boston since I was in college, and every time it’s just such a miraculous moment. You’re coming from the dark into the waters of Boston, which is just so fantastic. It’s just a moment where you’re like, “This is quite beautiful.” I don’t think I imagine it, but I think the T goes quiet when you leave the tunnel. It’s such a great view.
Author of White Hot Hate: A True Story of Domestic Terrorism in America’s Heartland
Payson Park Reservoir
We call it “the Rez,” which is short for Payson Park Reservoir. It’s an elevated area off Payson Road in Belmont. I go there almost every day. A lot of those visits are mandatory because I have a dog and need to walk her every morning. I can complain about it, but once I’m out there and have come home, I say, “Gosh, I’m glad I did that.” It’s always been this way to get out of the house and get out of myself. It just provides solace, especially during the pandemic. I’m always drawn to the Rez because you climb up, circle the park, and have a commanding view. At different times of the year, I might be able to see the lights at Fenway Park or some fireworks in the Seaport or a full moon.
It feels so much closer than if I just look out my window. It gives me this sort of “big sky” moment that really is refreshing.
Chef/Owner of Fox & the Knife
I love the Orpheum Theatre in Downtown Crossing, and have been going there since I moved to Boston 22 years ago. It’s one of the country’s oldest music venues, originally founded as the Boston Music Hall in 1852. I recently saw a drag show there, and it felt especially meaningful, as it was the first live event I’d been to since COVID-19. My spouse and I found our seats and talked about all the shows that we’ve seen there over the years—together and before we met. I love the nostalgia of the space, both the venue’s and my own. When I walk under the sign to enter the theater, I not only remember concerts I’ve seen in the past, but I think about all of the amazing shows that have been played there in the past decades. As our small and independent music spaces disappear from Boston and Cambridge, it feels especially poignant that the Orpheum is still standing.