Category Archives: Back Bay

Boston neighborhoods

The city of Boston is comprised of 23 neighborhoods. Many of the downtown neighborhoods span less than a square mile, but they are full of interesting sites and places of interest. To that end, this month I selected four downtown neighborhoods and shared my thoughts about what make them worth visiting.

South End

I started this series with the neighborhood I know best, the South End. I’ve lived here for nearly twenty years now but have been visiting since I moved back to Boston in the late 1990s.

The South End is incredibly charming. Built on landfill in the mid-19th century as a residential district for Boston’s growing upper middle-class, hundreds of Victorian Bow Fronts were built and today it’s the largest enclave of urban Victorian residential architecture in the country. The picturesque neighborhood is full of parks, unique shops and restaurants and cafes. While only a few gay bars remain in the South End, this was once upon a time an enclave for Boston’s LGBTQ+ community and while most of those businesses have closed or moved online, this is still where many in Boston’s gay community come out for dinner or to meet up with friends for drinks. Read my full profile of the South End here.

Back Bay

I moved into the Back Bay in the late 1990s after living in Atlanta for a few years. I thought I’d live in my apartment on Commonwealth Avenue for a year maybe two but ultimately, I stayed in the Back Bay for six years. I still consider it a homebase and love this neighborhood for all that it has to offer.

If you’ve visited Boston, you’ve probably spent time in the Back Bay. It is a centrally located, afluent neighborhood with some of Boston’s most iconic buildings, busiest streets, best restaurants, bars and shops. It is chock-full of office buildings, hotels, retailers, restaurants and of course residents. Tourists will love the parks (my favorite is The Esplanade) that run through this neighborhood, but Back Bay also has amazing architecture ranging from the modern I.M. Pei design of The Hancock Tower built in the 1970s to the beautiful McKim Building of the Boston Public Library and its hidden Italianate Courtyard that dates back to the late 1800s. In addition, this neighborhood has no shortage of restaurants, bars and shopping so there is plenty to see and do when here. Read my full profile of the Back Bay here.

christopher sherman

Beacon Hill

I never lived in Beacon Hill but one of my best friends went to Suffolk University which is located here. I also spent many hours at bars in this neighborhood in my late 20s and early 30s.

Beacon Hill is a popular destination for visitors due to its many historical sites, with some dating back to the 1600s. While this neighborhood is less than a square quarter mile in size it contains a lot to see and enjoy with its pretty as a postcard streets to its many Freedom Trail sites of interest to great restaurants and good pubs. While the neighborhood’s stodgy image is well deserved there is still plenty of fun to be had here and my favorite time of year to visit is in the summer when you can sit outside and enjoy the people watching along Charles Street. For more information about this historic and interesting neighborhood, read my full profile of Beacon Hill here.

North End

The North End is where my maternal grandmother grew up as a kid. My brother briefly lived here and at the moment one of my cousins call the North End home. While I’ve never lived here, it is this familial connection to this tiny neighborhood that makes me feel connected to it.

The North End is charming unless you’re driving then it is a nightmare. The neighborhood is comprised of a maze of narrow, meandering streets that are chock-full of Italian restaurants, bakeries and cafes. The tiny neighborhood is hemmed in between Boston’s inner harbor to the North and East and The Rose Kennedy Greenway (a.k.a. The Greenway) to the West and South. This neighborhood is for those who love American History (esp. American Revolution) and for those who love food. For more information about Boston’s “Little Italy”, read my full profile of the North End here.

Boston neighborhood profile: Back Bay

View of Back Bay and the Charles River from Cambridge

If you’ve visited Boston, you’ve probably spent time in the Back Bay. It is a centrally located, afluent neighborhood with some of Boston’s most iconic buildings, busiest streets, best restaurants, bars and shops. It is chock-full of office buildings, hotels, retailers, restaurants and of course residents.

In the late 1850s the Back Bay was built from reclaimed land from the Charles River basin to accommodate the city’s growth so this is one part of town that won’t be on the Freedom Trail but it has plenty of history. The neighborhood was built for Boston’s well-to-do families who were looking for more space. Unlike older neighborhoods, this was built on a grid with intersecting streets running north to south in alphabetical order (Arlington, Berkeley, Clarendon Street, etc…). The massive landfill was completed by 1900 and wealthy families flocked to these new Victorian brownstones like The Gibson House, The Ames Mansion, and The Ayer Mansion to name a few.

Boston Public Library McKim Building

About The Back Bay: Back Bay is one of Boston’s wealthiest neighborhoods in America and while it is home to nearly 20,000 residents, it really serves as a commercial center, as well as a playground for tourists, day-visitors and residents from all over the city. Residences dominate the streets closest to the Charles River and Esplanade (Beacon Street, Marlborough Street, Commonwealth Avenue). Shopping and dining options take center stage on Newbury and Boylston Streets and as you move further south larger, commercial buildings designated for hotels and office space dominate the skyline along St. James Avenue, Stuart Street and Huntington Avenue.

When you visit the Back Bay, leave your car behind, because parking is scarce and expensive. The neighborhood is pedestrian-friendly, but if you don’t want to walk the MBTA’s Green Line runs down Boylston Street with three stops in the neighborhood (Arlington, Copley and Hynes) and the Orange Line Back Bay Station is across from the Copley Mall. While many books and movies use the Back Bay as a backdrop, Boston’s Back Bay in the Victorian Era is worth reading to learn about the neighborhood’s history, the people who helped build it and the many prominent familes who moved here in the mid- and late-1800s.

Boston Public Garden

What to do in the Back Bay: If you like architecture, you’ll love the Back Bay. The neighborhood has many churches built in the late 1800s (e.g., Christian Science Church, Trinity Church, and Arlington Street Church to name a few). These aren’t on the scale of Europe’s most famous cathedrals but they do enhance the streetscape and are beautiful. However, my favorite building is the Boston Public Library (a.k.a. the BPL). I love the original McKim building (1895) and the “new” addition that opened in 1972 as well as the many rooms inside but my favorite part of the library is the Italianate courtyard. It is a wonderful place to relax and grab a coffee.

However, I think the most photographed building in the Back Bay is probably I.M. Pei’s Hancock Tower built in the 1970s. It’s mirror reflection of the original Hancock Building (now the Berkeley Building) captures the spirit of Boston; modern, bold and forward thinking but proud and mindful of its past. Pei intentionally designed the Hancock Tower to reflect the (original) 1947 beaux arts Hancock building, ensuring we remember and learn from our history. If his design and architecture looks familiar it is because Pei would go on to become one of the most admired architects of the late 20th century. He would famously go on to create the glass pyramid for the Louvre in Paris.

The Back Bay has some of the city’s most beautiful parks. The homes lining Commonwealth Avenue look out onto the Commonwealth Mall, which is decorated with sculptures on each block and framed by large elm trees. I think it’s most beautiful in the summer and in December when the trees are full of tiny white lights. It is also the narrowest part of Boston’s chain of parks referred to as the Emerald Necklace. From the Mall, you can stroll up to the Public Garden, which is the oldest part of the Back Bay and where the marshland was first filled. It is the nation’s oldest public garden and dates back to 1837. Then there is my favorite park in the city, The Esplanade, which stretches beyond the Back Bay and has paths for walking, jogging and biking. There is always something happening here and it is an idyllic setting for a jog, a picnic with friends or in my sister’s case, a marriage proposal.

Restoration Hardware Boston in the Back Bay

Shopping in the Back Bay: Newbury Street is a favorite destination for shopaholics and window shoppers alike. Many luxury brands and art galleries can be found at the start of the street with more ecelectic shops (like my personal favorite, Trident Booksellers & Cafe) and musicians busking for tips in the blocks that follow. If the weather isn’t cooperating, walk over to the city’s only downtown malls (Copley and Prudential), which are adjoined via a pedestrian walkway over Huntington Avenue.

Shops open and close with a speed that can make your head spin. Rising rents and online shopping has been the demise of many independent shops. I still miss Boston’s LGBTQ bookstore, Glad Day Bookstore in Copley Square, but there is always a new shop opening and there is something for everyone. Need an ancient fuse for your apartment that hasn’t been rewired since the 1970s? No worries, head over to Economy Hardware on Mass Ave. Need a statement gift for someone who already has everything? Go to Simon Pearce or Shreve Crump & Low. Want to grab a bottle of wine to bring to a dinner party later this week? Bauer Wines has you covered. There are also more clothing, shoe stores and salons than I could possibly list covering every trend and budget from Valentino to T.J. Maxx.

Sonsie Boston photo from TripAdvisor

Restaurants in Back Bay: This neighborhood has everything you could want from cheap eats to some of the priciest meals in the city. It would be difficult to do this neighborhood justice in a single post, but I feel compelled to share a few places I enjoy.

If you’re more of a cheap eats diner, head over to the stretch of Boylston Street just west of Massachusetts Avenue and join all the Berklee music students at the fast casual dining options set up along this stretch of Boylston. If you’re willing to stand in line (there is always a line), probably the best noodle shop in Back Bay is Santouka. While it isn’t a “cheap eats”, it is still on the cheaper end for dining and their all-day breakfast menu makes the Trident Booksellers & Cafe on Newbury a personal favorite. However, many people come to the Back Bay to eat outside and for years Sonsie has been the place to see and be seen. However there are a great many cafes and restaurants that offer streetside dining like Atlantic Fish Co., Stephanie’s on Newbury and Piattini to name a few.

For a more romantic setting, I love the hidden Mexican restaurant, Casa Romero’s private patio garden, or reserve a table at La Voile. For a finer dining experience Deuxave (French), Uni (Sushi and Asian), Sorellina (Italian), Grill 23 (Steakhouse) and the Fairmont Hotel’s Oak Long Bar + Kitchen (American) in Copley Square are all great options. A newcomer to the Back Bay dining scene, scheduled to open in June 2021, is the rooftop restaurant and bar, Contessa, at the newly remodeled and branded Newbury Hotel. The restaurant is gorgeous and the expectations for the food and service are high. It is worth putting on your list of places to try this summer or fall.

Although I’m not one to spend a lot of time discussing sweets, the Back Bay has something to tempt everyone. For me it is a small independent chocolatier based in New Hampshire with a shop in the Back Bay called L.A. Burdick. When I am in the Back Bay I try not to walk within a block of this cute shop and cafe, because I inevitably find myself buying something. In the winter I rationalize the calories by purchasing the best hot chocolate in the city to keep me warm.

Bukowski Tavern in the Back Bay

Favorite Bars in the Back Bay: So many bars have come and gone over the years and recently, the coronavirus has driven a stake through the heart of many long-standing bars. It is my hope that those remaining establishments will be able to pull through. Similar to other residential neighborhoods, most of the bars in the Back Bay are also restaurants so places like Sonsie, Oak Long Bar + Kitchen and Grill 23 (all previously mentioned) are popular places in part due to their large bars to grab drinks with friends. However, if you’re looking to sit outside, there are only a few bars that have patios. The best option is the Loews Hotel restaurant and bar, Precinct. Their large sunken, lounge-like patio with comfortable furniture is a popular place to meet up after work for a drink.

One of my favorite dive bars in Boston is (ironically) located in a parking garage. Bukowski’s Tavern, named after a German-American poet, is the only bar I regularly visited when I lived in the Back Bay that remains open. Back then, if you hesitated ordering a beer the Irish bartender would spin a wheel on the wall behind the bar (you can see it in the far right in the photo). Whatever it landed on was what you received. This happened to me once, and I was stuck with a $20 specialty Belgian beer. I never again hesitated.

What to do, man dancing

Gay Life in the Back Bay: This neighborhood has many LGBTQ+ residents. Moreover, this is where many travelers opt to stay when they visit Boston because of its central location, proximity to points of interest and Boston’s traditional (if no longer) gayborhood, the South End. Gay bars, bookstores and other shops moved out of the Back Bay mostly due to high rents by the late 1990s. My favorite gay bookstore in Copley Square, We Think The World of You, closed about 20 years ago. The last gay bar I can recall in the Back Bay closed before that. However, on any given night you will see gay friends meeting for drinks at many restaurants and bars in the neighborhood. If you are visiting and would prefer a gay owned establishment that markets themselves to the LGBTQ community go to Club Cafe on the Back Bay / South End line.

If you happen to be new to Boston or planning a visit, feel free to reach out to me with any questions. If you are familiar with Boston’s Back Bay, recommendations and comments are welcome.

Boston Public Library McKim building opened 125 years ago

BPLThe Boston Public Library (BPL) in Copley Square first opened its doors to the public on Sunday, February 3, 1895, and tomorrow marks the 125th anniversary of this iconic building’s opening. While this wasn’t the first home of the library, it is the only home anyone alive today would know.

The BPL is the 3rd largest public library in the United States behind only the U.S. Library of Congress and the New York City Public Library. However, it’s not the amazing amount of research nor its prized collections or priceless artwork  that make this such a beloved institution.

The BPL anchors the west side of Copley Square in the heart of Boston’s Back Bay neighborhood. It is where many important cultural and sporting events take place; such as the finish line of the Boston Marathon.

Since 1897, every April (on Patriot’s Day) tens of thousands of runners cross in front of the  Boston Library and every parade of note either lines up alongside or pass by these buildings.

BPL, Todd Van HoosearThe original building (a.k.a. The McKim building) and its gorgeous courtyard that was inspired by Rome’s Palazzo della Cancelleria are sanctuaries I go to often and places I show anyone who visits Boston. Bates Hall (shown below) on the second floor of the McKim Building features 50-foot-high barrel vault ceiling and is a must-see for any architecture enthusiasts. Travel + Leisure agrees with me too – check out their 2016 article about the BPL here.



Next time you’re in the Back Bay, take a few minutes to pay the BPL a visit and appreciate this cultural gem.

Sun setting over Boston’s Back Bay neighborhood

Earlier this week my friend Cyrus Dahmubed posted this gorgeous photo of the sun setting behind the Hancock Tower in the Back Bay (for all you wise asses, I know it’s now called 200 Clarendon but it will always be the Hancock to me).


Happy Easter

Here is a throwback to the spring of 2002 when Sergio and I lived in Back Bay and our neighbor was raising “show bunnies”; you read that correctly by the way.

We figured this would be our only chance to be photographed with so many bunnies so we took the opportunity and made the most of it.

Boston Public Garden

bret clancy, boston skyline, boston winterEstablished in 1837 The Boston Public Garden is a beautiful park in the center of town. I thought I’d share this gorgeous photo taken by Bret Clancy who has many photos of Boston on his IG account and available for sale on Etsy here. Much thanks to Arts Boston Instagram for posting this picturesque photo of kids playing hockey last month.

Trident Booksellers & Cafe has reopened

boston, independent bookstoreQuite possibly my favorite bookstore (certainly my favorite bookstore in Boston), Trident Booksellers and Cafe, was forced to close temporarily after a fire broke out in late February, but last week the bookstore reopened after undergoing extensive renovations.

The Trident’s cafe / restaurant was a favorite location of mine when I lived in the Back Bay so even if you’re not much of a reader you can go enjoy some food then check out their monster magazine rack or purchase a few funny cards. Keep in mind, the Trident now has daily entertainment / programming every evening so there really is never a bad time to stop by and see the newly renovated space.

While I’ve yet to have a chance to visit the bookstore I wanted to help get word out and encourage everyone to visit the Trident on Newbury Street between Hereford Street and Massachusetts Avenue.

Show this local business some love.

Trident Booksellers and Cafe
338 Newbury Street – Back Bay
Store Hours:  8AM to Midnight daily

Back Bay Boston Pride block party today

gay bostonAlthough the annual Back Bay Boston Pride block party isn’t the official closing party, for many of us who have to work on Monday morning, it signals the end to another Boston Pride.

The outdoor block party runs from 1PM – 9PM. For more information click here. Below are a few photos from years past.

gay bostongay bostongay bostongay bostongay bostonHappy Pride Everyone

Back Bay/South End Gateway project is approved

boston real estate, boston development

Click on image to enlarge  ||  Source:

ICYMI, another HUGE project was approved by the city of Boston last week. Boston Properties received unanimous approval from the Boston Planning and Development Agency board last Thursday for their air-rights project above the MBTA’s Back Bay Station.

The project will add 1.3+ million-square-feet of mixed-use development, including a new 34-story building,office building with ground floor retail, two new residential buildings, a one- to two-story vertical retail expansion of the existing Back Bay Station building, and the partial redevelopment of the existing 165 Dartmouth Street Garage. For more information visit

Newbury Street open to only pedestrians this Sunday

Boston, Back BayThis Sunday, July 23rd (from 10AM – 6PM), Newbury Street will be open only to pedestrians between Arlington Street and Massachusetts Avenue.

The event, officially known as “Open Newbury”, has many retailers hosting promotions to entice pedestrians who are expected to come and enjoy the one mile promenade through Back Bay.

Boston Public Garden at night by James Sutherland

About three weeks ago James Sutherland snapped and shared this beautiful photo of the Boston Public Garden. Since then the Public Garden has transformed as the trees have flowered and the buds have been replaced with leaves, but I loved this photo with Boston’s Back Bay off in the distance, seemingly enveloped in fog.

Back Bay / South End Gateway proposal updated

boston real estate, Back Bay T Station

Back Bay/South End Gateway proposal will include 1,260,000 sq ft

Last month the development team for the Back Bay/South End Gateway project shared their revised plans to transform the MBTA Back Bay station, the neighboring 100 Clarendon St. parking garage, as well as the entire block bound by Dartmouth, Stuart, Clarendon streets and Columbus Avenue, which also includes four air-rights parcels.

Their plans call for a sprawling mixed-use complex that includes three new high-rises that would accommodate residential, retail and office space, including an office tower with ground level retail. In addition, a new 11,000 square-foot public plaza has been proposed for the Clarendon Street side of the station.

Images below were provided from the February 1, 2017 documents shared with the Boston Planning and Development Agency. All images are from the Back Bay / South End Gateway Project Draft Environmental Impact Report. Click on the images below to enlarge.

Source: The Back Bay / South End Gateway Project Draft Environmental Impact Report Source: The Back Bay / South End Gateway Project Source: The Back Bay / South End Gateway Project

More modifications will likely be made before it gets board approval. Public comments on the project will be accepted until April 16 and can be directed to Michael Rooney, project manager for the Planning & Development Agency, at For more information on the project link here.

1000 Boylston proposed in the Back Bay

boston real estate, 1000 Boylston

Photo courtesy of Weiner Ventures

Did you hear? A developer has asked the city to review a proposal to build two residential towers over the Massachusetts Turnpike where Mass Ave and Boylston Street meet.  According to the article on Curbed Boston, one building would be 39 stories and the second would be 24 floors; combined they would include as many as 330+ condominiums / apartments.

Boston has a checkered past approving developments that span air rights because the cost often requires developers to build towers taller than neighborhood groups like. I’m curious to see how this proposal is received because I would LOVE to see the pike covered all the way down to Fenway.

Peebles Corp., Back Bay real estateNOTE: The shorter S-shaped image next to the proposed 1000 Boylston is not part of the developer’s proposal. That is a separate development called The Viola that is expected to start construction in 2019 and will include a 156-room hotel, 88 condos, 138 parking spaces, community areas and 26,000 square feet of retail space. The building’s footprint will stretch from Mass. Ave to Dillon’s Restaurant & Bar on Boylston Street and would feature a distinctive s-shape.

Newbury Street becomes pedestrian walk way on Sunday, Aug 7

Boston, Back BayNext Sunday (August 7) the city plans to shut down Newbury Street to traffic for one day only, offering a pedestrian-friendly street free of traffic from 10:00 a.m. to 6:00 p.m. The idea is being borrowed from other pedestrian-friendly cities like Paris where the Champs-Élysées is now closed one day per month to cars.

The city is promoting the event using the hashtag #OpenNewbury on Twitter.

Boston’s Love Locks



Back in 2013, in honor of the death of DOMA, three small heart shaped locks were shackled to the ugly chain link fence over the Massachusetts Turnpike on Massachusetts Avenue in the Back Bay.

Since the summer of 2013, many more locks have been added and now the chain link fence is covered by several hundred padlocks; each presumably to symbolize and commemorate relationships here in Boston. Some of the locks have names, dates, or quotes written on them, which you can read if you look closely.  Boston Love Locks