Boston neighborhood profile: Beacon Hill

Louisburg Square on Beacon Hill – photo from Wikipedia page

Beacon Hill is a popular destination for visitors. It’s chock-full of history and historical sites, with some dating back to the 1600s. While Beacon Hill is considered a very desireable neighborhood and one of Boston’s (and the nation’s) wealthiest addresses, that was not always the case. As early as the late 17th century, the south slope of Beacon Hill earned the nickname, “Mount Whoredom”. From the 1930s through the 1960s, Beacon Hill was home to many nightclubs and bathhouses that catered to “pansies” who would then spill out onto the Boston Common to cruise for sex. Those days are long gone and difficult to imagine today, considering Beacon Hill’s current prim repute.

I never lived in Beacon Hill, but I spent plenty of time here especially in college and my late 20s. My most vivid memories of Beacon Hill involved the much dreaded moving days for my friend Tom who attended Suffolk University. He always seemed to live on the top floor of every building. Getting furniture up and down those tiny, twisting walk-ups was torture. I distinctly recall hurling pillows out of Tom’s 3rd story window on Joy Street, and him running back and forth in the street trying in vain to catch the flying projectiles. Moving day always resulted in a significant amount screaming profanities at each other. Fortunately, there was always a cold beer (or twelve) after the move.

Massachusetts State House sits atop Beacon Hill

About Beacon Hill Beacon Hill is home to more than 9,000 residents. Despite it’s sky high rents, many Suffolk University students and Mass General Hospital (a.k.a. MGH) residents live here. The neighborhood is also awash with State government employees and lobbyists who spend a lot of time at the Massachusetts State House. Many politicians make this their home, like former US Senator, 2004 Democratic Presidential candidate and Joe Biden’s Special Presidential Envoy for Climate, John Kerry who lives in Louisberg Square.

This tiny neighborhood, which barely spans a square quarter mile, is divided into three sections: the South Slope, facing Beacon Street and The Common; North Slope, facing Cambridge Street and Mass General Hospital; and the Flats, which like its name suggests is not a hill and is sandwiched between Storrow Drive (think Boston’s version of the Henry Hudson Parkway) and the Public Garden.

Acorn Street in Beacon Hill is a favorite spot to snap a photo

What to do in Beacon Hill This is an historic neighborhood known for its Federal-style rowhouses, narrow streets lit by gas lamps and bricked sidewalks. The best examples of this are Louisberg Square and Acorn Street. The neighborhood also has the good fortune of being surrounded by some of Boston’s most beautiful parks including the Boston Common, The Public Garden, and Esplanade. These parks are full of interesting sculptures like this personal favorite in The Public Garden, and in 2022 I’m looking forward to the unveilling of the Martin Luther King and Correta Scott-King memorial on The Common. The parks host many free outdoor workouts, movie nights, concerts and events throughout the year including (my favorite) free performances of Shakespeare on the Common in the summer.

The Freedom Trail traverses Beacon Hill and will guide you to the Park Street Church, King’s Chapel and Burying Ground, Old Granery Burying Ground and State House, but Beacon Hill has more to offer like Boston’s African American National Historic Site, Nichols House Museum, and the William Hickling Prescott House. While it lacks historical significance, those of a certain age may recall the MTV series Real World, filmed in the late 1990s in Boston. I’ve been known to break-up Freedom Trail visits with a quick stop outside the former Boston firehouse at 127 Mt. Vernon Street where Real World Boston was filmed.

When you get tired of walking around and photographing this quaint neighborhood, you’ll likely find yourself drawn to Charles Street which stretches several blocks from Beacon Street to Cambridge Street along the Flats. Here you’ll find an array of ateliers that include gift shops, antique stores, local grocers and other specialty retailers. There are also more than a few coffee shops and cafes but my favorite is the Tatte Bakery & Cafe because of its central location and outdoor seating. There is a complete list of Beacon Hill shops online here, but I recommend strolling around. It’s a short walk and to quote Boston poet Ralph Waldo Emerson, “it’s not the destination, it’s the journey.”

Beacon Hill
Contrary to what NBC told you – nobody knows your name here

Food and Drink in Beacon Hill: Cheers, which is located in “The Flats” below The Hampshire House, remains the most famous establishment in Beacon Hill some thirty years after the popular NBC TV show went off air. However, there are far better places to drink and certainly better places to eat. Even though this is one of Boston’s most expensive neighborhoods, there are many good, reasonably priced restaurants. Some of my favorites are 75 Chestnut, which has a lively bar if you can nab a chair. If you’re hungry for pizza, I’ve always enjoyed Todd English’s Figs on Charles Street and right next door is the Paramount, which serves breakfast in addition to lunch and dinner daily.

Beacon Hill also has its share of fine dining if you’re in the mood to celebrate. One of the city’s best restaurants, No. 9 Park, run by Chef Barbara Lynch is just steps from the State House and is the perfect destination to share a romantic dinner. Just around the corner is one of Boston’s best hotels XV Beacon. Their restaurant, Mooo, is an excellent steakhouse, but I prefer their brunch, which they offered pre-pandemic. If you’re craving Italian, the subterranean Grotto Italian restauant behind the State House and Lydia Shire’s Scampo (technically in the West End) are favorites.

Although I rarely go to Beacon Hill for drinks, at one point in my life I clocked a lot of time at The 21st Amendment and The Sevens Ale House. Both are great pubs and fun places to meet up for a drink after work. If you’re more into wine or cocktails, go to Mooo’s bar. I’ve yet to try Peregrine, a relatively new restaurant in Beacon Hill’s newest boutique hotel, The Whitney, but it is on my list of places to try. In good weather, the best option for a drink outside is the patio at Liberty Hotel’s lounge, Alibi.

Destiny Boston is werqin‘ it at Drag Me To Brunch

Gay life in Beacon Hill: Beacon Hill is not a gay neighborhood. It hasn’t had a gay bar or shop for decades, although there are plenty LGBTQ+ residents. Prior to the pandemic, Carrie Nation in Beacon Hill had one of the best drag brunches in Boston called, Drag Me To Brunch hosted by Destiny Boston and Dee Dee de Ray on Sunday afternoons. Fingers crossed this will return later this year. As you can see from the photo above, it is predominantly attended by straight (and loud) women out for a fun afternoon rather than gay clientele.

If you happen to be new to Boston or planning a visit, reach out with questions. If you are familiar with Boston’s Beacon Hill, recommendations and comments are welcome.

Scruffy Sunday

This week’s image comes from the Fearsome Beard blog which post this photo last month, here.

Previous Scruffy Sunday Posts

Saturday morning coffee

Much thanks to Rob Orange who writes the blog Seduced by the New who posted this last month. It makes for a great Saturday morning coffee post, don’t you think?

Saturday morning comics

ADAM & ANDY is set in the fictional New England town of Woodfield, CT. You can learn more about Adam and Andy and purchase a copy of “the definitive collection of Adam and Andy” by visiting,

Click on this week’s comic strip to enlarge

Click here if you would like to see  the previous Adam & Andy

Furry Friday

It is an itsy, bitsy, teenie, weenie pretty pink speedo bikini.
And he wears it perfectly.

Past Furry Friday

BosGuy brain teaser

riddle, exercise for your brainEach Friday morning I post a riddle to get you to think outside the box and exercise your brain. If you are stumped, share it with a friend or colleague and see if you can figure out the answer together.

Leave your answer in the comment section. I’ll approve responses later in the day to give people a chance to respond without seeing any spoilers.

This week’s brain teaser:  If you were running a race, and you passed the person in 2nd place, what place would you be in now?

Like riddles? Check out past week’s brain teasers.

Pre-Stonewall exhibit of a 1950s gay haven

Safe / Haven: Gay Life in the 1950s Cherry Grove

Are you planning a trip to New York City later this year? The New York Historical Society Museum and Library has a free, outdoor exhibit that might be of interest to you. Entitled, Safe / Haven: Gay Life in the 1950s Cherry Grove, will run from May 14 – October 11, 2021 in the Museum & Library back courtyard. Out of consideration for public health, social distancing is required and timed-entry tickets need to be reserved here.

During weekends and summers in the pre-Stonewall era, gay men and women, including many New Yorkers, traveled to the secluded beach town of Cherry Grove on Fire Island where they found opportunities for sexual exploration and self-expression—behavior that was both stigmatized and criminalized in the US. Together with creative figures like Truman Capote, W.H. Auden, Carson McCullers, and Patricia Highsmith, visitors partook in costumed parties, theatrical events, and liberated atmosphere that this gay sanctuary provided. The exhibition explores the gay and lesbian community that flourished during the 1950s in Cherry Grove through some 70 enlarged photographs and additional ephemera from the unique holdings of the Cherry Grove Archives Collection. 

More information about the 70 photographs that comprise this unique exhibit is available here.

Vintage gay

Much thanks to my friend Jim L for sharing this playful photo of what I’m assuming are three friends that dates back to the 1910s. There are two lines of text embossed at the bottom of the photo that I can’t quite make out. I beleive the second line is “Eyesville” but I couldn’t find any references online and cannot be certain. Does anyone have any guesses where this may have been taken?

I dedicate this weekly post, featuring vintage gay photographs, to the men and women who lived in a more critical time where being true to yourself and loving who you want wasn’t always an option and came at a great price. Do you have a photo you would like to share? Email me at

Previous Vintage Gay Photos

This week on Instagram: robzoppo

I’m back again with another Instagram account that is designed to distract, but is relatively unknown with barely 6,000 followers. Rob Zoppo is a former team USA lacrosse captain turned actor, model, strength and performance trainer who is based out of Los Angeles. I don’t know much else about this man and was first made aware of him after a reader of this blog suggested he would make for an ideal Furry Friday (thank you John F!) I posted Rob as a Furry Friday last month, here.

For some reason I can’t make WordPress embed a photo directly from his IG account so you can follow this week’s featured account on Instagram here.

Check out previously featured IG accounts here.

Caption this photo

Hopefully the caption I’ve shared below inspires you to offer up one of your own in the comment section.

“And this little piggy said, ‘screw the market’, and took a long, relaxing bath”

The Emancipator

Earlier this year The Boston Globe and Boston University Center for Antiracist Research announced that they would be teaming up to launch The Emancipator to share opinions, ideas on journalism, and featuring contributions from experts and community voices.

The publication’s name is a nod to America’s first abolitionist newspaper which started in the early 19th-century. The hope is the online publication will create a forum to help reframe the national conversation on race.

“Even when The Emancipator was first founded in 1820, it was very difficult for people to believe that slavery, 45 years later, would be no more. Just as I think there are many people today who can’t imagine there could be a nation without racism and inequality,”

Ibram X. Kendi commenting in the video Announcing: The Emancipator

For more information follow them on Twitter at @the_emancipator or visit them online at to learn more and sign up to be added to their mailing list.

Temptation Tuesday

Past Temptation Tuesday Posts

Men in kilts

I have to admire his matching shorts.

Previous Men in Kilts Posts

Monday morning mancandy

If this is what the guys in the office looked like, I’d be counting down the days ’til the office reopens. 

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.