Here’s how to spend the perfect day in Beacon Hill

Sharon Durkan, a Boston City Councilor for District 8, takes us through her perfect day in Boston’s Beacon Hill neighborhood.

The Massachusetts State House is seen in the last gasp of sunlight on Beacon Hill. (Jessica Rinaldi/Globe Staff)

July 29, 2024 | 10:44 AM

In Boston.com’s Perfect Day series, we’re talking to a local expert in each of Boston’s 23 neighborhoods about how they’d spend their perfect day. See what makes this city so special to your neighbors, and share your perfect day with us at [email protected].

Beacon Hill, Boston’s historic gem, is known for its picturesque streets, elegant brownstones, and vibrant local businesses. Whether you’re a Boston local or a visitor, a day in this charming neighborhood promises an experience filled with unique finds, delightful eats, and scenic beauty.

Sharon Durkan, District 8 Boston City Councilor. *(Jonathan Wiggs /Globe Staff)*

For Sharon Durkan, Boston City Councilor for District 8 (which encompasses Back Bay, Beacon Hill, Mission Hill, the Fenway, Kenmore and the West End), the neighborhood is both her place of work and the place she calls home. The Georgia native has lived in the same apartment on Anderson Street since moving to Boston eight years ago, and said she considers herself lucky to have stayed in the neighborhood as long as she has.

“As a renter, I feel a lot of stability, having the same address and living in the same place for so long. A lot of residents of Boston aren’t that lucky, and they don’t have the opportunity to really plant roots,” she said.

Durkan was initially drawn to the neighborhood for its history, charm, and close proximity to the State House – which was “something that I really took a lot of pride in, being so close to City Hall and to the center of government and commerce,” she said.

Beacon Hill is one of Boston’s most storied neighborhoods, and has a rich history dating back to the 17th century. It played a significant role during the American Revolution and was home to notable events such as the 1830s abolitionist movement, with several residents being active in the fight against slavery.

The African Meeting House on Joy Street in Beacon Hill is the oldest black church edifice still standing in the United States, built in 1806. It’s part of the Museum of African American History, which specializes in interpreting and conserving the contributions of African Americans in New England from the colonial period through the 19th century. *(Michele McDonald/Globe Freelance)*

In the mid-20th century, the Historic Beacon Hill District was established to protect the area’s historic buildings from modern development pressures. Today, the neighborhood remains a symbol of Boston’s historic, political, and cultural heritage, highlighted by landmarks such as the Massachusetts State House and well-preserved 19th-century architecture.

The neighborhood’s appeal also comes from its small business community, Durkan said, which is exhibited by the shops lining Charles Street.

Acorn Street in Beacon Hill. (*David L Ryan/Globe Staff )*

“I think Charles Street is a commercial street like none other. Everything is so special, and there’s a lot of character to all of the businesses on the street,” she said.

For Durkan, a perfect day in the neighborhood involves a mix of exploring the neighborhood’s shopping, restaurants, and stores along with “a lot of utility,” she said.

“I have a lot of things that are on my to-do list,” she added.

Follow this curated itinerary for a taste of the neighborhood’s best spots, enriched with local insights from resident Durkan.

Here’s how she’d spend a perfect day in Beacon Hill.

Morning | Afternoon | Evening | Map | Share your perfect day in Boston

Morning: Breakfast at Peregrine and gift-shopping

Durkan begins her day by dropping off her laundry at Suds and Duds Laundry (64 Anderson St.) before heading to Peregrine (170 Charles St.) for breakfast. The restaurant, located inside the Whitney Hotel, is most known for its dinner offerings, but Durkan said it’s also an underrated breakfast spot.

Peregrine at The Whitney Hotel. *(Pat Greenhouse/Globe Staff)*

“Even though it is inside the Whitney Hotel, it doesn’t feel like a hotel restaurant,” she said. She’ll order the scrambled eggs with jamón serrano added on top, or their L.E.S. Platter. She also recommends one of their many breakfast sandwiches.

Down the street from Peregrine, Durkan will head to Sloane Merrill Gallery (75 Charles St.) She enjoys peering into the gallery, noting, “I love just being outside and looking in at the artwork. It’s owned by a great business owner, Ali Ringenburg, who is very involved in Charles Street.”

After soaking in some art, she’ll visit Gus & Ruby Letterpress (99 Charles St.) and Rugg Road Paper Co. (105 Charles St.) for unique stationery. Sharon often stops here for thank-you notes and small gifts for her staff and coworkers, appreciating the local touch.

“Maybe it’s the southerner in me (I’m originally from Georgia), but I really, really try to center myself in a lot of gratitude for the people that do things for me. When you’re an elected official, you don’t do it alone, you’re always doing it with other people. So two of my stops are to that effect, for thank you notes,” she said.

The Beacon Hill Books & Cafe on Charles Street in Beacon Hill. Irene MacDonald looks at a book on the first floor. *(John Tlumacki/Globe Staff)*

Around the corner from the stationary stores, she’ll make a quick stop at Rouvalis Flowers (40 W Cedar St.) for “the most beautiful bouquet you’ve ever seen.”

Then, she’ll finish her morning shopping spree with a visit to Beacon Hill Books & Cafe (71 Charles St.). Durkan enjoys grabbing a book here or finding a gift for a friend, thanks to the store’s “endless supply” of offerings.

Afternoon: Savory eats and a secret garden

After a morning spent walking up and down Charles Street, it’s time for lunch. Durkan recommends FLORINA Pizzeria & Paninoteca (16 Derne St)., an Italian pizza and sandwich shop.

“I invite my whole City Hall team here,” she says. “Their pizza is amazing, and they have a great group setting table perfect for team meetings.” She also loves their arancini, pasta specials, and the Florina salad.

Cheese Pizza at Florina on Beacon Hill. (Jonathan Wiggs/Globe Staff)

Post-lunch, she’ll run a quick errand at Beacon Hill Instant Shoe Repair (126 Bowdoin St.), where she’ll drop her shoes off to get re-cobbled. Durkan appreciates owner Vadim Kotlyar’s dedication to the craft and his humor with customers: “He’s a known entity in Beacon Hill and he kind of shames you if you don’t treat your shoes right,” she said with a laugh.

Next, she’ll visit Crane River Cheese Club (138b Cambridge St.) to pick up a bottle of rosé and some fresh strawberries for an afternoon hangout with her friends (“my Beacon Hill ‘parents’”) Bob and Janet in their backyard garden on Joy Street.

Beacon Hill is home to many “hidden gardens,” emblems of the neighborhood’s nineteenth century architectural style and layout. To cultivate these gardens, The Beacon Hill Garden Club was founded in 1928 by a group of residents devoted to urban gardening. It has held an annual hidden garden tour since its founding.

From “Hidden Gardens of Beacon Hill,” fifth edition, published May 2013. The different levels of this Beacon Hill garden take advantage of the neighborhood’s slope. *(Thomas Lingner/Globe Freelance)*

Durkan’s friends’ garden is one of the stops on the tour, and features a fountain and small pool. The gardens are a hidden treasure in the neighborhood that Durkan said she loves all the more because of their clandestine nature.

“The things that you have access to when you have friends and you live here are these back garden spaces that from street level, you might not actually be able to see,” she said. “Knowing the neighborhood, you might have a different experience than someone who’s just walking through.”

Evening: Dinner, Shakespeare, ice cream, and a stroll

As evening approaches, Durkan will stop by Charles Street Supply (54 Charles St.) to pick up cat litter for her cat, Ocho, named after her District.

“I got Ocho as a kitten after I was elected, and it was a personal reward for winning,” she explains. Durkan praised Charles Street Supply for its convenience as well as its unique services, like holding spare keys for tenants nearby.

“If you lock yourself out, they can be the person who will let you into your apartment,” she said.

Former Harpoon CEO Rich Doyle at the Hill Tavern bar. *(Joanne Rathe/Globe Staff)*

For an aperitif, Durkan will head to The Hill Tavern (228 Cambridge St.) to catch a couple innings of a Red Sox game before grabbing dinner with her boyfriend at The Paramount (44 Charles St.).

“People often think of it for breakfast, but their dinner menu is fantastic,” she said. “It’s not cafeteria style seating at night, it’s a great casual date spot.” She appreciates the free avocado spread with the bread, and her favorite dishes include the special braised short rib raviolis, the ragu bolognese pasta, and their hearty salads with added protein.

After dinner, she and her boyfriend will head to the Parkman Bandstand on the Boston Common for a performance by Commonwealth Shakespeare Company. This year, the theater company is performing The Winter’s Tale through Aug. 4.

The annual Shakespeare in the Common event is special for Durkan because it was where she had her first date with her boyfriend last year, and it was one of the first speaking engagements she did after being elected. Not to mention that the plays are free to the public and performed by professional actors.

Audience members watch a Free Shakespeare on the Common performance of “The Tempest.” *(Ben Stas for The Boston Globe)*

“It’s a great equalizer. It’s just everyone getting access to these world class actors,” she said.

Durkan will bring her perfect day to a close with a sweet treat from J.P. Licks (150 Charles St.). She’ll mix Yogurt X, a frozen yogurt, with pink lemonade sorbet to create the perfect summer confection.

“It’s tart and refreshing, especially in hot weather,” she said. Last but certainly not least, she’ll end her evening with a leisurely stroll along the Charles River Esplanade, reflecting on a day well spent in one of Boston’s most enchanting neighborhoods.

Find all of Sharon Durkan’s recommended spots below.