Here’s How to Spend a Perfect Day in Beacon Hill

In Boston.com’s Perfect Day series, we talk with a local expert from each of Boston’s cities. 23 districts on how they would spend their perfect day. Find out 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 quaint streets, elegant brownstones, and vibrant local businesses. Whether you’re a Bostonian or a visitor, a day in this charming neighborhood promises an experience filled with unique discoveries, delicious food, and beautiful scenery.

For Sharon Durkan, Boston’s 8th District councilwoman (which encompasses Back Bay, Beacon Hill, Mission Hill, Fenway, Kenmore and the West End), the neighborhood is both her workplace and her home. Originally from Georgia, she has lived in the same apartment on Anderson Street since she moved to Boston eight years ago and says she considers herself lucky to have stayed in the neighborhood this long.

“As a renter, I feel a lot of stability because I have the same address and I’ve lived in the same place for so long. A lot of people in Boston don’t have that opportunity and don’t have the opportunity to really settle down,” she said.

Durkan was first drawn to the neighborhood for its history, charm and proximity to the State House — which was “something I was really proud of, being so close to City Hall and the center of government and commerce,” she said.

Beacon Hill is one of Boston’s most historic neighborhoods. Its history dates back to the 17th century. It played an important role in the American Revolution and was the scene of significant events such as the abolitionist movement of the 1830s, with many of its residents active in the fight against slavery.

In the mid-20th century, the Beacon Hill Historic District was created to protect the area’s historic buildings from the pressures of modern development. Today, the district remains a symbol of Boston’s historical, 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, as evidenced by the boutiques that line Charles Street.

“I think Charles Street is a unique shopping street. Everything about it is so special and all the businesses on the street have a lot of character,” she said.

For Durkan, a perfect day in the neighborhood involves a mix of exploring the area’s boutiques, restaurants and shops as well as “a lot of utility,” she said.

“I have a lot of things 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 would spend a perfect day on Beacon Hill.

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

Durkan starts her day by dropping off her laundry at Foamy and frothy laundry detergent (64 Anderson Street.) before heading towards Pilgrim (170, rue Charles) for breakfast. The restaurant, located inside the Whitney Hotel, is best known for its dinner offerings, but Durkan said it’s also an underrated breakfast spot.

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

Down Peregrine Street, Durkan will head towards Sloane Merrill Gallery (75, Charles Street.) She enjoys checking out the gallery, noting, “I just like being out and looking at the art. It’s owned by a great business owner, Ali Ringenburg, who is very involved in Charles Street.”

After admiring the art, she will visit Gus & Ruby Typography (99 Charles St.) and Rugg Road Paper Company. (105, Charles Street.) for unique stationery. Sharon stops by often for thank you notes and small gifts for her staff and colleagues, appreciating the local touch.

“Maybe it’s my Southern side (I’m from Georgia), but I really try to focus on being grateful to the people who do things for me. When you’re elected, you don’t do things alone, you always do them with other people. So two of my stops are in that vein, for thank-you notes,” she said.

At the corner of the stationery stores, she will make a quick stop at Rouvalis Flowers (40 Cedar Street West) for “the most beautiful bouquet you have ever seen.”

Then she will end her morning shopping trip with a visit to Beacon Hill Books & Café (71, rue Charles). Durkan enjoys buying a book or finding a gift for a friend there, thanks to the store’s “endless supply” of products.

Afternoon: savory dishes and secret garden

After a morning spent strolling Charles Street, it’s time for lunch. Durkan recommends FLORINA Pizzeria and sandwich shop (16, rue Derne)., an Italian pizzeria and sandwich shop.

“I bring my whole city hall team here,” she says. “Their pizza is amazing and they have a great group table that’s perfect for team meetings.” She also loves their Arancini, pasta specialtiesand the Florina Salad.

After lunch, she will go for a quick run to Instant Shoe Repair in Beacon Hill (126 Bowdoin Street)where she drops off her shoes to get them repaired. Durkan appreciates owner Vadim Kotlyar’s dedication to his craft and his humor with customers: “He’s a known entity in Beacon Hill and he shames you if you don’t treat your shoes right,” she said with a laugh.

Then she will visit Crane River Cheese Club (138b, Cambridge Street.) to pick up a bottle of rosé and fresh strawberries for a relaxing afternoon with his friends (my “Beacon Hill” parents) Bob and Janet in their back garden Street of Joy.

Beacon Hill is home to many “hidden gardens,” emblematic of the neighborhood’s 19th-century architectural style and planning. To cultivate these gardens, the Beacon Hill Garden Club was founded in 1928 by a group of residents devoted to urban gardening. It has hosted an annual Hidden Garden Tour since its inception.

Durkan’s Friends Garden is one of the stops on the tour. It features a fountain and a small pond. The gardens are a hidden gem in the neighborhood that Durkan says she loves all the more because of their clandestine nature.

“The things you have access to when you have friends and you live here are these green spaces that you can’t see from the street,” she said. “Knowing the neighborhood, you can have a different experience than someone who’s just walking around the neighborhood.”

Evening: dinner, Shakespeare, ice cream and a walk

As evening approaches, Durkan will stop Supplying Charles Street (54, rue Charles) to collect litter for his cat, Ocho, named after his district.

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

“If you lock yourself out, they’re the ones who will let you into your apartment,” she said.

For the aperitif, Durkan will go to The Hill Tavern (228 Cambridge Street.) to watch a few innings of a Red Sox game before going to dinner with her boyfriend in The Paramount (44, rue Charles.).

“People often think of this restaurant for breakfast, but their dinner menu is fantastic,” she said. “It’s not a cafeteria-style place at night, it’s a great place for a casual date.” She appreciates the complimentary avocado spread with the bread, and her favorite dishes include Special ravioli with braised short ribsTHE Bolognese Pasta with Ragoutand their copious salads with added protein.

After dinner, she and her boyfriend will head to the Parkman Bandstand on the Boston Common Park for a performance of Commonwealth Shakespeare CompanyThis year, the theatre company is presenting The Winter’s Tale until August 4.

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

“It’s a great equalizer. Everyone has access to these world-class actors,” she said.

Durkan will end her perfect day with a sweet treat from JP Licks (150, rue Charles). She will mix Yogurta frozen yogurt, with pink lemonade sorbet to create the perfect summer confection.

“It’s tangy and refreshing, especially on a hot day,” she said. Finally, she’ll end her evening with a leisurely stroll along the Charles River Esplanadereflecting on a day well spent in one of Boston’s most enchanting neighborhoods.

Find below all the spots recommended by Sharon Durkan.

Map: The Perfect Day in Beacon Hill