How to Spend the Perfect Day in Beacon Hill

In Boston.com’s Perfect Day series, we speak with a local expert in each of Boston’s neighborhoods. 23 neighborhoods about 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 on [email protected].

Beacon Hill, Boston’s historic gem, is known for its quaint 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, delicious food, and scenic beauty.

For Sharon Durkan, Boston City Councilmember for District 8 (which includes Back Bay, Beacon Hill, Mission Hill, Fenway, Kenmore and the West End), the neighborhood is both her workplace and her home. The Georgia native has lived in the same Anderson Street apartment since moving to Boston eight years ago and said she counts herself lucky to have stayed in the neighborhood for so long.

“As a renter, I feel a lot of stability because I have the same address and have lived in the same place for so long. A lot of Bostonians aren’t that lucky and don’t have the opportunity to really put down roots,” she said.

Durkan was initially drawn to the neighborhood because of 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 storied neighborhoods, with a rich history dating back to the 17th century. It played a major role in the American Revolution and was home to notable events such as the abolitionist movement of the 1830s, during which several residents were active in the fight against slavery.

In the mid-20th century, the Historic Beacon Hill District was established 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, with landmarks such as the Massachusetts State House and well-preserved 19th-century architecture.

According to Durkan, the neighborhood’s appeal also comes from its small business community, which is characterized by the shops along Charles Street.

“I think Charles Street is a commercial street like no other. Everything 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 combination of exploring the shops, restaurants and other amenities nearby, she said.

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

Follow this curated route and discover the best spots in the neighborhood, enriched with local insights from resident Durkan.

This is how she would spend a perfect day in Beacon Hill.

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

Durkan starts her day by dropping off her laundry at Suds and Duds Laundry (64 Andersonstraat.) before you go to Peregrine Falcon (Charlesstraat 170) for breakfast. The restaurant, located in the Whitney Hotel, is best known for its dinner options, but Durkan says it’s also an underrated breakfast spot.

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

Across the street from Peregrine, Durkan will be Sloane Merrill Gallery (75 Charlesstraat.) She enjoys looking around the gallery, noting, “I love just being outside and looking at the artwork. It’s owned by a wonderful entrepreneur, Ali Ringenburg, who is very involved with Charles Street.”

After looking at some art, she will visit Gus & Ruby Letterpress (99 Charles St.) and Rugg Road Paper Co.. (105 Charlesstraat.) for unique stationery. Sharon often stops here for thank you notes and small gifts for her staff and colleagues, 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 who do things for me. When you’re an elected official, you don’t do it alone, you always do it with others. So two of my stops are for that reason, for thank-you notes,” she said.

Around the corner from the stationary shops she will quickly stop at Rouvalis flowers (40 W Cedar St.) for “the most beautiful bouquet you have ever seen.”

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

Afternoon: Savory snacks and a secret garden

After a morning of walking up and down Charles Street, it’s time for lunch. Durkan recommends FLORINA Pizzeria & Paninotheque (16 Dernestraat), an Italian pizzeria and sandwich shop.

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

After lunch she quickly goes to do some shopping Beacon Hill Instant Shoe Repair (Bowdoinstraat 126)where she drops off her shoes to be re-patched. Durkan appreciates owner Vadim Kotlyar’s dedication to the craft and his humor with customers: “He’s a well-known figure in Beacon Hill, and he kind of shames you if you don’t treat your shoes right,” she said, laughing.

Then she will come to visit Crane River Cheese Club (Cambridgestraat 138b.) to pick up a bottle of rosé and some fresh strawberries for an afternoon out with her friends (“my ‘parents’ from Beacon Hill”) Bob and Janet in their backyard on Joy Street.

Beacon Hill is home to many “hidden gardens,” symbols of the neighborhood’s 19th-century architectural style and layout. To cultivate these gardens, The Beacon Hill Garden Club was founded in 1928 by a group of residents dedicated to urban gardening. Since its founding, the club has organized an annual hidden garden tour.

Durkan’s Friends’ Garden is one of the stops on the tour, and features a fountain and a small pool. The gardens are a hidden treasure in the neighborhood that Durkan said she appreciates even more because of their secretive nature.

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

Evening: Dinner, Shakespeare, ice cream and a walk

As evening approaches, Durkan drops by Charles Street Offer (Charlesstraat 54) to collect 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 explained. Durkan praised Charles Street Supply for its convenience and unique services, such as holding spare keys for renters in the area.

“If you lock yourself out, they may be the ones to let you into your apartment,” she said.

For an aperitif, Durkan goes to The Hill Tavern (228 Cambridge Street.) to watch a few innings of a Red Sox game before going to dinner with her boyfriend at The Paramount (44 Charles Street.).

“People often think of it for breakfast, but their dinner menu is fantastic,” she said. “It’s not cafeteria-style seating in the evening, it’s a great casual date spot.” She appreciates the free avocado spread with the bread, and her favorite dishes are the special stewed ravioli with short ribsthe ragu bolognese pastaand their warm salads with added protein.

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

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

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

Durkan will end her perfect day with a sweet treat from JP licks (150 Charlesstraat.). She will mix Yogurt Xa frozen yogurt, with pink lemonade sorbet to create the perfect summer treat.

“It’s sour and refreshing, especially in hot weather,” she said. Last but not least, she’ll end her evening with a relaxing stroll along the Charles River Esplanadelooking back on a successful day in one of Boston’s most enchanting neighborhoods.

Below you will find all the places recommended by Sharon Durkan.

Map: The Perfect Day in Beacon Hill

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