Beacon Hill: Old-School Boston in a New Light

A neighborhood guide to the many charms and surprises of Beacon Hill.

At the risk of sounding a tad biased, we reckon that Beacon Hill is right up there among the prettiest and most fascinating city neighborhoods in the entire world. From the golden dome of the State House to the charming shops and pubs of Charles Street, via the residential red-brick nirvana that flanks Boston Common, Beacon Hill is a truly great location for chillin' and leisurely exploration: part Boston time-machine, part first-class ticket to old-school swankyville and, further back, the roots of the American story. Every visitor is supposed to grab a photo of achingly picturesque Acorn Street (above), but you don't have to follow the herd.

Corks in the window at Grotto

Where to Eat in Beacon Hill

Submerged below street level on the slope that points towards the North End, Grotto sets a high bar in the 'candlelit Italian hideaway' category. Here you'll finding lashings of black truffle oil, pan-toasted mozzarella, lush panna cotta and all the other classic signposts for culinary romance.

The Paramount (since 1937) on Charles Street is the very definition of an honest, friendly neighborhood joint, favored over the years by political movers and shakers, and just the place for a proper breakfast or a burger—the housemade black bean burger is great. They serve wine too.

Round the corner 75 Chestnut is worth the reservation for its excellent Nantucket seafood stew, and this fall they'll be cooking up a bunch of specials for the Annual Beacon Hill Neighborhood Oktoberfest.

Wares at December Thieves

Great Beacon Hill Shops

At some point in the past, a fine mist of quirkiness must have descended on Charles Street like autumn fog from the adjacent Charles River, because there's no shortage of stores that deal in unique, brilliantly crafted gifts. One of the most interesting is December Thieves—companion store to nearby Heist—where you can browse a well-curated range of clothes, accessories, curios and more.

Over at Black Ink, the range of the desirably unusual spans ninja coffee mugs, ceramic origami swans and cat-shaped cream jugs.

Tip Tap Room

Unbeatable Beacon Hill Bars

The test of a great Beacon Hill watering hole is its ability to remain staunchly unchanged through intense seasons of summer tourism and winter blizzard-ism.

The Tip Tap Room fits that bill, with its extensive and rotating selection of craft brews and picture window view of the classic brutalist concrete structure that houses the Massachusetts Department of Unemployment Assistance—way cooler than it sounds.

The Sevens Ale House on Charles is patronized by literary types and has a dart board while the 21st Amendment serves generous cocktails, including an "Angry Arnold Palmer," splashes of political gossip and the very essence of Kennedy-era Boston.

Boston Athenaeum

Things to Do in Beacon Hill

In the 19th century, most African-American Bostonians lived on the north slope of Beacon Hill, and that era comes alive at the Museum of African American History and adjacent African Meeting House: the perfect place to start a walk along the Black Heritage Trail.

You don't have to be a member to enjoy the pleasures and treasures of the Boston Athenaeum, enticingly located at 10½ Beacon Street: the library, founded in 1807, is packed full of gorgeous tomes, art and sculptures and holds regular events and tours, such as the Art and Architecture Tour.

For boaters who fancy taking to the river during the warmer seasons, there's Community Boating Inc., which rents kayaks and sailboats to all-comers.