On a day trip into Boston, you may feel compelled to visit all the traditional sights: walk the Freedom Trail, take a duck tour, or grab a drink at Cheers. But if you’re a little more adventurous and want to step slightly off the beaten path, consider taking a day to explore the city’s South End. More intimate than the Back Bay and more idiosyncratic than Beacon Hill, the South End is one of Boston’s hidden treasures. Although it is close to the heart of downtown and directly borders the ever-popular Back Bay, the traditional tourist barely ever sets foot in the South End. Nonetheless, this historic neighborhood has grown at an incredible rate, owing its vibrancy to world-class restaurants, unique shops, lush green spaces, and a thriving artistic community. There is no shortage of history in the South End. Like the Back Bay, the South End was built primarily on filled land, occupying the area that once comprised Boston’s “Neck,” a narrow isthmus that connected old Boston to the town of Roxbury on the mainland. In the mid-19th century, the city began to fill in the marsh that surrounded this narrow strip of land, building up the neighborhood now known as the South End.

Old Boston — A map of old Boston.
*Photo Credit : Norman B. Leventhal Map Center at the Boston Public Library*

Modern Boston — Boston as it appears today. The South End neighborhood is highlighted in red.

Are you looking for green space in the middle of the city? You’re in luck! When it was developed, the South End was built in the garden-square style popular in London, with row houses surrounding a central private green space meant for promenading. The South End has five major garden squares as well as a number of smaller, more intimate residential parks scattered throughout the neighborhood. A number of other community-maintained pocket parks and urban gardens add to the profusion of greenery and color throughout the year.

Union Park 1916 — The South End’s Union Park in 1916.
*Photo Credit : South End Historical Society*

Union Park today.
*Photo Credit : Stacen Goldman*

The South End’s Blackstone Square ca 1860.
*Photo Credit : South End Historical Society*

Blackstone Square Fountain 1980s — The Blackstone Square fountain in the 1980s.
*Photo Credit : South End Historical Society*

Blackstone Square Today — Blackstone Square today.
*Photo Credit : Stacen Goldman*

The South End is home to a building, now the centerpiece of the Boston Center for the Arts, that once housed a cyclorama (a Victorian amusement that consisted of a viewing platform placed in the center of a 360º panoramic painting) of the Battle of Gettysburg. When cycloramas went out of fashion in the 1890s, the building hosted a number of other businesses, including a bicycle riding school, a garage, and the Boston Flower Exchange, before it became an event and gallery space. The BCA complex (which is the full block adjoining the Cyclorama), is home to a number of artist studios, black box theaters, and the celebrated Calderwood Pavilion, so consider taking in a show!

The Cyclorama in 1884-1885.
*Photo Credit : South End Historical Society*

Cyclorama 1890s — The Cyclorama in the 1890s.
*Photo Credit : South End Historical Society*

The Cyclorama in 1972.
*Photo Credit : South End Historical Society*

The Cyclorama today.
*Photo Credit : Stacen Goldman*

The South End is a neighborhood of many beautiful churches, the most striking of which is Cathedral of the Holy Cross. The seat of the Archdiocese of Boston, the Cathedral is the largest Roman Catholic Church in New England, and is certainly the grandest church in Boston. Completed in 1875, the Cathedral was designed in the Gothic Revival Style by renowned architect Patrick Keely (designer of 3 South End Churches in total). Make time to step inside and see the soaring vaulted ceilings and magnificent stained glass.

Cathedral 1907 — Cathedral of the Holy Cross in 1907.
*Photo Credit : South End Historical Society*

Cathedral of the Holy Cross in 1972.
*Photo Credit : South End Historical Society*

Cathedral of the Holy Cross today.
*Photo Credit : Stacen Goldman*

If you’re in town on a Sunday, consider stopping by the bustling SoWa (South of Washington) district for the South End Open Market, SoWa Vintage Market, and the SoWa Farmer’s Market. The Open Market and Farmer’s Market are only in operation from May until October, but the indoor Vintage Market is open year round. Speaking of vintage goods, the South End offers plenty of opportunities to bring some history home with you. Farm and Fable is your stop for vintage cookbooks and kitchenware, and if you time it right, you can stop in for classes in their full basement kitchen. For rustic home goods (old and new), stop by Pioneer Goods Company on Tremont Street. And if you’re more inclined towards fashion, visit Sault New England where classic Americana meets vintage menswear.

Pioneer Goods Company is a great spot to pick up rustic home goods (old and new).
*Photo Credit : Stacen Goldman*

If you’re inclined to bring your furry friend on your day trip, you couldn’t find a more dog-friendly neighborhood in Boston! The open spaces make the South End an ideal place for your furry friend to romp. Peters Park Dog Run is the oldest off-leash dog park in the city, and there is no shortage of dog-friendly businesses in the neighborhood. Bring your pup to D’Tails Pet Boutique on Columbus Avenue, take him for at a tasty treat at Polka Dog Bakery on Shawmut Avenue, or erase the effects of a long day of playing with a bath at Bark Place on Washington Street. So dog friendly is the South End that many businesses put out water bowls for thirsty pups on the go!

Shop dog. — This shop dog agrees… You can’t find a more dog-friendly neighborhood in Boston!
*Photo Credit : Stacen Goldman*

Peters Park dog run — Peters Park Dog Run is the oldest off-leash dog park in the city.
*Photo Credit : Stacen Goldman*

One of the most popular activities for visitors to the South End is admiring the historic brick rowhouses that line the streets. Although they may look very similar at first glance, there is incredible diversity of architectural style in the neighborhood.

Flemish architecture on Shawmut
*Photo Credit : Stacen Goldman*

Gothic in Rutland Square
*Photo Credit : Stacen Goldman*

Italianate
*Photo Credit : Stacen Goldman*

Victorian Eclectic
*Photo Credit : Stacen Goldman*

And if you find yourself yearning for a glimpse inside those beautiful buildings, now is your chance! The Annual South End House Tour, held in October, is a self-guided tour of private homes and public spaces throughout the neighborhood. Bound to be a favorite for enthusiasts of history, architecture, and interior design, the House Tour offers the perfect framework for a day trip. Take the tour at your own pace, and if it leaves you feeling inspired, you can stop in the neighborhood’s various shops and restaurants along the way. 2018 South End Historical Society House Tour: Saturday, October 20th, 2018 For ticketing and more information, visit www.southendhistoricalsociety.org This post was first published in 2015 and has been updated.

SEE MORE: New England Architecture | Guide to House Styles in New England Beacon Hill, Boston | Exploring Boston’s Most Famous Historic Neighborhood

Stacen Goldman

Tour of Boston’s Historic South End