Is the South End safe to walk at night?

Yes, the South End is generally safe, especially along well-lit main thoroughfares like Tremont Street and Washington Street. As with any city neighborhood, it is best to stay aware of your surroundings, particularly on quieter side streets after dark.

What is the best time to visit the SoWa Art + Design District?

The best time to visit is on Sundays between May and October for the Open Market, or on the 'First Friday' of every month when many artist studios open their doors to the public from 5:00 PM to 9:00 PM.

Are there many places to eat in the South End?

Absolutely, the South End is one of Boston's premier dining destinations. Tremont Street is lined with a variety of restaurants, often referred to as 'Restaurant Row,' offering everything from casual cafes to high-end dining.

Is the South End walking route accessible for strollers?

Yes, the route is mostly flat and stroller-friendly. However, be prepared for some bumpy rides on the neighborhood's historic brick sidewalks, which can be uneven.

Where is the best architecture in Boston's South End?

Union Park and the surrounding streets offer some of the finest French Second Empire and Victorian architecture in the city. The bowfront red-brick row houses are a signature feature of this district.

Can I visit Wally's Cafe Jazz Club during the walk?

Wally's is a working jazz club that typically opens in the late afternoon or evening. You can see the historic exterior at any time, but you should check their schedule if you wish to go inside for live music.

What is the nearest T-station to the South End?

The South End is served by the Orange Line (Back Bay or Massachusetts Ave stations), the Red Line (Broadway station), and the Silver Line bus (SL4 and SL5) which runs along Washington Street.

Zigway - The Guide Follows You

About This Tour

Step into a world of red-brick elegance and artistic evolution with this self-guided walking route through Boston’s South End. Once a marshy neck of land connecting Boston to the mainland, the South End was transformed in the mid-19th century into a neighborhood of grand Victorian squares and charming row houses. This audio walk invites you to explore the largest intact Victorian residential district in the United States at your own pace, moving from the refined architecture of Union Park to the gritty, creative energy of the SoWa Art + Design District. Throughout this neighborhood stroll, you will discover how the South End has reinvented itself time and again—from a high-society enclave to a jazz-age sanctuary and finally to the culinary and artistic heart of the city. Your journey begins at the Calderwood Pavilion, a modern beacon for the performing arts that sits atop the site of the historic National Theatre. From there, the walking route leads you through the 'Restaurant Row' of Tremont Street, where the aromas of world-class cuisine mingle with the historic atmosphere of gas-lit streets. You will experience the quiet tranquility of Union Park, a masterpiece of French Second Empire design that feels miles away from the city's bustle. As you move toward the Southwest Corridor Park, you will see how community-led green spaces have replaced former railway lines, creating a lush urban oasis. The walk also pays homage to the area’s deep musical roots at Wally’s Cafe Jazz Club, a legendary venue that has hosted jazz greats since 1947. Finally, the route concludes in the SoWa district, where industrial warehouses have been reborn as vibrant galleries and studios. This self-guided adventure is perfect for those looking to see a different side of a walking tour Boston experience, focusing on local favorites and hidden gems that many visitors overlook. Whether you are an architecture enthusiast or a food lover, this neighborhood exploration offers a deep dive into the soul of one of Boston’s most beloved districts. **Note:** This area is known for its ever-changing character. Street art, pop-up venues, and temporary exhibitions may differ from what's described. That's part of the adventure - you might discover something entirely new!

Highlights

Marvel at the French Second Empire architecture of Union Park

Explore the 'Restaurant Row' of Tremont Street

Visit the legendary Wally’s Cafe Jazz Club

Walk the lush paths of the Southwest Corridor Park

Discover contemporary art in the SoWa Art + Design District

See the stunning red-brick row houses and historic ironwork

Tour Stops (6)

Calderwood Pavilion

Welcome to the start of your South End exploration. The Calderwood Pavilion at the Huntington is a modern architectural addition to a neighborhood steeped in history. Opened in 2004, it was the first new professional theater built in Boston in over 75 years. It stands on the site of the old National Theatre, a massive 3,500-seat venue from the 1800s. Today, this space serves as a hub for local theater companies, bridging the gap between the neighborhood's historic past and its current status as a cultural center. Take a moment to admire the glass-and-brick facade, which reflects the classic South End aesthetic while signaling the area's ongoing revitalization.

Union Park

As you enter Union Park, you are stepping into what many consider the crown jewel of South End residential design. Laid out in the 1850s, this oval square is flanked by stately French Second Empire-style row houses, characterized by their mansard roofs and ornate ironwork. Note the central park with its Victorian-style fountains and lush greenery. This area was designed to rival the high-society squares of London. Though the neighborhood saw a period of decline in the mid-20th century, the meticulous preservation here offers a window into the opulent lifestyle of Boston's 19th-century merchant class. It remains one of the most photographed spots in the city.

Tremont Street

Tremont Street is the vibrant artery of the South End, famously known as 'Restaurant Row.' As you walk this stretch, you'll pass an incredible array of eateries, from cozy French bistros to innovative fusion spots. The architecture here is a mix of commercial and residential, with many ground-floor spaces hosting boutiques and cafes. This street captures the neighborhood's transition from a quiet residential district to a trendy, culinary destination. Keep an eye out for the small details: the cast-iron fences, the window boxes overflowing with flowers, and the distinct 'bowfront' windows that allow light to flood into the narrow homes.

Southwest Corridor Park

This linear park is a testament to community activism. In the 1960s, a plan was set to build a massive highway through this area, which would have demolished hundreds of homes. Residents fought back and won, resulting in this 4.7-mile greenway that sits atop the orange line subway tracks. As you walk through this section, you'll see community gardens where locals grow vegetables and flowers, as well as playgrounds and dog parks. It is a vital 'green lung' for the South End, connecting various neighborhoods and providing a peaceful, car-free path for commuters and strollers alike.

Wally's Cafe Jazz Club

You are standing outside a true Boston institution. Wally's Cafe was founded in 1947 by Joseph Walcott, a Barbadian immigrant who became the first African American to hold a liquor license in the city. During the mid-20th century, the South End and Lower Roxbury were the heart of Boston's jazz scene. While many other clubs have vanished, Wally's remains a sanctuary for live music, hosting performances 365 days a year. The club has served as a training ground for countless students from the nearby Berklee College of Music. Even if you aren't stopping for a set, the history of this small, unassuming brick building is legendary.

SoWa Art + Design District

Your walk concludes in SoWa, which stands for 'South of Washington.' This former industrial area, once filled with piano factories and shoe warehouses, has been transformed into a premier arts district. The massive brick buildings now house hundreds of artist studios, galleries, and design showrooms. If you are here on a Sunday from May through October, the area comes alive with the SoWa Open Market, featuring local makers, food trucks, and a vintage market. It is the perfect place to see how the South End continues to evolve, blending its industrial heritage with contemporary creativity. Please note that gallery hours and market events are subject to seasonal changes.

Frequently Asked Questions

This self-guided walk typically takes 90 to 120 minutes. The distance is approximately 1.5 miles, allowing plenty of time to admire the architecture and explore the SoWa galleries.