Boston Shopping Areas, Boston

Boston Shopping Areas (Self Guided), Boston

One of the top shopping destinations in the US northeast, Boston has a strong network of interesting stores, galleries and boutiques to visit along with its many high-class shops, some of which are nestled inside historical buildings. Shopping here in more than one way mirrors the city itself: an amalgamation of classic and vanguard, the handmade and the high-end, and both local and international sensibilities.

Take our self-guided tour to experience the best shopping Boston has to offer, starting with bargains aplenty in the Downtown Crossing area. If you're looking for more high-end design, Newbury Street has multiple stores offering a wide range of options. It also features cute little cafes, restaurants and bookstores, plus beautiful trees, perfect brick buildings and the vibe to go along with all that.

There’s equally much to see and explore on your walk along bustling Boylston St, running one block parallel to Newbury St. Definitely check out the remarkable architectural marvels such as the Boston Public Library, the Old South Church, and the Prudential Center while you’re there. The latter is famous for the skyscraper you can see from many parts of town as well as the indoor shopping mall.

For an additional high-end treat, end your trip at Copley Place Mall, which features Neiman Marcus, Saks, Tiffany’s jewelry and so much more. There’s something for everyone there!

If you want to mix great shopping with some great sightseeing, consider embarking on this self-guided shopping tour!
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Boston Shopping Areas Map

Guide Name: Boston Shopping Areas
Guide Location: USA » Boston (See other walking tours in Boston)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 6
Tour Duration: 2 Hour(s)
Travel Distance: 3.2 Km or 2 Miles
Author: anna
Sight(s) Featured in This Guide:
  • Downtown Crossing
  • Beacon Hill / Charles Street
  • Newbury Street
  • Boylston Street
  • Prudential Center
  • Copley Place Mall
Downtown Crossing

1) Downtown Crossing

Historically, Downtown Crossing has primarily been known for its shopping appeal, with its peak popularity occurring in the early 20th century. To alleviate the congestion caused by heavy traffic, this central shopping district at the intersection of Washington, Winter, and Summer streets was transformed into a pedestrian-friendly area between 1975 and 1978. Today, it's a vibrant place with street vendors and summer lunchtime concerts, boasting an appealing and picturesque atmosphere characterized by charmingly designed buildings.

While Macy's stands as the sole remaining department store in Downtown Crossing, the area offers a diverse range of other retail options, including bookstores, camera shops, and a thriving jewelry district. The bustling Macy's is part of a nationwide chain, with the most famous store located in New York. Across Summer Street, the former home of Filene's Department Store, now occupied by Arnold Worldwide, remains a notable local landmark. Following a decade-long redevelopment project, the original 1912 Beaux-Arts facade was preserved, and a sleek condominium tower was added. The complex also houses various shops and restaurants, including a Roche Brothers supermarket branch offering an abundance of fresh produce and take-out lunch choices.

Meanwhile, at 100 High Street, the High Street Place Food Hall showcases a diverse selection of 20 local vendors offering delectable and high-quality cuisine of all types. You can find gourmet doughnuts from Blackbird, porchetta sandwiches from Pennypacker's, Jewish deli delicacies from Mamaleh's, sushi at Fuji, and much more. It's a great place to satisfy your hunger anytime you visit!

The historic multi-story building at 333 Washington Street is colloquially referred to as the "jewelry building" due to its housing of over 70 small jewelry stores and jewelry repair shops spanning five floors. Feel free to stop by and admire the sparkling jewelry on display.
Beacon Hill / Charles Street

2) Beacon Hill / Charles Street

Most of the commercial activity in Beacon Hill nowadays centers around its primary street, Charles Street. In the not-so-distant past, this area was renowned for its antique shops, but in recent decades, upscale, independently owned boutiques specializing in gifts, jewelry, and women's clothing have established a presence and occupied the valuable commercial real estate in this affluent neighborhood.

Even if you don't visit any of the shops, you'll be captivated by the design and character of the homes and buildings, as well as the evident dedication of their owners to not only preserve but also showcase them in the best possible light. While many of the street's buildings date back to the 19th century, some received new facades during the 1920s due to widening efforts. The Charles Street Meeting House, designed in 1807, was constructed for a Baptist congregation known for practicing immersion in the nearby river.

For the most celebrated architecture in Beacon Hill, head to Upper Mount Vernon and Chestnut streets, where you'll find Federal-style mansions designed by Charles Bulfinch in the early 1800s. (The charming one-story structures between 50 and 60 Mount Vernon originally served as stables for the elegant residences on the adjacent block at 13, 15, and 17 Chestnut Street.)

Don't forget to take your time exploring Louisburg Square, a picturesque cobblestone street surrounding a central private garden that epitomizes Beacon Hill for many. The neighborhood's delightful Christmas Eve tradition of carolers, bell ringers, and candlelit windows originated here in the 1860s. Additionally, don't forget to wander down Cedar Lane Way and the block-long Acorn Street, the latter of which features cobblestone streets and charming small houses. These dwellings were originally constructed for the coachmen whose employers resided in the mansions on either side.
Newbury Street

3) Newbury Street (must see)

Traditionally for Boston, Newbury Street has embodied a fusion of fashion and trends, similar to New York's 5th Avenue, when it comes to high-end and designer stores. One defining characteristic of this street is its constant evolution, driven by changes in rents and prevailing trends, particularly over the past few decades. Due to Newbury's reputation as a shopping haven, numerous out-of-state chains have established a presence here, alongside a plethora of charming specialty shops, ultra-modern art galleries, salons, and dazzling jewelers (just take note that the closer you get to Arlington Street, the more upscale the stores become).

The landscape of restaurants, bars and cafes is also ever-changing and eclectic, with many offering patio seating and stylish bay windows, making this the perfect sunny-weather spot to see and be seen while indulging in coffee or exotic delicacies. Some notable highlights include the rustic Italian eatery Piattini; the intimate La Voile, celebrated for its authentic French cuisine; and the relaxed Pavement Coffeehouse, serving premium coffee, espresso drinks, tea, and baked goods.

Sidewalks are wide enough to accommodate foot traffic, and the street itself is lined with beautiful architectural details and lush foliage.

Why You Should Visit:
Boston's answer to Los Angeles' Rodeo Drive, Newbury Street is a haven for shoppers. Here, you'll find a diverse range of stores, catering to various budgets and tastes. From luxurious brands like Valentino and Max Mara to more budget-friendly options like H&M and ZARA, as well as charming specialty shops like The Fish & Bone, Newbury Comics, and MUJI, there's something for everyone.
Boylston Street

4) Boylston Street

The intersection of Boylston and Berkeley streets exemplifies the diverse and outstanding architecture found in Boston. On the west side stands an elegant French Academic-style building originally constructed for the Museum of Natural History, which eventually transformed into a home for upscale shops and restaurants. On the east side, you'll notice a tower designed by Robert A. M. Stern and an office building by Philip Johnson that bears a resemblance to a tabletop radio.

Amidst the array of restaurants and convenience stores, a few exceptional establishments stand out, such as Anne Fontaine, offering flattering women's clothing, Pompanoosuc Mills, renowned for its exquisite handcrafted furnishings, and Marathon Sports, catering to both serious and novice runners, as well as those who simply want to look the part.

Regardless of your reasons for being in the area, you're bound to cross paths with this street at some point, and it's especially enchanting in the evening when everything illuminates and beckons you to enjoy the vibrant atmosphere.

Why You Should Visit:
Arguably one of the most famous streets in Boston, recognized worldwide not only as the Boston Marathon's finish line but also for its abundance of monuments, prominent churches, and a wealth of top-tier restaurants and bars.

If you have a hankering for fresh seafood, like a delectable brown-butter lobster roll, pay a visit to Eventide at No. 1321, where you place your order at the counter. Providing great food at affordable prices, this offers a hassle-free and enjoyable dining choice in Fenway.
Prudential Center

5) Prudential Center

Embark on a journey to the 50th-floor observation deck of the Prudential Center for breathtaking views of the city and the stunning natural beauty of New England, or simply take some time to explore the building's vast interior at the tower's base. With an array of more than 75 specialty retailers, there's an excellent selection of shopping options for out-of-town visitors, as well as many dining spots available for every meal of the day. Even if shopping isn't your primary purpose, the experience of visiting an Italian marketplace is worth the stop – don't miss "Eataly", a sprawling area filled with restaurants and specialty shops that can overwhelm your senses! There's even a small Catholic chapel within the mall, known as the Saint Francis Chapel, where frequent masses are held.

The true hidden treasure of this location reveals itself as you step through one of the mall's doors, leading you into the South Garden – a space that transports you to another world. With its groves of trees, abundant shrubs, grasses, and perennials, including roses, astilbe, and rudbeckia, this 1.3-acre open-air plaza offers a serene sanctuary. The large fountain, resembling a black disk atop a sturdy oblong pedestal, drowns out the city noise, while the water feature integrated into the large sculpture in the southwest corner creates the illusion that those seated in that area are floating on water. The tables at the west entrance provide a comfortable spot to enjoy takeout food, read, or simply bask in the sun and surroundings. Children are often seen using the lush green lawn for cartwheels and somersaults, and even adults find solace here. Although it can get a bit crowded during peak times and at lunchtime, most of the time, you can discover a shady spot where you can unwind and escape from it all.
Copley Place Mall

6) Copley Place Mall

Copley Square is dominated by two modern architectural landmarks: 200 Clarendon (still commonly referred to as the Hancock), situated at the southeast corner, and the even more striking Copley Place skyscraper to the southwest. The latter, an upscale urban mall constructed between 1980 and 1984, includes two prominent hotels: the towering Westin and the Marriott Copley Place. This multi-level complex features numerous shops, restaurants, and offices thoughtfully arranged around spacious, well-lit indoor areas.

Connected directly to the Prudential Center, the elegant mall caters to a wide range of upscale tastes, featuring boutiques from renowned names like Chanel, Christian Dior, Louis Vuitton, Salvatore Ferragamo, and even Moncler. While it also includes several mid-range brands like J. Crew, Gap, and Sur La Table, the anchor store Neiman Marcus offers a selection of high-end products. Additionally, there are dining options such as Caffè Nero and Legal Sea Foods, with its legendary New England Clam Chowder.

Although the interior may lack architectural intrigue, its chic and well-spaced luxurious storefronts create an appealing ambiance. When combined with the shops at the adjacent Prudential Center, the network of glass walkways provides a safe and weather-protected way to traverse the Back Bay area at any time.

Outside, the inviting and verdant Copley Square serves as a hub for civic activities, especially during the summer months, when it hosts farmers' markets, concerts, and folk dancing events. This open space, adorned with trees, grass, and fountains, took shape in the heart of the city in the 1990s and continues to be periodically redesigned to meet the growing demand for outdoor public spaces.

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