Itinerary Walking Tour Boston Rainy Day

Exploring Boston’s Historic Center on a Rainy Day: A Delightful Walking Tour

Exploring Boston on a Rainy Day?

No need to confine yourself indoors!

Embark on a self-guided walking tour suitable for inclement weather, allowing you to discover one of the city’s oldest districts, settled nearly four centuries ago by the Puritans.

While you encounter various sites along the renowned Freedom Trail and other historic locations, what’s particularly advantageous on a rainy day is the abundance of establishments along the way where you can shop, dine, and remain sheltered from the rain if it intensifies.

The entire route covers a mere three-quarters of a mile, although you can extend it by venturing into intriguing areas that pique your interest.

As depicted in the photos on this page, the autumn season presents a marvelous time for this stroll due to the picturesque foliage adorning the path—despite the rain, the scenery retains its beauty.

Nevertheless, this walk can be equally enjoyable in any other season or whenever you desire to combine sightseeing with shopping and indulging in a snack or meal.

1. Commence your Stroll at Boston Common

Boston Common

Initiate your walk at Boston Common.

From any location within the Common, head towards Tremont Street, where you’ll come across the Tourist Information Center situated across from the intersection of Tremont and West Streets.

Boston Common Visitor Center

Now that you’ve reached the Tourist Center, you’ll follow Boston’s renowned Freedom Trail, distinguished by a red stripe.

To your left, you’ll observe the golden-domed Massachusetts State House perched atop a small hill.

The State House stands on the outskirts of Beacon Hill, one of the city’s oldest neighborhoods and presently one of the wealthiest.

On a less rainy day, you might want to explore Beacon Hill’s charming cobblestone streets, admire the lavish mansions, and traverse the path of the Black Heritage Trail, once a sanctuary for runaway slaves on the Underground Railroad.

Today, you have the choice to admire the State House from a distance or explore its interior. Admission to this Freedom Trail site is free, and it houses art, magnificent architectural features, and historical artifacts, including two state symbols: the Sacred Cod and Holy Mackerel.

2. Strolling Along the Freedom Trail

Over the next few blocks of your walk, you’ll delve into one of the most captivating sections of the Freedom Trail.

Saunter along Tremont Street following the red stripe of the Freedom Trail. In front of you, the white spire of Park Street Church stands at the intersection of Park and Tremont Streets.

As you proceed along the street, take a moment to appreciate Tremont Temple on your right—a building adorned with a beautiful blue spiral design on its peaked front gable. Erected in 1896, it replaced three previous structures destroyed by fire in 1852, 1879, and 1893. The first building on this site, constructed in 1827, initially served as a popular theater.

The Free Baptist Society, established in 1839 to combat slavery, transformed the building into a temple in 1842-43, hosting the first integrated church services in the country.

In 1848, Abraham Lincoln delivered a stirring speech here, and it was also the venue for the initial reading of the Emancipation Proclamation in Boston in 1863.

Park Street Church

Dating back to 1809, Park Street Church played a significant role in championing social justice and the abolition of slavery during the 19th century. Renowned abolitionist William Lloyd Garrison delivered his first public anti-slavery speech here on July 4, 1829.

The area in front of the church was once referred to as “Brimstone Corner”—either due to the gunpowder stored in the church during the War of 1812 or the fervent sermons delivered by Congregational ministers.

You may enter Park Street Church, a designated Freedom Trail site, unless a service is in progress (although you are welcome to attend the service if you wish).

Granary Burying Ground

Continue walking up Tremont Street, and just behind Park Street Church, you’ll come across Granary Burying Ground, the third oldest cemetery in Boston. The light rain contributes to its atmospheric allure.

Pass through the Egyptian Revival-style gates added in 1840 and explore the grounds. Signage will assist you in locating the graves of the most prominent figures buried here.

When you depart from Granary Burying Ground, turn left onto Tremont Street and follow the red line of the Freedom Trail.

Just before reaching the corner of School Street, you’ll notice Omni Parker House, one of Boston’s splendidly restored grand hotels.

Omni Parker House

Throughout its existence, Parker House has hosted numerous renowned and infamous guests, including Charles Dickens and John Wilkes Booth. It proudly holds the title of the oldest continuously operating hotel in the United States, although the building you currently see dates back only to 1927—the original structure was constructed in 1856.

However, the hotel’s lasting fame arises from three culinary creations: Parker House rolls, Boston Scrod (thick-cut fillets of cod), and Boston Cream Pie.

If you find yourself feeling even the slightest bit hungry during your walk, don’t miss the opportunity to savor Boston’s delectable dessert, which is, in fact, a cake filled with creamy vanilla and topped with chocolate ganache rather than an actual pie. It also serves as an excellent excuse to step inside and catch a glimpse of the hotel’s exquisite interior.

You can indulge in Boston Cream Pie at various locations within the hotel, so make your way to Parker’s Bar—a charming room adorned with wood paneling—unless you prefer a full meal in the elegant restaurant.

Omni Parker House Hotel

Whether you choose to continue your walk or take a break for a slice of pie, be sure to look upward and admire the exquisite design, slate and copper roofs, and the corner clock of the Omni Parker Hotel.

In fact, you’ll encounter numerous splendid architectural details along this route, many of which are situated above eye level—so remember to cast your gaze upward to spot them.

Two additional Freedom Trail sites, Kings Chapel and King’s Chapel Burying Ground, await on the opposite side of Tremont Street, just beyond School Street.

Both locations are worth exploring, so if you wish, take a detour to visit them and then return to the corner of Tremont and School Streets.

Additional Nearby Hotels

Your journey through historic Boston becomes even more delightful when you stay at one of these exceptional hotels along the route:

  • The Godfrey: A fabulous hotel conveniently situated on Washington Street near the theaters. Check rates and reviews.
  • Omni Parker House: An iconic hotel with a rich history, luxurious modern updates, and an array of excellent dining and drinking options. Check rates and reviews.
  • Ritz Carlton: Indulge in a splendid 5-star luxury experience overlooking the Common at this prestigious hotel. Check rates and reviews.
  • Hyatt Regency: Located adjacent to Boston’s theaters and Chinatown, offering a convenient and comfortable stay. Check rates and reviews.

3. Exploring the Freedom Trail and Noteworthy Sites on School Street

While some parts of the Freedom Trail’s red line may be difficult to spot, you cannot miss it when you reach the intersection of Tremont Street and School Street.

Embark on the Freedom Trail along School Street, immersing yourself in one of Boston’s oldest districts, steeped in layers of history that trace back to the arrival of the Puritans in the 1630s.

On your immediate left, a magnificent gray stone building in the elegant French Second Empire style catches your eye. This is Boston’s Old City Hall, constructed in 1865, which served as the office for nearly three dozen mayors until the current City Hall was established a few blocks away in 1969.

Boston Old City Hall

Before 1865, an older City Hall occupied this very spot. Even earlier, between 1704 and 1748, the location was home to Boston Latin School, the oldest public school in the United States. Although the school is now situated in the Fenway neighborhood, it originally held classes at this site.

Take a moment to explore the surroundings and appreciate the statue of Benjamin Franklin, erected in 1856. Being the first public statue of a person in Boston, it drew large crowds upon its installation.

Benjamin Franklin

Direct your gaze downward to the sidewalk in front of Old City Hall, where you’ll find an elaborate memorial paying tribute to Boston Latin School.

During his childhood, Benjamin Franklin attended Boston Latin School for a couple of years until his father could no longer afford the tuition. Back then, “public” education did not imply it was free, so Franklin had to withdraw from school at the tender age of 10.

Continuing your journey along School Street, you may unknowingly pass by two of Boston’s oldest brick buildings from the 18th century unless you’re tempted by a bagel or burrito.

The first building you’ll encounter, currently housing a Brueggers Bagel Bakery, dates back to 1722. Adjacent to it, at the corner, stands the Old Corner Bookstore, which also serves as a site along the Freedom Trail, Literary Trail, and Women’s Heritage Trail. This historic establishment was constructed in 1712.

Initially, the Old Corner Bookstore functioned as an apothecary shop with a residence on the upper floor. Throughout most of the 19th century and part of the 20th century, it housed various publishers and booksellers, attracting literary luminaries like Ralph Waldo Emerson, Nathaniel Hawthorne, Charles Dickens, Oliver Wendell Holmes, and Henry Wadsworth Longfellow, who frequented the nearby Parker House.

Delving further into the past, the site where the Old Corner Bookstore stands today was once the residence of the charismatic Puritan leader Anne Hutchinson from 1634 to 1638. Due to her promotion of a doctrine that questioned the authority of Puritan ministers, she and her children, along with her supporters, were excommunicated and banished from the Massachusetts Bay Colony.

Encouraged by Roger Williams, another religious exile who had already established the more tolerant Colony of Rhode Island and Providence Plantations, Hutchinson and her followers migrated south and established the settlement of Portsmouth.

If you previously explored the Massachusetts State House on this walking tour, you might have noticed a statue of Anne Hutchinson and her daughter Susanna on the lawn. Hutchinson and Williams are recognized as key figures in the development of religious freedom in the American Colonies.

Cross the intersection at Washington Street and take a left turn. Within a short distance, you’ll encounter Spring Lane, which resembles a narrow alley, as well as Water Street. These two streets represent some of the oldest thoroughfares in the city. Walking along either of them allows you to follow in the footsteps of Boston’s Puritan founders.

In a mere half-block, if you look across the street, you’ll notice Pi Alley, situated at the entrance of a parking garage.

Pi Alley

Pi Alley, alternatively known as “Pie Alley,” houses a few small shops and eateries, including Viga, where you can savor delicious Italian pizza and calzones. This narrow lane likely dates back to the Colonial era.

The names “Pi Alley” and “Pie Alley” evolved in the late 19th century and describe a scene that is no longer visible. At that time, the alley was lined with numerous newspaper printing shops, earning it the nickname “Newspaper Row.”

The alley was filled with small cafes serving meat pies, a popular delicacy of that era, much like pizza is today. Some establishments even humorously listed “Cat Pie” on their menus. The historic Bell in Hand Tavern, founded in 1795, was also located here (you can now visit it a couple of blocks away at 45 Union Street).

Due to the printers and typesetters’ haste while enjoying their meals, they would occasionally drop loose type or “pi” from their pockets. Over time, the accumulation of dropped type in the alley led to its name “Pi Alley,” a playful play on words.

Continuing up Washington Street, you will soon encounter several fascinating small shops on your right.

At this point, you face a decision: you can either continue walking north along Washington Street for another two blocks and arrive at Faneuil Hall Marketplace, where you can easily spend the remainder of your day indulging in shopping and dining, or you can turn around and return to the School Street intersection to continue this stroll.

In Need of Rain Boots or an Affordable Umbrella?

Walking in the rain becomes more enjoyable when you stay dry.

Require an umbrella or waterproof boots or shoes? Downtown Crossing along Washington Street, just one block from Boston Common, offers a range of options at bargain prices. Consider visiting these stores:

  • DSW – 385 Washington St, Downtown Crossing, 617-556-0052 – Typically offers a wide selection of affordable rain boots and umbrellas.
  • Eddie Bauer Outlet – 500 Washington St, Downtown Crossing, 617-423-4722 – Additional options for boots and umbrellas.

4. Historical Sites and the Freedom Trail on Washington Street

Assuming you decide to turn back, you’ll come across the Boston Irish Famine Memorial, situated across from the Old Corner Bookstore.

Boston Irish Famine Memorial

Created in 1998, the Irish Famine Memorial commemorates the 150th anniversary of the devastating potato crop failure that led to the starvation of approximately one-eighth of the Irish population, mostly in rural areas. During the famine years, over 1.5 million Irish immigrants fled to the United States, with many settling in Boston.

The statues represented at the memorial symbolize two distinct groups, highlighting the social disparities and economic inequities in Ireland that caused certain segments of the population to suffer more than others.

However, one can also view the healthy and joyful figures as a representation of the Irish immigrants in Boston who triumphed over initial discrimination, worked diligently, and thrived due to the opportunities America offered.

Diagonally across Washington Street from the Irish Famine Memorial lies one of the most historically significant sites along the Freedom Trail: Old South Meeting House.

Old South Meeting House

From our modern perspective, it’s difficult to fathom the immense role that the Old South Meeting House played in Colonial Boston.

Initially serving as a place of worship for a dissident group of Puritans who broke away from another congregation, Old South became a prominent gathering spot in the early 1770s, where the Sons of Liberty advocated revolution and independence from England.

Today, Old South stands as a Freedom Trail site renowned for being the location where a secret code phrase was shouted to initiate the renowned Boston Tea Party. If you want to learn more about the Tea Party, the Old South Meeting House houses an intriguing history museum with interactive exhibits, showcasing some of the actual tea thrown into the Harbor on that fateful night.

If time permits, take a break from your walk and venture inside the Old South Meeting House. There is a small entrance fee, but if you possess a valid GoBoston card, you can enjoy free admission.

5. Downtown Crossing: Shopping, Construction, and the Theatre District

After passing Old South Meeting House, you enter Downtown Crossing, a predominantly pedestrian shopping district.

This area boasts a captivating blend of large-scale fashion discount stores, a sprawling Macy’s department store, and an array of unique independently owned shops and boutiques.

However, one of the most renowned establishments along this stretch of Downtown Crossing, the Boston Jewelers Exchange Building, is easy to overlook if you aren’t actively searching for it. Simply keep an eye out for the prominent gold clock.

Jewelers Building Boston

Observing the exterior of the Jewelers Exchange, an art deco building dating back to 1922, one might not anticipate that it houses over 150 independent jewelers, artisans, and manufacturers. Many of these businesses have operated within the building since the 1940s.


Downtown Crossing has undergone significant transformation in recent years, with the addition of luxury condominiums, inviting outdoor plazas for leisurely seating, and upscale coffee shops and restaurants. These changes have seamlessly merged the district with the Theatre District.

As you continue walking past Macy’s, you’ll suddenly find yourself surrounded by Boston’s Theatre District.

This area is shared by two downtown-based higher education institutions, Suffolk University and Emerson College, resulting in a frequent sight of students working on laptops in the upscale coffee establishments.

Boston Theatre District

If you wish, you can explore the theaters further, peering inside to admire their lavish lobbies. Alternatively, you can continue walking for a block or two until you reach Chinatown, where the alluring aromas emanating from numerous Asian restaurants entice you to indulge in a flavorful meal.

However, if rain persists, you may prefer to head back to Boston Common, which is only a block away.

Make a right turn onto West Street, where you’ll find the Brattle Book Shop.

Brattle Book Shop.

On pleasant days, the mural-adorned parking lot next to the shop displays hundreds of books for browsing. There’s nothing quite as delightful as leisurely perusing books on a warm August afternoon.

But on a rainy day, step inside the shop, where you can easily lose yourself amidst the three floors of used and rare books. The Brattle Book Shop, established in 1825, has occupied various locations in Boston over the years and specializes in antiquarian books, first editions, maps, postcards, and other treasures. If you seek a unique gift, explore the “Boston” section, which often features intriguing out-of-print books about the city and its history.

At the end of West Street, cross Tremont Street, and you’ll find yourself back at Boston Common, where this walking tour concludes, bringing you full circle to where it all began.

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