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Rambles with Rachel

October 19, 2022

How to Spend One Day in Boston, MA

“She said I think I’ll go to Boston”

-Augustana

Honest opinion: I love Boston. Maybe it’s all the brownstones and cute alleyways. Maybe it’s how clean the T trains are compared to New York City’s MTA. Or perhaps it’s the fact that I can walk much of Boston in a day!

If you only have one day in Boston, fear not! You will be able to see much of what this famous city has to offer. Whether you are here for the US historical sites, for the food, or just to visit one of the many, many college students, a walk around Boston is absolutely worth it.

Flowers flank a pathway to a statue of George Washington in Boston Public Garden, with the city skyline in the background.

If you have a weekend in Boston, why not take a day trip to Salem, MA?

Boston is, of course, the state capital of Massachusetts. The area played a key part in the American Revolution, with events occurring such as the Boston Tea Party, the Boston Massacre, and the Battle of Bunker Hill.

Boston has been able to hold on to and/or renovate quite a few buildings from this time period. In fact, one of my favorite things about Boston is seeing how the architecture has evolved over the past few hundred years.

This one-day Boston itinerary will take you through many of Boston’s unique neighborhoods, so you’ll get a taste of each…like slices of a Boston creme pie.

So put on your best pair of walking shoes and explore all the best things to do in Boston in 24 hours!

A long residential building stretches into the water of Boston Harbor, with boats docked beneath it on a sunny day.

Getting There

Boston is quite easy to get to, especially from any big city on the East Coast. You can drive, of course, but if you’d rather not worry about traffic, parking, or the winding streets of Boston, try these alternatives:

  • By plane: Many major airlines fly in and out of Boston Logan International Airport. To get from the airport to Boston proper, take the Silver Line of MBTA (more on that below). Flights from NYC to Boston are about an hour and a half long.
  • By train: Amtrak trains and MBTA commuter rail lines go in and out of Boston’s South Station. A train ride from NYC takes about four hours.
  • By bus: Popular bus carriers, such as Greyhound, Peter Pan, and Megabus all go into the South Station Bus Terminal. A direct bus ride from NYC takes about four and a half hours.

Getting Around

If you are only in Boston for a day (and are able-bodied), I encourage you to walk as much as possible! Staying above ground is the best way to see a city (in my humble opinion).

However, if you need to rest your feet or need to reach a certain spot, you’ll most likely take the MBTA, most commonly referred to as “The T”.

The different T lines are referred to by their color like “the Red Line” and “the Green Line”. Inbound trains mean they are headed into the city center, while outbound trains mean they are headed to the end of their lines.

For more info on how to take the T, and how to purchase a CharlieCard, check out MBTA’s Guide to the Subway.

How to Spend One Day in Boston, MA

Get ready to walk and eat your way around Boston! This itinerary may be ambitious, but there are so many fun things to do in Boston, and you only have a day, so might as well make the most of it!

Breakfast at Trident Booksellers & Cafe

A closeup of a breakfast scramble and toast at Trident Booksellers & Cafe in Boston.

Begin your one day in Boston by fueling up with breakfast. Trident Booksellers & Cafe just happens to have two of my favorite things: books and coffee!

You can sit at the bar or by the windows and enjoy a delicious breakfast in a homey, laid-back atmosphere. Have a breakfast scramble or the ricotta-stuffed French toast!

After you have eaten your fill, take a wander through the book section of the store, and maybe pick up something for the trip home. Trident also has a bunch of fun items like games and puzzles.

Newbury Street

The brick facades of businesses along Newbury Street in Boston on a sunny day.

Trident is located right on Newbury Street, which is Boston’s main upscale retail district. Basically, it’s Boston’s version of NYC’s 5th Avenue.

You’ll find all of your favorite stores, but with pretty brownstone facades. Maybe swing into a Patagonia store so you can fit in with all the locals!

Commonwealth Avenue

The brownstone residences with windows reflecting the blue sky along Commonwealth Avenue in Boston.

If you’ve had your fill of window shopping, cut over a block to Commonwealth Avenue, which runs parallel to Newbury Street. Here you will find stunning brownstone residences and a beautiful tree-lined walkway dotted with statues.

(It’s a great place to dog-watch since everyone walks their dogs along here!)

Boston Public Garden

The bronze sculptures of a mother duck and her ducklings in Boston Public Garden.
Rachel sits in silhouette, underneath willow branches, looking out at the lagoon in Boston Public Garden on a sunny day.

If you walk east along either Newbury Street or Commonwealth, you will eventually hit Boston Public Garden. If I could only go to one place with my one day in Boston, it would be the Public Garden.

Boston Public Garden was established in 1837 and was the first public botanical garden in America. This peaceful green space is meticulously taken care of. Enjoy the beautiful flowers, the willow trees, the fountains, and the swan boats that cruise (seasonally) around the lagoon.

You might even come across the bronze statues that honor the beloved children’s book, Make Way for Ducklings by Robert McCloskey. Published in 1941, it tells the story of Mr. and Mrs. Mallard, who are in search of the perfect place to nest in Boston.

Boston Common

A chow chow dog runs across a paved path in Boston Common with trees ad the Boston skyline in the background.

Right next to Boston Public Garden is Boston Common. (Yes, they are technically two different parks.) Boston Common is like the Public Garden’s bigger, older sibling.

Dating back to the 1630s, Boston Common is America’s oldest park. Boston Common has evolved over the years- it’s no longer a mustering spot for Colonial militia, and you’re no longer allowed to graze cows there. However, it is still a spot Bostonians and tourists will flock to.

During the summer, you can see Commonwealth Shakespeare perform on the green, and in the winter you can skate across the Frog Pond.

Brattle Book Shop

Shelves of books for sale sit in a vacant lot surrounded by high brick walls at Brattle Book Shop.

If you are like me and cannot resist another bookshop, then exit on the east side of Boston Common and you will find Brattle Book Shop on West Street.

The Brattle is one of America’s oldest used book shops, but you don’t even have to go inside. They have extremely discounted books on shelves in the lot next door. (We’re talking $1-5 books.) You never know what you might find there!

The Freedom Trail

Black boots step over a large medallion in the sidewalk marking the Boston Freedom Trail.
The brick building of the Old State House with its white tower is dwarfed by the modern high rises around it in Boston.

You may notice a trail of red bricks while you’re walking around Boston. This is the Freedom Trail: a 2.5-mile trail throughout the city that connects areas of historical significance.

While it is not necessary to walk the whole Freedom Trail (unless you’re a big American history buff), it is easy to walk a bit of it during your one day in Boston!

If coming from Boston Common or Brattle Book Shop, I would pick up the Freedom Trail from Granary Burying Ground and follow it to Faneuil Hall. This way you will pass the Old South Meeting House, where the Boston Tea Party was organized, and the Old State House, outside of which the “Boston Massacre” occurred. (There’s a museum inside the Old State House detailing the incident and events leading up to it.)

Faneuil Hall Marketplace

The brick Colonial exterior of Faneuil Hall, seen from across the street on a sunny day in Boston.
Twinkle lights descend from the domed ceiling under which people dine within Faneuil Hall Marketplace.

By now you should have walked enough to have worked up an appetite! It’s time to get lunch at Faneuil Hall Marketplace.

Faneuil Hall Marketplace actually consists of four markets: Faneuil Hall, Quincy Market, North Market, and South Market. In 1742, Boston’s wealthiest merchant, Peter Faneuil, built the hall and gave it to the city.

Today it’s a popular spot to gather for food and shopping, while street musicians and magicians perform in the cobblestone courtyard.

For lunch, you can choose among 18 restaurants and counters. However, you’re in Boston, so why not have some seafood? Try a lobster roll or some lobster mac and cheese!

New England Aquarium

A seal rests vertically in the water with its eyes closed at the New England Aquarium in Boston.

Now you can either keep following the Freedom Trail…or you can take a fun little detour. If you keep walking east you will reach the water, where you can find the New England Aquarium.

You don’t even have to buy a ticket and go inside to see some cute marine animals! Part of the harbor seals’ enclosure includes a section outside where you can see them swim, play, and sleep. (I’m honestly convinced they know they’re on display and thus know how to be as cute as possible.)

You can then walk along the harbor walk that stretches along Boston Harbor. (Yep, the one they dumped the tea into.)

The North End

Round patina bay windows cover a four-story building in Boston's North End.
Shelves of Italian desserts, including five types of cannoli sit for sale at a bakery in Boston's North End.

Head north and you will be in Boston’s (aptly-named) North End. Known for being Boston’s oldest residential neighborhood, by 1890 the North End was known as Boston’s Little Italy.

It is here that you can find the best Italian food and desserts in town. Do a cannoli taste test between Mike’s Pastry, Bova’s Bakery, and Modern Pastry, or grab a slice of pizza.

The diamond-paned windows dot the brown wooden exterior of Paul Revere's house in Boston.
Patina bay windows cover the corner of a four story building in Boston's North End on a sunny day.

While in the North End, you can also swing by Paul Revere’s House for a tour. Paul Revere became an American folk hero thanks to Henry Wadsworth Longfellow’s poem “Paul Revere’s Ride,” (which was written decades after Revere’s death).

This was indeed his house in 1775 when he made the famous ride to alert Boston of incoming British troops. You can see the house in about 30-45 minutes, and learn about Colonial life in the 1700s.

Beacon Hill

The cobblestone sidewalks of the Beacon Hill neighborhood in Boston are lined with Victorian lamp posts.
Rachel, in an orange skirt and black boots, walks up the narrow cobblestone lane of Acorn Street in Boston's Beacon Hill neighborhood where an American flag hangs above a doorway.

About a half-hour’s walk back southeast will bring you to one of Boston’s most picturesque neighborhoods: Beacon Hill. Rowhouses with cobblestone alleys and Victorian street lanterns lend this area its charm. Thus, it also happens to be one of the most expensive neighborhoods in Boston…but it’s pretty!

Hunt for narrow, little Acorn Street for that quintessential Boston Instagram spot.

Charles River Esplanade

A Canada goose looks at the camera while walking along the Charles River Esplanade where the trees' leaves are just starting to change to yellow.

Keep walking west until you reach the river. Here you will find the lovely Charles River Esplanade. This peaceful park is a nice place to watch the sunset (or just to people and dog-watch).

The whole stretch one way is three miles long, but you can do an easy little loop circling the Storrow Lagoon.

Back Bay

After your very long day in Boston, it’s time for dinner!

Boston’s Back Bay neighborhood is one of the best places in the city to find food. From fancy to casual, you’ll be able to satisfy every palette.

Of course, there are plenty of seafood options, but you’ll also come across Mexican, Japanese, American Southern, and French-themed restaurants.

Honorable Mentions

If you have a bit more time in Boston (or are a super early riser), check out a few more things to do in Boston:

  • Liberty Lobby Bar: While you are walking from the North End to the Charles River Esplanade, a fun pit stop is at the Liberty Hotel. This unique hotel actually used to be the Charles Street Jail! You do not need to be a guest to have a drink in the lobby and wonder how such a pretty place can have such different origins.
  • Samuel Adams Boston Brewery: One of the things still on my Boston to-do list is to visit the Samuel Adams Brewery. The famous Sam Adams beer has a long history, plus the brewery offers tastings!
  • The Isabella Stewart Gardner Museum: If you are more an art buff than a history buff, after wandering Boston Common, take the Green Line E from Boylston Street to the Museum of Fine Arts T stop. The nearby Isabella Stewart Gardner Museum has a unique collection of art, personally acquired and arranged by the wealthy Isabella Stewart Gardner. Thirteen pieces (mostly by Edgar Degas) were famously stolen in 1990…and they have never been recovered! Don’t worry though, there are still plenty of impressive works.
The high, open ceiling of the Liberty Hotel with a large circular window and chandelier.
The Italian palace-like interior of the Isabella Stewart Gardner Museum, where palm trees live under a glass ceiling.

I hope you enjoy walking around Boston! This one-day itinerary is chock full of things to do in Boston, but it will mean you’ve earned those North End cannolis!

How do you like to spend one day in Boston? Let me know in a comment below!

Planning to spend a day in Boston? Save this post for later!

Posted In: Massachusetts, One Day · Tagged: Day Trips, Massachusetts, New England, Things to do in Massachusetts

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About Me

About
Hi there! I'm Rachel, lover of stories, history, and the great outdoors, with a penchant for the fantastical. Raised in the Adirondack Mountains of New York State and grown in New York City, I love sharing the best of both my worlds, while exploring new horizons. Come ramble with me!

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