This is the walk I take friends on when they come to visit me in Boston. Two historic neighborhoods, connected by a unique urban park. Also, snacks! This is a premium post for Wonder & Sundry subscribers and features a custom Google Map to guide you on your way. Not a subscriber? Sign up today (it's free)!

Take a Boston walk—and have snacks!

When friends visit me from out of town and the weather is fine, this walk tops my list of suggestions for an afternoon in Boston. This stroll through the North End, the Greenway, and Chinatown showcases old and new Boston, and provides a nice orientation if you’re new to the area. Plus, you know, snacks.

This walk will take you from one of Boston’s oldest neighborhoods, the North End, which became an Italian neighborhood around the turn of the twentieth century, along the Rose Fitzgerald Kennedy Greenway (just call it the Greenway), one of Boston’s newest parks, through to Chinatown, one of the oldest and largest in the country. 

Along the way, you’ll have a chance to check out the waterfront in (the unfortunately named) Christopher Columbus Park, visit the seals at the New England Aquarium, or perhaps grab a beer at Trillium or a glass of wine at City Winery in the summer months.

Depending on the time of day you take this walk, you might grab a slice of authentic Sicilian pizza, or a sweet treat at Modern Pastry (I’m not team Mike’s—you’ll understand) in the North End, and dumplings in Chinatown (or maybe some pho or a banh mi, if you prefer). Whatever you choose, you will have earned your snacks with the lovely walk you will have taken.

North End, Boston
Sal's Lunch, North End, Boston

Getting There

From the Haymarket T station (Orange or Green Lines), walk along Hanover Street through the first section of the Greenway. On the weekends, you’ll run into the historic Haymarket produce market, a raucous affair, with hawkers yelling out their specials. It’s an experience—just make sure to keep moving and don’t interrupt the flow of foot traffic.

First Stop: Boston’s North End

The North End is one of Boston’s oldest neighborhoods, containing the Old North Church (Revolutionary War fame), Paul Revere’s House, and Copps Burial ground, but since the early twentieth century, it has been the beating heart of Boston’s Italian community.

Recent years have brought a lot of change, with the passing of most of the immigrant community, gentrification, and time. While most of the restaurants in the North End are now more fun to look at than they are to eat in (there’s better Italian elsewhere in the city, if that’s what you’re looking for), there are still some tasty treats to be had here.

The streets are narrow, twisty, and often crowded, and it has a bit of an Old World feel to it. You could spend hours wandering around the North End, but we’re going to do a couple of the hits, have a quick bite, and go on our way. There was a lot of mob activity here back in the day (a friend of mine walked past the aftermath of a shooting when she was a student there), but that’s the stuff of stories and gritty Boston movies (so many gritty Boston movies) now.

All the history and food make this a super touristy area, but it’s definitely worth checking out. It’s pretty easy to get lost in the North End without a map, as the streets were made by drunk cows, but in the age of Google Maps, feel free to duck down a side street if things are too bananas. It’s fun.

North End, Boston
A North End institution since the 1930s, Bova's Bakery is open 24 hours

Stroll the North End

Wander through the Greenway section on the left-hand side. You’ll need to cross Cross Street to get to Salem Street, which is a lovely entry way to the North End (don’t worry—you’ll get to experience the rest of Hanover). Pass Polcari’s Coffee, this great old Italian shop, and you’ll then see a warren of restaurants. Most of these are more fun to look at than they are to eat in, but Al Dente has classic Italian-American fare.  You’ll pass Bova’s Bakery, a rare 24-hour spot that’s been there since the 1930s.

Old North Church, North End
One if by land, two if by sea . . . Old North Church, Boston
Old North Church and Paul Revere
Say hello to Paul Revere, riding in front of Old North Church, Boston

Old North Church and Paul Revere

Keep walking up Salem Street until you get to the Old North Church, of one if by land, two if by sea  Revolutionary War fame. If there isn’t a line and it’s open, take a quick spin through. Then walk along the side of the church through the park (this is part of the Freedom Trail), passing Paul Revere’s statue. Say hello to the man, and then take left onto Hanover Street. There’s an oddity that you’ll enjoy seeing.

All Saints Way, Boston
"Leave the Saints Alone," North End, Boston
All Saints Way
Admire, but do not mock, the saints

All Saints Way

Cross the street and keep walking until you see Battery Street. There’s a strange little shrine that admonishes you to, Mock all and Sundry Things, but Leave the Saints Alone. It’s known as All Saints Way. There are little saints statues, and, season permitting, lots of plants. Icons adorn the building. Snap a photo, turn around, and get back onto Hanover Street the way you came.

Snacks or lunch

Now you have a choice—is it lunchtime or snack time? If it’s lunchtime, and you’re lucky enough to get there in time, grab a piece of Sicilian pizza at Galleria Umberto (cash only—ATMs abound). This place often has a line out the door, and when they run out of pizza, they are done for the day. Trust me, you want a piece of that pizza.

Galleria Umberto
You want a piece of that Sicilian pizza.
Modern Pastry
The pastries are as big as your head at Modern in the North End


Now you have a choice—is it lunchtime or snack time? If it’s lunchtime, and you’re lucky enough to get there in time, grab a piece of Sicilian pizza at Galleria Umberto (cash only—ATMs abound). This place often has a line out the door, and when they run out of pizza, they are done for the day. Trust me, you want a piece of that pizza.

Or pastry?

Or, perhaps it’s not lunch time. In that case, get thee to Modern Pastry. Skip Mike’s and it’s ridiculous line. Stand in Modern’s line, and you will not be sorry. You might only eat a quarter of your treat (their lobster tails—my personal favorite—are the size of your head), but this is the good stuff. Modern does have a little “secret” restaurant downstairs with lunch/dinner grub, but you’re there for the pastry. You’ll probably want a coffee, too.

Christopher Columbus Park
Check out the Waterfront at Christopher Columbus Park, Boston

Let’s walk! Christopher Columbus Park

From either Galleria Umberto or Modern, head left on Hanover out of the North End. At the light, don’t cross the street, but just turn left and walk until you get to Christopher Columbus Park (a lovely park, despite the name). I like this park, as you can get down and look at the water a bit. The arbor is also lovely to walk under. Depending on the time of year, you’ll also see roses near the fountain.

Now let’s cross the street and head to the Greenway.

The Greenway

The Rose Fitzgerald Kennedy Greenway is an urban park that replaced the Central Artery as a result of the Big Dig. So much better than the ugly elevated highway, but goodness, that project took forever. The Big Dig started in 1991 when I was in high school, and the Greenway was finally completed in 2008.

The Greenway has several features, including fountains, open spaces, trees, and public art. Ai Weiwei had an exhibit here, and another one featured twentieth century neon signs. Toward South Station, in Dewey Square, there’s a rotating mural exhibition. There’s often open markets, food trucks, and other happenings along the paths, especially during the summer months.

However, there are also some quiet spots, where you briefly forget that you’re in the heart of the city. Until you look up and see some of the historic buildings in the Financial District, like the Custom House.

If you wanted you could cross the street to the New England Aquarium and check out the seals (a good choice if you happen to have kids with you, along with the fountain). If you took one of the Boston Boat Rides, you’ll  recognize the area.

Trillium on the Greenway
If you fancy a beer, there's an excellent brewery along the Greenway
Wine on the Greenway
Wine on the Greenway

Grab a beer?

If you’re walking between April and September, you could stop for a beer at the Trillium beer garden. Trillium is an excellent local brewery, and the setting is a lovely one for a cold beer on a hot summer day. There’s a small wine garden near South Station in Dewey Square, but I would recommend Trillium for the atmosphere. Trillium looks onto the Boston Harbor Hotel, where you can catch outdoor movies on Friday nights in the summer.

From Dewey Square to Chinatown

While the Greenway continues into Chinatown, it does take a little break. After you’ve hung out and enjoyed the art installation at Dewey Square, head toward Chinatown. You’re headed to JFK Surface Road. Basically, you want to keep South Station to your left and cross Summer Street. You want to be on the sidewalk to the right.

It’s about a five-minute walk to the Chinatown section of the Greenway, which is an Asian themed garden with a water feature. If it’s a little later in the evening, you might want to peek before walking, but generally, it’s pleasant. It’s a small section, and you’ll come out into a park and see Chinatown Gate.

As you walk toward the gate, you might find a group of people playing Mahjong. This is strictly a residents thing, so don’t try and insert yourself in the crowd, but I do like to peek over.


Boston’s Chinatown is one of the largest in the country, and the last surviving Chinatown in New England. There’s loads of eateries and shops, and you can find Vietnamese food here, as well as Chinese. When I was young, Chinatown was pretty rough, and I avoided it, but the area around it has gentrified (luxury housing has replaced strip clubs on Washington Street), and it’s gotten much safer.

Find street art

There’s some good murals in Chinatown (while it got tagged almost immediately, there was briefly a Banksy there). Walk around and see what you find! Personally, I find it a lot more fun to discover those on my own.

Let’s eat!

I love walking around Chinatown. It’s like a vacation. There’s fun shops, but mostly, we’re here to eat. I take people to one of four places:

  • Gourmet Dumpling House
  • Taiwan Café
  • Banh Mi at Vietnamese Sandwich (or the new Banh Mi Huong Que)
  • Pho Pasteur

Gourmet Dumpling House has the pork dumplings that angels eat in heaven when they’re happy, and the veggie ones are good too. There’s a line out the door; it’s tiny; and the tables are communal. Over the years, famous people have shown up, and their faded photos are on the walls. It’s so good, and my friends always thank me when I take them there. It’s not far past Chinatown Gate to the right; you won’t miss it.

Taiwan Café is a bit bigger and a little less chaotic, and also has excellent dumplings, along with other things. One time I went there with friends during Chinese New Year, and the parade came to us.

If you’re not starving, but could use a little something something, get a Bahn Mi at the very creatively named Vietnamese Sandwich. Be prepared for lots of crumbs, but the sandwiches are tasty. The dearly departed New Saigon Sandwich has been replaced by a new Vietnamese Sandwich spot that’s tasty. If you get a sandwich, walk back to the park to eat it.

Pho Pasteur has been around since the 90s and specializes in pho. While the best Vietnamese food in Boston is found in Dorchester, Pho Pasteur is good. You might wind up at a communal table, and that’s part of the fun.

Jia Ho Supermarket is a fun place to walk through, and you can find some treats there you can’t get elsewhere.

Greenway, Boston

Getting Away

I hope you enjoyed your walk! To get away, there are several nearby T stations.

  • Chinatown: Orange Line
  • Downtown Crossing: Red Line
  • Park Street: Green Line/Red Line

The Silver Line buses also stop around here, but, to be honest, I hardly ever take those. If you haven’t taken the Silver Line before, I’d suggest sticking with the subway unless you don’t have a choice.

Take this Boston Walk! Map and tips

Here is a custom map to guide you on your way, and below are a few notes to help make it enjoyable.

IMPORTANT! Don’t walk in the middle of the road!

The map markers were placed by an amateur. The connecting line is a representation only and meant to help you follow along. If it looks like the line is in the middle of the highway, I don’t mean for you to walk in the highway!

Obviously, please use crosswalks and basic common sense in negotiating traffic.

Distance and time to allow

The Greenway stretch is just about a mile and would take you just about 20 minutes. Add in the twisty turnies I’m suggesting, and you’ll probably looking at about two miles. If you stop for snacks and to see the seals and wander through the park, you’ll have a lovely afternoon.

General Considerations

This is a pleasant city walk—all flat, with plenty of places to stop. I encourage you to be leisurely about this. It’s part of the fun.

Safety and solo female travel

I’ve done this walk alone days and evenings. I don’t walk through the especially thick areas alone at night, but this is a popular walk. Normal urban street smarts apply, especially in the North End and Chinatown.

Accessibility considerations

The Greenway is accessible, with sidewalks, in addition to the garden paths. The North End is less so, as the streets are quite narrow in parts, as are the crowded sidewalks. The section of Chinatown I’m suggesting is OK-ish, I would think (the side streets probably aren’t). There are stairs going into the Gourmet Dumpling House. If you’re not sure, I would suggest sticking with just the Greenway section.

Many, but not all, T stations are accessible, though sometimes things aren’t working properly. It would be good to check the MBTA accessibility guide for more details. Wheelchair Travel also has information about transit.

What did you think?

Did you take the walk? What did you think? Please let me know in the comments! If you have friends who you think might like adventures like this, please encourage them to subscribe!

Looking for something else to do?

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