Walking Itinerary for Boston, Massachusetts

Spending time in Boston made me realize how great of a city it is for walking. Here, the journey is often the destination. Around every corner is an intriguing shop, restaurant, historical building, or park.

If you would also like to walk around Boston and discover its magic, here are some landmarks, restaurants, and activities you should add to your itinerary!

Freedom Trail

The Freedom Trail is a 2.5-mile red line along the ground that leads to 16 of Boston’s most significant historical sites. This itinerary loosely follows the Freedom Trail but sprinkles in a few of my favorite stops along the way. Following this path makes it easy to see all of Boston’s highlights. You can either start at the Bunker Hill Monument and end at Boston Common, or vice versa.

Bunker Hill Monument

At the top end of the Freedom Trail is Bunker Hill Monument. This impressive monument sits at the site where the Battle of Bunker Hill took place during the Revolutionary War in 1775. Until 1880, its obelisk was the tallest structure in the United States. Today, visitors can climb up 294 steps to reach the scenic observation platform to see impressive city views. The grounds around are a tranquil place to walk around.

North End

Cross over the Leonard P. Zakim Bunker Hill Memorial Bridge, and you’ll find yourself in North End. This Boston neighborhood, also known as “Little Italy,” has been around since the 1600s. Italian food lovers are in heaven in North End. You’ll find countless pizzerias, food markets, restaurants, and bakeries serving up delicious bites to eat. In addition to its tasty cuisine, it also has an exciting harborwalk and several historical monuments to explore.

The Paul Revere House

One of the most famous monuments in the North End along the Freedom Trail is the Paul Revere House. It is the historic home of the prominent patriot Paul Revere, renowned for warning militia that the British were coming during the Revolutionary War. This two-story townhouse dates back to 1680, but Paul Revere lived there from 1770-1800. Today, visitors can see this masterfully restored building that recreates the original look and feel of the home.

Mike’s Pastry

A local North End legend for some mouthwatering pastries is Mike’s Pastry. Mike’s Pastry has been a neighborhood favorite since 1946. Local Bostonians and tourists both love this place. This spot is famous for its cannolis and “lobster tail,” a cream-filled pastry in the shape of a lobster tail. Aside from cannolis and lobster tails, this bakery also has delicious cookies, pies, and cakes. It’s a great place to visit while on your Boston walking tour.

Faneuil Hall and Quincy Market

If you follow the Freedom Trail across the Rose Kennedy Greenway, you’ll find Faneuil Hall and Quincy Market. Faneuil Hall is a historic building where many of the most important meetings, protests, and debates have occurred. Abolitionists, labor unionists, and women’s suffragists have all fought for liberty in this space. Across from Faneuil Hall is Quincy Market. Inside this marketplace are delicious local eateries and shops. The North and South Market surrounding it are also exciting places to explore.

New England Aquarium

A little bit off the Freedom Trail, but nearby Faneuil Hall is the New England Aquarium. If you’re a sea animal lover, you can enjoy a giant ocean tank housing over 200 different species of marine life. You can find every type of fish under the sun, marine mammals, and other exciting critters. For more education, there is a theater that plays educational films.

Boston Common

If you follow the Freedom Trail to the end, you’ll end up in Boston Common. Along the way, you’ll pass by the Boston Massacre Site, Old Corner Bookstore, and a few other historical sites. Boston Common is Boston’s version of Central Park. It’s not nearly as large as Central Park in New York, but it is a welcome oasis within the bustling city. There are numerous ponds and green spaces where you can take a break

Downtown Crossing

After finishing the Freedom Trail, you can spend time shopping in Downtown Crossing. This district is the retail center of Boston. You can find every brand you can think of within this area. There are clothing and apparel stores, markets, jewelry retailers, and many other places to explore. Additionally, there a few tasty restaurants and eateries nestled between the shops to sample.

Chinatown

Down the street from Downtown Crossing is Chinatown. This cultural center has an iconic gateway to mark its borders. After a whole day of walking, you’ll find a variety of different mouthwatering eateries to grab dinner. While the area has some of the city’s best Chinese fare, there are also excellent Vietnamese and Japanese eateries. Throughout the year, this area has some exciting festivals, including Lunar New Year and Moon Festival.