Your Weekend in Boston Itinerary: 2 Days of History & Architecture!

Boston is the largest city in Massachusetts (and all of New England, for that matter), and at the heart of the region’s cultural scene.

It’s also one of the most important cities when it comes to early American history, sprinkled with historical sights practically everywhere you look.

Luckily, Boston is a compact and walkable city that also has excellent public transportation for exploring other neighborhoods of Boston that are a bit outside the city center area.

If you’re planning a trip to Boston, this Boston weekend itinerary will be your guide!

Your Weekend in Boston Itinerary: 2 Days of History & Culture

Day One of Your Boston Itinerary

Go for a morning stroll in the Boston Public Garden.

The artificial lake at the heart of Boston Public Garden with swan boats in it - where to start your weekend in Boston itinerary
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Dating back to the 19th century, Boston Public Garden is one of the greenest spaces in the city center.

It features a large artificial lake at its center where people often rent swan boats to go out for a paddle on the ‘lagoon’.

Another famous site you’ll find is the sculpture called Make Way for Ducklings, named for the children’s book of the same name.

This is a common Boston photo spot, so grab a snap here if you want!

Grab a coffee at Thinking Cup.

sign at Thinking Cup, a Boston cafe near the Boston Common, with hand written menu on a chalkboard

We have a busy day ahead, and you’ll be walking a lot, so I suggest grabbing a cup of coffee at one of the coffee shops along the edge of the Boston Public Garden and Boston Common.

I enjoyed my coffee from Thinking Cup quite a bit — they also had tasty breakfast items like a breakfast burrito that was great to snack on while walking through Boston!

Walk the first portion of the Freedom Trail.

Historic church along Boston's Freedom Trail starting at Boston Common

Starting at Boston Common, the Freedom Trail covers 2.5 miles of ground, visiting 16 different historic sites downtown Boston that you can follow via pathways marked with brick on the ground.

Your first stop will be at Boston Common, the oldest public park in the United States of America, which was established in 1634.

You can type “Freedom Trail Starting Point” into Google Maps to find the exact place to start, so you can follow the path from there — no need to look at your phone once you start, as the route is laid ahead of you with bricks!

The first ten stops along the Freedom Trail route will take you to the Massachusetts State House, the Park Street Church, the Granary Burying Ground, King’s Chapel and Burying Grounds, the Ben Franklin Statue and Boston Latin School, the Old Corner Bookstore, the Old South Meeting House, the Old State House, and the Boston Massacre Site.

These sites include important historical sites from Boston’s colonial days, the American Revolution, the Boston Massacre, and so on!

Take a gander at Faneuil Hall.

The Faneuil Hall market complex in downtown boston, a historic and touristy place to visit

The next stop on the Freedom Trail is Faneuil Hall, one of the most touristy spots in Boston that’s still worth taking some extra time to peruse.

There are a lot of different eateries here, especially in Quincy Market, but I suggest waiting — we’ll have even better places to eat later on in our Boston itinerary!

Continue your Freedom Trail walk until Copps Hill.

Gravestones sticking out of the green grass at Copps Hill, one of the freedom trail sites

We have just a few more stops on the Freedom Trail walk, so next up, you’ll visit the Paul Revere House, the Old North Church (the oldest church in Boston), and Copp’s Hill Burying Ground.

There are two more stops on the Freedom Trail — the USS Constitution and Museum and the Bunker Hill Monument — but we’ll skip them in the interest of time unless you really want to go see them, as they’re a bit further afield and take us away from the rest of the itinerary.

Check out the “Spite House”.

Narrow gray house sandwiched between other larger houses in Boston

Right across from Copps Hill, you’ll find the so-called “Spite House”. But where did it get this quirky moniker?

Supposedly, it was built by an angry brother who felt stiffed by his end of a land deal — and then built this tiny house on the remaining land to block his brother’s views!

The house recently sold for $1.25 million — pretty amazing considering it’s only 10 feet wide!

Grab something to eat in the North End.

A sign in Boston's north end

The North End is Boston’s “Little Italy”, full of Italian restaurants and bakeries. You could just grab a cannolo at a local bakery if you just want a snack, but now is probably time for a hearty lunch.

I just wandered around and ate at a random place and found it a bit subpar and overpriced, so I recommend doing some research first — this guide by Eater to where to eat in Boston’s North End looks like a good place to start.

Stroll along the Boston Harbor.

A red building on stilts above the water with a walkway leading to a boat similar to those that would have been used during the Boston tea party

The Boston Harborwalk is a great place to go for beautiful views of Boston’s waterfront.

Walking along the Harborwalk, you’ll pass the Boston Tea Party Ships & Museum, a museum that hosts reenactments of the famous event!

Cross to the other side of the harbor via one of the bridges for a gorgeous view of downtown Boston!

Have dinner at The Barking Crab.

lobster roll in a bun with salad

Boston is known for its seafood, especially New England clam chowder and its tasty lobster and crab rolls!

There are lots of seafood restaurants along Boston’s waterfront but one of the most famous is The Barking Crab, which is pricy but a Boston classic!

Day Two of Your Boston Itinerary

Start the day either at Fenway Park or at the Isabella Stewart Gardner Museum.

green press building at fenway park boston
Photo Credit: Bernard Gagnon, CC BY-SA 3.0, via Wikimedia Commons

With only two days in Boston, we’ll need to make some sacrifices — and one is deciding between Fenway Park and the Isabella Stewart Gardner Museum.

It’s a pretty simple question to figure out — are you more of a sports fan or an arts fan?

Fenway Park is where the Boston Red Sox play, and if you’re a baseball fan, it’s a must to make a pilgrimage here!

interior of the isabella stewart gardner museum with beautiful architecture and lush plant life
Photo Credit: Amoran002, CC BY-SA 4.0, via Wikimedia Commons

Meanwhile, the Isabella Stewart Gardner Museum is one of the premiere arts museums in Boston, with beautiful art housed in a stunning building that combines a palatial and a jungle aesthetic.

It’s located right next to the Museum of Fine Arts, and if you really want to go museum-crazy, you could knock out both museums in one go if you keep a quick pace.

Wander through Back Bay.

ivy covered brick house with american flag in back bay boston

The stunning houses of Back Bay make up one of Boston’s most scenic neighborhoods, and taking a stroll through here — and perhaps stopping for brunch along the way — is simply a must-do.

Don’t miss a stroll down Newbury Street, which has some of the most beautiful houses in Boston!

If you’re getting peckish, grab something at Levain Bakery or local chain Tatte Bakery for a quick bite.

If you want something more substantial, Buttermilk & Bourbon is great for a weekend Southern-themed brunch.

Check out the Boston Public Library.

the stunning courtyard of the boston public library on a sunny summer day

The Boston Public Library is one of the most beautiful places in Boston, and it’s totally free to visit!

Besides visiting the beautiful main reading room and the murals by Sargent, you should also check out the courtyard, which is a really peaceful and tranquil site.

Admire Copley Square and Trinity Church.

flowers in bloom in front of trinity church in copley square in downtown boston

A (very) short walk from Boston Public Library, you’ll arrive at Copley Square, a cute small public park with a beautiful church at its heart.

Trinity Church is another site worth seeing while in Boston, built in 1877 and known for its beautiful stained glass windows and its impressive organs inside.

Wander through the streets of Beacon Hill.

Allison walking around Beacon Hill on Acorn street

The charming neighborhood of Beacon Hill is another one of Boston’s cutest neighborhoods.

The houses here are stunning, shaded by trees in a place that feels a world away from downtown Boston!

Don’t miss the most scenic street of them all, Acorn Street, which runs between W Cedar Street and Willow Street for one short but photogenic block!

Head over to Harvard Square.

sign reading harvard book store established 1932 with books in the window

Technically not part of Boston but rather a neighboring city called Cambridge, the area around Harvard University is effectively a neighborhood of Boston in terms of how you experience it (as it’s connected by metro).

The Harvard Square area is a cute little shopping district — don’t miss the Harvard Book Store and the great coffee shops in this area!

Wander around Harvard University.

the harvard campus with beautiful buildings and green spaces

Centered around Harvard Yard, it’s fun to get to walk around this famed Ivy League school and imagine you go here!

The campus is really beautiful, so take your time to enjoy a walk around Harvard Yard, admiring the university’s halls, quads, and libraries.

Grab dinner in Cambridge.

Before heading back to your Boston hotel, you might as well grab something to eat in Cambridge, since this is a great foodie destination!

Not sure where to eat? This list of great restaurants near Harvard Yard should help you out!

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