Best of Boston in One Day: The Freedom Trail and Beyond

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New England’s cultural hub, Boston takes its name from Boston, England. With a history spanning almost four centuries, the state capital of Massachusetts is one of the most historically significant cities in the United States.

With historic sights aplenty, two world-famous universities and a thriving foodie scene, Boston is an unmissable stop on any visit to the North East. Great transport links with New York and Washington, and a walkable city center make Boston an ideal day trip or short break destination. Boston is also the gateway to Nantucket, one of the best places to visit in the U.S. in summer.

Is Boston worth visiting?

You probably know Boston best for its important role in U.S. history. First as the largest British settlement in British America and later as the birthplace of the American Revolution. Boston is also home to Harvard University, consistently ranked among the best universities in the United States.

A few of Boston’s other claims to fame include being the birthplace of baked beans, home to Fenway Park (the oldest baseball stadium in the country) and as the site of the first ever telephone call. Scottish inventor Alexander Graham Bell made the world’s first successful call to his assistant, Thomas Watson, on March 10, 1876, in Boston. He simply said, “Mr Watson, come here. I want to see you.”

Top attractions include Quincy Market (a foodie paradise), Boston Common – the oldest city park in the States – and the Freedom Trail, which is the focal point of our one day in Boston itinerary.

Getting to Boston

By air

Boston’s Logan International Airport is just 2.5 miles from downtown Boston, making it one of the easiest airports to get to and from. There are hundreds of daily flights serving destinations across the U.S. and Canada.

Direct flights are also available from London (Gatwick & Heathrow), plus a number of cities in mainland Europe. You can also find direct flights as far afield as the Middle East, China and Japan. To find the best options for your trip, compare flights before booking.

By public transport

Luckily for us, the North East corridor is one of the best connected areas in the United States by public transport. Amtrak’s Acela Express and North East Regional trains offer several daily services between Boston, New York, Philadelphia and Washington DC.

Acela trains are slightly quicker (from Washington it’s just under 7 hours, Northeast Regional takes 8 hours), and usually more expensive. For the best fares, you should book as far in advance as possible.

A more cost effective way to reach Boston from New York is to take the bus. Flixbus, Greyhound Lines and a number of local operators run the route several times a day. Journey times start at just over 4 hours. To get the best price, we always recommend you compare options.

How to spend One Day in Boston

9 am: Breakfast in Back Bay

Starting your one day in Boston in Back Bay puts you not only in one of the city’s trendiest neighborhoods, but just steps from Boston Common and the starting point of the Freedom Trail. Thinking Cup is a cozy spot whose divine coffee will set you up for a day of exploring.

Their breakfast menu is simple and inexpensive. Some of my favorites here include flaky, freshly baked pastries, bagels and burritos.

9:30 am: Public Garden & Boston Common

Walk east from Thinking Cup for a couple of minutes and you’ll find an entrance to the Public Garden on the west side of Boston Common. This quiet spot has been providing a retreat for Bostonians since the late 19th century. Check out the statue of George Washington on horseback and take a stroll over the ornate bridge across the lake.

Cross Charles Street from the Public Garden and you’ll come into Boston Common itself. Covering 50 acres, the Common was first opened in 1634 when the governor of Boston bought the land back from a European settler, paid for by a tax on all city residents.

10:30 am: Start the Freedom Trail

Head to the south-eastern corner of Boston Common, directly south of Frog Pond, to find the starting point of the Freedom Trail. The trail, conceived in 1951, runs for 2.5 miles from the Common to Bunker Hill, passing 16 significant historical monuments.

The trail starts by running north through Boston Common to the Massachusetts State House. Built in 1798, the State House is the state capitol building.

The trail then turns immediately south to pass Park Street Church which dates back to 1804 and the Granary Burying Ground. One of Boston’s oldest cemeteries, the Granary, is the final resting place of Paul Revere, a folk hero of the American Revolution. The three signatories of the Declaration of Independence, Samuel Adams, John Hancock and Robert Treat Paine, are also buried here.

Continuing east, the trail passes King’s Chapel to arrive at the site of Boston Latin School, the oldest school to still exist in the United States. Founded in 1635, based on the idea of English Grammar Schools, the school was the first in the city (and British America) to offer a free education to all.

Pass the Old Corner Bookstore (sadly, now a Chipotle Mexican restaurant) and Old South Meeting House and you’ll arrive at the Old State House.

12 pm: Old State House and Faneuil Hall

One of the most iconic sites on the Freedom Trail, Old State House served as the state’s General Court from its inception in 1713 until it was replaced by the current State House which you passed earlier. It was here, in 1770, that the first shots of the American Revolution were fired and, in the same spot six years later, the Declaration of Independence was read out.

Whilst you won’t have time to spend long at all of the stops along the Freedom Trail with one day in Boston, it’s well worth allowing time to go inside the Old State House.

Just around the corner, Faneuil Hall is an 18th-century marketplace which was the site of important speeches which led to the American Independence movement. Samuel Adams and James Otis held several speeches here in the run up to the Revolution, earning the hall the nickname “the Cradle of Liberty.”

1 pm: Lunch at Quincy Market

The central hall of Faneuil Hall, Quincy Market is not just a great place for lunch, but another of Boston’s historic sites. Completed in 1826, it was named to honor mayor Josiah Quincy, who ordered its construction.

There are 34 restaurants in Quincy Market and choosing where to grab lunch from is almost impossible. Iconic Boston pizza joint Pizzeria Regina and local favorite Union Oyster House are our top picks. If you’re not able to make it down to Nantucket or Cape Cod, don’t miss the Boston Chowda Company for an excellent clam chowder

2 pm: Continue the Freedom Trail

As you leave Quincy Market, walk for around 10 minutes until you reach the Paul Revere House. The oldest house in Boston, it was built in 1680 and was home to Revere and his family from 1770 to 1800.

This is another of the Freedom Trail sites which is well worth going inside.

The trail continues north past the Old North Church and Copp’s Hill Burying Ground to Charleston Navy Yard.

3:30 pm: USS Constitution

The oldest naval warship still afloat, USS Constitution was built by Boston shipbuilder Edmund Hartt in 1794. She saw action in the Quasi War, First Barbary War and the War of 1812 between the United Kingdom and United States.

Be sure to pay a visit to the museum before stepping aboard the ship. Keep in mind the ship is closed on Mondays.

5 pm: Bunker Hill – the end of the Freedom Trail

Just half a mile from the USS Constitution museum, the Freedom Trail draws to a close at the impressive Bunker Hill Monument.

Fittingly, the monument is also the most modern stop on the trail. Completed in 1843, the monument marks the site of the Battle of Bunker Hill. One of the first major battles of the American Revolution in June 1775, the Battle of Bunker Hill saw the British capture Charlestown.

5:30 pm: Reward yourself with a beer

Walking the Freedom Trail is thirsty work, but thankfully, there’s an excellent tavern just steps from Bunker Hill. Follow Pleasant Street downhill from the monument and you’ll find Warren Tavern on the corner of Pleasant and Warren Street.

If there were ever a time for a ‘Sam,’ this is it. On a summer day, make the most of the weather on Warren’s outdoor terrace.

7 pm: Dinner time

There’s no shortage of great places to eat in Boston, but our favorite neighborhood for dinner is always Harvard. One of Boston’s trendiest spots, there’s more to Harvard than the university. Harvard Square is buzzing all hours of the day, and has some fantastic quirky restaurants.

Alden & Harlow is our number one recommendation. This bright and airy underground restaurant has a real family feel. Their menu is ever changing, but whenever you go, you can be sure of delicious American classics. There’s a strong focus on fresh seafood; it is Boston after all.

More time in Boston

There are far more things to do in Boston than meets the eye. If you have a little more time in Boston, we’ve prepared an itinerary for Boston for two days so you can see the best of what Beantown has to offer.

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