After a solid night’s sleep in a surprisingly comfortable room at the Omni Parker House, we were ready to explore Boston properly. The plan for Day 10 was simple — walk the Freedom Trail, soak up some history, and end the day with good food and tired feet.
We started the day with a walk down to Quincy Market for breakfast. Two freshly made bagels, smothered in cream cheese, and a couple of takeaway coffees made the perfect start to the morning. Sitting outside in the sunshine, watching the city come to life, was exactly how a Boston day should begin.
After breakfast we wandered through the market itself — a mix of delis, fruit and veg stalls, and souvenir shops — before exploring Faneuil Hall and the surrounding area. Then it was time to start the day’s main adventure: following the red brick line of the Freedom Trail.
Walking the Freedom Trail
The Freedom Trail is a 2.5-mile route through Boston that links 16 of the city’s most historic sites. It traces the steps of America’s revolution, from colonial marketplaces to battlefields and shipyards. Or, as I jokingly called it (quietly, in case any locals were listening), the “Traitor Trail.”
From Faneuil Hall to the North End
We started outside Faneuil Hall and followed the trail past historic taverns and public houses into the Italian district of the North End. The air smelled of espresso and garlic, and we made a note of several restaurants that looked perfect for dinner later. The narrow streets, lined with flags and flowers, felt distinctly European — a lovely contrast to the modern city we’d seen the day before.
Paul Revere’s House and the North End
Along the way we stopped at several statues and historic buildings, including the home of Paul Revere — one of the key figures of the American Revolution. Revere was a silversmith and patriot famous for his “Midnight Ride” in April 1775, when he rode from Boston to Lexington to warn colonial militias that British troops were advancing. His house, built around 1680, is the oldest remaining building in downtown Boston and a fascinating glimpse into life during that era.
Copp’s Hill Burial Ground
Our next stop was Copp’s Hill Burial Ground, Boston’s second-oldest cemetery, dating back to 1659. Many notable figures from the city’s early history are buried here — including ministers, shipbuilders, and craftsmen who helped shape colonial Boston. From the top of the hill, the view over the harbour was superb, and the old gravestones told quiet stories of a city centuries in the making.
Over the Charles River to Bunker Hill
From there, we followed the trail over the Charlestown Bridge and into a quieter, residential part of the city. The colourful clapboard houses and flower-boxed windows gave the area a small-town feel. We wandered up the hill to the Bunker Hill Monument — a 221-foot granite obelisk that commemorates the Battle of Bunker Hill (1775), one of the first major conflicts of the American Revolutionary War. It was here that colonial forces famously stood their ground against the British, giving rise to the phrase “Don’t fire until you see the whites of their eyes.”
The Naval Yard and Old Ironsides
A short walk from the monument brought us to the Charlestown Navy Yard, home of the USS Constitution — nicknamed “Old Ironsides.” Launched in 1797, it’s the world’s oldest commissioned warship still afloat and played a key role in the War of 1812. Nearby sits the USS Cassin Young, a Second World War destroyer that saw service in the Pacific. We found the Cassin Young more interesting — perhaps because we’ve seen similar ships to the Constitution back in the UK — but both were worth the stop.
Returning by Ferry and Exploring Boston Common
After miles of walking, we decided to rest our legs and take the Charlestown Ferry back across the harbour. The views of the Boston skyline were spectacular — the perfect reward for our morning’s effort. Back on land, we picked up the rest of the trail and made our way through Boston Common and Beacon Hill, weaving in a bit of shopping along the way. The afternoon sun made the old brick buildings glow, and the city felt far more alive and welcoming than it had the day before.
Italian Dinner in the North End
By early evening we were back at the hotel for a quick change before heading out for dinner. We retraced our steps to the North End and found Antico Forno on Salem Street — a proper local Italian restaurant with a warm atmosphere and wood-fired oven. We tucked into pizza, pasta, tiramisu and a few well-earned beers, all of which were excellent.
No visit to the North End would be complete without dessert from Mike’s Pastry, so we joined the queue and came away with a pair of their famous cannoli filled with sweet ricotta. Delicious, messy, and absolutely worth it.
Ending the Day
We ended the night back at the hotel bar with a couple of drinks before heading up to our room, exhausted but happy. We’d walked more than 27,000 steps, learned a little history, eaten very well, and seen Boston at its best. After yesterday’s slightly underwhelming start, the city had completely redeemed itself.
