Stepping Through History- Boston

Boston has a way of pulling you right in. The mix of old-world history and modern city energy is pretty cool. On our first day, we dove straight into the heart of it with a Red Sox game at Fenway Park. There’s something electric about being in that ballpark: the crack of the bat, the crowd singing “Sweet Caroline,” and the feeling that you’re part of a tradition that’s been alive for more than a century. After the game, we carried the excitement into dinner at Union Oyster House. Stepping through the doors of the oldest continuously operating restaurant in America felt like walking back in time. The wood-paneled dining room has hosted everyone from Daniel Webster to JFK.

The second day was all about the Freedom Trail. We decided to do the entire thing by foot, starting at Boston Common and following that famous red line through centuries of history. Along the way, we stood before the Old State House, imagining the fiery debates that helped spark a revolution, and paused at the Paul Revere House, picturing the midnight ride that has been told and retold for generations. The Granary Burying Ground was both humbling and haunting, with the resting places of patriots like John Hancock, Samuel Adams, and Paul Revere himself. Boston Harbor was breezy and beautiful, reminding us of the tea party that changed the course of history, while Beacon Hill charmed us completely with its narrow cobblestone streets and flickering gas lamps. We climbed up to Bunker Hill, and lastly almost crawled to the USS Constitution, proud, triumphant and a little sore at the end of the trail. My Apple Watch proudly flashed 25k steps and we earned every single one.

So how do you celebrate a day like that in Boston? With oysters and spritz, of course. We found a spot called Warren Tavern established in 1780, offering $1 oysters. We paired them with an ice-cold beer and a crisp Aperol spritz, the perfect treat for tired feet.

Dinner that evening took us to the North End, Boston’s “Little Italy,” where the food is as much a part of the culture as the history. Plates of fresh pasta with, a spicy lobster sauce. The polpetta has been named Boston’s best meatballs, tender, rich, and served with sauce that had been simmering all day. Just when we thought we couldn’t eat another bite, tradition called us to Mike’s Pastry. No trip to Boston is complete without one of their legendary sweets, leaving its mark as we walked down Hanover Street, smiling like true tourists.

Two days, thousands of steps, unforgettable meals, and so many layers of history, it’s safe to say Boston was a great trip. This is a city best experienced on foot, fork in hand, with a little bit of dolce to end it.