Corner any local in Boston and ask them what you should do on your visit to this city, we guarantee 9 out of 10 times the Freedom Trail will be a part of their answer. That’s because when it comes to Boston, the city has made a name for itself in walking tours. But for those visitors who want to get a nice walk in with a little less history, we’ve put together a route that hits all the best spots.
TIP: Boston’s streets are old, so there are two things to remember when you hike. First, when it comes to shoes, choose function over fashion—you’ll be walking along stone, brick, and cobbled streets, so a comfortable pair of shoes will get you a lot farther (I’ve lost a few good pairs to these streets before). And second, make sure you have a map and/or GPS on your phone—Boston streets are winding and can get confusing at times, so without some guidance you might end up walking in circles.
North End: We start our non-Freedom Trail walk on the Freedom Trail (ok, yes we admit that is a bit confusing). While this historic neighborhood is home to some of the top Revolutionary sites in the city, it is also home to some of the most delicious food. Take a moment to wander through the Old North Church, and onto Hanover Street, where you can pick up some snacks for later—cheese, charcuterie, cannoli, they’ve got it all! (Note: This is home to the famed Mike’s Pastry. We try to get there early to beat the lines, but you can stop by at any time to get your Italian bakery fix if you’re ok waiting in line.)
Faneuil Hall and the North End Park: Over the years, Boston has made more of an effort to increase its green spaces in the city. One such example is the North End Park, which has become a staple for both locals and visitors in the summer months. Here, you can lay out a blanket and have a picnic (stop by the Boston Public Market for other food options), play in the water fountains, or sit at one of the tables and read before continuing on. Just south of the park you’ll find one of Boston’s top attractions—Faneuil Hall. Here, you can shop, eat, grab a snack, or just wander through and catch a street performance.
The Boston Common: Climb the stairs past Boston’s concrete City Hall (a product of 1960’s geometric design and often described as one of the ‘Ugliest Buildings in America’), and turn left onto Tremont street. Follow the curve until you reach a large open green space. This spot, known as Boston’s Common, has existed since colonial times and was once grazing land for Boston’s livestock. Look north to spot the gold-domed State House, the hub of Massachusetts’ government, and continue west past the Frog Pond, which in summer months is a swimming spot for children, and in the winter transforms into a fun ice skating rink.
TIP: Before you walk through here, read up on the famously obese squirrels—they are adorable!
Beacon Hill: North of the Common, one of our favorite areas to walk is Beacon Hill. Here, you’ll see the true historic beauty of Boston’s architecture, with brick streets and brownstone homes lit by picturesque street lamps—you feel like you’re taking a step back in time. Wandering through here doesn’t take long, but it’s a must-see for architecture and history nerds.
Boston Public Garden: From Beacon Hill, turn left onto Charles Street heading back towards the Public Garden. One of our favorite stops is the Make Way for Ducklings statue, commemorating the 1941 illustrated book by Robert McCloskey about a family of ducks that trekked through the city in the most adorable way. If you’re looking for real ducks, head over to the pond and watch the swans and ducks swim around, or if it’s the right season, take a ride around the pond on one of Boston’s swan boats.
Newbury Street and Copley Square: By now you’ve walked a few miles through historic Boston, so you’ll be in need of some refreshments. Wander down Newbury Street for a taste of high end shopping plus a selection of restaurants. One street over is Boylston, which brings you to the heart of Copley Square and some of our favorite Boston Landmarks—Trinity Church, Boston Public Library, the Prudential Center—there’s plenty to do in that space.
TIP: When on Boylston Street, be sure to look for the Boston Marathon Finish Line (in front of Marathon Sports), but be careful of cars when snapping photos!
Kelleigh Welch 