The city of Boston is one of my “second” homes. From historical battle fields, to Irish pubs, a mix of colonial and modern architecture, the fusion of blue collar values and lofty academics leaves me feeling relaxed and welcomed. The city is smaller than most capital cities and boasts a host of unique neighborhoods. It’s more intimate than it’s rival New York, and it’s easy to escape for those dreaming of New England sea coast villages or the mountain wilderness of New Hampshire and Vermont.
Boston is where my mother’s family is from, where I went to school, it’s where all of my best friends live, it’s my first stop during any trip home, and it’s one of those places you could spend years exploring and never really figure it all out.
Bostonians are proud and loyal, with good reason. The city can lay claim to the nation’s oldest public park, first public library, first subway system, the first public school and as you will see everywhere the key role the city and its loyalists played in the American Revolution. I get asked over and over where to go and what to do in Boston. Here are 5 Uniquely Bostonian things you should do on your next visit to Boston.
The Freedom Trail
This is perhaps the most quintessential Boston tourist activity you can do. However, just because it’s popular doesn’t mean its not worth it. The Freedom Trail is a walking introduction to Colonial Revolutionary Boston. The trial brings walkers on a tour through the historic past of the city, covering 16 colonial sites over the course of 2-3 hours. The sites are connected by a red brick path serving as a guide through the city. At over 2.5 miles the trail combines museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.
You can take a self-guided tour or one of the many tours available through the Boston Common Visitors Center at 148 Tremont Street or the Bostix Booth located at Faneuil Hall. I prefer to walk, but you can also take trolleys that allow you to get on and off.
Oh, and stick around Faneuil Hall for some historic touristy shopping. Don’t forget to stop by my uncle’s bar, The Ames Plow Tavern for a beer and a reminder of what the area used to be like when it was an agricultural marketplace. Have a look at the bar and you’ll see pictures of my great grandfather and his blacksmith shop.
Catch a Red Sox Game
Fenway park is not only the oldest baseball park in the United States, but the Boston Red Sox are the best baseball team. Well, OK, I might be slightly biased, but it is hard to imagin coming to Boston and not experiencing a night at Fenway. The fans are loyal (when we win), loud (all the time), and the sausages and beer are excellent (if overpriced). During and after the games is when you will get to the heart and soul of any Bostonian. Buy a ticket well in advance as games are almost always sold out, or test your luck with the scalpers lining the road to the stadium.
At the very least park yourself on a bar stool at one of the thousands of bars across the city during a game and you will see what true passion, and bitterness is all about.
The North End is Boston’s oldest residential neighborhood with people living there since the 1630s. The area has gone through many face lifts and demographic shifts, from the wealthiest segment of Boston, to the first community of freed slaves, to mostly Irish, to a major Jewish center, and finally in the 20th century the center of the Italian American Community. If you are hungry this small 1/2 square mile area boasts over 100 small authentic Italian restaurants.
Your walk along the Freedom Trial will take you through the North End, so don’t forget to save room for Italian cannoli, a tour through the Old North Church and Paul Revere’s House.
Ok, to be fair I would give this advice anywhere in the world. But Boston sports two of my favorite small scale breweries, Samuel Adams and Harpoon. These two classic American Breweries will have you laughing in the face of anyone who tries to convince you that American Beer taste like water. Rich in flavor, and steeped in history they will also knock you on your ass if you drink too many.
The Samuel Adams Brewery offers a tours with a tasting afterward for a suggested donation of $2. Tours run weekdays and weekends but fill up quickly and tickets are only available in person. Harpoon Brewery has a free tasting on Weekdays and a $5 Weekend tour with a tasting afterward.
Nothing quite says New England cuisine like a large helping of seafood. From fresh lobsters, to New England Clam Chowder (psst that’s the white one), to raw oysters, you can not leave Boston without diving into the Atlantic ocean. You will find no end to places to eat lobster, which come boiled or steamed, with a fashionable plastic bib, drawn butter for dipping, a nutcracker for the claws and a pick for the legs. Eating lobster can be an expensive proposition and they are sold by the pound with market prices changing everyday. Personally, I’m a clam chowder and crab cake kind of a guy.
There are too many great fresh seafood restaurants to name them all. While my favorites are simple shacks in the small coastal towns near Boston, if you are in the city you can’t go wrong with Legal Sea Foods. Go to the one near Long Wharf and you can stroll along the water before or after dinner and watch the seals for free just outside of the Boston Aquarium.
Of course there is plenty of truly unique Bostonian adventures to be had in this culturally packed little city. We would love to hear your own recommendations.