I have been to Boston more times than I can count and will continue to go back annually for the rest of time. It is quite simply my favorite city I have been to! It is big enough to provide great night life, a sprawling pro sports market, all sorts of festivals and events, and enough to do to keep you busy for weeks. But, it is small enough for it to feel tremendously safe, super clean, and you won’t feel like you have to run the Boston marathon just to get across town!
Boston is home to about 655,000 people. For history buffs and sports fans, the city is a playground, providing revolutionary era tidbits at every turn and deploying some of the most successful sports franchises in the Red Sox, Celtics, and Bruins. If neither of these get you excited, the food scene is sure to not disappoint. Home of some of the best seafood in the world, you are surrounded by lobster rolls and clam “chowdah”.
1.) Freedom Trail
While not necessarily a trail, the Freedom trail is a 2.5 mile route through the City of Boston that will take you past some of it’s most historical landmarks. It can be self guided or you can tag along with a Park Service Ranger. The starting point is typically out front the Old State House, where the site of the Boston Massacre is displayed by a large monument in the side walk. From here you can head either North or South and will pass sights such as Paul Reveres home, the Old North Church (church in which Revere Was signaled from…”The British are coming, the British are coming!”), Boston Common (the oldest public park in the US), Faneuil Hall, the burial ground of Samuel Adams, and many more! It is truly a must do on your Boston trip and offers many opportunities to pay your respects to our great Founding Fathers!
2.) Faneuil Hall marketplace
Right in the heart of downtown Boston, Faneuil Hall Marketplace is a bustling hub of activity where you can choose from about 100 different spots to grab lunch and catch a street performer or two. Dating back to 1742, the market provides many different lunch and shopping options. Located in close proximity to the Old State House and within walking distance of the North End and the Harbor, it is a great place to take a break and grab a bite to eat.
3.) Fenway Park
Or, Fenway Pahk. I am a little biased here and would put this #1 if I could! There is nothing quite like watching the cities beloved Red Sox in one of the oldest ballpark’s in America. It is ballpark that mimics the city in which it is one of the smaller ones in the MLB and has seen minimal changes over the years. Even if the Sox aren’t playing, be sure to wander over to the Fenway neighborhood and check it out, maybe stop for a beer or two at The Bleacher Bar, a restaurant located under the outfield bleachers with a window that looks directly onto the field.
4.) Pop Culture stops
If you are fan of Hollywood then Boston has some spots for you! The iconic TV Show Cheers was filmed in Los Angeles but uses an exterior shot of the Bull & Finch Pub on Beacon street as its shot of the bar. You can now have a beer at the famous bar and place yourself next to Woody Harrelson’s seat if you choose.
Many films, including Good Will Hunting, The Departed, and The Town, are set in Boston and you can visit many sights from the movies. You can even head over to Boston Common and sit on the exact bench that Matt Damon and Robin Williams shared a special scene.
5.) The Food!!
If you ask any Bostonian, they will claim their city as the Seafood Capital of the World. They may just have a case. Home to famous clam chowder, lobster rolls, clams, scallops, oysters, and much more, you may not find seafood more fresh anywhere else. Boston is a harbor city and they take pride in their food. The Union Oyster House, located in the north end, is Bostons oldest restaurant, standing for over 250 years and has been serving locals since 1826. Their stalls and Oyster Bar are in their original positions and there is a no feeling quite like it to be able to eat lunch in the same stalls as our Founding Fathers! Make sure you head across the street to get a drink at the Bell in Hand Tavern, America’s oldest tavern where the first drink was poured in 1795.
A city that oozes and history at every corner, Boston will make you want to return time and time again. A very family friendly city, there is something to do for everyone!