Boston is known for a lot of things: its rich history, its educational institutions, its passionate sports fans, its colorful autumns (and brutal winters), its culture, and its pride. Whether you're dining on a high-class dinner or watching a Patriots game at a local bar, you'll feel the love for this city's strong personality.
Start your weekend in Boston off by stepping way back in time, to the first battle of the American Revolution: the Battle of Bunker Hill. Even though the Americans lost the battle, the British were left maimed by the engagement, finally understanding just what they were up against. A massive granite obelisk marks the battle, and there's a free museum across the street where you can delve more into the story of the skirmish.
Faneuil Hall Marketplace has been the place to eat and shop in Boston since 1742. Today, there are tons of vendors selling all kinds of delicious things to eat and drink, plus souvenirs, and other wares. Sure, it's pretty touristy, but if it's your first time in Boston, you should stop by and at least appreciate the historical vibes.
It seems like every square inch of Boston is somehow historically significant. That's why it's a good thing that the city decided to help tourists out by specially marking out some of the most important sites by creating the Freedom Trail. It's a 2.5-mile-long path (marked with brick) that winds through the city past 17 spots of particular historical interest, mostly pertaining to the American Revolution, in which Boston played a huge role. Walking along the trail, you'll see all kinds of fascinating places, from ships to cemeteries, and essentially follow the path from colonial rule under Britain to American independence.
Once you're done walking the Freedom Trail, you're probably going to be famished. The last thing you probably want is to wait in line, but don't let a wait deter you from eating at local favorite Neptune Oyster. They really do have the best seafood in Boston. Everyone raves about the raw bar and the hot buttered lobster roll... and once you taste the food here, you'll see why! And as for the wait, grab a drink at the bar and make the most of the people-watching.
If you can, snag tickets to a game at Fenway Park. It's the oldest baseball stadium in the country (built in 1912!) making it a veritable pilgrimage for sports fans. Seats on top of the Green Monster, the massive green left field wall, are harder to come by, but if you can swing it, it's worth it. Otherwise, enjoy a hot dog and a few beers and watch the Red Sox... the team is a local institution!
(If the Sox aren't in town, catch the game at a local bar, and if it's the off season, a Patriots or Celtics game is just as entertaining.)
After that, head for a nightcap at Wink & Nod, a cocktail bar with old-school drinks and a modern culinary incubator that lets up-and-coming chefs take over their food menu for six months at a time. The drinks ain't cheap, but they're worth it: the cocktails are imaginative and feature fresh, unique ingredients!
There are tons of awesome boutique hotels in Boston, but the Inn at St. Botolph is unique. For starters, the fact that it's in a brownstone in a more residential neighborhood, and the fact that there's no lobby or doorman (you get a key and can enter like it's a private residence) make it feel like you're a local. Of course, it has the classic hotel amenities, like a hotel lounge and fitness center, as well. Basically, you get the best parts of staying in a hotel and staying in an Airbnb, all for a great price.
Since you spent the whole first day exploring Boston's North End and downtown, make your way north to the cool neighborhoods of Cambridge and Somerville for day two. Cambridge is home to MIT and Harvard, so you get Ivy League history and cool college town vibes, and Somerville is an artsy little suburb that has started to become the hotspot in the Boston area: Lonely Planet named it one of the best places to visit in the whole country! Start with breakfast or brunch at The Friendly Toast. Whatever you're craving that morning, whether it's a Benedict, a scramble, a stack of waffles or pancakes, something healthier, or even just a cup of coffee, this quirky local staple is the perfect place to start your morning.
Okay, so not everyone can get into the Massachusetts Institute of Technology (BKA MIT) but everyone can get into the MIT Museum on their campus. Science, math, and technology collide with art and history here: displays of vintage slide rules, old polaroid cameras, stunning glass, robotics and AI, holography and more will have you oohing and ahhing at the beauty and intrigue of science and technology.
After MIT, keep the brainy vibes going by exploring Harvard Yard. This is their quad, a green, grassy area surrounded by historic buildings. The churched, libraries, museums, and even dorms that line the yard are stunning, and you can even go into some of them. Go to the Smith Campus Center and head out on a student-led historical tour of the Yard for a great guided adventure!
Head back to Kendall Square for lunch at Area Four. They're known for their pizza, which is totally one-of-a-kind, thanks to their crust dough, which is made from a 12-year-old starter, fermented for 30 hours, and cooked in a wood-fire oven after being topped with all kinds of delicious things. And, since this is a college town, they offer locally-roasted coffee drinks as well.
Pro tip: they also serve brunch, which includes a mouth-watering breakfast pizza and other goodies cooked in the wood-fire oven. Drool.
Harvard has more than a few world-class museums, so spend a few hours exploring one or two of them. The Peabody Museum of Archaeology is awesome. Their collections contain artifacts from across time and the globe: pottery and dolls from the American Southwest, Aztec figurines from Mexico, textiles and metalwork from South America, and tons more.
For a more offbeat museum experience, head up to Somerville to check out the Museum of Bad Art. Yep, this is a real place, folks... a museum dedicated to the paintings that you'd never find in a real art institution. Are the masterpieces here actually that bad? What even is "bad art"? That's all for you to decide after you visit this surprisingly thought-provoking spot.
After all that exploring, you deserve a beer. Aeronaut Brewing Company in Somerville is the perfect place to unwind with a craft brew (they make a lot of stellar IPAs) and maybe a game on their Nintendo (hooked up to a huge screen, of course). The huge, open, industrial space with a few off-the-wall decorations make for a great environment to chill out for an hour or two.
Simultaneously paying tribute to the punk rock dive that once occupied the space and to the incredible local food produced around Boston, Kirkland Tap and Trotter is the kind of restaurant you would be a regular at if it was in your hometown. Think, tacos made with softshell crab, burgers made with grass-fed beef and housemade kimchi Russian dressing, and crispy fried pork ribs. Instead of cheap beer, you can find craft brews, barrel-aged cocktails, and tons more.
End your trip with a strong beverage from the hefty A-Z cocktail menu at the Green Street Grill. Head into the dark, cozy space and ask the bartender for "The Bible", which is the unabridged cocktail menu listing every. Single. One of their many drinks. Whether you're craving a fruit tiki drink, a stiff whiskey beverage, or a classy martini, they have it. Careful, though: they're pretty strong!
Spring, summer, and fall are the best times to visit Boston. Winters are frigid and can bring a ton of snow, but prices then are a good bit cheaper. Fall is probably when Boston is at its best: the New England region has tons of old-growth trees that change to their vibrant autumn colors, apples and pumpkins abound, and the weather isn't so hot that you can't stay outside exploring without needing some AC.