14 Experiences to Add to Your Boston Bucket List

There's no better way to kick off your trip than by following the red-brick path of the Freedom Trail. Not only is this 2.5-mile-long path one of the country's most historic walking trails, but it also serves as a fantastic way to get to know the city.

Starting in the Boston Common and concluding at the Bunker Hill Monument, this trail passes along 16 locations that hold significant value to the history of the United States. From iconic museums and meetinghouses to notable burying grounds — and even Paul Revere's residence — each step you take will unveil a new story.

One of the most popular destinations along the Freedom Trail is the Faneuil Hall Marketplace. Located in the heart of downtown, this marketplace is actually four great places in one location: Faneuil Hall, North Market, South Market, and Quincy Market.

If you've managed to work up an appetite from all that walking and exploring, make a pit stop at Quincy Market. With over 36 international food vendors inside, this market serves as the largest food hall in all of New England. There is no doubt you'll be able to satisfy practically any craving. A word of advice: indulge in as much seafood as possible. Fresh steamed lobster, half-shelled oysters, creamy chowder, and sacred cod are just a few of the many local specialities!

But because the inside can get quite crowded, I recommend bringing your food findings outside to the cobblestone promenade. There is always some kind of outdoor performance taking place here. Whether it's jugglers, magicians, or musicians, this area is a great place to sit and take a breather.

Simply put, you can't visit Boston without indulging in some sort of decadent sweet treat from Mike's Pastry. You just can't. While this renowned Italian bakeshop is most famous for its cannolis — they've been cranking out these cream-filled pastries since 1946 — the truth is, everything is out-of-this-world delicious.

Yes, there will probably be a line out the door. But don't let that stop you, as top-quality brownies, cookies, and eclairs are awaiting your arrival inside.

Looking to learn more about the craft-brewing process? If so, carve out time to visit the Samuel Adams Brewery. During this free brewery tour, you'll taste specialty malts and smell the Hallertau hops used to brew Samuel Adams Boston Lager, all while learning more about the Samuel Adams brand. And yes, there will be plenty of time to sip and sample, too!

Did you know you can experience "America's Most Beloved Ballpark" without the crowds? It's true! For $18 per person, you can tour the historic grounds of the Fenway Park and sit atop the iconic Green Monster. But that's not even the best part. Your pass will also provide access to watching the players during batting practice. How cool, right?

While Beacon Hill might be small in size, this neighborhood is certainly big in history. Overlooking the nation's first public park, as well as the Massachusetts State House, these cobblestone streets are teeming with fascinating things — not to mention beauty — which is why this area makes for a glorious afternoon stroll!

After taking in the stately homes and quaint alleyways, be sure to make your way over to Charles Street. Here, you can feast your eyes on even more delights thanks to all the colorful boutiques, shops, and galleries.

For a quintessential Boston experience, hop aboard a swan boat and glide across the lagoon in the Public Garden. At just a few dollars per ticket, this boat ride is one of the most relaxing and picturesque ways to tour through the serene garden. Plus, the swan boats have become quite the cultural icon for the city, as they have been in operation since 1877!

When it comes to the Boston Public Library, this building is more than just a house for books. This place is truly an architectural masterpiece! Established in 1848, this institution became the first large free municipal library in the United States. And with over 23 million items in its collection today, it has remained one of the largest public library systems in the country.

With intriguing attractions — such as biweekly courtyard concerts in the Summer and a near-daily afternoon tea service in the Courtyard Restaurant — this library is certainly worth checking out.

Another place to add to your "must-see" list is the city's Museum of Fine Arts, which happens to be the fourth-largest museum in the United States. With more than 450,000 works of art, meandering through this museum will make for an unforgettable afternoon, as there are endless exhibits to discover.

Just don't be too disappointed if you can't explore them all! After spending several hours here, I didn't even scratch the surface during my visit. But it's just another reason to return, right?

Of course, what would be a visit to Boston without touring the oldest college in the United States? You know the one I'm referring to: Harvard University.

While there are numerous historic buildings, halls, and landmarks to discover, make sure to carve out time to stop by the infamous Harvard Yard. This lush grassy area is the oldest part of the campus and is a popular spot to plop down and roll out a blanket for a picnic.

Once you've indulged in a bit of rest and relaxation, don't forget to explore the charming streets of Cambridge right outside the University's gates.

Get ready for a boost in creativity and inspiration when visiting Boston's South End, as this is the home to the blossoming SoWa, the city's leading art destination. Here, you will find a vibrant art community, comprised of artist studios, local boutiques, design showrooms, and buzzing weekly markets.

One market in particular not to miss is the award-winning SoWa Open Market. Bringing together the area's best designers and creative entrepreneurs, this market provides a unique shopping experience and is a phenomenal place to find one-of-a-kind pieces and collectibles.

OK, history buffs, this is for you! If you're looking to visit the grounds of the first major battle of the American Revolutionary War, make your way over to the Bunker Hill Monument. Located across the Boston Harbor in Charlestown, this 221-foot granite monument marks the end of the Freedom Trail. However, if you want to avoid crowds, consider following the trail backwards so you can visit this landmark first!

Although it's a bit of a workout, visitors can climb the 294 steps to the top of the monument for a spectacular view of the city as well as the harbor.

Speaking of spectacular views, soar 52 floors above the Back Bay and have the happiest of hours at the Top of the Hub. Situated atop the Prudential Tower, this restaurant offers one of the most romantic dining experiences in all of Boston.

Yet because the tabs can become quite pricey, if you're looking for a less expensive option, opt to sip on cocktails in the restaurant's lounge. This way, you can relish in the sublime panoramic views without forking over your entire travel budget.

Even if you're not a classical-music fanatic, attending a performance by the Boston Symphony Orchestra is an absolute must when visiting this pocket of the Northeast. While the BSO started performing back in 1881, today, the world-renowned symphony plays over 250 shows each year. Due to the increased popularity of these shows over the years, tickets can be quite hard to come by, so if you manage to score passes, go!

However, don't fret if you aren't able to purchase tickets to a performance, as you can still tour the magnificent Symphony Hall. And the best part? These tours are free!