With a long and illustrious history of revolution and reform, Boston has a rich heritage and fascinating culture that spans more than 400 years. It is the site of many significant historical events and home to some of the country’s most prestigious academic institutions and championship sports teams. Plus, its harborside location makes it one of the most beautiful cities in Massachusetts!
Originally established in 1630, Boston has a tangible sense of the past that makes it a fascinating place to visit. The vibrant and diverse neighborhoods – such as the incredibly hip Allston-Brighton and the restaurant-filled North End (Little Italy) – are perfect for immersing yourself in the culture of the city. If that’s not enough, the historic landmarks and famous sports stadiums are ideal places to explore on a visit to the area.
Whether you’re looking for fantastic food, live music, stunning architecture, lively sports games, wildlife, or history, Boston has everything you could need and more. In fact, there are so many things to choose from that we have put together a list of the best things to do in Boston to help you get started. Stick to these fun and unique Boston bucket list recommendations, and you’ll have the time of your life exploring the City of Champions!
- 15 Fun and Unique Things to do in Boston
- 1. Catch a game at Fenway Park
- 2. Get a culture fix at the Boston Museum of Fine Arts
- 3. Stroll along the Freedom Trail
- 4. Dance to live music at Brighton Music Hall
- 5. Enjoy a play at Cutler Majestic Theatre
- 6. Grab a drink at the original Cheers Bar
- 7. Wander through the Faneuil Hall Marketplace
- 8. Visit Harvard University
- 9. Explore Boston’s culinary delights with a Boston Foodie Tour
- 10. Take a day trip to Salem
- 11. Go on a sightseeing tour in an amphibious bus
- 12. See the stars at Coit Observatory
- 13. Head out on a boat to go whale watching
- 14. Climb the Bunker Hill Monument
- 15. Take a scenic sunset cruise
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15 Fun and Unique Things to do in Boston
1. Catch a game at Fenway Park
Nothing quite beats the thrill of cheering on a local team in a famous stadium, and this is especially true of watching the Boston Red Sox play at the legendary Fenway Park!
Since opening in April 1912, Fenway Park has hosted the World Series 11 times, with the Red Sox winning six titles and the Boston Braves winning one. The park is the oldest ballpark in Major League Baseball and was added to the National Register of Historic Places in 2012.
To get here, you’ll need to take the subway to Kenmore Square off the Green Line or the MBTA bus to Brookline Ave & Yawkey Way. But one of our favorite ways to get here is by bike! Biking is quick, inexpensive, and a great way to take in the sights of Boston on the way.
Tickets range from around $35 for the cheap seats to a whopping $1,500 for a fancy field box. It’s a good idea to book tickets in advance, but limited numbers do go on sale up to 90 minutes before the game. Make sure you get a photo in front of the Green Monster and the famous Boston Red Sox sign while you’re there!
2. Get a culture fix at the Boston Museum of Fine Arts
The Museum of Fine Arts houses one of the most exceptional collections of art and artifacts in the world. Filled with world-renowned paintings by Gauguin, Van Gogh, Rembrandt, and Monet, as well as vast collections of sculpture, ceramics, photography, and textiles, the museum is the perfect place to soak up the culture and admire beautiful works of art.
For an afternoon of inspiring art, seek out the beautiful John Singer Sargent collection before heading to the impressive Arts of Islamic Cultures Gallery and the Claude Monet gallery in the European Wing.
If it’s ancient wonders of the world you’re interested in, then head to the Arts of Ancient Egypt wing, which contains more than 65,000 antiquities. Here you can see everything from coffins and mummies to weapons and mosaics. All of the artifacts were acquired during excavations led by American archaeologist George Andrew Reisner Jr. between 1905 and 1942.
There are further extensive collections of art and historic artifacts from Asia, Ancient Greece and Rome, Europe, the Americas, and Africa around the museum, so it pays to set aside a day to explore them all. Adult tickets start at $27, and the museum is open from Thursday to Monday between 10 am and 5 pm.
3. Stroll along the Freedom Trail
The Freedom Trail is an exploration of the history of Boston and the beginning of the United States as we now know it. This 2-hour walking tour follows the famous 2.5-mile red brick line through some of the most important and historic sites and neighborhoods in Boston, giving visitors a glimpse into the complicated history of the area.
Many of the sites are notable for their role in the American Revolution. At some point, all of the sites on the trail have been involved in political and social movements that subsequently shaped the city and the country as it stands today.
Visitors can walk the trail end to end, pick a few sites of interest and explore those, or take a guided tour from the National Park Service staff or private organizations. Some of the sites on the route charge admission fees, so if you are on a budget, it is worth planning ahead and picking out the places you would prefer to see before you head off.
Don’t miss the USS Constitution, a warship originally launched in 1797, and Boston Common, which is considered the oldest public park in the United States.
4. Dance to live music at Brighton Music Hall
Boston has a plethora of live music venues to choose from, but one of the most coveted is the Brighton Music Hall. Located in the heart of Allston, Brighton Music Hall is an intimate performance venue hosting every kind of act, from new local bands to internationally renowned stars.
Since first opening its doors in 2010, the stage has seen bands such as Imagine Dragons, Weezer, and Dropkick Murphys, as well as stand-up comedians, spoken word poets, and DJs from around the world.
Although the 500-capacity venue is on the smaller side, it means you are always within 60 feet of the stage, so you are pretty much guaranteed a great view!
There are three fully staffed bars, so queue times are minimal, and there are pool tables in the back if you need to take some time out from the crowd. It’s a great venue to check out new or established artists – just be sure to buy your tickets in advance, so you don’t miss out.
5. Enjoy a play at Cutler Majestic Theatre
Designed as a Beaux-Arts-style theater by architect John Galen Howard, the Emerson Cutler Majestic Theatre opened its doors in February 1903 as the second performance venue in Boston’s historic Theater District.
The refined architecture and flawless acoustics of the venue were originally intended for opera. However, the theater was also used for vaudeville, theater, and movies throughout the years, until it fell into decline in the 1970s.
Emerson College purchased the building in 1983 and restored the architecture to its former glory. After years of anticipation, it finally reopened in 2003 as an award-winning 1,186-seat auditorium with state-of-the-art theatrical facilities.
While visitors come for the world-class performances, some get more than they bargained for. There have been several sightings of ghosts in the balconies, which have led to the theater being included in one of the city’s famous ghost tours!
Whether you’re into dance, theater, music, or opera, there is always a performance here worth seeing. Just remember to watch out for those shadows on the balcony! To get to the venue, you need to take the Green Line to Boylston/Theatre District or take the Orange Line to Essex/Chinatown.
6. Grab a drink at the original Cheers Bar
Ever wanted to go where everybody knows your name? Well, while you’re in Boston, you can visit Cheers, the real-life pub that inspired the iconic TV show. Originally founded in 1969 as the Bull & Finch Pub, the intimate and friendly setting became the inspiration for the hit TV show Cheers after producers went searching for the quintessential American bar.
After visiting other bars in Boston, the producers returned to Bull & Finch and decided to use it as the inspiration for the set in the show. Cheers first aired in 1982 and is still regarded as one of the best American sitcoms of all time.
The bar holds regular live music shows, trivia nights, and promotion events, so be sure to check out what’s happening while you’re in town. While you’re ordering a drink at the bar and recreating your favorite Cheers moments, you can also grab a bite to eat from the Cheers-inspired menu.
Sample Sam’s Turkey Sandwich and Frasier’s Chicken Panini or take the Giant Norm Burger Challenge to get your name on the Norm Burger Hall of Fame!
7. Wander through the Faneuil Hall Marketplace
The historic site of Faneuil Hall has been a bustling marketplace since 1743. Located near the waterfront, this eclectic market is filled with boutique shops, department stores, food stalls, bustling restaurants, and live performers.
There are four indoor and outdoor spaces arranged around a cobblestone plaza: Faneuil Hall, Quincy Market, North Market, and South Market. The Quincy Market Food Colonnade is set in a neoclassical building designed by architect Alexander Parris. Opened in 1976, the food market was one of the first food halls in the US, setting a trend for the rest of the country.
The North Market building is packed with chain stores and independent boutiques, while the South Market has clothing stores to suit all tastes. Finally, the historic Faneuil Hall is home to the Visitor Center and a Museum Shop where you can learn all about the historical significance of this building.
This is a great place to grab a bite to eat while strolling through the stalls and boutiques and admiring the world-class street performers on every corner. To get here, take the MTBA Subway Blue Line to Aquarium/Faneuil Hall or hop on one of the many tour buses that come here every day.
8. Visit Harvard University
Harvard University is an iconic Ivy League university that counts Henry David Thoreau, Gertrude Stein, W.E.B. Du Bois, and seven US presidents among its alumni.
Famous for being America’s oldest learning institution, the campus was founded in 1636 as the “New College” to educate clergy. The name was changed to Harvard University in 1639 following the death of John Harvard, who had donated his entire library and half of his estate to the school in his will.
The best way to take in the history and significance of this prestigious institution is by a free student-led tour which lasts between 45 to 60 minutes. Visitors are guided through the campus to see the library, Memorial Church, Massachusetts Hall, and Memorial Hall while learning all about the history of the buildings.
It is said that touching the shoe of John Harvard’s statue will bring you luck, so make sure you make a stop here on your tour as well!
The red brick colonial architecture and the views of Charles River provide a beautiful backdrop for photos, particularly in the fall, so pack your camera when visiting. Due to its prestige, visiting Harvard University is one of the must-do things in Boston.
9. Explore Boston’s culinary delights with a Boston Foodie Tour
Boston is famous for its pubs, sports, and historical significance, but it is also on the map for its wide range of delicious food options. To get the full experience of local food and first-class eateries, join a multi-award-winning foodie adventure tour group. One of the most fun things to do in Boson, Boston Foodie Tours will take you on a gastronomic adventure through the streets of Boston’s historic neighborhoods.
Boston Foodie Tours offers two public tours: the North End (Little Italy) Neighborhood Tour and Boston Public Market & North End Tour. Each tour lasts up to 3.5 hours and includes the history of the area, visits to award-winning restaurants and food markets, and plenty of the best food in Boston!
The North End Neighborhood Tour includes stops at many of the “Best of Boston” winners, where you can sample some of the finest Italian-American sandwiches, pizza, and cannoli in the city. The Boston Public Market & North End Foodie Tour is a walking tour through Boston Public Market and Haymarket Market where you can sample local foods such as clam chowder, lobster rolls, and infused maple syrups followed by sweet treats from the local bakery.
10. Take a day trip to Salem
Boston’s historic seaport is the ideal place to hop on a ferry and take a day trip to nearby “Witch City!”
Head to the seaport to catch the high-speed ferry service between Long Wharf, Boston, and Blaney Street in Salem. In less than one hour, you’ll arrive in the famous city of Salem, where you can hop on the Salem Trolley and take a narrated tour of Salem. The tour crams in 400 years of history into just one hour as you pass through Salem’s neighborhoods and stop at all the major attractions.
Set aside some time to visit the Salem Witch Museum to discover the story of the 1692 Witch Trials before heading to Omen Psychic Parlor and Witchcraft Emporium to have your fortune read. There are plenty of food options to choose from in Salem, but Finz Seafood & Grill offers fresh seafood with unbeatable views of the waterfront.
After grabbing a bite to eat, wander around and check out the famous House of the Seven Gables. After that, finish your trip with a drink at The Landing at the Salem Ferry bar, where you can enjoy your refreshments while overlooking the harbor and waiting for your ferry to come in.
11. Go on a sightseeing tour in an amphibious bus
One of the most unique things to do in Boston is exploring the city on a Duck Tour! These amphibious vehicles collect sightseers from the Prudential Center, the Museum of Science, or the New England Aquarium and head out on a narrated adventure through the city streets before finally taking a dive into the Charles River to admire the views of the Boston and Cambridge skylines.
The 80-minute Duck Tour cruises through some of the most historic sites in Boston, while the “ConDUCKtor” provides an entertaining narrative packed with facts, information, and plenty of jokes, making this an ideal trip for families and those looking for a fun way to explore the city.
The WWII-style amphibious vehicles travel just as well on water as they do on land, making this a sightseeing tour to remember. You can also opt to stop for lunch or dinner or another Boston attraction on your journey to create the perfect outing. Prices start at $48.99 for adults, and the tours run every hour, seven days a week.
12. See the stars at Coit Observatory
If it’s romance you’re looking for, then it doesn’t get better than the Coit Observatory. Stargazing is a great way to spend an evening, and the best part is that on the Observatory’s Public Open Nights, this activity is completely free. However, this does mean that it is incredibly popular, so it is very important to reserve your free tickets ahead of time.
The observatory is named after Boston University’s first astronomy professor Judson B. Coit and is used by undergraduate and graduate-level students for astronomy courses and projects. The public is permitted to enjoy the celestial views through the Schmidt-Cassegrain telescopes and binoculars while guided by the observatory’s manager, who helps you find and identify stars, planets, and constellations.
The Public Open Nights are held on Wednesdays and begin at 8:30 pm in the spring and summer and 7:30 pm in the fall and winter, weather permitting. Tickets are made available each Thursday for the following Wednesday. Space is limited, so tickets do get booked up very quickly, and it is worth checking whether the event has been canceled due to rain or clouds.
13. Head out on a boat to go whale watching
Each summer, the Boston area is home to an abundance of humpback whales, finback whales, minke whales, and dolphins who have migrated to the warmer waters of Massachusetts. The Boston whale watching season begins in late March and runs through mid-November. It’s the perfect opportunity to tick a Boston bucket list adventure off your list!
Whale sightings are practically guaranteed between May and October, so if you happen to be in the area at that time, a whale-watching tour is an absolute must. Climb aboard one of Boston Harbor City Cruises’ high-speed catamarans, which will take you to the feeding grounds 30 miles east of Boston. Here naturalists from the New England Aquarium provide information about the magnificent mammals.
After a once in a lifetime experience of seeing the whales in their natural habitat, head to the New England Aquarium, where you can learn all about the native species of penguins, seals, stingrays, barracudas, and sharks before getting up close and personal with a few of the animals.
To dive a little deeper into the Whale Trail, head over to Harvard Museum of Natural History, where a pod of whale skeletons is suspended in the Great Mammal Hall. Admire the enormous and rare North Atlantic right whale and be mesmerized by the majestic fin whale, which can weigh over 100 tons in the wild!
14. Climb the Bunker Hill Monument
Bunker Hill was the site of the American Revolution’s first major battle between New England soldiers and the British Army in June 1775. Fifty years after the event, the Marquis De Lafayette set the cornerstone in what would become a 17-year project of building the 221-foot-tall obelisk, which now stands as a tribute to the bravery shown, the lives lost, and the activism that took place on this land.
Take a stroll through Charlestown’s hilly roads and follow the Freedom Trail up to the Bunker Hill Monument. You can even opt for a guided tour from one of the Park Rangers to learn more about this significant site.
After taking in the solemn surroundings of the monument, head to the Bunker Hill Museum, where the exhibits and dioramas go into detail about the Battle of Bunker Hill, the construction of the obelisk, and the fascinating history of the Charlestown district.
The monument is open every day between 10 am and 5 pm, with the last entry to climb to the top at 4:40 pm. There is no elevator, so climbing the 294 steps can feel like a bit of a workout, but the view makes it all worthwhile!
15. Take a scenic sunset cruise
If you’re looking for a view of the city with a difference, take a Boston cruise on a sailboat or a luxury yacht at sunset! Whether you want to finish your day in style or start your evening with a bang, sailing through the Boston Harbor on a boat is the ideal way to set the stage and take in beautiful views of the city as the sun goes down.
Choose from an elegant sailing boat or a lavish motor yacht, then kick back and relax while you sip champagne from the bar and enjoy the exceptional hospitality from the onboard crew during the 2-hour cruise. Bring a date to admire the stunning views of Boston as the sunset paints the skyline with oranges, reds, blues, and pinks, or meet with friends to enjoy a few drinks while the sun dips below the horizon.
The cruise will take you by the U.S.S. Constitution at a dry dock in the Charlestown Navy Yard where you can listen for the cannon fire that announces the setting of the sun. Prices start at $40 per person and are dependent on the season and weather.
There you have it! The 15 best things to do in Boston. What’s your favorite thing to do in the City of Champions? Let us know in the comments below!
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