15 Unique Things to Do in Boston as Recommended by Locals

From cobblestone streets echoing tales of the Revolutionary War to the cutting-edge corridors of renowned academic institutions, Boston is a dynamic blend of past and present, where tradition meets innovation at every turn.

The city has a rich cultural scene, with world-class museums and opportunities to appreciate the performing arts. Educationally, it’s a powerhouse with prestigious universities like Harvard and MIT calling it home. And let’s not forget the passionate sports culture—Bostonians really rally around their sports teams. Plus, the city’s blend of old architecture and modern developments gives it a unique charm. And, of course, the delicious seafood and the vibrant atmosphere make it quite an exciting place to be!

Whether you’re a resident living in Boston or simply visiting as a tourist, there are many things that you can do here. To give you the inside scoop, we asked locals to give us their insight and their favorite hidden gems in Boston. Here’s what they told us.

1. Visit a historic home

Chris Amaral, the owner of Safe Responsible Movers, knows a thing or two about where to find the most fascinating properties in the city for history buffs.

“In our many years of helping folks move in and around Boston, we’ve seen all of the different neighborhoods and what they have to offer. One of our favorite, lesser-known historic homes is the Loring Greenough House in Jamaica Plain. Built in 1760, it’s a gorgeous example of Georgian Colonial architecture, located on a beautiful green lot of former farmland close to the bustling center of Jamaica Plain. The grounds of the house are open to the public, and there are frequent events hosted by the house, including tours of the home, outdoor movies, “Thursdays on the Lawn” featuring local mobile food trucks, and other fun times.”

2. Visit Faneuil Hall Marketplace

When visiting the beautiful city of Boston, Paula Marrero, Wedding Planner and Owner of Marrero Events highly recommends checking out Faneuil Hall Marketplace. “It’s a can’t miss when visiting Boston,” she says. “Quincy Hall within Faneuil Hall Marketplace offers a wide variety of restaurants, shops, and a myriad of fun local flavor and items at their kiosks strewn throughout the property. It’s also a great place to see street performers!”

3. Check out the Seaport District

Marrero also suggests a trendy evening out in the Seaport District, “a thriving area where you can enjoy rooftop dining at the Omni Hotel, dine at incredible restaurants, enjoy bowling at King’s, an aperitif at Tuscan Kitchen’s first-floor cocktail bar and a harbourfront walk of the city.”

4. Enjoy a day trip in the great outdoors

“Fall is a great time of year to get out of the city,” says Carina Clingman, founder and CEO of Recruitomics Consulting. “Bostonians often take day trips up to New Hampshire, Maine, and Vermont for amazing fall foliage. You can hike the beautiful White Mountain trials just two hours north of Boston. They get very crowded on the weekends, but if you can drive up on a weekday, you’ll find far fewer people. Some popular hikes are the Little Haystack summit via the Falling Waters trail and Cardigan Mountain.”

“For non-hikers, there are some wonderful scenic drives, including the Kancamagus Highway through the White Mountains and the Mt. Washington Auto Road,” she said. “Along the way, visitors should choose one of the many apple orchards to pick apples, get some fresh cider, and try a cider doughnut. Fall in New England is truly sensory overload, in all the best ways.”

5. Immerse yourself in the Boston music scene

The team at local moving and storage company Born to Move recommends exploring some of Boston’s dynamic music venues. “Since the 1960s, Boston has grown a thriving music scene. With fantastic young musicians studying at Berklee and a surplus of quality venues, seeing a live show is a must,” they said. “One of our favorite places is The Beehive in the South End. Every Thursday through Sunday, they host different musicians with soulful singers and full jazz bands. Complete with mouthwatering food and cocktails to match, it’s a place that can’t be beaten.”

6. Spend some time on Castle Island

“Before leaving the City, we highly recommend visiting our South Boston landmark, Castle Island,” added the folks at Born to Move. “Tour the oldest fortified military site in British North America that boasts cannons as well as the best view of the harbor. It’s also home to the “sugar bowl,” a scenic walking trail that’s the perfect place to listen to waves crash and watch planes take off right above your head.”

7. Catch a Red Sox Game at Fenway

Corinne Morahan, professional organizer, mom, and founder of Grid + Glam, recommends making a “loose plan that leaves some room for spontaneity.” To make the most of the day, she suggests, “picking one main activity like catching a Red Sox game at Fenway Park plus making a dinner reservation at a great restaurant is the perfect start.”

Morahan also suggests attending a show in the Theatre District or jumping on a Duck Boat tour. Taking a walk through the Common is also on the to-do list. “The Common is a must-do activity to get a feel of the city and check out some of the surrounding historic buildings.”

8. Do a little shopping on Beacon Hill

“For shopping,” she adds, “Beacon Hill has great shops to pop into, and, of course, window shopping on Newbury Street is always a good time. When you need a break from shopping and walking, find a Tatte Bakery to regroup and get a little caffeine boost.”

9. Learn about Boston’s most famous institution of higher learning

“For a unique Boston trip, start at Harvard University and feel the academic atmosphere,” recommends the team at Flash Moving Company. They also suggest continuing your afternoon sightseeing a few miles down the road in historic Beacon Hills with its “cobblestone streets, historic homes, and old-fashioned gas lamps.”

10. Visit the Mapparium at the Christian Science Center

“If you’re into geography, check out the Mapparium at the Christian Science Center, where you’ll walk inside the world’s only inside-out globe,” says Chris Stephens, director of marketing and group sales for Boston Hidden Gems. “Standing 30 feet in diameter, it was built of stained glass in 1935 and shows the world as it was then. It’s also an echo chamber, so you and your group can stand on opposite ends and whisper to each other!”

11. Seek out the city’s lesser-known attractions

Stephens also had fantastic suggestions for tourists looking for something more off the beaten path. “In Downtown Crossing, stop by Winthrop Lane. The alley seems unassuming, but it’s actually a public art project! Look at the ground to see the “Boston Bricks.” Created by local artists, each showcases a different aspect of the city’s history and/or true character.”

“Across the river in Cambridge, under the Longfellow Bridge, you’ll find a hidden collection of beloved trophies. No one knows who put the first trophy there in 2014, but now anyone can add theirs. Today, dozens of awards from the City of Champions line the walls. Try to find the oldest!”

12. Visit Hammond Castle

Stephens told us that Hammond Castle is another of Boston’s most fascinating hidden gems. Designed by eccentric inventor John Hays Hammond, the castle features “80-foot ceilings, a Tuscan village, imported medieval-era doors, stories of Hammond’s love of pranks, and information about his inventions, many of which you likely still use today,” he said. “It’s unlike anything else in the region.”

13. Hire a pedicab to cruise the city’s landmarks

“If you want to see Boston on an intimate level, hire a pedicab driver,” says Christian Matyi, co-owner of the TrikeHub, a Boston-based pedicab company. “The best Boston trips aren’t based on going to a list of places, so much as they are about wandering through a chain of places. Don’t hunt sites; do explore neighborhoods. Boston becomes what you make it; it will reveal nothing if you don’t poke at it.”

If you do decide to embark on a pedicab adventure, Matyi recommends a trip to the South End. “Most of our clientele rave over the South End. Gems like Bond and Ringold, Union Park, Montgomery Park, and Rutland Square have that “quaint Boston” vibe and are still close to the main parts of the city.”

14. Visit the city’s most unique libraries

“Another spot that tourists drop to their knees thanking us for is the Copley Public Library,” Matyi says. “Most would think a library would be dry and boring, but if you are a romantic, you will swoon inside this palace. There is hardly an angle in any room that doesn’t evoke charm and whimsy. You’ll find marble staircases, installed Sargent paintings, gardens, fountains, and nooks (and probably some books as well). Do not pass up the Map Room, grab high tea, and for sure, get your camera ready. You have never seen anything like this in the United States.”

“There are two favorite “private” libraries in Boston that are both charmers and perfect for those quirky “no tourists do this one” peeks,” he continued. “On the erudite end, you have the glorious and fascinating Athenaeum atop Beacon Hill – so posh that some sections are forbidden to non-members. Then, on the far opposite end of the spectrum, you have the working-class-artist side of things with the equally fascinating little Puppet Library in Back Bay. Both have limited hours, making each feel like a clandestine secret mission. Come see the real story behind why Boston is a city of books and letters – and puppets!”

15. Visit a national park right in the city

Matyi also tipped us off to where you can enjoy the great outdoors just a stone’s throw away from the city. “One of the most often overlooked things to do in the city is visit one of our national parks that are right in town,” he said.

“The favorite above all is the Boston Harbor Islands National Park. There are dozens (literally) of small islands polka-dotting the harbor, and most are designed to welcome visitors. With its spooky and romantic ruins, George’s Island makes you feel like you’re in another time. Spectacle Island feels like you’re on a wilderness hike. Or maybe just hop on a whale watch (guaranteed sightings – whales love us) and scope out islands from afar.”

Good to know: the public ferry to the islands only runs from May through September, so plan accordingly.

Come and See the Best of Boston!

We can see why the locals here are passionate about their city and all the unique things it has to offer. Whether you’re a history buff eager to trace the footsteps of early patriots, a nature enthusiast looking to enjoy the beauty of New England, or a seeker of knowledge drawn to the intellectual epicenter of renowned universities, Boston offers something truly special for every visitor!