Top 7 Fun Things To Do in Boston

Ready for a city break that’s bursting with history, foodie heaven, and secret spots even seasoned travelers don’t know? If you’re googling “fun things to do in Boston,” you’ve landed in the right place. From wandering cobblestone streets to catching killer skyline views, Boston offers epic adventures for every kind of explorer. Whether you’re packing your bags and hunting flights to Boston or you’ve already booked that ride, prepare yourself for a trip you’ll brag about for years. No stale travel guide stuff here—just insider tips, real local flavor, and everything you need to tick off your bucket list of Boston things to do.

1. Stroll the Freedom Trail Like a True Patriot

Forget about cookie-cutter tours; follow the bright red brick Freedom Trail with a local guide who turns dates and facts into gripping stories. You’ll start at Boston Common, the oldest public park in the U.S., and wind past Paul Revere’s House, the Old North Church, and the site of the Boston Massacre. Along the way, you’ll hear juicy tidbits—like how a midnight ride nearly derailed due to an escaped pig! This 2.5-mile trail mixes fresh air with deep history, and you’ll learn why “the shot heard ’round the world” mattered far beyond New England. 

Pro tip: snag tickets online in advance to skip the line and catch that perfect Instagram moment. Whether you’re a history buff or just love a scenic walk, it’s one of the best things to do in Boston.

2. Indulge in a Seafood Feast at Quincy Market 

Ask any local for Boston things to do and they’ll point you straight to Quincy Market. This historic, L-shaped hall inside Faneuil Hall Marketplace is your seafood HQ. Lobster rolls, clam chowder, and oysters on the half shell await—plus global eats if you’re craving a break from New England staples. Watch the ice carvers transform blocks into art or catch a street performer juggling fire! Insider tip: head there just before lunch to avoid the crowds and score a seat overlooking the harbor. You won’t find bland bites here—everything’s fresh, flavorful, and often sourced straight from the docks. It’s the ultimate spot to fuel up between Boston adventures and a must-do when planning flights to Boston.

3. Catch a Game at Fenway Park and Feel the Roar 

You can’t claim to know Boston until you’ve cheered at Fenway Park—America’s oldest ballpark. Grab a classic “Fenway Frank” (hot dog) and some cold brew, then join the scramble for a front-row glimpse of the Green Monster. Even if you’re not a die-hard Red Sox fan, the chants, waves, and camaraderie will give you goosebumps. Want a behind-the-scenes peek? Book the Fenway Park Tour to wander the dugout, press box, and even the broadcast booth. Tours sell out fast, so lock in your spot early. Baseball, history, and heart-thumping fun collide here: it’s unmissable among fun things to do in Boston.

4. Explore the Vibrant Streets of the North End

Boston’s “Little Italy” pulses with aromas of fresh basil and garlic at every corner. The North End is a maze of narrow lanes lined with family-run bakeries, cozy trattorias, and espresso bars that have fueled storytellers for generations. Don’t leave without tasting a cannoli at Mike’s Pastry (the ricotta is legendary) or sampling a slice of Amalfi pizza down the street at Pizzeria Regina. History lovers will appreciate that Paul Revere’s home is tucked right here, too. Ask a local for their off-menu wine suggestion—you’ll get a recommendation that transforms dinner into a genuine Italian feast. Perfect for a leisurely afternoon or evening crawl, this culinary hotspot ranks high among fun things to do in Boston.

5. Glide Across the Charles River on a Kayak 

Swap crowded boardwalks for an active adventure: kayaking on the Charles River. Launch at Community Boating in the Esplanade and paddle your way under the city’s skyline. You’ll float by MIT’s modern towers, catch sight of sailboats gliding by, and maybe even challenge a crew team practicing for the Head of the Charles Regatta. Don’t worry if you’ve never kayaked before—free basic lessons are included, and friendly staff will make you feel confident in minutes. Sunset trips are dreamy, painting the water golden as rowers push past. Bring a waterproof phone case—you’ll want epic snaps. Paddling here is one of those unforgettable fun things to do in Boston when you crave both fitness and fresh air.

6. Get Cultured at the Museum of Fine Arts 

Boston’s Museum of Fine Arts (MFA) houses more than 450,000 works, covering ancient Egyptian artifacts, Impressionist masterpieces, and cutting-edge modern art. Skip the generic tour and download the MFA mobile guide to follow curator-led “fast takes,” which dive deep into hidden gems you’d never spot on your own. Grab a latte at the on-site cafe, then head upstairs to see Monet’s Water Lilies and Van Gogh’s self-portrait without elbowing your way through crowds. Friday evenings often feature live music in the courtyard which are free to attend, transforming the museum into a social hotspot. Whether you’re a serious art enthusiast or just looking to escape a rainy afternoon, this stop tops many lists of things to do in Boston.

7. Sip Craft Cocktails in Back Bay’s Secret Speakeasies 

Looking for evening fun? Back Bay hides some of Boston’s coolest speakeasies behind unmarked doors and phone-booth entrances. Start with the velvet-lined lounge at Backbar in Somerville: order a “Vieux Carre” for a smooth, spirit-forward treat. Then, wander toward the South End to find Deep Ellum’s secret back room, known only to those in the know (hint: it’s off the main taproom). Each spot pairs cozy ambiance with masterful mixology—think house-infused spirits, hand-crafted bitters, and whimsical garnishes. Reservations aren’t needed, but arrive early to snag plush seating. Perfect for date nights or a night out with friends, this bar-hopping adventure is a standout among fun things to do in Boston after dark.

Final Thoughts: Plan Your Boston Adventure Now!

There you have it—7 fun things to do in Boston that prove that the city is more than a history lesson. Whether you’re securing flights to Boston with Experian Airfare, craving chowder, or hunting secret speakeasy doors, this city delivers surprises at every turn. Pack comfy shoes, an adventurous spirit, and your appetite—Boston’s waiting to show off its best-kept secrets. Ready for an unforgettable trip? Boston’s calling! Also Read: Free Places To Visit In Boston

FAQs

Q- What are some of the fun things to do in Boston with kids?

Walk the Freedom Trail to trace history, relax in historic Boston Common and the Public Garden, stroll the Rose Kennedy Greenway’s public art installations, browse Harvard’s campus in Cambridge, attend free outdoor concerts or movies on the Esplanade, catch the free TAC tram at the ICA.

Q- What is the best time to visit Boston?

Spring (May–June) and autumn (September–October) are ideal for visiting Boston. Mild temperatures, blooming gardens, and fall foliage mix with fewer crowds and seasonal festivals. Summers burst with outdoor concerts and boat rides, while winter draws cozy holiday markets. Plan around school breaks to avoid peak tourist rush.

Q- Suggest some things to do in Boston for free?

Boston delivers free fun things to do for kids: splashing with sharks at the New England Aquarium, exploring dinosaurs at the Museum of Science, meeting animals at Franklin Park Zoo, sailing Swan Boats on the Public Garden pond, riding Duck Tours through streets, hands-on exhibits at the Children's Museum, and playground time on Boston Common.