20 Fun Things to Do in Boston: The Local’s Guide
March 02, 2026
I may be biased because I live here, but I’ll say it anyway: there really is no place like Boston. We’ve got 17th-century taverns, cobblestone streets, modern skyscrapers, world-class sports teams, and some of the best restaurants and bars in the country. And don’t even get me started on our city’s incredible history. With so much to do and see, planning a trip to Boston can feel a little overwhelming.
That’s why I put together this local’s guide to Boston. While I won’t recommend you do every touristy thing, there are some iconic "bucket list" items you should see. Here’s my list of the best things to do in Boston, including both tourist attractions and local spots.
1. Walk the Freedom Trail
I know, shocker. But this is at the top of every list of things to see in Boston for a reason. It’s easy to follow the red-lined path, which leads you past 16 historical sites, like the location of the Boston Massacre and the USS Constitution. If you do the whole thing, the trail weaves through the city's most beautiful neighborhoods like Beacon Hill and the North End.
Quick tips:
Hit the highlights: If you aren't up for the whole Freedom Trail, start at Faneuil Hall and head north into the North End. You’ll see the famous Boston sights like the Paul Revere House and the Old North Church before ending up in the city’s Italian food hub.
Do a digital tour: Skip the crowded group tours and download the Freedom Trail Foundation’s official audio walking tour. It’s free and you can pause it when you want to explore local shops, grab a drink at a pub, or stop for a snack.
Eat local: If you’re hungry, avoid Faneuil Hall. Hold out until you hit the North End and grab a slice at Ernesto’s or a sub at Monica’s Mercato.
2. Experience Upscale Dining in Boston
Downtown Boston has some of the best bites, and you can’t go wrong with my favorite steakhouse in the city. Vermilion is an elegant, modern chophouse from a Michelin-starred chef specializing in dry-aged steaks with inventive, vegetable-forward dishes. Plus, definitely check out the bar to see the famous vermilion sculpture.
Quick tips:
Hit Happy Hour: From 3-6 every weekday, they do a solid happy hour at the bar. They have a big book full of wine, beer, and cocktails. Plus, they have bar snacks.
Order the signatures: You can’t go wrong with the caviar sandwich or French onion dumplings. I also love the espresso martini.
Reserve a table: Seats fill up fast at Vermilion, so make sure to book your table ahead of time.
3. Catch a Game at Fenway Park
You can't talk about Boston without talking about Friendly Fenway. It’s the oldest MLB stadium in the country, and while the seats are cramped and the tickets aren't exactly cheap, it’s 100% worth it. I’m not even a baseball fan and I have fun every time I go. Check the Red Sox schedule to find your game.
Quick tips:
Eat before the park: The food in the park is overpriced and underwhelming. Instead, grab something on Jersey Street or hit Tasty Burge right around the corner.
Skip the drive: Parking near Fenway is a nightmare and can cost as much as a ticket. Just take the Green Line to Kenmore and walk the five minutes over.
Score cheap seats: If you’re a student, sign up for the Students program to get tickets starting at $5.
Check Gate E on game day: Sometimes they release a limited number of tickets 90 minutes before the first pitch.
4. Explore Harvard & Cambridge
With Cambridge just across the river, you should explore the stunning Harvard campus. However, it’s the neighborhood around it that has all the fun. So definitely walk through Harvard Yard, but don’t miss the local bars, independent bookstores, and cute coffee shops in the area.
Quick tips:
Explore the local spots: Grab a burger at the famous Mr. Bartley’s or a slice at Pinocchio’s. If you’re a book person, The Harvard Book Store is a classic.
Go to the museums: If it’s a rainy day, the Harvard Museum of Natural History is great. It’s famous for the "Glass Flowers” and puts on cool exhibitions regularly.
Visit Mount Auburn Cemetery: Walk 15 minutes to this beautiful park where people like Henry Wadsworth Longfellow, Winslow Homer, and B.F. Skinner are buried. Plus, the views from the top of Washington Tower are hard to beat.
5. Eat Your Way through the North End
The North End is Boston’s oldest neighborhood and our version of Little Italy. It’s a maze of narrow streets that smell like garlic and espresso, and some of the best cannoli you’ve ever had. Fair warning: it’s almost always packed with tourists, but it’s worth pushing through the crowds for some of these restaurants that have been in local families for generations.
Quick tips:
Join the Great Cannoli Debate: Chances are you’ve already heard about Mike’s Pastry. But make sure you also try Modern Pastry across the street or Bova’s Bakery. Bova’s is open 24/7, so you can grab a Florentine or a cannoli whenever the craving strikes.
Explore Hanover and the side streets: Don’t skip Hanover Street, but make sure you explore the side streets too. Daily Catch is tiny and cash-only, but their black pasta is legendary. Try Antico Forno for brick-oven pizza or La Famiglia Giorgio for a rustic vibe and huge portions. Caffe Vittoria is one of the oldest Italian cafes in the US and feels like stepping into 1920s Italy.
Bring cash: Many of the best spots in the North End are cash-only and don't take reservations, so come prepared. You should also mentally prepare yourself for long wait times, especially in the evenings and on weekends.
6. Grab a Pint at a Historic Downtown Tavern
We have some of the oldest taverns in the country, and most of them were once headquarters for some names you might recognize. Of course, the touristy ones aren’t something I normally do because I live here, but it’s definitely worth grabbing a drink if you’re visiting Boston — it’s like stepping back into the 1700s.
Quick tips:
Hit the "Big Three": Start at The Bell in Hand, which claims to be the oldest tavern in America, dating back to 1795 and started by a town crier. Right around the corner is Union Oyster House, where you can sit at the same bar Daniel Webster did. Then pop over to The Green Dragon Tavern, the "Headquarters of the Revolution," where Paul Revere and John Hancock are said to have planned the Tea Party.
Avoid the weekends: These downtown spots are in the middle of the Faneuil Hall madness (and yes, they’re on every list of the top things to do in Boston). If you go on a Friday night, it’ll be standing room only with a loud crowd.
Try a more local option: Walk five minutes over to The 21st Amendment near the State House. It’s an old-school basement pub that’s a favorite among locals who like to immerse themselves in history (without the crowds).
7. Explore the Seaport District
I remember when this area was nothing but parking lots and fishing piers, but now it’s one of the hottest neighborhoods in the city. It’s a mix of modern skyscrapers, high-end offices, and some of the best views of Boston’s skyline. It can feel a little corporate during the week, but it’s the place to be if you want a night out on the town. Plus, it’s within walking distance of the Boston Tea Party Ships.
Quick tips:
Try the seafood: This spot can be a little touristy, but I love it for its food, vibe, and views. The Barking Crab is a bright red-and-yellow tent that you really can’t miss (it’s a local landmark). It’s loud, messy, and perfect for cracking open a lobster and drinking a beer on the water. Because it’s an indoor/outdoor vibe, they’re closed in the off-season.
Visit the Children’s Museum: One of the best things to do in Boston with kids is the Boston Children’s Museum. It’s located right on the Fort Point Channel (look for the giant 40-foot milk bottle outside). The three-story climbing structure in the lobby alone will keep them busy for hours.
Check out the local favorites: You can find Trillium breweries throughout Boston, but I love their Seaport location. It has an awesome roof deck and some of the best New England IPAs in town. For a quick bite, grab a sandwich at Flour Bakery & Cafe.
8. Go Brewery Hopping
Boston is a beer city, and no, we’re not talking about Sam Adams. The brewery scene here is huge, and in the summer, beer gardens pop up all over town. Whether you’re into double IPAs or just want to sit outside with a light pilsner, there’s at least one brewery in almost every neighborhood.
Quick tips:
Check out the big names: Trillium, Harpoon, and Night Shift are all over the place. They all offer a variety of food and bar snacks like pretzels and pizza. I love the Nite Lite from Night Shift, it’s crisp and light and perfectly refreshing.
Find the local favorites: Head to Dorchester Brewing Co. with its glass-walled rooftop "Hopservatory" that has killer views of the city. If you’re in East Boston, Downeast Cider has a tasting room where you can try experimental flavors you won't find in stores. For a true neighborhood vibe, hit Lamplighter Brewing Co. in Cambridge. It's a coffee shop by morning and a taproom by night.
Game and drink: If you’re a fan of old-school tech and games, go to Aeronaut Brewing in Somerville. It’s a quirky, science-themed space that feels like a big garage party with live music and retro arcade games.
9. Eat and Shop in Back Bay
Back Bay is one of the most picturesque parts of the city and one of my favorite places to visit in Boston when people come to town (my friends always want pictures of the Victorian brownstones and cute cafes). Newbury Street is eight blocks of pure shopping, from luxury designers to quirky thrift stores and record shops. It’s the best place in the city to spend an afternoon exploring, even if you’re just window shopping and people-watching.
Quick tips:
Walk from lower to upper: The "Lower" end (near the Public Garden) is where you’ll find high-end stores like Chanel and Tiffany & Co. The "Upper" end (near the Pru) is more local and laid-back. Make sure to duck into Trident Booksellers & Cafe, a local favorite where you can browse the stacks and grab a delicious breakfast.
Explore the side streets: Don't spend all your time on Newbury. Commonwealth Avenue is just one block over and has a massive, tree-lined mall with lots of great stores. Parallel to that is Marlborough Street, which is mostly residential and great for pictures of our iconic Boston brownstones.
Don’t eat in just one place: There’s so much good food here, I recommend stopping in multiple places for small bites. Grab a sidewalk table at Sonsie or Stephanie’s On Newbury for some prime people-watching. Saltie Girl is pricey but has some of the best fish and lobster rolls in the city. The Salty Pig near Copley Square is great for shareable plates like charcuterie boards and pizza.
Check out the Boston Public Library: I normally don’t recommend libraries, but I love the history and architecture here. The Italian-style courtyard is free and great for taking a quick walking break.
10. Stroll Through Boston Common
Boston Common is the oldest public park in the country and is considered the "start" of the Freedom Trail. But for us locals, it’s just a beautiful place to soak in some nature. Plus, there are plenty of events and activities all year round.
Quick tips:
Check out Frog Pond: If you’re here in the colder months (good luck!), go ice skating at the Frog Pond. In the summer, it turns into a spray pool for kids and has a carousel area. It’s also where the city hosts Shakespeare on the Common, featuring free outdoor plays in July and August.
See the sights: When it comes to what to see in Boston Common, find the Soldiers and Sailors Monument or the Boston Massacre Monument for a bit of history. If you’re a fan of Good Will Hunting, the famous bench where Robin Williams and Matt Damon sat is just across Charles Street in the Boston Public Garden. Don’t forget to check out the swan boats, too.
Hang out at Brewer Fountain: During the summer on the Tremont Street side, the city sets up a bunch of café tables, chairs, and food trucks.
11. Explore Beacon Hill
When you think of historic Boston, Beacon Hill is exactly what you’re picturing. It’s all steep hills, gas-lit lanterns, and hidden gardens tucked behind wrought-iron fences. Be warned: it’s one of the most expensive neighborhoods in the country, but it’s free to wander around in. You’ve probably seen that the Cheers bar is here, but it’s crowded, touristy, and I’d recommend skipping it unless you’re a big fan. Go to The Sevens Ale House instead.
Quick tips:
Go to Acorn Street: This is one of the last true cobblestone streets in the city, by which I mean uneven and difficult to walk on. People actually live in those tiny houses, so try to be quick with your photos and keep the noise level down. Plus, walk down Louisburg Square to see where the real Boston elite have lived for centuries.
Shop and eat on Charles Street: This is the neighborhood's main drag. Check out antiques at Upstairs Downstairs or browse books at the super cute Beacon Hill Books & Cafe (trust me: don’t skip the little cafe in the summer).
Walk the Black Heritage Trail: This tour starts at the Robert Gould Shaw and 54th Regiment Memorial (across from the State House) and takes you through 15 sites important to Boston's 19th-century Black community.
12. Explore Our Famous Museums
With so much history, it’s not surprising that Boston has some of the best museums. My two favorites are The Museum of Fine Arts (MFA) and the Isabella Stewart Gardner Museum, which are less than a ten-minute walk from each other.
Quick tips:
The Gardner Heist: The Isabella Stewart Gardner Museum is famous for a Venetian-style courtyard that’s always in bloom, but it’s even more famous for the 1990 art heist. Look for the empty frames hanging on the walls. It’s been said that, per Isabella’s request, they should stay empty until the stolen paintings are returned.
Don’t MFA all day: The Museum of Fine Arts is huge. Don’t try to see it all in one day or you’ll be exhausted. If you’re short on time, head straight to the Art of the Americas wing. It’s a four-story glass atrium that houses everything from Paul Revere’s silver to giant John Singer Sargent portraits.
Get in for free: If your name happens to be Isabella, you get into the Gardner Museum for free. If you’re a Boston resident, the MFA is often free to visit on specific days and students at many local colleges get in for free with their ID.
13. Enjoy the Esplanade
On warm days, this is one of my favorite things to do. The Charles River Esplanade is a three-mile stretch of paved paths, docks, and green space that runs along the water between the Museum of Science and the BU Bridge. In the summer, keep an eye out for the Night Shift’s pop-up beer garden right on the riverbank.
Quick tips:
Walk the "Lampson" Bridges: To get the best views of MIT across the water, use the pedestrian footbridges (like the Arthur Fiedler Footbridge) to cross over Storrow Drive. The "Island" area near the Hatch Shell is the best spot for a picnic or to watch the sunset over the Longfellow Bridge.
Get on the water: You can rent a kayak or a paddleboard at Community Boating Inc. or Paddle Boston.
14. Walk or Cruise the Boston Harbor
The Harborwalk is a massive, 43-mile park that connects the city’s waterfront neighborhoods, and it’s the best way to see the skyline. You can also head out on the water in everything from commuter ferries to vintage sailboats.
Quick tips:
Take the ferry: You don't need a $60 tour ticket to get on the water. The MBTA Commuter Ferry runs from Long Wharf to the Seaport or Charlestown for just a few dollars. If you want something more fancy, Classic Harbor Line does sunset sails on yachts and sailboats.
Go island hopping: The Boston Harbor Islands are a hidden world just a 20-minute ferry ride away from the city. Head to Spectacle Island for hiking and a rare sandy beach, or Georges Island to explore Fort Warren (which is supposedly haunted by the "Lady in Black"). Ferries leave from Long Wharf, check out the ferry schedule to learn more.
15. Visit the New England Aquarium
The New England Aquarium is right on the harbor waterfront and easy to get to from most places in the city. My favorite part is the Giant Ocean Tank, a four-story reef with a stunning spiral walkway. This is a great option for rainy days or if you’re visiting Boston with kids.
Quick tips:
See the penguins: This huge, open-air penguin colony is loud, busy, and one of the best parts of the museum. If you time it right, you can watch the frenzied feeding.
Buy tickets online: This is one of the most popular Boston attractions, especially on weekends and school holidays. The line for walk-up tickets can be brutal, so book a timed-entry slot on their website to skip the wait.
Check out the seals for free: If you’re just doing the Harborwalk, you can see the harbor seals in their outdoor tank right in front of the building without buying a ticket.
16. Explore Southie & South End
No, they’re not the same thing. But they’re two of Boston’s coolest neighborhoods, right next to each other. If you want a night of incredible food and cocktail bars, stay in the South End with its stylish bars and restaurants. If you want to end the night dancing on a crowded patio, head over the bridge to Southie.
Quick tips:
Go to Tremont Street in the South End: You’ll find plenty of delicious food in South End. For a local legend, go to The Beehive for a subterranean bohemian bar with live jazz and a wild brunch. If you want a more intimate vibe, Barcelona Wine Bar is always packed and great for tapas.
Party in Southie: For the real Southie experience, head to West Broadway. Lincoln Tavern & Restaurant is always loud, fun, and their spicy wood-fired pizzas are delicious. You also can’t go wrong with late nights at Loco Taqueria & Oyster Bar.
Go to the SoWa Market: In the summer and fall, the South End hosts the SoWa Open Market with food trucks, local artists, and a beer garden.
17. Go Whale Watching
Yes, you read that right — we really do have whales here. We’re close to the Stellwagen Bank National Marine Sanctuary, which is a massive feeding ground and means you can see humpback, finback, and minke whales.
Quick tips:
Get your tickets early: The New England Aquarium partners with City Cruises for tours. I’d recommend booking the first trip of the morning (usually around 9:00 AM or 10:00 AM). The water is often calmer, the crowds are slightly smaller, and you’ll be back on land early enough to spend the rest of the day exploring.
Dress appropriately: It’s always about 10–15 degrees cooler out on the open water once the boat is moving. Bring a windbreaker or a sweatshirt. Trust me — you won’t regret it.
18. Take a Day Trip to Salem
If you’re looking for interesting things to do near Boston, head 30 minutes north to Salem — chances are you’ve heard of it. Salem is famous for the Witch Trials, but it’s also a beautiful coastal city with a deep maritime history, incredible architecture, and great places to eat and drink. Head to Finz for seafood on the water or Gulu-Gulu Cafe for a cute vibe and great beer.
Quick tips:
Take the ferry: Take the Salem Ferry from Long Wharf for a scenic 50-minute ride, or hop on the Commuter Rail from North Station for a $16 round trip. It’s faster, cheaper, and drops you right in the center of town.
See the sights: Go to the Salem Witch Trials Memorial and the Old Burying Point Cemetery. For world-class art and maritime history, the Peabody Essex Museum (PEM) is actually one of the best museums in the country.
Walk the McIntire District: If you want to see the "Hocus Pocus" houses and stunning Federal-style mansions, head over to Chestnut Street. It’s one of the most beautiful streets in the city and it feels like it transports you back in time.
19. Book a Boston Duck Tour
There’s a lot of touristy stuff to do in Boston, and Boston Duck Tours is one of the best. You hop into a silly-looking amphibious vehicle and drive past the major landmarks before splashing directly into the Charles River. The tour guides are often local actors or historians, so get ready for a lot of "wicked" jokes and Boston accents.
Quick tips:
They leave from three spots: the Museum of Science, the Prudential Center, and the New England Aquarium. If you want to shop afterward, go with the Pru. If you want to hit the North End for dinner, pick the Aquarium.
Book early: In the summer and on fall weekends, these sell out completely. Don't show up expecting a walk-in spot. Book your tickets online at least a few days out.
The tours run rain or shine: The vehicles are covered, but if it’s a windy or rainy day, the sides are open to the air, so you’ll want to bring a jacket.
20. Try Candlepin Bowling
If you’re not sure what to do in Boston on a rainy day, you can’t go wrong with candlepin bowling. Candlepin bowling was invented in Worcester in 1880 and it’s a true New England tradition. The balls are small enough to fit in your palm, the pins are thin like candles, and the "deadwood" (fallen pins) stays on the lane between throws.
Quick tips:
Head to Southie: Sacco’s Bowl Haven in Somerville is the gold standard for the old-school vibe, but if you're staying in the city, Southie Bowl is the spot. It’s been around since 1960 and serves cheap beer and hot dogs.
Three balls, not two: In Candlepin, you get three rolls per frame. Because the pins are so light and the balls are small, it’s rare to get a strike. You’re playing a game of physics and using the fallen pins to help knock down the ones still standing.
Join Us at Vermilion for the Best of Boston
There’s no shortage of things to do in Boston, Massachusetts. For an even deeper dive, don’t miss this guide on the best hidden gems in Boston.
No matter how you spend your time in Boston, don’t skip Vermilion. With the stunning massive 55-foot bar, iconic Chihuly sculpture, and innovative menus from Michelin-starred Chef John Fraser, no one does upscale dining like we do. Check out the menu or book your table today.