This post was originally published on A Globe Well Travelled in 2016. The content has been revised and updated with fresh information.
Planning a weekend in Boston felt surprisingly exciting for me
I’d been to the US a few times, but this was one city I’d always skipped. So when my husband and I finally booked a trip, I was determined to make the most of it. Boston instantly won me over with its mix of history, cosy neighbourhoods, beautiful green spaces, and incredible food (hello, North End cannoli).
Over two days, we wandered charming cobblestone streets, followed the iconic Freedom Trail, explored Harvard’s campus, warmed up inside the stunning Boston Public Library, and ate our way through markets and Italian bakeries. It turned into the perfect Boston weekend itinerary — full of classic sights, easy walks, and a few hidden gems that I hadn’t expected.
If you’re a first-time visitor wondering about the best things to do in Boston, here are the 12 essential activities I’d recommend packing into your weekend in the city.
Quick summary:
If you’re planning a weekend in Boston, this guide covers the city’s absolute essentials. I also share my favourite spots, where to stay, and a few uniquely-Boston experiences you won’t want to miss.
Recommended tours:
🚶 Freedom Trail Walking Tour — See the city’s most important historical sites with context and stories from a local guide.
🎓 Harvard Campus Tour — Explore the world-famous Harvard grounds on a student-led walking tour.
🍝 North End Secret Food Tour — Taste Boston’s Italian heritage through cannoli, clam chowder, lobster rolls, and more.
Where to stay in Boston
🛏️ My husband and I based ourselves at the HI Boston Hostel near Chinatown. It was seriously the perfect location from which to explore the city – it was an easy walk to 2 subway lines and had a bunch of cheap eats nearby.
As an eco-conscious traveller, I was super impressed with the hostel’s green initiatives with recycling bins and power saving lights in every room. Plus, who could say no to warming up next to that cosy fireplace after a day of exploring in the cold?
12 best things to do in Boston:
1. Wander around Beacon Hill
Beacon Hill has got to be one of the most adorable neighbourhoods on the planet. Its narrow, gas-lit streets and perfectly preserved 19th-century brick row houses make it one of the most photogenic places in Boston. We spent about an hour just wandering, but honestly, you could easily spend half a day here if you love architecture and charming city nooks as much as I do.
Make sure you walk down Acorn Street, often called the most photographed street in America, though Chestnut Street is just as dreamy and far less crowded. Beacon Hill is also home to cute boutique shops, independent cafés, and plenty of doorways that made me stop every two seconds for a photo. I followed this guide for the route along Chestnut Street and Acorn Street.
2. Check out Boston Common
Boston Common is the oldest public park in the United States, and it feels like the city’s communal backyard. In summer, the lawns are filled with locals having picnics, playing ball games, or simply lying in the sun. I visited in winter, and was lucky enough to see the park dusted in snow.
The Common lies right in the heart of downtown and is the official starting point of the Freedom Trail, making it an easy and essential stop on any Boston weekend itinerary. You’ll also find the famous Frog Pond here, which turns into an ice-skating rink in colder months.
3. Stroll through Boston Public Garden
Right next to the Common is the Boston Public Garden, the city’s first public botanical garden. Think elegant bridges, landscaped flower beds, winding paths, and weeping willows cascading into the water. It’s peaceful, picturesque, and one of the best places in the city for a relaxed walk.
If you’re visiting between April and September, this is where you can take a ride on a swan boat, which have been gliding around the lagoon since the 1870s. Even from the shore, the views are stunning — the mix of greenery and skyline makes it one of Boston’s most beautiful outdoor spaces. Don’t skip the little footbridge across the lake; it’s one of the garden’s signature photo spots.
4. Follow the Freedom Trail
Yes, the Freedom Trail absolutely deserves its spot on every list of things to do in Boston. It’s touristy, sure — but also one of the best ways to understand the city’s past while seeing a huge slice of downtown on foot. The trail is 2.5 miles (4 km) long and marked by a red brick line that winds past 16 historic landmarks, including the Massachusetts State House, Granary Burying Ground, Old South Meeting House, and Paul Revere’s House.
If you want to do the trail independently you can follow this map. I loved how easy it was to follow — you can simply start at the Boston Common Visitor Center and walk at your own pace. It’s a choose-your-own-adventure kind of trail: linger at the spots that interest you, skip the ones that don’t, and stop for food whenever you’re tempted (which… is often).
If you want deeper insight into the Revolutionary War history, joining a Freedom Trail walking tour with a costumed guide is a fun upgrade.
If you’re short on time or energy, you can stop at Copp’s Hill Burying Ground in the North End, which cuts the walk in half while still giving you a great feel for the trail.
5. Eat at Quincy Market
Locals will tell you Quincy Market is touristy — and they’re not wrong. But you know what? It’s also full of delicious (and surprisingly affordable) food, and the architecture alone is worth seeing. The main hall is a long, historic marketplace lined with food stalls offering everything from clam chowder and lobster rolls to flaky pastries, Greek platters, mac and cheese, and baked goods galore.
It’s a great lunch stop if you’re exploring downtown or finishing the Freedom Trail. Grab food from a few different stalls and head outside to the surrounding plazas to eat and soak up the lively atmosphere.
6. Sample some Boston Cream Pie
You can’t visit Boston and skip its namesake dessert — even if it’s technically a cake! Boston Cream Pie is a soft yellow sponge filled with creamy custard and topped with glossy chocolate ganache. You’ll find it at bakeries around the city, and it’s a fun mini food mission to add to your weekend trip.
I picked up a slice at Café Bella Vita in Beacon Hill (which has since closed), and while it was decent, there are plenty of other spots that now serve excellent versions. Modern Pastry in the North End is a classic option, and Flour Bakery has a great reputation for pastries. No matter where you get it, it’s a sweet way to tick off a uniquely Boston experience.
7. Explore the Boston Public Library
If you’re into architecture, photography, or simply beautiful indoor spaces, the Boston Public Library is a must-see. It’s one of the most stunning libraries I’ve ever visited, with a grand marble staircase, arched windows, and a European-style courtyard that feels like it belongs in Italy rather than New England.
The highlight for me was the Bates Reading Room — a long hall lined with lamps and green-shaded lights that make the whole space glow. It’s quiet, atmospheric, and incredibly photogenic. A quick tram ride on the E Line takes you straight there from downtown, making it an easy stop to add to your Boston itinerary.
8. Harvard University
Harvard is one of the most famous universities in the world, and visiting the campus gives you a glimpse into centuries of academic history. It’s only a 15-minute ride on the Red Line from downtown Boston, and once you arrive in Cambridge, it’s an easy walk to Harvard Yard.
On this visit, we downloaded the self-guided walking tour off the Harvard website but to be honest, we found it rather difficult to follow.
🎓 Alternatively, you can book a guided Harvard Campus Tour which are run by university students. I did this the first time I visited Harvard, and it was great — the guides mix history with funny anecdotes and give you insider knowledge you’d never get on your own.
9. Museum of Fine Arts
The Museum of Fine Arts is one of the largest and most impressive art museums in the United States. You can easily spend a few hours wandering its vast galleries, which cover everything from ancient Egyptian artifacts to European masters, Asian art, and contemporary pieces.
Entry is usually $30 USD (as of 2025), which can seem steep — but it’s absolutely worth checking the museum’s website ahead of time, as they sometimes offer free admission on certain holidays or community days. We happened to visit on one of those days (winning!), and it ended up being one of the cultural highlights of our weekend in Boston.
If you love art, this is a no-brainer. And if you’re not a huge museum person, it’s still an excellent indoor activity on a cold or rainy day.
10. Eat Italian food in North End
Boston’s North End is the city’s Little Italy — a maze of narrow streets packed with Italian restaurants, bakeries, gelato shops, and centuries-old buildings. It’s one of the oldest neighbourhoods in Boston and one of the tastiest.
🍝 If you can’t decide where to eat, a North End secret food tour is a great way to sample chowder, lobster rolls, cured meats, pastries, and more while learning about the area’s history.
11. Go to an Irish Pub
Boston has a famously strong Irish heritage, which means you’ll find more Irish pubs here than in almost any other US city. Visiting at least one is practically a rite of passage. We chose JJ Foley’s, a historic local favourite that felt like a blend of traditional pub and sports bar — lively atmosphere, friendly bartenders, and hearty comfort food.
If you want something more classic and old-school, there are plenty of iconic pubs scattered around the city. Whichever one you choose, grabbing a pint in an Irish pub is a fun and authentic Boston experience.
12. Try Candlepin Bowling
Candlepin bowling is a quirky New England tradition — and Boston is one of the few places where it’s more common than standard ten-pin bowling. The pins are tall and narrow (like little candles), the bowling balls are small and don’t have finger holes, and the gameplay is strangely addictive.
We headed to Boston Bowl to give it a try, and it was such a fun way to spend an evening. It feels familiar but distinctly different, and it’s a great rainy-day or post-dinner activity. You can find a list of candlepin lanes around Boston here if you want to try something truly local.
*I was a guest of HI Boston Hostel during my stay in Boston. I’m proud to be an honest and transparent blogger, so every opinion expressed on AGWT is a true review of my experience!
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