3 Days in Boston: A Perfect Long Weekend Itinerary

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Planning a long weekend in Boston? Keep reading for the perfect itinerary for 3 days in Boston, Massachusetts!

From food to American history to parks and museums galore, Boston is a fantastic place to spend some time. You could spend years here like we have and still stumble across new treasures while out and about. The city is a definite must for any New England bucket list.

Whether this is your first visit to “Beantown” or you’re contemplating another visit, we’ve compiled a weekender guide with everything you’ll need to know to spend 3 days in Boston. We’ve included some top travel tips for you, as well as a sample itinerary, taking into account different activity levels and the potential for some of that super-fickle weather New England is known for!

If you have longer than a weekend to spend, we’ve also included our favorite hiking, biking, and day trips as a bonus at the end. For all the best tips for hiking, biking, and travel in the region, we hope you’ll check out our Boston and New England landing page here

This post was written by Tegan George and Alex McKenzie, Boston locals and travel bloggers at Why Not Walk.

A World in Reach contains affiliate links. If you make a purchase through these links, I may receive a commission at no cost to you! Read my full disclosure here.

3 Days in Boston: A Perfect Long Weekend Itinerary featured image - Boston skyline with purple pink sky

3 Days in Boston: Top Boston Travel Tips

Boston Basics

  • Location: New England, Northeastern USA
  • Currency: US Dollar
  • Language: English
  • Tipping: US standard, 18-20%
Sunset over downtown Boston, Massachusetts - 3 days in Boston itinerary

Getting around Boston

Boston has a great public transit system called the MBTA (Massachusetts Bay Transit Authority). There are several train lines (blue, green, orange, red, and silver), as well as an extensive system of buses.

To venture outside of Boston, check out the commuter rail. It departs from large stations (such as North and South Station) and often has special weekend passes – $10 for unlimited rides. We highly recommend booking accommodation near a train or bus line.

Relatedly, we do not recommend renting a car or driving in Boston unless you really need to – the traffic was ranked the “worst in the U.S.” in 2019, and parking is very limited, expensive, and hard to find. It is so much easier to take the train, bus, or walk – Boston is a super walkable city with a relatively small “city center” area, so eminently walkable!

When to Visit Boston

Boston, contrary to popular belief, is a great place to visit in all seasons. It is especially popular in the summer and fall, as summers are famously mild and enjoyable in New England, and the fall is peak “leaf-peeping” season for gorgeous foliage and astounding autumnal colors.

However, we would recommend Boston in shoulder season, especially the spring, as the tulips are in full bloom and there aren’t so many tourists. Winter in Boston is super charming, with beautiful snowfalls, outdoor ice skating, and pop-up hot cocoa bars to enjoy.

Despite a reputation for arctic winters, Boston is far more temperate than other places further inland and north due to its coastal location. A lot of winter weather is broken up over the ocean, leading to milder temperatures.

A few dates and annual events to note:

  • Sunday closest to St. Patrick’s Day: The St. Patrick’s Day Parade in South Boston, said to be home to almost as many Irish people as Ireland itself. Note that this parade can get a little rowdy, so get there early to avoid fighting crowds.
  • Third Monday in April: the Boston Marathon finishes in Copley Square, and the last few miles are packed with spectators with signs, cheering on the runners and watching. Note that if you’re not partaking in Marathon festivities, it’s best to avoid visiting this weekend, as the city is jam-packed with visitors and public transit is closed the day of the marathon. But if you are in town, it’s a lot of fun to spectate.
  • Late May: Boston Calling Music Festival at Harvard Stadium
  • Second Saturday in June: Boston Pride Parade, celebrating the LGBTQI+ community in Boston and surrounding areas  
  • Fourth of July weekend: Boston Harborfest, a “birthday party” celebrating American independence
  • Last Sunday in August: St. Anthony’s Feast, dedicated to patron saint St. Anthony, has been celebrated every year in the North End since 1919. There are concessions, games, and food and fun galore. 
  • Late August to early September: Peak sunflower field blooms
  • Late September to late October: Apple-picking season, a quintessential New England activity! There are tons of farms around Boston to spend a half-day picking apples and sampling apple-related treats.
  • Late September to mid-October: Fall foliage. “Peak weekend” falls at different times each year, so it’s a good idea to do some research if you’re trying to time your visit.
  • Penultimate weekend in October: Head of the Charles Regatta, one of the most famous rowing races in the world, as well as the largest. It has taken place on the Charles River since 1965, and over 11,000 participants compete each year. 
  • Early December: SoWa Winter Festival, a beautiful holiday-themed winter market 

What to Pack When Visiting Boston

if you’re visiting Boston in fall, spring, or winter, pack those layers! The weather in New England is known for being quite fickle, and Boston is no different.

While milder than other places in the region due to its coastal location, the weather can change rapidly and dramatically. We recommend bringing along a packable rain jacket if you have one, as well as layers that are easy to take on or off as the temperature changes over the course of the day.

If you’re visiting in winter, keep in mind that the wind can be fierce at times. To mitigate this, it’s a good rule of thumb to make sure your neck, wrists, and ankles are covered (and maybe even your ears and head!) Scarves, beanies, and warm footwear (like Uggs or Timberlands) is a good idea.

As for footwear year-round, Boston is a very walking-heavy city. Definitely wear comfortable shoes with good support for walking, like sneakers. Similar to New York City, you’ll notice that a lot of women in Boston have “commuting shoes” and “office shoes” that they change into when they arrive.

Money Saving Tip: Make sure to pack along your Go Boston All-Inclusive Pass – you can save up to 55% on admission costs on some of Boston’s top attractions and activities including the Boston Duck Tour, the New England Aquarium, and the Boston Hop-On Hop-Off Trolley! Make sure to read the fine print as certain attractions aren’t included unless your pass is valid for at least 3 days.

A building covered in greenery and an American Flag in Boston's Beacon Hill neighborhood
Boston's Chestnut Hill neighborhood during winter

3 Days in Boston: Where to Stay

Accommodations in Boston can be quite expensive. Due to a fairly severe housing crisis, there seem to be fewer hotels in Boston than in other cities, leading to fairly high prices.

As always, we recommend looking on Airbnb or VRBO first, as that is often cheaper. If you’re on a budget, check out areas like Brookline or Jamaica Plain, which are close to downtown and on train lines, but a little more budget-friendly. Another budget-friendly option is to stay at a hostel like HI Boston.

The Verb Hotel is a good 3-star option located close to the iconic Fenway baseball stadium, and if your lodging budget is a bit higher, check out the Fairmont Copley Plaza, known for playing host to every U.S. President since William H. Taft. For more hotels in the Boston area, check out Booking.com.

READ MORE: The Best Hostels in North, South, and Central America

Where to Eat in Boston

We could go on and on about the Boston food scene, but in a nutshell, Boston has options for every budget, palate, and craving.

While known traditionally for comfort food (e.g. lobster rolls and traditional Italian fare in the North End neighborhood), there has been an emerging foodie scene in the last few years, as well as a few food halls and markets to note.

We have woven in food recommendations in our itinerary below, but here are a few favorites:

  • Upscale Italian + mouthwatering hand-made pasta: Giacomo’s (note that they don’t accept reservations and the interior is very small, leading to long wait times: people sometimes start lining up outside at 2PM! Since they make their pasta from scratch every day, when they run out of pasta they close for the night. We realize this can be a bit of a commitment for a short visit, but it’s the real deal!)
  • Pizza: Regina’s (the best pizza in Boston, in our humble opinion. Also doesn’t take reservations, but the line moves fairly quickly. Try to go at off hours to avoid the line, or sit at the bar.)
  • Chinese (dumplings): Gourmet Dumpling House (definitely a “no frills” experience, but absolutely delicious. Expect to be seated with another party if you’re a party of less than 4.)
  • Locally-Sourced Bowls: Dig Inn (great for lunch and quick bites!)
  • Options: Faneuil Hall (great for groups, as there are tons of options, as well as lobster rolls and clam chowder! Located on the Freedom Trail, so a very convenient location as well.) 

Want to try all of Boston’s best treats? Go on a Boston food tour!

The outside of Faneuil Hall and Quincy Market in Boston, Massachusetts
Faneuil Hall and Quincy Market

3 Days in Boston – The Perfect Itinerary

3 Days in Boston: Day 1

If you arrive on Friday afternoon/evening, check into your accommodation and check out the South End neighborhood for beautiful Victorian row house architecture, trendy eateries, and hip bars. Stop in at the Beehive for a drink and live jazz music, or Barcelona Wine Bar.

Day 2 in Boston: Explore Boston’s Top Sights

Take the MBTA or a ride-share to the Boston Common to start the Freedom Trail, a 2.5-mile tour of some of the most significant historical sites in the U.S., including the site of the Boston Massacre, the State House, and a variety of churches, museums, meeting houses, and more. The trail technically takes about 90 minutes to complete end-to-end, but we recommend allotting a full half-day in order to really enjoy everything it has to offer.

The snow-covered ground and bare trees in Boston Common during winter
Boston Common in winter

As far as staying on the trail, just follow the brick path (often 2 bricks wide in the center of the sidewalk) and you won’t get lost. There are 16 stops total. For a complete step-by-step guide to the Freedom Trail, check out Why Not Walk’s guide here.

The State House in the snow in Boston
The State House in the snow

The “sister trail” to the Freedom Trail is the Black Heritage Trail, which comprises 10 stops in the Beacon Hill neighborhood important to Black history and culture in the area, including the oldest Black church in the U.S.– the 1806 African Meeting House. We highly recommend adding these stops in!

The Freedom Trail ends at the memorial to the Battle of Bunker Hill in Charlestown, so spend some time exploring the area, including the U.S.S. Constitution and its accompanying (free) museum, or begin to make your way back downtown for some lunch.

For quick bites downtown, check out the enormous sandwiches at Sam LaGrassa’s, or you can also grab a bite while you’re on the Freedom Trail itself at Faneuil Hall. This is a good place to try lobster rolls and clam chowder, if that’s on your list! 

Save some room, though, because in the afternoon, you’re going to tour the North End, where you’ll have the opportunity to sample a myriad of Italian treats that strike your fancy – we especially recommend cannoli or Italian cookies! A note about cannoli: there is an epic rivalry between neighboring cannoli shops Mike’s Pastry and Modern Pastry. We recommend trying both to see where you stand in this age-old stand-off!

A restaurant called "Ciao Bella" in Boston's North End
Boston’s North End
A walkway in Boston's Christopher Columbus Park
Christopher Columbus Park

The North End has a lot to offer other than food, though. As you saw on the Freedom Trail, it is Boston’s oldest neighborhood (continuously inhabited since 1640!) and is located right by the Boston Harbor, where you can stroll around Christopher Columbus Park, go for a whale-watching tour with Boston Harbor Cruises, and more.

You can (and should) absolutely stay in the North End for dinner, choosing one of many restaurants (you can’t go wrong!) We love the squid ink pasta at Trattoria Monica and the lasagna at Antico Forno, but as we said before, the pizza at Regina’s or fresh pasta from Giacomo’s are our top picks.

Day 3 in Boston: More of Boston’s Must-Sees

Since you spent pretty much all day in and around downtown yesterday, start your day today in Copley Square. Here, you can visit its beautiful churches, as well as the iconic Boston Public Library and the Prudential Center. 

In Copley Square proper, check out the Old South Church and Trinity Church. Behind Trinity Church is the tallest building in New England, the John Hancock Tower (we joke that it looks a bit like a PlayStation 4!)

The Boston Public Library is one of our favorite “local tips” to impart. It’s such a gem, and so often overlooked! It was built in 1888, and we guarantee your jaw will drop when you go inside. There are murals by John Singer Sargent, imposing staircases, an interior courtyard, and the cherry on top– the Bates Room. Located on the 2nd floor of the library, it is the epitome of “old-school study vibes,” complete with antique bookshelves and lamps.

A fountain at the Boston Public Library
Boston Public Library

Next, meander along Newbury Street, perhaps stopping in one of its eateries for brunch, like Stephanie’s. Newbury Street is an excellent window-shopping street, with upscale brands and beautiful storefronts galore. As you keep walking, you will come across the Prudential Center, a large shopping complex that is very popular with tourists and locals alike. There is a really fun Italian market inside called Eataly.

In any season, you can’t miss a stroll down the Commonwealth Avenue Mall, a beautiful promenade next to the Public Garden (and one block over from Newbury Street!) where the trees arch over the walking area. 

For lunch, you can head over to the aforementioned Dig Inn for customizable, locally-sourced bowls (our favorite!) or perhaps try some seafood at Saltie Girl.

A mural at Boston's Fenway Park stating "Go Red Sox!"

After you’ve had some lunch and a bit of a rest, head over to the nearby Fenway area (you can take the green line or walk) to visit the Fenway Baseball Stadium, home to the Red Sox; the enormous Museum of Fine Arts; and the Isabella Stewart Gardner Museum. If you’re in the mood to keep walking afterward, 3 of the 6 parks that comprise what is known as “the Emerald Necklace” – the Fens, Olmsted Park, and the Riverway – are interconnected and absolutely beautiful. 

For dinner, you can check out Lolita in the Back Bay for Mexican fusion and amazing margaritas in what we like to call a “dungeon-glamour” setting, or head back downtown for dim sum or dumplings in Chinatown, or even head across the river to Cambridge for Mediterranean fare at Oleana or more Italian at Giulia

Spending more than 3 days in Boston?

If you’re spending more than 3 days in Boston, here are 6 day or half-day trips to consider:

  • Cambridge: This one is a no-brainer, since it’s right across the river from Boston. Cambridge is home to Harvard University and MIT, as well as lots of fun activities at the Central Square, Davis Square, and Porter Square red line stops. If you take the red line to Harvard Square, you can explore much of the area by foot. 
  • Hiking: there are tons of options for hiking near Boston and in New England. New Hampshire is a short drive away, and boasts 48 4000-footers. If this sounds a bit daunting, there are countless trails to explore in Massachusetts, Maine, and New Hampshire at all skill levels. Note that we don’t recommend hiking in winter unless you’re very experienced, as the wet weather can make a lot of the trails very slick. Here are a few options less than a few hours’ round trip:
    • New Hampshire: Hike Mt. Major for stunning wraparound views of Lake Winnipesaukee and the Alton Bay area. 
    • Boston: Skyline Trail at Blue Hills Reservation or exploring Middlesex Fells Reservation (both MBTA-accessible!)
    • Massachusetts: World’s End Reservation in Hingham (once considered as UN Headquarters!) or Break Heart Reservation in Easton.
  • Biking: While not typically considered a biking-friendly city, Boston has really committed to adding more bike lanes, and there are tons of options within the city to explore. You can rent bikes per hour or per day through the fabulous Blue Bikes program, and there are docks all over the city.
    • Southwest Corridor: stretching from the Back Bay to the Forest Hills area and Jamaica Plain, biking along this corridor is a fantastic way to explore several Boston neighborhoods: the above-mentioned Back Bay and Jamaica Plain, as well as the South End and Roxbury. 
    • The Emerald Necklace: mentioned above as a walking destination, the interconnectedness of the Emerald Necklace also doubles as a fantastic biking destination 
    • The Charles River Esplanade: our favorite place to bike in Boston, this beautiful Esplanade follows the path of the Charles River on both the Boston and the Cambridge side 
    • Minuteman Bike Path: this is a bit more advanced (about 25 miles total) and not technically in Boston, but very flat and well-paved if you’re seeking a longer ride. Built on an old train line, the Minuteman starts in the Alewife area of Cambridge and takes you by several sites from the American Revolution, including where it all began in Lexington.
  • Sunflower Fields: if you’re visiting in late August/early September, check out the awe-inspiring sunflower fields at Colby Farm – sunflowers as far as the eye can see! 
  • Apple Picking: if you’re visiting in late September to late October, there are lots of options to pick apples in the region.
  • Beach Day: in the summer, it’s lovely to spend a day at the beach, coupled with exploring quaint coastal towns! Three beach towns that we highly recommend (that are on the commuter rail) are Newburyport, Rockport, and Gloucester.
Boaters on the Charles River Esplanade in Boston, Massachusetts
The Charles River Esplanade is one of Boston’s best places to ride a bike.

Boston is a great city that should be on your USA bucket list – there’s so much to offer! Spending a long weekend in Boston is a great way to get an introduction to the city, and there’s a ton to do if you have more time during your visit.

Have you been to Boston?

About the Author: Tegan and Alex are travel, hiking, and biking enthusiasts currently based in Boston, USA. There is nothing they love more than exploring new places by walking, and they have visited over 30 countries together since they met in 2015. Their love for “walking the world” led them to found Why Not Walk, a travel guides site. Follow them on Instagram, Facebook, or Pinterest to start planning your next adventure.

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7 thoughts on “3 Days in Boston: A Perfect Long Weekend Itinerary

  1. Sunetra says:

    I was in Boston a couple of years ago during autumn and loved the vibe of this city! Would love to return and do some of the activities I missed on my last visit!

  2. Megan says:

    I would love to visit Boston. It is so rich in history, but also so beautiful. And it looks like there’s a lot of fun things to do and see as well! Great guide!

  3. Melissa says:

    Oh my gosh these are great tips! I would love to come to Boston in the fall. I’ve only been in the winter when it was like a snowpocalypse haha! Very intrigued by the dumpling place you mentioned too. Thanks for sharing this!

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