Boston Still Has Lots Of Family Friendly Fun Despite The Cold

(So Bring A Coat And Take Advantage Of The Lack Of Crowds)

Why You Should Go

Boston is one of my favorite cities in America to visit, especially with kids. I love that it has so much history to explore and that the city has made it so easy to do just that by making the Freedom Trail an actual permanent “ brick trail” in the sidewalk for kids to follow in a fun scavenger hunt. I love the city’s enormous food scene, from fancy to fast casual choices to suit any tastes. I love its dedication to its sports teams-- that the mood of the city can entirely depend on how the Red Sox do.

Most especially, I love that Boston has its neighbourhoods (23 of them in fact) with their own individual feel. Beacon Hill is not like Charlestown which is not like North End or Fenway. Plus, there are nearby municiplaities that are an easy T stop away that add even more places to explore--Cambridge and Wellesley come to mind. Spend 30 minutes on the commuter rail and you can even get to farther out places like Salem, Lexington, or Concord.

All of this awesomeness means that Boston is an extremely popular tourist destination, especially in the summer when sidewalks are crowded and lines for museums are long. So why not go in winter when you can take advantage of inexpensive hotel rooms, cheap flights, and having Paul Revere’s house all to yourself?

The Weather

I am sure you are thinking “I don’t want to go to Boston in January because it is cold and rainy and snowy.” And yes, it can be like that some days, but it can also be more temperate than you might think because of its proximity to the ocean.

January/ February averages:

• Temperature: a high around 37-41 degrees and a low of 23-28 degrees

• Rain: about 8 days a month which is the same year-round

• Snow: less than an inch each month

• Wind: 9 mph (versus average of 5 mph in June). This is the biggest negative as anyone who has lived on a coast knows that the wind can make all the difference.

We made sure we came prepared with hats, gloves, scarves, and good jackets and we did fine. Most of our days were spent popping in and out of historic sites so it is not like you are spending hours outside anyway.

Truly the biggest issue for us visiting in winter versus summer was the early sunrise and sunset due to its location so far east. Boston has only about 9 hours of daylight in January, with the sun rising around 7 am and setting before 5 pm. This is a bit of an issue when attractions don’t open until 10 am. That means you are either squeezing all the sights into a shorter amount of time or you are happy seeing some attractions in the dark. Which is actually okay. The Bunker Hill Monument is beautifully lit at night for instance.

*February is a bit better than January with 10-11 hours of daylight and a sunset after 5 pm.

Getting Around Boston In Winter - Walking, Ride Share, And Public Transportation

We walked everywhere on most days since we were staying downtown and sightseeing mostly in downtown as well. Boston is a very walkable city and we generally spent 10-45 minutes walking or exploring outdoors, then hopping inside a historic site, museum, or restaurant for awhile before heading back outside to walk to the next place.

Ride Share

For places too far away to walk (Cambridge or Fenway for example) or for getting back and forth to the airport, we used Uber/ Lyft and public transportation. Ride sharing is very popular in Boston and you won’t have any problem finding a ride. Short rides around the city will cost you $8-$10 while the airport might cost $15-$40 depending on time of day and distance.

Public Transportation

Boston’s has a really good public transportation system of subway, buses, street trams, commuter rail, and ferries. The subway system is known as the “T” and is the one you will use the most as it has lots of stops downtown. There are 2 types of tickets- a CharlieCard (this is a plastic rechargeable card used by locals and is not something you will need) or a CharlieTicket (a durable paper card for single fares and short term visitors- this will be what you get).

Each ride on the subway is $2.90 no matter the destination or time of day. Kids 11 and under ride free. Buy a CharlieTicket at one of the fare machines in each station. Machines take cash, credit, and debit cards and you can select how much you want to load onto each ticket - one fare or multiples thereof. You will then feed your CharlieTicket into the turnstile gates to enter the station. Unlike say, New York City, you can only use one CharlieTicket per person so everyone will need one.

Getting the 1 Day or 7 Day Pass for Public Transportation

If you think you are going to ride the T at least 8 times during your stay, then go for the 7 day pass for $22.50. It gets you unlimited travel on the subway, bus, Charlestown ferry, and inner commuter rail zone. If you are here for only one day, look at the 1 day pass for $12.75. Even if you don’t quite make it pay for itself, it is nice to be able to go straight to the turnstiles and skip the fare machine. The passes are issued on a special CharlieTicket stamped with the time and date.

Getting Back and Forth From the Airport

It is quite easy to get into town from the airport using public transportation. Boston has free airport buses that take you to 2 subway stations (why don’t more cities do this?!).

Catch the Silver line (this is a bus despite being colour coded like a subway line) to South Station for the Red line -- this is a free transfer so you get to ride the Red line for free too. Or take a Massport bus (either # 55 or # 22) to the Airport Station for the Blue line (not a free transfer and you will have to buy a CharlieTicket to get on the subway here). All of the free buses pick up right outside baggage claim in their appointed area. Look for the signs for each bus pick-up.

Half of our family took an Uber to our hotel in Charlestown from the airport and half took the airport bus/ subway combo. The Uber beat the public transportation people by 5 minutes and that’s only because we had to walk from the station.

Going to the airport from town is just as easy but if you are taking the Silver Line from South Station, you will have to pay a normal fare as the ride is only free coming from the airport, not going to it. The Massport shuttles to and from the Airport Station (serving the Blue line) are always free.

Learn more about using public transport to/ from Logan Airport here.

What To Do In Boston In Winter

Lots of the main touristy things are open year-round and you will find that you are not the only people who have decided that New England in winter sounds like fun. We had 20 other people on our USS Constitution tour for instance, but 20 people is way better than a 100 people you’d be likely to find in summer.

Here is the list of the things we did on our 3 day January trip to Boston in 2020.

• Freedom Trail- We split this into 3 days and only did a quick walk by of some of the historic sites due to time constraints or weather (Boston Common isn’t that fun when it’s super windy). But at some of the other historic sites, we spent a good deal of time exploring and enjoyed having them (almost) to ourselves.

• Explore Cambridge- We walked around MIT and Harvard, admiring the campuses, enjoying cheaper food, and poking around the shops.

• Tour Fenway- An excellent way to take advantage of the offseason. Great for the sports fans but fun enough for anyone with even a passing interest in baseball or Boston history.

• See a Celtics Game- Not exactly a cheap outing but an absolute highlight if you can swing it. TD Garden is the big arena right downtown so it’s easy to get to. The Bruins also play there if hockey is more your thing.

• Eating so much good food- The Italian restaurants in the North End were a particular hit, but we also tried some historic taverns and were pleasantly surprised by the friendliness and food quality in such obvious tourist sites.

The Freedom Trail

2.5 miles long, 16 historic sites, extends from Boston Common to Bunker Hill

The Freedom Trail is the number one tourist attraction in Boston and rightfully so. Anytime of year that you happen to be visiting, you should make an effort to walk at least part of this trail. It takes you through the heart of the oldest parts of Boston, surrounding you with charming architecture, lots of good restaurants, and plenty of history.

There are 16 sites on the trail: 1) Boston Common, 2) Massachusetts State House, 3) Park Street Church, 4) Granary Burying Ground, 5) King’s Chapel and Burying Ground, 6) Boston Latin School Site/ Ben Franklin Statue, 7) Old Corner Bookstore, 8) Old South Meeting House, 9) Old State House, 10) Boston Massacre Site, 11) Faneuil Hall, 12) Paul Revere House, 13) Old North Church, 14) Copp’s Hill Burying House, 15) USS Constitution, and 16) Bunker Hill Monument.

It really doesn’t matter which end of the trail you begin, so just plan your visit based on the weather and your interests.

It will take about 2 hours to walk the entire trail straight through with a minimum of stops to read information plaques and taking only a few pictures. But I recommend that you plan on doing the trail over at least 2 days so you have time to go inside most of the sites and explore. In the winter, not only will it be a nice respite from the cold (and probably windy) day outside, but you can really take advantage of the lack of other tourists to pester guides with questions or get tons of solo photos. (We did both of those things. A lot.)

Plus, most kids will have a history overload after about 5- 6 sites on the trail so best to do it over more than one day. If you only have one day, just plan on doing whatever part of the trail interests you most and leave the other parts for your next visit. I promise you, everyone will enjoy it more.

We split the Freedom Trail over 3 days:

• Copp’s Hill Burying Ground to Faneuil Hall on day 1 (0.8 miles)

• Bunker Hill and the USS Constitution on day 2 (0.5 miles between the 2 sites). Bunker Hill and the USS Constitution are good to do together as they are both in Charlestown, a neighborhood just across the Charles River from downtown Boston, easily accessible across a bridge with a wide sidewalk

• Boston Massacre Site to Boston Common on day 3 (0.7 miles).

*My mileage doesn’t add up to 2.5 miles because I am leaving out some of the Freedom Trail between the sites since we kept leaving and coming back to the trail on different days.

Details

• All of the sites remain open in winter at least some days, with the exception of Park Street Church (which is only open in summer). The State House is closed on weekends, King’s Chapel is closed Tues/ Wed/ Thur in the winter, the Paul Revere House is closed on Mondays in Jan/Feb/March, and the USS Constitution is closed on Mon/Tue in the winter.

• Everything is closed on Thanksgiving, Christmas, and New Years Day. Some places are also closed on Christmas Eve or close early.

• Plan on opening hours of 10-4 for most places everyday, although a few open at 9 or close at 5 pm. Many of the churches won’t open until 12 or 1 pm on Sundays. We tried to be out of the hotel before 10 am and were usually back by 4 or 5 pm for a break. Then we headed back out for dinner around 6 pm.

• Four places charge admission- Old South Meeting House ($6 adults/ $1 kids), Old State House ($12/ free), Paul Revere House ($5/ $1 CASH ONLY), and Old North Church ($12/$2). There is a “build your own” Go Boston card that includes the Old State House, Paul Revere House, and the Old South Meeting House and will save you about $5 per adult (kids aren’t worth it, only saves you 40 cents).

• Two places ask for donations but are technically free- King’s Chapel ($4 per adult) and the USS Constitution Museum ($25-50 per family). The ship itself is free, only the museum is a donation. (And is completely worth it in our estimation.)

For a complete rundown of all the sites we saw on the Freedom Trail, including what the kids loved and what we found skippable, you can read my very detailed blog about it that includes everything I could think of. “Boston’s Freedom Trail In Winter- What To Do, What Is Closed, And What Is Still Awesome”

Tour Fenway Park

Although I think the only way to really experience Fenway is to see a game there, you can still take a tour of the historic stadium in the offseason. You get to see parts of Fenway that a regular ticket holder doesn’t get to see, like the press box or the visiting team’s locker room.

The hour long tour is pricey but worth it if you are a fan or even have a passing interest in baseball or Boston history. The tour can also be done in any kind of weather, a big plus in winter. The tour guides are knowledgeable and passionate about Red Sox history so the tours are pretty fun. And, in the winter, they probably won’t have to use their megaphone because there may only be 8 people in your group like we had.

Our favorite part was sitting on top of the Green Monster and hearing its history. I had no idea it was built that tall because originally there was a car dealership next door when they built the park so they did not want any balls going over the top and damaging the cars. It was those nifty little trivia bits that made the tour so interesting.

I also did not know that Fenway has a rooftop garden where they grow vegetables for their concession stands. Not sure how much it actually provides percentage-wise but a nifty idea nonetheless.

Details

• The park is open 10- 5 in the winter and tours leave every hour. Adults $21/ kids 3-12 $15.

• You can add the Fenway tour to the “build your own” Go Boston card for some savings. See my comparison of passes at the end of this blog for more details.

• Be sure to check the website ahead of time to make sure of the hours and to see if they are doing any maintenance that might close down something you really want to see like the Green Monster. Concerts can also affect hours.

• Be aware that you have to go through metal detectors and bag checks. They won’t allow bags bigger than 16”X 16” X 8”. It is not as strict as it is for actual games so a water bottle was fine. See the security policy here.

Explore Cambridge (MIT and Harvard)

Most people don’t realize that Cambridge is its own municipality and not part of Boston, giving it a bit of a small town feel in the middle of a big city. The fact that they have 2 world class universities in a town of 100,000 people makes it a very smart small town too (76% of the population has at least a bachelor degree). I remember having a beer at the MIT student union years ago and realizing that, while I was discussing the nuances of Ross and Rachel’s relationship, the people next to me looked like they were solving cold fusion on a napkin.

Visiting Cambridge during the winter has its drawbacks-- all the cute little beer gardens and pocket parks look a lot less cute when it is 35 degrees, as does wandering both of these sprawling campuses. But on the plus side, you won’t be elbow to elbow with other tourists (Harvard in particular suffers from an overload of people with selfie sticks) and there is plenty that you can see without having to walk too far from the T station.

Cambridge also has lots to see “inside” on a cold day-- pop into some of the campus buildings, visit one of their world famous museums, or just take advantage of the more budget conscious food choices in such a student heavy population.

MIT (Massachusetts Institute of Technology)

If you want to explore MIT, you will want to do it on a nicer day as the campus is huge and the main part of it is about 0.5 mile from the nearest T station. It probably won’t be that interesting for young kids but anyone who thinks technology and science is awesome will get a kick out of walking around. I personally think it is a beautiful campus that tends to be overlooked by most tourists who head straight up to Harvard for the T-shirt and photo. You can walk down some of MIT’s halls and see the state of the art labs or admire the campus’s modern architecture with buildings by IM Pei, Frank Gehry, and Eero Saarinen.

Getting To MIT

From downtown Boston, take the T or Uber/ Lyft. The T’s Red line stops at Kendall/ MIT Station which is on Main Street, one of the main commercial arteries adjacent to MIT’s campus. You will find a smattering of food choices right around the T stop. If you are ride- sharing, then head to 77 Massachusetts Ave. That is the Rogers Building where MIT’s Visitor Center is located. It is a good central place to start.

From the Kendall/ MIT station, it is 0.5 mile walk from the station to the Rogers Building but at least it is thru the campus so you can tour while walking. Walk 2 blocks west on Main St, then turn left onto Vassar St. You will go a couple of blocks on Vassar, passing the crazy looking Ray and Maria Stata Center. This is a large building designed by Frank Gehry so of course it doesn’t believe in silly things like right angles. Turn left onto Mass Ave and walk another block until you see the massive, neoclassical Rogers Building on your left and the open plaza on your right.

Do a Short Campus Tour

Walk into the Rogers Building, which is almost always open even when undergraduates aren’t there, to find the Visitor Center where you’ll get a brochure for a self- guided tour. You can also print out or download the self-guided tour at home from the website, but you should still head to the Rogers Building to start exploring even if you skip the Visitor Center. Most of the important stuff is right around there, so it is a good place to start.

The Rogers Building connects to the main building housing the Great Dome. This is the postcard building of MIT and you can walk out the big double doors to the large courtyard to get the iconic photo. The corridor that you are walking down is known as the Infinite Corridor. It is a super long hallway that connects several buildings. You will walk by some labs and classrooms where people appear to be doing super cool things way beyond my comprehension. We had fun reading the bulletin boards for all the clubs and meetings on campus.

After walking the Infinite Corridor and staying warm, head back out of the Rogers Building and cross Mass Ave to the open grassy area in front of you. The Student Union is on your right if you are looking for some snacks or a bathroom. The nondescript brick cylindrical structure on your left is the MIT Chapel, designed by Eero Saarinen to be used by any and all faiths. It is beautifully simple inside and only open to non-MIT students M-F 10-1130 am and 130-230 pm. So if you are on campus during those times, go straight there first.

*If you want to do MIT and Harvard in one trip, there are several ways to get to Harvard Square from MIT. One is Uber/ Lyft- the fastest way and will cost somewhere between $10 and $15 usually. Or take Bus 1 from right outside the Rogers Building for a 20 minute ride ($2 cash for a ticket one way that you can buy on the bus, kids 11 and under ride free, or use your pass). You can also walk 0.7 miles up Mass Ave to Central Station and take the Red line 1 stop up to Harvard. This is not a bad walk as you will pass more restaurants and shops on the way. Now you are really getting into the heart of Cambridge.

Harvard

The T’s Red line runs right through Harvard Square, which is the heart of the commercial area of Harvard. The square is also conveniently located adjacent to Harvard Yard, the picturesque, tree-lined grassy area that contains Harvard’s oldest buildings. A T ride from downtown’s South Station out to Harvard Square will take you about 18 minutes and cost $2.90. Kids 11 and under are free.

Harvard Yard- 30 minutes is plenty of time to walk around the Yard and join the other selfie-taking tourists. Even in winter you will join a larger than expected number of them, so you can imagine what summer is like. Massachusetts Hall (1720) is the oldest building at Harvard and housed some of our founding fathers when they attended the school (John Adams, Sam Adams, and John Hancock). Look for it by the Johnston Gate off Peabody Ave—the building has a helpful plaque on it.

You can rub the left toe of the statue of John Harvard for luck like all the other tourists, but I don’t think any actual Harvard students do this. I do believe they do other things to the statue that will make you not want to touch it. Read more about Harvard Yard’s history and what it means to the community in The Harvard Crimson’s article.

Harvard Bookstore is a must for any bibliophile, especially the downstairs which carries hugely discounted used and overstock books. They have been selling books since 1932, so it is definitely an institution and worth a visit. I think their collection is wonderfully curated and I seem to always find a perfect book for myself or someone else every time I visit. It makes a unique gift. The bookstore is just down the street from Harvard Square on Mass Ave at the corner of Plympton St, across from Harvard Yard.

Harvard Arts Museum puts all 3 of Harvard’s arts collections (Fogg, Busch- Reisinger, and Sackler) under one roof and has a remarkable amount of artists that most people will recognize- Degas, Monet, Klimt, Renoir, Van Gogh, Sargent, etc.

I spent about 2 hours here and never even saw the 3rd floor, which has ancient Mediterranean art (Greece, Roman, Egyptian). The second floor has the collection of American and European art from the 17th- 19th centuries so it is where most people head straight to because it has the most amount of artists they recognize.

Do not miss the Wertheim Gallery on the main level. A 1906 Harvard graduate, he went on to accumulate an astounding amount of Impressionist and Post- Impressionist art before donating it to his alma mater. I also particularly liked the galleries on the main level covering Secessionism and “Art in Germany Between the Wars”. I had never seen so much art from that time period gathered together and presented as a group. It was very interesting to see how themes ran in common and the progression of ideas.

One admission price covers all 3 collections and is $20 for an adult but free for kids and any students with a university ID. The Harvard Arts Museum is open 10- 5 and is located across from Harvard Yard on Quincy Street. The building has a cafe (Jenny’s Cafe) and a Renzo Piano designed glass covered courtyard which is a pretty great place to sit and enjoy your not terribly-priced meal. The soup ($5) and kids meal ($5) are both good deals. Read more about the museum in the NYT’s article.

Harvard Museum of Natural History and the Peabody Museum are two more worthy museums on Harvard’s campus. Neither are huge compared to say New York or London’s Natural History Museums but they are jam packed with exhibits. Plus, one admission gets you into both museums since they are in adjacent buildings. You could easily spend 3-4 hours seeing both of these museums.

The Museum of Natural History is fun for about any age as it has dinosaurs, lots of mounted wildlife specimens, and a gorgeous collection of glass flowers, made for a Harvard botanist so he could teach his students.

The Peabody focuses on Native American history with exhibits from all around the country and other parts of the Americas. It is very well organized with some interesting displays but you need to be able to read the signs to get the most out of it so probably not for younger kids.

Open 9-5 daily (except the major winter holidays) and costs $15 adults/ $10 kids. The museums are an option on the “build your own” Go Boston card, so if you are planning on seeing at least one other site from this blog on the card (Fenway, Old State House, Paul Revere House, Old South Meeting House), you could save 20%.

The museums are a little bit away from Harvard Square, a o.5 mile walk to be exact. Walk across Harvard Yard to the north exit and take the pedestrian bridge across Cambridge St. From there, head diagonally right, keeping the beautiful sort of gothic brick building on your right. When you hit Oxford Street, go up 2.5 blocks until you see the Natural History Museum on your right.

Places To Eat Around Harvard Square

This is a great place to find cheaper eats thanks to all the students. These are just some of my favorites.

• Mr. Bartley’s Gourmet Burgers is next door to Harvard Bookstore and has been slinging burgers at students since 1960. One of your best bets for a value meal around here plus it has a kids menu plus the burgers are often named after current events so it’s pretty funny. Has vegetarian options and amazing frappes as well. If you can’t tell, I like this place even if all the tables are crammed in. Closed on Sundays and Mondays and no beer.

• A student at Harvard Bookstore recommended I try Russell House Tavern as that is where they went for beers after work. Not cheap but not terrible prices either, and the food was very good and creative. No kids menu but does have a decent sized margherita pizza for $13. The beer list is extensive and focuses on New England beers, which I liked. If you are at the Harvard Square T station, then head down JFK Street and the Tavern is half a block down on your left.

• If your like your food fast and casual, with a side of locally grown and ecologically sustainable ethos, then Clover Food Lab is for you. What started as a food truck and an idea from a MIT grad has now become 13 locations and some dedicated cult status. Serves breakfast, lunch, and dinner for decent prices. My fav is having one of the soups of the day with a tomato cheese sandwich. The menu changes everyday based on what they get from their farmers. Even has beer (local of course). Between Harvard Bookstore and the T station.

Catch a Celtics or Bruins Game

If you happen to have some extra disposable income (or perhaps won a recent lottery in the case of Bruins tickets), you can watch Boston’s passionate sports fans in action at TD Garden, right in the heart of downtown Boston. Tickets ain’t cheap but the “gahden” is like no other and something the kids will remember forever. My brother and his wife gave Boston Celtics tickets as a Christmas present and it might have been the greatest night of my ten year old nephew’s life. Check the website of the Celtics and the Bruins for schedule and prices.

*We bought our tickets resale on Vivid Seats and looked for a game against a bottom dwelling team that wasn’t much of a rival. That made prices slightly more manageable. Slightly.

Other Tourist Sites That Are Great Ideas In Winter

We did not get to everything in Boston this trip; it being a big city and us only being there for 3 and a half days. So there are tons of things we did not get around to that I have either loved in the past or I am dying to try.

• The New England Aquarium- one of Boston’s top attractions and sure to be a hit for anyone that loves fish, not huge though and can be crowded

• The Boston Childrens Museum- a blast for the under 10 crowd, maybe a bit too basic for older kids

• The Museum of Science- huge place with a planetarium and lots of interactive exhibits

• Museum of Fine Arts- has one of the largest collections of Monet paintings outside of France

• Explore Back Bay- go to the Sywalk Observatory at the top of the Prudential Building, eat large quantities of Italian food at Eataly, or see the world’s largest walk-in globe.

Where To Stay In Boston

This can depend on lots of factors: Do you have a car? How many people in your group? Do you want to have a kitchen or free breakfast so you don’t have to eat out every meal?

Thanks to excellent public transportation, I don’t generally have a car when I visit Boston so I can stay downtown without worrying about paying $40 a day parking fees. If you have a car, you are probably going to want to stay a bit farther out and use the T or commuter rail to get into the city everyday.

Anywhere downtown is going to be convenient for the sites mentioned in this blog, just try not to go farther out than I-90. It is nice to be able to nip back to the hotel during the day for a break or nap times or to grab extra jackets or gloves if needed.

Where We Stayed

We stayed at the Residence Inn in Charlestown, just across the bridge from downtown and next to the USS Constitution. This was a fabulous hotel for 2 adults and 4 kids, because it had 2 bedrooms (1 King, 1 Queen) with 2 baths and a common room between with a pullout sofa (double). Try and get rooms overlooking the marina as the sunrise is gorgeous.

Our room also had a full kitchen and the hotel offered an extensive free breakfast (waffles, scrambled eggs, sausage, yogurt, fruit, oatmeal, baked goods, etc). Between the breakfast and being able to refrigerate and reheat leftovers, we saved a good bit of money feeding 4 kids.

We also stayed at the Hotel Indigo across from TD Garden for part of the trip (we added more people to the group and now needed 2 rooms). This was also a nice hotel that I would stay at again. It has a great central location steps away from North Station so super convenient for the T.

The hotel is clearly in an older building that they have redecorated into a more modern boutique hotel. So it has some quirks, like tiny elevators and squeaky floors, but the furnishings were comfy and the rooms were spacious. The kids were sold when reception gave them each a humongous brownie one afternoon.

We had 2 rooms (not adjoining) at the Hotel Indigo-- a 2 Queen Room that had enough space to put a kid on the floor as well as a King Suite with a separate living area containing a pullout sofa, table, 4 chairs, and a desk. The pullout sofa was small and we had just one kid in it but the room itself was much larger than I was expecting. It became the gathering place for our family group of 7.

Each hotel room had a fridge and coffee maker but no microwave. The hotel does not offer free breakfast, but there is a coffee/ pastry place next door that we frequented.

Other Lodging Options In Boston

Try to stay as close to center of the peninsula as possible, not going farther south than Interstate 90 and not too far across the Charles River. It is worth it to be within walking distance or a short subway ride of the Freedom Trail and the other main sites downtown.

*Some of these links are affiliate links, meaning we may get a commission (super small but every bit helps) but it doesn’t affect the price for you at all. We don’t recommend places based on commissions, only if we have stayed or would stay there with our own families. Full Disclosure Statement.

Where To Eat In Boston

Boston is loaded with good restaurants everywhere you turn and they run the gamut from takeaway counter to fancy dress. You can find a fair amount of tourist traps as well, especially around Faneuil Hall, but even then, I am often surprised by the quality of the meal even if I am wincing at the price. When in doubt, aim for a tavern, especially one that looks like it has been around awhile and has lots of locals.

Here are my specifics from this last trip:

The North End

Much of this area is basically Little Italy and while some of it is clearly for the tourists, it is also the kind of place where you see locals gathering outside the bakery at 9 pm for fresh cannolis. Hanover Street is the main drag through Little Italy but all of the surrounding streets will have places to eat.

Mike’s Pastry is the famous bakery on Hanover but if the line is out the door or you don’t have cash, try Bova’s Bakery just one block away, at the corner of Prince and Salem St. It is open 24 hours a day in case you get a midnight tiramisu craving. Bova’s also takes credit cards if you are like me and never have cash on you.

For an awesome Italian dinner, try Riccardo’s Ristorante, catty corner to the Paul Revere House on North Street. We went there with our family party of 7, including 4 kids, and they made us feel right at home. You can tell it is a family-run place.

Riccardo’s didn’t have a kids menu per se but they offered to make any of the dishes into a smaller portion. We just ordered a bit of everything and shared. It was one of our favorite places on the trip. Open for dinner M-Th, lunch and dinner on Fri-Sun. You might need reservations in summer, but in January, we walked right in on a Saturday night.

Around Faneuil Hall

The Green Dragon Tavern is on the Freedom Trail a few blocks from Faneuil Hall and is one of many taverns lining the quaint cobblestone streets in that area. I have usually avoided these places in the past, thinking they were too touristy, but hungry kids and a warm, cozy interior convinced me to stop on this January trip. And it was great.

Not cheap, but we got the cup of soup which was filling and warm on a cold winter’s day and only $6. The kiddos ordered off the kids menu, which was your typical grilled cheese, pasta, chicken tenders, etc. with drink and fries all in for $8. Throw in a decent selection of New England beers, and we were happy as clams not in chowder.

The kids enjoyed reading about the history of the original Green Dragon Tavern-- the British plans for marching on Lexington and Concord were overheard here. Not sure how accurate that is but it made for interesting reading. The tavern is located on the picturesque cobblestone Marshall Street, just off Hanover Street and by the New England Holocaust Memorial.

* Just up Marshall Street from the Green Dragon is the Boston Stone, a large millstone embedded in the wall of a building and inscribed Boston Stone 1737. Nobody really knows why the stone is there but people have lots of ideas. The most likely is that somebody in the 19th century created it as a phony landmark in imitation of the London Stone to drum up business. The fact that marketing is still just as shady as it has ever been makes me laugh.

There are several historic places right around the Green Dragon that are about the same price, atmosphere, and historic claims. The Bell In Hand Tavern (America’s oldest tavern- 1795) and the Union Oyster House (America’s oldest restaurant- 1826) are probably the two I would choose.

If you don’t care about history or you’re wanting to save some money, then head to Quincy Market (just behind Faneuil Hall). It has an abundance of takeaway stalls in its famous food colonnade. You will find just about anything you want there along with tables in the middle of the market to sit down and eat.

In Charlestown

In this charming neighborhood just a short walk from downtown Boston and home to the Bunker Hill Monument and the USS Constitution, you can find a couple of good choices.

The Warren Tavern is very near Bunker Hill and makes an excellent place to have a meal after you have seen the monument. It was established in 1780 and calls itself Massachusetts oldest tavern, making it older than the Bell in Hand but I am sure that there is some technicality that makes them both right. Anyhow, it was named for Dr. Joseph Warren, the famous Revolutionary leader and doctor, who was killed during the battle of Bunker Hill. It is a cozy place with a low roof and warm interior that was a welcome stop on a windy night.

Prices were pretty typical for a restaurant in Boston, but my fried haddock sandwich was well worth its $15 price tag. They do have a basic kids menu as well, and the place is full of locals, from people watching the game at the bar to families grabbing a bite to eat. It was a wonderful atmosphere.

Warren Tavern can get busy so try and hit off peak dining hours. Luckily in winter, it is a bit less of an issue than in summer. Open for lunch and dinner everyday plus brunch on Sat/Sun. On the corner of Pleasant and Main St; 2 blocks from the Bunker Hill Monument.

* The tavern was also a Freemason Lodge, like so many other historic buildings in Boston, and so was frequented by leading patriots of the time, like Paul Revere, who were all apparently Freemasons. George Washington also came here in 1789 (also a Freemason, just pointing that out as I was unaware just how many of our founding fathers were members).

Blackmoor Bar and Kitchen was super close to the Residence Inn where we were staying, so we ended up eating there twice. Serving New American food in a large modern interior, this place is family friendly and can handle large groups. They had a basic kids menu, a fantastic nacho appetizer that could feed all of us, and an extensive beer list. Two thumbs up. Open for lunch and dinner everyday, plus brunch on Sat/Sun. On the corner of Washington St and Chelsea St by the Charlestown Bridge. Near the USS Constitution.

Brewer’s Fork is also close to the USS Constitution (o.2 miles from the USS Constitution heading north) and has great pizzas as well as sandwiches, small plates, and an extensive craft beer list (and pretty good wine list as well). They don’t have a specific kids menu but are family-friendly. They believe in kids getting to eat adult food and not be relegated to chicken tenders all the time.

*To get back to downtown Boston from Brewer’s Fork or elsewhere in Charlestown, you can either walk across the Charlestown Bridge or you can take the MBTA ferry that leaves from the Charlestown Yard Naval Terminal and takes you to Long Wharf by the New England Aquarium. It is a great way to take a cheap tour of the harbour; $3.70 adults/ kids 11 and under ride free. You can buy tickets at the booth on the pier or use your one day or 7 day pass you got for the T. Ferries are every 15-30 min from 645 am- 815 pm weekdays and 1015 am- 615 pm on Sat/ Sun.

Should You Get An All Inclusive Pass for Multiple Attractions?

That depends on what you intend to do. If you like museums and are one of those people that will want to go inside all the sites on the Freedom Trail plus a few more places, then yes, a pass will probably save you money. The biggest question is whether you think you will see more than one of the pricey attractions in Boston like the Aquarium, Fenway tour, Museum of Science, Children’s Museum, etc. That is where the pass can really save you some cash.

If you just want to do the sites on the Freedom Trail, you do not need a pass or you may want the “Build Your Own Pass” from Go Boston. Most of the sites on the trail don’t cost much anyway, so you won’t make your money back on the more expensive passes. You especially don’t need it for kids.

Keep in mind that some of the included attractions on many of the passes aren’t even an option in winter, like a Red Sox game or a Whale Watching tour. The hop-on-hop-off-trolleys often only operate on the weekends as well. Passes are often discounted in the winter to make up for this, but not enough to make up for it.

* None of the passes include public transportation- you will need a separate CharlieTicket for that.

So think realistically about what you are going to be able to accomplish in the days you are in Boston. The multi- attraction passes are usually $70- $100 and may not cover what you want to see.

We have not found the passes to be useful for us with the exception maybe of the “Build Your Own Pass” from Go Boston. We have not bought that pass though, because then you are then locked into seeing those sites and we have liked the freedom to rearrange things based on weather and what we feel like doing.

There are 2 main passes to choose from:

1) The Boston CityPass

• includes the 4 main attractions in Boston-- 1)New England Aquarium, 2) Museum of Science, 3) Skywalk Observatory (in Back Bay), 4) Harvard Museum of Natural History or a Boston Harbour Cruise.

• Not really applicable for this blog since we did not go to any of those attractions. Price $64 adults/ $54 kids.

2) The Go Boston Pass has 3 options:

• All Inclusive- Pick the number of days you want and go see any of the listed attractions. Expensive, covers way more than you could possibly see, and some things included aren’t open in the winter or are limited. Only good if you intend to spend all your time at high dollar attractions like the Aquarium, Museum of Science, Children’s Museum, Fenway, etc. A 3 day pass is $126/ $85.

• Explorer- Pick a card good for 3, 4, or 5 attractions. Same limitations as the All Inclusive- some included attractions aren’t open in winter, only has good value if you were planning on going to the most expensive attractions. A 4 attraction pass is $98/ $65.

• Build Your Own- The only pass really worth considering if you plan on spending most of your time on the Freedom Trail plus maybe one pricier attraction. Pick as many of the attractions you want from the list to add to your card and save a standard 20% over regular prices. It is a good deal if you have a pretty firm idea of what you want to see.

As you can see from the chart above, we would not have made the All Inclusive pass pay for itself nor saved much had we gotten the Build Your Own pass. If we had gone to the Museum of Science or another museum covered by the Go Boston passes instead of the places we went (like Harvard Art Museums), we would have saved enough to make it worth it.

Here is hoping you enjoy yourself as much in Boston as we did. The kids are already asking for a return trip. We may aim for spring or late fall, or maybe even next winter. I really enjoyed being able to see everything without waiting in line or pushing my way through people as can so often be the case when it gets super crowded in summer. We even got a day nice enough to walk along the Charles River, what more could you want?!

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