Baby Steps through Boston

Sample Itinerary:
Day 1: Boston – visit the downtown area, strolling through Boston Public Gardens, Boston Commons and Beacon Hill before walking to Quincy Market and Faneuil Hall for lunch then check out the Boston Tea Party Museum, Children’s Museum or the New England Aquarium before finishing the day in Boston’s North End for a delicious Italian dinner.
Day 2: Boston – Spend the morning in Brookline enjoying local cafes before checking out the Isabella Stewart Gardner Museum and/or the Museum of Fine Arts then enjoy walking through the neighbouring park on your way to the Boston Public Library for mid-afternoon tea time and end the day by taking a sunset cruise along the Charles River.
Day 3: Amherst – Amherst is a cute place to stroll: start in the town’s core and also visit the campuses (especially Amherst College). There are also interesting museums to explore like the Emily Dickinson Museum and the Yiddish Book Center.
Day 4: Northampton & Amherst – Take a morning trip to Northampton where you can wander Thorne's Marketplace and Smith College campus before grabbing lunch at Familiars (a converted rail car turned restaurant). Spend the afternoon in Amherst checking out areas or museums you haven’t yet seen.
Day 5: Cambridge - You could spend days visiting the different museums that dot Harvard’s campus like the Museum of Natural History, so I’d suggest one day in and around Harvard’s campus and Harvard Square. Enjoy dinner at Harvest or Alden & Harlow.
Day 6: Cambridge – Some people only spend time at Harvard but it’s also worth exploring areas like Porter Square and maybe even checking out a movie or show at the 100+ year old Somerville Theatre. For treats, you can’t go wrong with a chain like Tatte or L.A.Burdick but there are a lot of delicious, local places as well like Formaggio Kitchen or Honeycomb Creamery. For a great meal make sure to visit Giulia, Season to Taste or Barcelona (all three are beside each other).

Overall Tips for Travel with a Baby:
- Let the airline know in advance if you’re bringing a lap infant (and confirm that travel is free because some destinations and airlines will charge tax for them, e.g., cross-border flights) or make sure you purchase a ticket for your baby if you want to take them in a car seat on the plane
- Write out your packing list in advance and travel with as few bags as possible - check whatever you can, e.g., gate check the stroller, check the pack n play in a large suitcase with extra diapers, wipes, clothes, bibs, etc. and check a suitcase with your own items
- Carry back ups, e.g., change of clothes for you and baby in case of blow out, delayed flight or lost luggage
- Feed your baby during take off and/or landing by breastfeeding or bottle feeding, if possible, so that the pressure is lessened for their little ears. If not, try to bring a pacifier or teethers so that they have something to suck on
- Try to play with your baby as much as possible before the flight so they’re more likely to nap on it
- Before you fly, consider what you use on a daily basis and whether some of those items will be available when you arrive vs. what to bring with you (note that there are baby item rental services in many places) e.g., determine whether you’ll need a stroller or prefer to just use a baby carrier and if you’ll take your car seat or just rent one with a rental car etc.
- Don’t expect travel to be like it was before the baby – plan for fewer activities each day, make space for nap times, and consider accessibility
- Bring some entertainment, e.g., a couple of teethers, painter’s tape, books and small toys
- Always make sure you have the hygienic items and medications you might need, e.g., face and hand wipes, diaper rash cream etc.

Where to Stay:
Boston & Cambridge: Boston Marriott (Long Wharf or Copley Place)
Amherst & Northampton: Inn on Boltwood (in Amherst) or one of the chains like Comfort Inn etc.

Where to Eat:
Great "chains": L.A. Burdick, Tatte, Bueno y Sano
Boston: Boston Sail Loft (seafood), Mike’s Pastry (Italian)
Cambridge: Giulia (Italian), Barcelona (Spanish), Harvest (local American), Alden & Harlow (local American), Formaggio (deluxe grocery store), Honeycomb Creamery (ice cream), Yume Ga Arukara (Japanese)
Amherst: Antonio’s Pizza (Italian)
Northampton: Familiars (café snack foods)

My Travel Diary
This trip was special for me because it was the first time I was flying, or going anywhere more than a couple hours from home, with my baby daughter. This was my first trip as a mother. It required a lot more planning than usual and was also a lot more rewarding because I could experience all these places through my daughter’s reactions too. Initially, my nervousness was centered on how she’d fly because I, like most people, have experienced the incessant shrieking of a baby becoming the soundtrack of an entire flight. And I don’t fault babies for being upset. A plane is an overwhelming setting: you’re surrounded by strangers, flying high in the air, met with loud noises, and worst of all for babies, your ears are popping uncomfortably for much of it. That’s why we timed our first flight early in the morning so that it would align with her first feed of the day. She drank on the way up, played with us for a bit and then napped on me. I hadn’t expected her to be comfortable napping on me because she was already 6 months, past the point of the newborn nap-anywhere phase. But she was adaptable everywhere we went – she napped on us, in her stroller, in the car, and in the pack ‘n play we brought for her to sleep in. It was a good lesson to be prepared for the worst, but pleasantly surprised when the baby is more flexible than you expected.

Over the course of a six-day trip, we spent time in three towns and two cities – staying overnight at two different places. The baby only had one rough night and I too had a lot of difficulty sleeping that night. When you’re used to living in a city, it can be jarring to be met with the silence and darkness of the country. By the second night, I embraced the tranquility and slept like a (sound asleep) baby. Our time in more rural areas of Massachusetts was spent predominantly in Amherst, but we also briefly visited both Concord and Northampton. Massachusetts is known as a state that values higher education, home to some reputable institutions like Harvard and the Massachusetts Institute of Technology. As if we were scouting out future universities for our baby, we toured multiple campuses in both the cities and country, noting their facilities (UMass Amherst was impressive), views (Amherst College won, hands down - see photo below!) and even the sporting aptitude of students (Harvard came in last, unsurprisingly). I have friends who seek out the same sites when they travel, like visiting local cinemas, for example, and I could understand the appeal of seeking out university campuses when traveling. It’s interesting to see how they are organized because it’s indicative of what they prioritize. Smith College in Northampton, a private liberal arts women’s college, felt like an apt representation of the town – peaceful and creative. That said, everyone was too well dressed and as we walked through Northampton’s Thorne’s Marketplace, I kept thinking that this town was too condescendingly cool for me.

Everywhere we went had an air of old juxtaposed with new. In Northampton we ate outside an early 20th century converted railcar, now a delicious modern café. In Boston, we walked down cobblestone streets from centuries ago to get to a restaurant built in the last few decades. And in a different sense, navigating all these places felt fresh despite my having visited both Boston and Cambridge before and that’s because I was seeing the world through my baby’s eyes. Traveling with my daughter was such a rich experience because everything was a first for her. Boston is on the Atlantic Ocean, so she got to see that body of water for the first time. My sister has a puppy, so she got to spend quality time with a dog for the first time. She had never visited any of the sites we saw in Massachusetts and although she’s too young to truly engage with them, she’s observant enough to enjoy being in those places. It brought her dad and I a lot of joy watching her live through all of these firsts. Most of our time was spent in Cambridge and although I’ve visited it a few times before, I previously always felt like the only thing to really do was spend time at Harvard’s campus. I was being elitist without even being a part of the elite! This time, my sister showed me how flawed that approach was. Cambridge (and Somerville) has a number of nice communal areas to stroll through, including large parks like Danehy Park, which is perfect to visit with dogs or kids, and gathering places like Porter Square and Davis Square, which are surrounded by delicious eateries. Despite eating some great meals like at Giulia, I was very disappointed with the café drinks. Everywhere we went, I tried to get a drink but never found anything flavorful. It’s unclear whether the issue is Boston beverages being bland or pregnancy irrevocably altering my taste buds.

My favourite meal of the trip (not including my sister’s cooking) was hands down at Giulia in Cambridge. It’s a small Italian restaurant where an entrée will run you about $30. My sister and her partner were kind enough to babysit our daughter one night so that we could get a date night, which happens very infrequently in Chicago (unfortunately). We decided to go somewhere nicer, so out of fear of fancy meaning insubstantial my husband decided on route to go for a pre-dinner dinner and we stopped at a ramen place called Yume Ga Arukara in Lesley University’s Porter Campus. He had heard great things. It didn’t entirely disappoint. We decided to get takeout because the place is just so tiny (it’s in a small food court), but that meant that he had to eat ramen on a bench outside in the cold. It’s likely the way in which he ate which detracted from the meal more than the food itself. By the time we sat down to eat at Giulia I was starving, and he was semi-full. We still managed to share fresh focaccia and two pasta dishes. Mine was better, as usual. Somehow, he always ends up liking whatever I order more than his own meal – it’s a talent I’ve honed over the years. I really enjoyed our time in Cambridge because it feels like home. It’s full of families and dogs and very safe for both visitors and residents. Living in Chicago I have to be hyper vigilant at all times, but in Cambridge I could relax more. It’s not an exaggeration to say that the majority of people we passed one day were either with child or dog and would actually smile at you or even sometimes share a greeting. One of the more bizarre interactions was while walking past a local grocer where we saw a very young child wandering alone. The grocer came out and tried asking the little boy questions, but to no avail. My sister and I stayed with the grocer and child trying to brainstorm what to do until finally a very frazzled man showed up on a bike and started screaming at the child. He hurriedly thanked the three of us for watching his son, muttered something about his daughter and took off on the bike with his boy in tow. We watched them bike down the street, still hearing distant yelling until the dad abruptly stopped his bike beside an older girl. Judging by then body language, we surmised that the older sister had been entrusted to start walking her younger brother to school and that the dad would catch up on his bike. Instead, she must have decided she wanted to ditch her annoying mini-me, so she left him to fend for himself at the grocery store. No wonder the dad was distraught.

We spent most of our time walking so we covered a great deal of Cambridge and Somerville, including, of course, the Harvard campus. It really is very beautiful, and the museums are fantastic so in my mind it still is the top destination in Cambridge, but I now acknowledge that there’s much more to see too. This trip involved very little time in Boston proper. We went in the Saturday before St Patrick’s day to see the main tourist sites that I really like, including Quincy Market and Fanueil Hall. Both were built built in the 18th century and it felt a bit like a time warp watching so many people of all ages getting drunk there before noon. Then again, I know nothing of drinking culture in 2024 so maybe 10 am is the new shot o’ clock. We didn’t partake in festivities ourselves, but I enjoyed seeing the sea of green. There’s nothing like travel on a holiday: the excitement is palpable, and the congestion is unbeatable. By some miracle, we were able to find parking right near Boston Common and walk everywhere. Parking may be the one thing in Boston that’s actually affordable because living there comes with a huge price tag from the cost of housing to the cost of food. In any case, Boston Public Garden and Boston Common are wonderful areas to stroll or even picnic. They’re great for some classic Boston photoshoots too. We took photos in front of the foot bridge and as everyone rushed off toward Beacon Hill, I managed to snap a shot of the iconic ducklings statue. Besides the statue being adorable, I appreciate that each time I’ve visited someone has clothed them in something new! They’re very stylish little statues.

I made sure to dress the baby in some classic New England styles like a collared shirt and wool sweaters. You never know when a surprise country club invite may appear. Her look elicited many compliments from locals, and I felt like a successful stylist. One thing to keep in mind, especially when traveling over a holiday, is that Boston’s sidewalks are extremely narrow and there are many local people trying to go about their day while trying to pass the stagnant tourists taking selfies. This can lead to some awkward traffic jams, which are usually exacerbated by a giant stroller trying to either park or push through. Be aware that walking in some areas of Boston and Cambridge may be easier to navigate while wearing the baby instead of letting her carriage dominate the path (which is what our baby did). In the Beacon Hill area, you’ll find picturesque streets and houses, but also very cute little stores like the nut one in the photo below. I really liked Beacon Hill Chocolates and could have happily spent more time taste testing there if not for everyone else’s desire to find a washroom (use the nearby hotel!). Speaking of hotels, Marriott Long Wharf has a wonderful lobby in case you’re walking around the harbourfront area and in need of an indoor break. In our case, we got takeout from Boston Sail Loft, the wait would have been hours otherwise, and then suddenly the temperature dipped, and we were frantically looking for somewhere to eat indoors when the Marriott occurred to us. In Boston, like in Chicago or Toronto, it’s important to be aware that weather can change on a dime so you should leave your accommodations prepared for at least one season. I’ve visited Boston in summer, fall, and winter and I can confidently say that there’s enough entertainment to keep you occupied in each season. We were lucky on this trip because although it was March, we were able to spend a considerable amount of time outdoors. On my next trip to Boston, I’d like to visit in the spring and do a harbour walk that includes multiple stops at restaurants and cafes in the North End, an area known for its delicious (and adorable) Italian eateries.

Apart from the meal at Giulia, the next best food was in rural Massachusetts. In Amherst in particular, I was pleasantly surprised by how delicious the pizza was from a small place called Antonio’s. Apparently, Harrison Ford used to frequent it on his trips to visit his kid at Amherst College - I can’t speak for his movies, but he clearly has good taste in food. Northampton, the other town we spent most of our time in, has also attracted celebrities in the past – not for its food, but for its culture. Apparently, it has a vibrant music culture, which used to bring in famous performers. Judging based on the murals (two shown below), ornate buildings, and prevalence of bookstores, it still seems to have a thriving arts scene. We visited multiple bookstores and art galleries while in town, but the highlight was a flavorful lunch on the patio of a converted railcar turnd café called Familiars. We tried to make an effort to eat at small local eateries everywhere we went because that fit with the spirit of these towns. It’s always encouraging traveling to smaller cities and towns that have been thriving and innovating, rather than being taken over by box stores or left to crumble. To me, it felt like towns in Massachusetts and North Carolina are great examples of how successful small towns can be when there’s investment in local culture.

Amherst and Northampton may be small, but they have numerous, sizeable college campuses. The presence of Smith College lends an air of prestige to Northampton as it’s part of the small group of famous, historic women’s colleges in the Northeast known as “the Seven Sisters”. Amherst has also played host to very prestigious figures including Nelson Mandela to whom they bestowed an honorary doctorate in 2005. Globally he’s had a massive impact, but locally he’s also left a legacy that includes the inclusion of scholars from South Africa to Massachusetts, building bridges and advancing academia. For me, Amherst was most appealing because of our local connection. We were able to stay with extended family on a large rural property. There was livestock across the street, down the street, and seemingly everywhere! I don't think they were as amoosed by us as we were by them though (photographic evidence presented below). We don’t get the chance to eat many sit-down meals together in the city because of my husband’s work schedule so I really appreciated being home with my sister and her in-laws, sitting around and chatting about nothing and everything while enjoying delicious food. Luckily for us, my sister happens to be a great cook. She’s also a curious person and an academic, so I’m always open to her recommendations for things to do and places to see when traveling. In Amherst, she was adamant that we visit the Yiddish Book Center. She also highly recommended the Emily Dickinson House Museum, but unfortunately, we only had time for one.

Amherst is not known for having many Jewish people; however, it houses the only Yiddish “museum” in the country (and arguably in the world). We spent a couple of hours there exploring the exhibits and feeding the baby. Although there’s not a large lounge, there is a comfortable entrance area with a couple of couches where my husband could tend to the baby while I explored. I found it fascinating listening to the Yiddish music, seeing the collection of postcards from different Jewish neighbourhoods prior to the Holocaust and learning about the history and cultures connected with the Yiddish language. There’s also a small gift shop, which sells items like onesies that say “my little matzah ball” and Jewish trivia games. It’s a nostalgic place to visit despite never having learned Yiddish.

One of the more surprising sights we saw on our trip was during a brief stop in Concord. It should be noted that once you leave Boston on your way to Amherst there aren’t rest stops like what you would experience in southern Ontario (Canada), for example. With a baby you have to expect to stop at least once every two to three hours because she needs to be taken out of her car seat and may get antsy or hungry. In our case, we hadn’t timed our drive very well and almost immediately after leaving Cambridge she wanted to eat, so we stopped in Concord which was basically the only place to stop on route to Amherst. It worked out well because it’s a lovely little town with nice parks, cafés, and pretty, historic buildings. I didn’t expect to see much about international conflict in rural Massachusetts, so I was caught off guard when, while wandering, we came across a memorial to the thousand plus Israeli victims of Hamas on October 7, 2023. It looked to be created on someone’s private property, but along a busier area in town such that it was highly visible. They had planted an Israeli flag for each person murdered. There was no commentary about the political situation apart from one larger sign (pictured below), whereas once back in Cambridge, I noticed the visible political statements – particularly in the form of posters. Around town the messaging was explicitly anti-Israel.

Harvard has been in the news a lot in the past year, so I was anticipating some protests or loud gatherings while visiting its campus; however, it was quiet. This was probably attributable to us visiting during spring break, which I highly recommend. There were still open museums, cafes, and restaurants but without the throngs of academics everywhere. Whenever you visit a new city or town it’s so helpful to look into both the local culture and the local calendar! I learned my lesson when I haphazardly visited Hong Kong and Macau during a Chinese national holiday without realizing so many Chinese tourists from the mainland would be descending on both popular destinations. St Patrick’s day in Boston, although popular, was extremely manageable and even the flights were fine because we still had an empty seat for the baby both ways (without paying!) and I appreciated that it coincided with spring break.

Traveling with a baby makes you more aware of your surroundings and focus more on logistics. You can’t travel as casually, you have to plan for as much as possible, but you also need to accept how much is outside of your control. We really appreciated how much nature we could explore and how safe we felt everywhere in Massachusetts; however, accessibility is a barrier there from the narrow sidewalks to cobblestone streets to lack of ramps and automatic doors. That said, we managed just fine even with a stroller and probably would have felt it less were we baby-wearing. This trip made me realize that you don’t have to limit your destinations, but rather make accommodations for what’s feasible wherever you travel.