East Coast Road Trip: Headed to Boston (Connecticut, Rhode Island, Cape Cod, Plymouth)

PS I have a young, frugal friend who lived in Boston for several years. I have copied an email she sent us right before going. (you may already be halfway done, but just in case). It was invaluable information for us. We loved our trip to Boston!

This may turn into a novela, but doing Boston with littles can be tricky and I want you to have a good experience.

Parking: Honestly, I would recommend budgeting for a parking garage. We sometimes used a free app called Spot Hero to find the best garage prices in the area we wanted to spend time in (if we weren’t taking the T or doing street parking). Street parking is doable, but it can be a PAIN and a time waster- especially if you have limited time. So many streets are resident only, 2 hours only, left side of the street only, etc. and parking spaces are a premium, anyway. With kids, I DEFINITELY recommend having ease and peace of mind by going with a garage. One that we have used several times and is located in a decent-ish spot along the Freedom Trail is in Post Office Square. It’s not right at the beginning of the Trail (which starts at the Boston Common), but it is very close to the Old State House, Faneuil Hall, and Quincy Market. If you want to see Bunker Hill and the USS Constitution (the very end of the Trail), there is a parking garage right across from the Constitution. Those two sites are quite a distance from other things on the trail and don’t have great T access. Also, if you, for some reason, decided to purchase T passes/pay as you go, your kids will ride free.

Boston has several trolley and duck boat tours, if you just want to go that route and have a lot of variables removed. It’s a little pricey, though.

Here’s my recommendation for seeing some things/having fun with littles:
1. Start at the Boston Gardens (right across from the Common). It’s beautiful, there are lots of ducks, usually family-friendly street entertainers, and the swan boats are only a few dollars per person to ride. Kids LOVE it! If your children have ever read “Make Way for Ducklings,” the gardens are where that story is set. There is a brass monument of the ducks that kids like to see/climb on. There is *usually* a decent amount of metered, 2-hour parking around the gardens, which would enable you to do the gardens and even walk over to do some stuff in the Common, if you decide not to do a garage at that point.

2. There is tons of space to run and play in the Common (right across the street from the gardens). There is a playground, street vendors, and it is the beginning of the Trail. There is information (and BATHROOMS) in the visitors center in the Common. The State House (gold dome building), several statues, and Park Street church are all right there, so you get some fun kiddie stuff and some historical sites all in one place. There is also a Burger King and Dunkin Donuts, should you need them, right across from Park Street Church.

3. The Freedom Trail is marked by a red brick path from beginning to end, leading you along the sidewalks so you don’t get lost, so plan to follow the red brick road (path). Immediately beside Park Street is the cemetery where Paul Revere and quite a lot of other historical figures are buried. Tip: sometimes there is a guy who stands at the entrance to the cemetery and hands out folders with TONS of information. He does it as a public service and just asks that you return the folder on the way out. It comes across as crazy at first, but take him up on it! The folders are fascinating.

4. Follow the path from there, cross the street, and you’ll find a slough of Trail sites clustered together, including the site of the first Latin grammar school and old City Hall. Along that strip there are several food places, if you need them. Boloco is a local burrito chain that is a pretty good option for kiddos (and you can fairly easily squeeze a stroller in- not the case everywhere).

5. Several blocks down, you’ll come to the Old State House/ site of the Boston Massacre. It’s a neat spot, but in the MIDDLE of downtown, so keep an eye on everyone.

6. A few blocks from that are Faneuil Hall and Quincy Market. There are usually fun street performers down there that kids love. There are lots of interesting things to read and see inside FH. Sometimes they’ll even have free tours that start from FH. I haven’t done one, so I can’t comment on it. QM has a lot of restaurants inside, but it is often CRAZY in there with very little seating. You can get seafood, if you’re looking for it, but it can get tricky with littles. FH is a great place to buy souvenirs. Also, if you were ever “Cheers” fans, there is a Cheers restaurant/memorabilia site in QM. Also, the weathervane atop FH is in the shape of a grasshopper. Children seem to like that, too.

*Across the street from FH is the outdoor Holocaust Memorial. It’s beautiful and so interesting. It’s free, in a park, and I definitely recommend it.

7. I don’t know how much walking you want to do, but if you keep following the trail for, I don’t know, maybe half a mile (maybe more?), you’ll get to Hanover Street. This is in the Italian district, and you’ll find the Old North Church and Paul Revere’s house. You have to pay to do Paul Revere’s house/museum, fyi. I, personally, love this part of the Trail. It might be my favorite.

8. My personal recommendation is to do lunch at Regina’s (http://www.pizzeriaregina.com/), which is just a few streets over from Hanover and is an interesting walk through the district. I think they open at 11:30, and if you get there when they open, you won’t have too much trouble getting a seat (like most things in Boston, it’s tiny inside). The pizza is fabulous (the margherita pizza is a personal favorite), and it has SO MUCH local color. The employees are VERY Bostonian, and they generally love kids. They may ask you to leave your stroller in the alley right outside. We have with no problem, but you can also take a bike lock, if it gives you peace of mind. There is a *tiny* but clean bathroom. After pizza, I would always take visitors back to Hanover street to get canolis from Mike’s pastries. They are incredible. And just a few blocks down is Old North Church. There are free presentations inside, which are interesting for adults.

9. At this point, the Trail might be losing its hold on littles. It’s a good deal of walking to this point and there is a lot more walking after this point. Not too terribly far is the Boston Tea Party museum, which costs, but might be interesting for y’all. If you prefer to go “off book,” a few blocks away from Hanover Street is the Harbor. In my experience, kiddos really like to look at the boats and walk along the water. There are also a couple of parks (not with playground equipment but with plenty of room to move around safely). We would often take our canolis over there to eat/sit/etc.

10. If you want good seafood/lobster rolls, Yankee Lobster Co. is on the Harbor (it will be a walk), family friendly, and yummy. If you want to drive over, there is parking along the side of the building.

You can definitely continue the rest of the trail after Hanover, but you will walk A LOT. Including over a kind of intense bridge. If you want to do the Constitution and Bunker Hill monument, I recommend driving over to Charlestown and parking in a garage, rather than walking with the kids. Also, you can climb the Bunker Hill monument, which is fun, but exhausting (and not always fun with kids). Charlestown is an interesting little slice of Boston culture, though, and kind of fun to walk around. There’s a guy who sets up his ice cream truck not too far from Bunker Hill and has been selling ice cream for a long time. He knows all the locals, has lots of Boston trivia, and is an interesting guy to listen to.

Tip: take advantage of any bathroom you can (Faneuil Hall, Bunker Hill office) because they aren’t as prevalent as you may think (or establishments will require you to buy something…and will keep the bathroom locked until you do).

I know you didn’t have the time to spend in RI but if you get the chance to go back you have to try some regional favorites. Clam cakes, stuffed quahogs, and Del’s Lemonade. You have to have Del’s with a pretzel rod. And Colt State Park in Bristol is an awesome place to spend the day picnicking, walking, biking etc and I don’t think it cost anything to park. Also, if you drive down Papasquash Point in Bristol to Coggeshall Farm, it is a cool replica of a tenant farm from the 1790s. There is so much history in that tiny little state. I’m biased because I was born there but I’ve lived in 3 New England States and RI is my favorite.

This is, quite possibly the saddest thing I’ve ever heard that you have never had fried dough. We grew up eating it at street fairs and carnivals…have you had funnel cake before? (I think that counts as fried dough.)

My mom says that her mother, who was from Italy, would make fried dough every Saturday for them! I guess they didn’t really know how unhealthy it was back then!