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

Welcome to my 14-day series on our East Coast Road Trip where I share our adventures along the way, how we’re doing this on a budget, honest reviews of attractions & restaurants we visit, and money-saving tips and ideas. If you missed it, read Day 1 here, Day 2 hereDay 3 hereDay 4 hereDay 5 here, Day 6 here, and Day 7 here.

Well, we had planned to get to Boston by late afternoon, but the day didn’t quite pan out like that…

We were just going to drive through Connecticut (our first time to visit the state!), but we stopped to buy a case of water (it’s SO much cheaper to buy water by the case than to buy individual bottles!) and 2 $6 footlongs to split at the Subway in Madison.

(Need an inexpensive but somewhat healthy meal option? We love to split footlongs — especially whatever is the special of the day priced at just $6 per footlong.)

We wanted to eat outside, but there was no place to eat outside at the rest stop. So we drove to the sign that said Hammonasset State Park and were going to pull in and eat at a picnic table there. Only it was $22 to park in the park — which we didn’t want to pay (of course!) since we were just planning to make it a quick 20-minute stop to eat our lunch!!

We found a nearby (free!) parking spot at the Shoreline Trail. There were signs about the beach and I just couldn’t really bear the thought that we were so close to a beach and couldn’t see it because of the trees. (If you know me well, you know that the beach is my happy place!)

I figured the beach must be super close so I asked Jesse if I could take the Shoreline Trail for a bit and go find it. Kaitlynn wanted to come with me. So off we went!

And I’m so glad we did — even if it ended up being a much longer walk than we had anticipated, because the beach was absolutely gorgeous!!! And the weather was perfect.

I called Jesse (who was still back at the trail head with Kathrynne and Silas) and was like, “I know we were only planning to stay here for 20 minutes, but this beach is AMAZING! Is there any way that you could walk here and meet us? I don’t think you’ll regret it!”


Always one for adventure, he walked to meet us at the beach and we all had fun playing in the water (well, as much as the kids could since they didn’t want to get completely drenched!) and just enjoying the beautiful view!

So much for the 20 minute pit stop! We were probably there at least an hour and half! But it was worth it!

We then drove on through Rhode Island (our first time to be there!) and made it to Massachusetts (another new state for us!) We stopped at Cape Cod for a short while (it was beautiful!) and then headed to Plymouth.

Plymouth was quite the hopping place, which somewhat surprised us — especially since it was past 8 pm on a Saturday evening. We got dinner at a total tourist-y place (Pebbles Restaurant) because it was the only place close and we were so hungry! But it ended up being great food and I got to try Fried Dough for the first time (yum!!)

We pulled into our hotel in Boston only to discover Jesse had booked it for the wrong night on accident and they were sold out. So 11 pm found us sitting in our car searching online for a hotel in a good area that was a good rate that didn’t charge $40 for parking! We finally found one and crashed there around midnight!

Have you been to Connecticut or Rhode Island before? Any suggestions for the best free or inexpensive places to visit there?

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  • Beth says:

    The east coast is great! Have fun! I like reading your thoughts on travel!

  • Heidi Leasure says:

    You are in Massachusetts on Friday, there are free for cultural type events every Friday for the summer. I am sure there will be something in the east coast of Massachusetts that would be close. You can check their website Highland Street Foundation. It is called free fun Fridays

  • JoDi says:

    I have no ides what it costs now, but Mystic Seaport in Ct is a great place to visit. Your kids would love it!

  • Lisa says:

    Rhode Island is so much more than a “drive through” state. There’s so much to see and do. It’s so much more than a “connection” between two states.

    • Yes! We wanted to stop and spend time there, but we ended up not having time on this trip. We hope to go back and have more time in the future! But we went ahead and drove through it so that at least we could say we’ve been there (sort of!) now! 😉

  • Jeanine says:

    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!

    • I have had funnel cakes, but I’ve never heard of just taking a big flat piece of dough and frying it like they did! I honestly had no idea what “Fried Dough” was going to be; I just ordered it because I guessed that it was something I needed to try! 🙂

    • Maryalene says:

      So is fried dough essentially the same as an elephant ear or something else?

  • Sami says:

    While in Boston go and visit the Holocaust Memorial. It’s truly beautiful, hauntingly so, but gorgeous and it would be quite the lesson for your kiddos.

  • Kelly says:

    Madison, CT is my home town! Glad you enjoyed “Hammo”. There’s nothing like Madison in the summertime.

    I live in San Francisco now, but brought my brood to CT the same week you were there for a family reunion & feel in love with it all over again. We spent time in Branford, which is only 2 towns away from Madison but I’d never spent time on the shoreline there. It was amazing. We took a boat tour around the gorgeous Thimble Islands.

    Enjoy the rest of your epic trip!

    • I really, really want to go back and spend more time there! I’m so glad we spontaneously decided to stop there!

      • Libby says:

        And I live in the town next to Madison! So you’ve discovered Shoreline CT!

        More things to love & visit next time you are in CT: Mark Twain’s House, go onto a REAL submarine at Sub Museum in Groton, Mystic Seaport – a living museum of an 1800’s whaling village, the Mashantucket Pequot museum is fascinating with a life size recreated Native American village also a great exhibit on how people hunted in CT during the ice age, almost every town has at least one historical house museum, the museums at Yale are free.

  • Courtney says:

    Hi – I’m a local. Double back to Providence for Saturday night. It’s Waterfire, a wonderful free event with a street fair. Easy drive or only about 45 m-50 min by train.

    Hard to describe but definitely an RI classic and unique civic experience. You won’t regret checking it out.

    Train schedule, ~$20 round trip. Not sure if there are kid discounts.

  • Kat says:

    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.

    • Thank you SO much for these suggestions! We definitely want to go back in the future!

    • Libby says:

      Even though I’m a nutmegger, I think RI swamp yankees have the best beaches in New England – warm-enough water for swimming and miles of sand. Check out East Beach at Watch Hill in Westerly. Beach is free but parking costs. GREAT boogie boarding

  • Margaret says:

    Dont know if you are anywhere in the area but when we visited boston and maine two summers ago, we happened accidentally upon the hammond museum (a huge castle/house) in gloucester. It was one of the highlights of all our trips. We loved it! Lots of secret passages, drawbridge, and cool stuff. And the designer was an inventor. Fabulous grounds too. It was relatively inexpensive to visit and worth every penny! I highly recommend you google it and go if you are within an hour. It is a maritime town too so interesting other things as well.

  • MArgaret says:

    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 (, 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).

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