New England Road Trip

One of my friends that came on the Boston trip (hi, Allison!) has a goal to see all the US states by a certain year. She also has a more realistic goal of seeing the continental states first. She had quite a few New England states to check off of her list, and since we were already going to Boston, she mentioned that she would stay an extra day or two and go on a little mini road trip, and anyone was welcome to join her. So I thought “I have some PTO to burn and I want to see those states, too…. ok I’m in!!!”

So we started making plans on where we wanted to go, what we wanted to see, and making sure that logistically we could fit in visits to Connecticut, Rhode Island, Maine, New Hampshire, and Vermont before we had to be back at the airport in Boston. I did a lot of Google-mapping and making timelines and figuring out where to go, and before too long our New England road trip was all planned!


We got up EARLY to hug and say goodbye to one of our friends who was heading to the airport for an early flight, and then the remaining 3 ladies took an Uber to get to one of the girl’s car (she lives in New York so she drove to Boston). We got in her car and started driving toward Hartford, CT! Once we got to Hartford, Allison and I got our rental car and then we all drove to Washington Depot. If that name sound familiar at all, it’s probably because that’s the adorable little town that was the inspiration for Stars Hollow from Gilmore Girls! Yes – we sure did drive all the way to western Connecticut just to do some Gilmore Girls fan-girling!

We ate at the cutest little cafe, Marty’s, we went into a little bookshop, we stopped in the cute market (and Allison re-enacted when Rory stole some corn starch but SHE DID NOT STEAL IT it went safely back on the shelf!!), and we stopped in a little boutique and talked to the owners who were ALL about Gilmore Girls tourists!

We also stopped in the next town over which also has some Gilmore Girls claims – they have a gazebo!!! So obviously we had to stop and take some pictures with it! We listened to a lot of Sam Phillips while driving around (featured heavily on the show) and it just all felt so magical!

After getting our fill on Gilmore Girls, we said goodbye to our friend – she headed back to New York, and Allison and I got in our car and headed toward Rhode Island. By the time we got to the state we were both getting kind of tired, so we just made a quick pit stop across the border (at a Walgreens – it counts!!!) before heading back to our AirBnb where we ordered takeout for a late dinner (it was pouring rain) and stayed in for a cozy night.


This was an EARLY day for us – we were in the car and out the door by 6am!! We were on a tight schedule since we had to get to the airport by 3:30pm to turn in our rental car, and we didn’t want to push it by sleeping in too late.

Our first stop was the Nubble Lighthouse in York, Maine. It’s one of the most iconic lighthouses in the country and it also just so happens to be on the very southern tip of the state – so convenient for two gals on a schedule! We also got some bagels while in town (delicious) and made a fun new friend (we named him Sergio and he loved our warm car.)

Our next destination was New Hampshire. Literally anywhere in New Hampshire. As we were on the road, I saw that we would go right by the state capital, so we decided to stop and look at their gold-topped capitol building. And I’m so glad we did! Not only was it very pretty, BUT they have a liberty bell replica out front! How fun and random is that?!?

Our final state on the road trip was Vermont. We stopped in Brattleboro (right on the border) and walked around a bookstore before eating lunch at a little country store just south in Guilford. At this point in the trip, we were both kind of tired and growing tired of the rain, but SO happy that we got ALL of the states in!

The only thing left on our journey was to get back to the airport to turn in our rental car, which we did with a few minutes to spare! It was such a fun little trip and we saw so many gorgeous leaves while driving through New England! Allison and I have taken a lot of road trips together over the years (I think the longest was from Missouri to Virginia Beach) and we have a good rhythm in the car, and so it was nice to have such a great road trip buddy to drive around with!

One thought on “New England Road Trip

  1. Pingback: 73 Questions | My Name Is Not Katie

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