Dylan in the Details is a travel interested in culture, history, and giving you the best recommendations for your next trip!

Road Trip Route: Connecticut Highlights

Road Trip Route: Connecticut Highlights

Even though I logically know how small of a state Connecticut is, it still amazes me that you can drive across the entire state in around two hours. While some may take this as a sign of Connecticut’s inevitable lack of interesting sites, I see it as a level of accessibility that allows a traveler infinite options. If planned correctly, this geography can only work in your favor and allow you the flexibility to see more of the state. That all being said, depending on what you like, there may not be a ton of must-see things for you in Connecticut. I think the weekend was more than enough time for me. However, that doesn’t mean there aren’t worthwhile sites hiding in the Nutmeg State.

Day 1

Philadelphia, PA to Rocky Hill, CT

While Google Maps saying this drive should only take around four and half hours, do not be fooled. Any route from the Philly area up North usually takes us somewhere near New York City and that inevitably adds at least another thirty minutes, if not more. If you have a schedule to keep, make sure to pad your time accordingly.

Dinosaur State Park - Rocky Hill, CT

I don’t think it’s a stretch to say that the absolute coolest thing in Connecticut is Dinosaur State Park. While it is small (as many TripAdvisor reviews note), there is nothing like seeing dinosaur remnants in real life. Whether fossils or bones or footprints, I feel like an awe-struck kid every time. (A feeling which was probably helped by the fact that we played the ‘Jurassic Park’ theme song in the parking lot.) This stop will probably take less than an hour (maybe more if you have kids or want to watch the introductory video), but it’s worth the effort. The main exhibit is simply the slab with the footprints, but there are some explanatory panels and interactive spaces. If nothing else, these are the types of museums where I never mind paying admission – small, but unique and worth supporting.

Trying mimic the T-Rex behind me, I'm not sure it worked...

Trying mimic the T-Rex behind me, I'm not sure it worked...

Rocky, Hill, CT to Middletown, CT

Going from Rocky Hill to Middletown after driving from PA is, admittedly, a little bit of backtracking, but we wanted to make sure that we had plenty of time to visit our priority, which was Dinosaur National Park. Also, the nice thing aboutt CT, is that backtracking really only means about fifteen minutes or so.

Wild Bill's Nostalgia - Middletown, CT

I'm not sure there is truly a way to describe Wild Bill's without experiencing it. It is an eclectic store full of new stuff, old stuff, strange stuff, and some stuff that is obviously junk. There is also art and buildings and some strange aesthetic sculptural choices on the land surrounding the store. Worth a quick stop just to witness the oddities. (Note: While nobody bothered us or talked about politics, there was a fair amount of Trump paraphernalia adorning the shelves.)

The buildings behind Bill's

The buildings behind Bill's

Middletown, CT to Union, CT

Union is as far north in Connecticut as you can go before crossing the border into Massachusetts. Depending on where you’re coming from, it may seem like a bit of a drive, but even from Rocky Hill/Middletown, which are right around the middle of the state, it's only an hour or so.

Traveler Restaurant - Union, CT

Trust me, the Traveler Restaurant is worth the drive up north. I was originally drawn to the place by the advertised promise of three free books with every meal. Regardless of the food quality, I knew that the bibliophile in me needed that experience. However, the food quality lived up to the book excitement. Sitting 'near the birds’ (by the window that faced the birdfeeder), we had onion rings that actually stayed in their batter (as opposed to the frustrating bite full of onion and then an empty batter shell) and great buffalo chicken tenders. The relaxed atmosphere worked for both the couple behind us, who seemed to be regulars, and the daughters with their mom who stopped off the highway for a quick root beer float. And yes, I did get my three books.

(If you’re already in Union and like beer, you’re only about fifteen minutes from Rapscallion Brewing and Homefield Brewing in Sturbridge, MA and about thirty minutes from Tree House Brewing in Monson, MA. Both of which are absolutely worth the detour.)

Union, CT to Hartford, CT

While our ultimate destination the next day was New Haven, we ultimately decided to stay over in Hartford. It gave us an excuse to see another part of CT and we didn't have to drive the length of the state from Union to New Haven after a full day. It is just under an hour to get from Union to Hartford.

The Goodwin Hotel - Hartford, CT

The Goodwin is a boutique hotel in downtown Hartford. While the breakfast is great, the parking situation is a little tenuous. We ended up street parking, however, I do think there is a valet option. More than anything else, learn from our mistake, and don't set your GPS to take you to the Goodwin Apartments in West Hartford. (Yes apparently West Hartford and Hartford proper are two distinctly different places.) Shout-out to the girl who walked into the lobby only to find us trying to figure out how to get the door open. Thankfully she cleared up our confusion while also being visibly suspicious of us.

Day 2

Hartford, CT

As a bonus, if you’re interested in obscure presidential statues, there are two worth seeing in Connecticut. (Just me who is interested in weird presidential stops? Ok cool…) One is a statue of Jack, the first turkey to receive a presidential pardon from good ol’ Abe Lincoln. He is located a short walk from the parking lot in Riverside Park in Hartford. This is worth a look if for no other reason that the novelty of a statue dedicated to a turkey. If that isn't enough to convince you, the park is quiet and beautiful as well.


 Hartford, CT to New Haven, CT

The drive from Hartford to New Haven only takes about forty minutes, but extending it by a half hour or so will afford you the chance to see the Gilmore Girls highlights that Connecticut has to offer. See my other post dedicated to the getting the Gilmore experience.

Claire's Corner Copia - New Haven, CT

As we were headed to an event at the Cooperative Arts and Humanities High School in downtown New Haven, it made sense to park once and find a place to eat nearby. We probably picked the busiest place on the entire block, but Claire's was worth the wait. Interesting food pairings plus a great selection of ice drinks and smoothies. I love a good restaurant that has a sense of social responsibility and flexible options.

RJ Julia's Cecile Richards Event - New Haven, CT

While we did not get to actually visit the store, this staple of the CT independent book scene put on a great event. We planned this whole trip around going to Cecile Richards' book signing and it did not disappoint. The staff from RJ Julia's were so kind and gave everyone space to chat and take pictures after the event. I am so grateful to them and, obviously Cecile herself, for a great event. There was no question that it was worth the drive. And, yes, I'm going to brag with a picture of Cecile and I.


Amistad Memorial - New Haven, CT

After meeting Cecile, we had to stop at the other presidential memorial in CT. It is a memorial to the bravery of those slaves who rose up on the Amistad and were successfully defended by (then former) president John Quincy Adams. A beautiful three-sided piece focused on the story of the brave passengers is tucked next to New Haven’s City Hall building. JQA is my favorite president, so we couldn't leave without stopping by.


After that we headed back to face the NYC traffic and, finally, get home. Happy Adventuring!

Stories from the Road: Ford Presidential Museum - Grand Rapids, Michigan (May 25, 2018)

Stories from the Road: Ford Presidential Museum - Grand Rapids, Michigan (May 25, 2018)

My Favorite Things: Gilmore Girls Sites in Connecticut

My Favorite Things: Gilmore Girls Sites in Connecticut