Nicole and I have been best friends for years, and we’ve decided to take this friendship on the road. Together we have several traditions: trading The Book of Everything that chronicles our adventures since we were 16, throwing a piece of paper with a Spanish tongue twister on it at each other since we were 15, watching Marvel and Disney movies, going to a new amusement park every year, and now an annual road trip to take us somewhere new. This is our second road trip together, and it has an added challenge. Now that we’re 21, we’ve decided to undertake the 50 State Drink Challenge. In every state we go to (including Canadian provinces), we must find a local bar and order the most iconic drink of that state. The map that we’re following is at the end of the blog for reference. So yes, if you picked up on it, Nicole and I fully intend on traveling to all 50 states and 10 Canadian provinces together, meaning that our future is filled with many more road trips and blog post recaps.

This is The Nicole & Sydney Road Trip Chronicles: New England & Canada

Also check out The Nicole & Sydney Road Trip Chronicles: North Carolina & Virginia!

Day 1: We left Arlington in the late morning and hit the road. The drive through Virginia and Maryland was quick and easy, and once we hit Pennsylvania we were smooth sailing. In between bursts of storms we could see green hilltops, rolling clouds, and curving roads. I couldn’t even count the amount of times we said “I love Pennsylvania.” By the time we reached the Pittsburgh Zoo, it was sunny and warm. Without checking the weather, we hopped out of the car and walked into the zoo with no rain covers for ourselves or my camera. We spent over an hour checking out the animals and exhibits, and spent the most time with baby elephants and 12 week old baby clouded leopards. By the time we were going towards the aquarium, it was getting very dark and overcast, and before we could comprehend what was happening, the sky unleashed upon us. We sprinted to the aquarium and watched in despair through the windows to see the heaviest storm of the day trapping us inside. With a fifteen minute gap in the rain some time later, we ran for the exit and got in our car right as the rain came back. Filled with adrenaline, we drove to Pittsburgh. We got dinner in the city, had our Pennsylvania Yuengling, and met up with my Hellfish friend Pichael for milkshakes and a walk to Point Park. We drove up to Mount Washington to see the cityscape at night, but the cold and mist made the stop short. That night, we crashed on Pichael’s couches to the sweet smell of the brownies his mother made for us.

Day 2: We left early in the morning and headed straight for Kane, Pennsylvania. If you read my Family Road Trip series, particularly Part 3, you would recognize this 8th Man-Made Wonder of the World! I absolutely loved the Kinzua Sky Bridge when I went a few years ago with my family, so we made sure to stop by! The trip was made even better by the people scared of heights, glaring at us as we rolled around on the glass bottom at the end of the bridge, with a few hundred feet drop below us.

We said good bye to Kane and drove straight to Niagara. You’ll recognize the Cave of the Winds from my Family Road Trip Part 2, which is a MUST DO every time you go to see the falls. We were absolutely soaked by the end, but it was the most fun we had that day. After soaking up the falls as much as we could, we escaped and shared New York’s Long Island Iced Tea, which took more than a minute to get used to. After a lunch of packed sandwiches, we crossed the border and headed to Toronto for dinner, where we shared what we guessed could be Ontario’s province drink: a local pale ale. We couldn’t find an official list, so we Googled the best we could, and were both very happy with the ale. After watching the sunset over the cityscape, we drove into the night as far as we could and stayed in a hotel on Lake Ontario.

Day 3: We spent literally all of day 3 driving, totaling to over 10 hours in the car. However, it was an extremely nice 10 hours. Instead of taking the highway from Toronto to Montreal, we took the scenic byway that ran along the lake. We stopped in multiple little towns to take in the views and explore Canada as best we could on a timeline. We adored 1000 Islands and drove through Long Sault Parkway, which was a road that connected 11 little islands and turned them into camp grounds and picnic areas. We even saw a beaver.

By the time we got to Montreal, it was nearly dinner. With a map in hand with marks with key monuments, Nicole drove around downtown while I directed and acted as tour guide. Big mistake. I would tell Nicole to take a left at the next road. Construction, road closed. Okay, turn left at the next road. One way, going in the opposite direction. Okay, turn left at the next road. Light was too short, there were too many pedestrians. Okay, let’s get the heck out of here. After over an hour in the madness, we had only gone about 10 blocks, and we had to fight our way to our chosen restaurant for dinner. Once we finally got there, we enjoyed a classy meal and shared Quebec’s province drink: a local cider.

We barely escaped the city without bloodshed from Nicole, but once we did it was absolutely our favorite part of the trip. The drive from Montreal, across the border, and into Vermont at sunrise was the most beautiful landscape I have ever seen. Pure countryside, golden light, red barns, no one on the two-lane road, then suddenly we were in the green mountains with the pink sunset surrounding us entirely.

We made it to Burlington, where we met up with my Hellfish friend Travis for our Vermont local craft beer and pizza, then spent the night at his place.

Day 4: This is part 2 of the most beautiful landscape I’ve ever seen. While Vermont was beautiful in the twilight, to me it was even more beautiful in the daylight. We were completely surrounded by mountains, fields of wildflowers, rivers, forests, and lakes. At this point, Vermont might be my favorite state. Travis’s mother suggested Little River State Park, and we walked along the river, waterfalls, and dam which created a reflective still lake. Afterwards, we toured the Ben & Jerry’s factory. We watched them make the flavor of the day, cookie dough, and walked into the tasting room with excitement. To our disappointment, cookie dough was the production flavor of the day and not the tasting flavor. Instead, we were handed samples of Strawberry Cheesecake, which Nicole took a few bites of then threw away.

We left Vermont behind and hit the corner of New Hampshire, so of course we had to stop. We found the Everyday Cafe & Pub and stopped for a local craft beer, the state drink. We stayed for over an hour and talked to the locals and the bartender, who told us he was the owner’s uncle. We asked questions about which maple syrup is best, what happened to the Stony Man, and what they did around New Hampshire. They asked us questions about our travels, where we had been and where we were going to go. The bartender told us he applauded us for exploring places he had never gone, even though they were so close, and he wanted to share in the adventure. He gifted us a hat and told us to tag the bar, and that way they could all be part of our trips. Whether he knew it or not, Nicole and I both promised each other at that moment that we would take that hat everywhere we went, even beyond this road trip. We bought some homemade muffins, then left that little bar and cafe, hoping to come back one day.

We drove all the way to Boston with intention of exploring the city. Saddened by the clouds and rain, we decided to stop and catch a movie instead before heading to my Hellfish friend Motta’s house to stay the night, where we enjoyed their many cats and homemade cake.

Day 5: At this point we realized we were very far from home and had to be in Arlington that night, so we picked our spots strategically and prepared for another day full of driving. We left Boston and found the bar that opened earliest, Alberto’s, and were surprisingly not the first ones in. We shared Massachusetts’s state drink, Sam Adams, and talked to the bar tender and a man who seemed like he was in charge. Again we talked about our travels and connected as well as we could to these locals. We asked our maple syrup questions and they asked travel questions. They resonated with our mission so much that we got our second sponsor of the trip. The Alberto’s tshirt and the Corona tshirt and necklaces have been added to our travel suitcase and will continue to see our trips.

We continued on and stopped in Providence, Rhode Island for lunch and a Dark and Stormy. We drove through the state pretty quickly, but it seemed like a nice place. We made it to Connecticut, where we stopped at the Gillette Castle. Although this was a random stop that Nicole found, it couldn’t have been more perfect. William Gillette is an idol and someone we really enjoyed learning about. He was a playwright and actor that was immensely successful and lived his life to the fullest. He lived on a boat, and while sailing through Connecticut he saw a hilltop he liked and decided to build himself a castle, so he did. He designed it all, filled with secret passageways, unique doors, spy mirrors, overhangs for his 30 cats, and a train on a railroad that ran around his property that he would take his famous visitors on. The views were incredible, making this stop amazing. As a serious Sherlock Holmes fan, I was delighted to learn that this was the man that brought the detective to the stage and gave him his hat, pipe, violin, and coined the phrase, “Elementary, my dear Watson.” It was the coolest house I had ever been in, and completely unforgettable through and through.

We later stopped for dinner and our Connecticut local white wine, then continued on. We hit terrible traffic going through New York City, but were pleased to see the city skyline in the sunset. By the time we made it back to Arlington, it was 1 AM. Exhausted but happy, we did it.

This adventure started out as just a road trip between two best friends, but it ended as much more. We created a new challenge for ourselves, and although it involves having 50 drinks together, it mainly shows our dedication to each other to visit all 50 states together and create a tradition. Road trips have been part of me ever since my family moved to the East coast, and instead of flying from California we drove the whole way and made countless fun stops. Road trips are how I see the world and take in the things around me, and more than anything they show that I enjoy the journey more than the destination.

After talking to so many locals across New England, we’ve realized that not everyone can do what we love to do. They’re stuck dreaming about seeing the things we see, doing the things we do, and having the freedom of the open road that Nicole and I are addicted to. We are reminded of this every time we see the Everyday Cafe & Bar hat and Alberto’s tshirt, and we will continue to carry them with us in our travels to remind us every day. We are lucky to have these road trips, and I feel like it’s my duty and honor to share these adventures with you. I can’t wait for the next trip, because who knows what it will bring us? It is only fitting that Nicole keeps the banner I gave her years ago on her car dashboard: “Road trips make me happy.” They sure do.

If you’d like to follow along or take the challenge for yourself, here are the most iconic drinks of every US state!