I’ve been a West Coaster all my life. I won’t say I’ve seen all there is to see, but I know it like anyone knows their home. I’ve driven up and down its beautiful coastline more times than I’ve flown to New York City, which is will be nine this year. However, New York was the only place I’d been on the east coast at all, and as soon as I heard I was visiting Boston, I was excited to change that.

Emily and I left from Indiana at nine o’clock on a Saturday morning, with Syracuse, New York as our destination for the day. Crossing state lines I’d never seen before was thrilling despite the familiar road signs and similar scenery.

Columbus, Ohio was a place I was slated to visit last year before plans fell through. It’s never been a place high on my list (Midwest metro areas tend to blend together), so driving through seemed like an appropriate way to see the city for the first time. I’ve heard it’s home to amazing botanical gardens and a booming German village, both places that sound right up my alley. The only thing I really noticed was the striking art-deco LeVeque Tower as we passed. 
 

Columbus Eats: Mission Coffee  |  Portia's Cafe  |  The Suisse Shop

As soon as we crossed into Pennsylvania, the scenery changed from Midwest quirk to colonial charm. It was like we had driven into a different time period. All I could think about was Felicity Merriman as we drove by farmhouse after farmhouse. Her life and family may have been set in Virginia, and a hundred years before western Pennsylvania was developed, but she's my tie to the colonial days.
 

Pittsburgh Eats: Big Dog Coffee  |  Randita's  |  La Gourmadine Bakery
 

Upstate New York is almost exclusively open forests with bare trees, broken up by hunting stands high up in the trees, which were surprisingly close to the roadway. It seemed so quaint to see signs for Manhattan—the City for the rest of the world is just their metro area. The prospect of driving in New York City terrifies me, but from 300 miles away, it doesn’t sound as daunting. There are also a ton of American Revolution historical sites in upstate New York. Most of the major battles were fought on its grounds. Near Buffalo, Old Fort Niagara is rumored to be haunted by a fallen French soldier, and also housed something like 1,200 German soldiers during World War II as a POW camp.

With a low-to-no-budget hotel room on our horizon, we decided to pull off in Buffalo for a look at Niagara Falls. I’ve always wanted to go, but it seemed for some reason like a pipe dream that would never be accomplished—a silly thing to think for someone in the midst of traveling the world. My only advice for visiting Niagara Falls is this: investigate the park situation before you get there. We happened to go when it was closed for the season and all of the viewing points were closed off. We saw a corner of its majesty and didn’t want to accidentally end up in Canada, so we turned the car around, less than impressed. With one final state line to cross, we set out the next morning with Starbucks and a dream.
 

Buffalo Eats: Public Espresso + Coffee  |  Ashker's  |  Wheatberry Bake Shop
 

Massachusetts was a different shade of green than what I’m used to in Washington state. Beautiful and bright, and nothing like the vibrantly melancholy evergreen that anchors our hillsides. Around every corner is another level of idyllic meadow or river or town that I'm not used to seeing on our country's younger coastline. I've been to Colorado a dozen times. I've driven the Oregon coastline up and down and down and up. Maybe I have seen it all. When I road trip, I expect to zone out pretty quickly and get into whatever else I'm doing, whether it's a podcast or a crossword or belting out an entire Broadway musical. Things on the east coast felt new and exciting, and I couldn't peel my eyes away from the windows. It was nice to take actually take a journey instead of spending a quarter of the time and just flying over it all. Although we were anxious to get to our destination, it set the gears in motion to plan a more substantial road trip next summer. Of course, to somewhere new.

I wrote about road trip eats for Urban Outfitters last month: click below to read my tips for snack-packing!

Boston is a city of great variety and great stature. My excitement about meeting it has grown exponentially in the last two or three years with a developing interest in American history—a subject I passively glazed over from grade school to high school—but it’s also a vivaciously dynamic city with much more going for it than just its revolutionary tales. I’m sharing five of the best places I visited during my week in town. Unintentionally, many of them do happen to have great historical significance; the city’s fabric is just woven too tightly with the thread of a nation’s beginning to ignore.

Boston Public Library — 1848

If you’re asking a librarian (which you are) it doesn’t get much more romantic than city libraries, and the Boston Public Library easily clinches a spot in the top three of several I’ve been lucky enough to visit. Established in 1848, everything from its art collections to the courtyard fountain to the building itself, its stateliness is overwhelming and beautiful, and an entire afternoon could easily be dedicated to combing through its extensive collection. Don’t miss Bates Hall to get the iconic and studious green lamp shot.

Beacon Hill — 1795

One of the oldest neighborhoods in America, there’s nothing to dislike about Beacon Hill. Also home to one of the most photographed streets in America (Acorn Street), prepare for perfection abound in every lane. Take a few minutes and stroll through each street for as long as you can handle it. Every exquisite home is unique in its façade, and some even stand out as historical gems with a bit of a back story. It presents itself as the ideal neighborhood, and it should be. It’s had the most practice out of anyone on the mainland.

Freedom Trail — 1634-1809

You can’t do Boston without doing the Freedom Trail. A major revolutionary hub, just about everything happened in this city short of signing the Declaration. It’s extremely entertaining to start at the head of the green line—there’s a literal paint line along the sidewalk that takes you by each landmark—and follow the crowd along the 3 mile stretch of history. The highlights? The Old Granary Burial Ground, where you can pay your respects to Paul Revere and Mother Goose; The Old North Church; and my personal favorite, the Old Corner Bookstore (frequent visitor Louisa May Alcott’s work was published here!) which is now, sadly, a Chipotle.

Regina’s Pizza — 1926

Not everything in Boston is as old as the hills. Like every other city in the world, everyone in Boston has their own opinion about the best slice. The only one I made time for was Regina’s Pizza, and I can still taste the perfectly seasoned sauce. A small, always-bustling space in the lively and cozy North End, the atmosphere is warm and joyful because everyone sitting there wants to be (be prepared to wait in an outdoor line). The pizza is served fast and hot, and the bathrooms are laughably small. It’s exactly what you’d expect from a family-run space tucked into a city corner, draped in twinkle lights and autographed celebrity headshots.  

Harvard University — 1636

I went to Harvard for Legally Blonde, and I stayed for all the other reasons. Harvard surpassed any expectations I may have set for it (I don’t recall if I had any, now that I’ve been), but I felt its importance in every step on the pavement. Besides the fact that it’s Frasier Crane’s alma mater, thousands of vastly important (real) people have attended and walking in the footsteps of some of the smartest people in the world made me wish I had a sliver of their commitment to learning. It’s been around since 1636. Let that sink in. It’s also home to the second largest collection of secular stained glass in the world, which happens to be housed in the freshman dining hall. It’s this kind of weighted casualness that makes walking the campus a progressively humbling experience. Learning historical facts about a place when you’re standing literally in the middle of it always tends to strike a stronger chord.

“That’s my whole thing,” Alyssa shakes her head, still smiling, “If you have to ask what’s good on the menu, the answer is probably nothing.”

Answering my question about what to order from the pride and joy of Bannister’s Wharf, The Coffee Grinder, Alyssa Cerceo doesn’t beat around the bush. I settle on a simple latte and ask how long she’s been in business. In return, I get a story about how she missed the establishment’s 10th anniversary, shaking her head the whole time. I get where she’s going with her answer. The days run together.

Much of Newport’s charm is the people and the places that have been there for as long as tourists can remember. Shop owners and wait staff are comfortable chatting, cycling through thousands of tourists a day, and they’ve learned their way around friendly and captivating conversation.

The quick but memorable experience easily gets Coffee Grinder a spot on my return list, and I spend the rest of the afternoon weaving in and out of open docks and public harbors, admiring the boats and sights along the seaside. The next best thing I put in my mouth is an order of fish and chips from The Wharf Pub, enormously satisfying as it’s the second time I’ve eaten fish in the last eight years.

As I walk, I get a message from my friend. “You have, have, have to go to St. Mary’s Church,” it reads, “Where JFK and Jackie were married!” I feel like I’ve failed as an American for not knowing until this moment, but I swing a right anyway and walk up the Memorial Boulevard hill. There’s a tourist group already snapping photos, but once they’re gone, I’m the only one on the premises. I can feel the history of the place weighing my feet to the cement, a feeling I usually get only around places that are centuries old, but it’s the romance of this one that presses on me. It’s a lovely moment.

It’s a fifteen minute drive to the lighthouse at Ragged Point, and I leave just in time for sunset. It takes me twenty-five, thanks to scenic viewpoints and my inability to simply drive by a beautiful vista, but it’s worth it. I park at Castle Hill Inn and I’m not sure where I’m going as I leap over the fence and off the cliff, but after cavorting across a hundred feet of scraggly rocks, I finally see a glimpse of what I came for. It’s at this moment that I feel immensely proud of what I’ve accomplished. I traveled across the country on my own to see this, and I’m seeing it.

It’s windy and beyond out there on the rocks. I can’t feel my hands anymore after taking a thousand photos of my phone—I can never take enough. My nose is red and my eyes are watering, but I can’t leave the Castle Inn Lighthouse. Maybe it’s because I know there’s a chance I’ll never be here and see this again. I’m cursed with a terrible memory, and as many times as I try to press the image into my skull, I know it will be gone before I’m ready to say goodbye. The sun sets, and I’m surprised I make it back across the night-black rocks alive.

My bed at Gilded Hotel is extra that night. Extra soft, extra plush, extra comfortable—just extra. The only thing that can make it better after an hour-long soak in their perfectly-sized bathtub is the promise of Ma’s Donuts the next day (get the s’mores and honey dipped flavors, and iced coffee with cream and sugar). Newport’s quiet seaside ways have given me much needed pause from a nonstop road trip down my country’s eastern coastline, and from my hectic life that always seems to be speeding up. I don’t remember ever feeling quite this comfortable.