A Rom-Com–Inspired Road Trip From NYC to Kennebunkport, Maine

While some kids spent their childhood playing with LEGO or hanging out at the local mall, I was on the couch watching rom-coms. Particularly, the kind that were set in a quaint town—usually on the East Coast, but in a pinch, the Pacific Northwest would do—where the trees never lost their leaves and the streets were lined with Victorian-style homes owned by quirky, well-intentioned neighbors. I walked to school everyday trying to embody the rom-com main character archetype I always envied (Laney Boggs, Kat Stratford, Sally Albright, to name a few). She was beautiful in an understated way, clumsy yet elegant, witty without hurting anyone’s feelings, and the object of at least one dreamy guy’s affection. Becoming an adult helped me realize that while such a woman likely doesn’t exist, the places she inhabited still did—the East Coast is brimming with hamlets and small towns that still retain the movies’ old-school charm, and I wanted to see them with my own eyes.

Who am I: I’m Kelsey, an associate editor at Thrillist, and, if it’s not obvious, a rom-com obsessive. (Further evidence: I once watched 10 Things I Hate About You everyday for a month straight). I’ve lived on the East Coast for eight years but have stuck to big cities like Boston and NYC, so I’m thrilled to leave the littered, rat-ridden streets behind and drive into a film backdrop.

Any song where the artist is overcome by deep yearning. Irma Thoma’s 1966 album Take A Look is an upbeat melodic take on love, while Mitski’s Bury Me At Makeout Creek is a scream-inducing foray into wistfulness and heartbreak. The Magnetic Fields’ 69 Love Songs is exactly what it sounds like—a three-volume concept album featuring two hours and 45 minutes exploring the ecstatic psychosis that being in love induces.

A novel to read while you’re sitting alone in a coffee shop or at dinner—this is a surefire way to attract a mate, or at the very least, make you look mysterious and fiercely independent. To fit with the theme, I recommend an epic romance, and no one does the genre better than Jane Austen. On all of my trips, rom-com themed or not, I bring hand sanitizer spray and vitamin C gummies because I can’t bear the idea of getting sick while traveling.

The East Coast is an excellent road-trip region for its nature-filled highways, drive-thru Dunkin’ Donuts, and accessibility to a variety of states, each with its own delicious cuisines and historic landmarks. Within an hour of leaving New York City you can be in an entirely new state, which, as a California native, came as a pleasant shock.

It’ll take just under three hours to drive to Mystic, Connecticut, the setting of the film Mystic Pizza, where rom-com veteran Julia Roberts got her big break. Park in the downtown village, where your first stop, naturally, should be the titular restaurant, Mystic Pizza, on West Main Street. The pizzeria has a full dining room, but to feel more one with the locals, grab a slice at the bar. After lunch, stock up on some pastries at Sift Bake Shop; I recommend the bakery’s signature treat, the Ebbieoche, which is braided croissant dough stuffed with cinnamon and sugar. Before hitting the road, grab a coffee at Lamplighter Trading Co., a cafe stocked with books, knick knacks, and a kind owner who will talk with you about all things Taylor Swift. On your way out of the city, drive 10 minutes over to the Stonington Community Center Thrift Shop, where you’ll find antique Pyrex dishes, vintage Merrells, and the biggest DVD collection to exist since the closure of Blockbluster.

Depending on how much time you have, Mystic has one of the country’s best aquariums, where you can even have a private painting session with a seal (yes, you read that correctly).
 

Westerly, Rhode Island, home to multiple rocky beaches and Taylor Swift’s Watch Hill mansion, is just a 15-minute drive away. Much like Mystic, Westerly’s downtown looks like it popped out of a postcard. (Are you sensing a theme here?) Martin House Books is the city’s shining star and a fitting spot to have your Notting Hill moment. While the selection is respectable (a mix of classics and contemporary releases, tons of cookbooks, and an adorable children’s section), it’s the cozy atmosphere that will make you want to abandon your everyday life and become a bookseller. Just note that it is unfortunately not owned by the swashbuckling Hugh Grant.

If you’re like me and the owner of Lamplight Trading Co. (ie, a Swiftie), drive 15 minutes toward the coast to get a peak at Swift’s $17-million-dollar mansion, previously known as Holiday House. But don’t loiter. Instead, walk over to the Watch Hill Lighthouse for a truly awe-inspiring view of the Atlantic Ocean. Listen to the waves roar, take in the salty air, and pretend to be the man in Caspar David Friedrich’s Wanderer above the Sea of Fog. Just note that the lighthouse is on a private road that is open to pedestrians but not cars—so park a few streets away.

It’s a quick, 45-minute drive to your final destination for the night, Providence, Rhode Island. Grab dinner at one of the city’s best restaurants, like Al Forno, which is an RI staple and credited with creating the grilled pizza. Then, wander around Brown University’s campus, which is open to the public, and pretend to be one of the many bookish rom-com leads that hail from the school—Sandra Bullock in Two Weeks Notice, Julia Roberts in My Best Friend’s Wedding, Blake Lively in The Sisterhood of the Traveling Pants are just a few examples.

Though it has close to 200,000 residents, Providence feels more like a whimsical small town. Kick off your morning in the quaint Federal Hill neighborhood, with its cobblestoned streets and perfectly preserved historic homes. Nitro Bar, a cafe located in a Dash Bicycle Shop, may have become TikTok famous in the past couple of years for its uniquely flavored drinks (caramelized banana, cinnamon coconut, and strawberry are a few), but it still retains a neighborhood feel. Park yourself at the large windowsill (which doubles as seating) and sift through the free local newspapers while enjoying a latte and an egg and cheese before setting off.

After driving on the highway for a bit, you’re going to be ready for some sustenance. When you pull off, make sure to take note of New England’s incredible array of architecture—you’ll notice homes in all kinds of styles, including Colonial, Georgian, and Greek Revival. Get out of the car to wander the grounds of the family-run Ward’s Berry Farm in Sharon, Massachusetts. Stroll through the farm’s rows of perennial, annual, and edible plants, all of which are for sale. Then hop over to the playground, where you can run amongst the farm’s chickens a la Elizabeth Bennett in the opening scene of Pride and Prejudice. If you’re there on the weekend, you can even go for a hayride around the farm. Once you’ve seen enough of the property, peruse Ward’s Berry Farm’s market. It’s far more romantic to pick up road trip snacks from a local farm stand—where offerings include maple cotton candy, soft-serve smoothies, and freshly baked pies—than a gas station.

You’d be remiss to not make a pitstop in Portsmouth, New Hampshire. The Portsmouth Downtown Historic District is right on the water and makes for a restorative stroll after driving for hours.

A tenet of practically every rom-com is the third space, usually a coffee shop or a bar, where the characters hang out and the love interests “serendipitously” run into each other. The hand-drawn chalkboard menus, string lights, and active community bulletin board make Cup Of Joe the perfect real-life version of this. Stop by for a late lunch and a cup of coffee, or, depending on your mood, a specialty cocktail.

It’s just another 30 miles to your final destination, Kennbunkport, where part of Taylor Swift’s music video for “Mine” (which is basically a rom-com concentrated into four minutes) was set. Once you’ve settled in at your hotel, walk five minutes north to Kennebunkport’s waterfront, full of restaurants, charming gift stops, and sailboats. Grab dinner at Alisson’s Restaurant and make sure to finish it off with a slice of blueberry pie—Maine’s wild blueberries are small, sweet, and likely the best you’ll ever have. If you have time, take a short 10 minute drive to Christ Church, one of the main locations of Swift's iconic music video. 

Luxuriate in Rhode Island’s gorgeous seaside and take the ferry from Point Judith to Block Island, a less than 10 square mile archipelago off the coast. Go for a beach day, hunt for glass floats, and visit the alpacas, goats, and camels at Abrams Animal Farm.
 

Get to know Massachusetts. From Boston to Ponyhenge to Walden Pond, there is a ton to see in what is considerably quite a concentrated state. If you really want to feel like you’re Rory Gilmore in Stars Hollow, your best bet is exploring Concord, the home of literary greats like Louisa May Alcott, Ralph Waldo Emerson, and Henry David Thoreau. Here’s our guide to the bookish small town.

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