There’s nothing like a good road trip—windows down, snacks stocked, and an epic playlist ready to go.
And this one? It’s next-level.
We’re talking charming coastal towns, jaw-dropping ocean views, and enough lobster rolls to make you question your life choices (in the best way possible).
You’ll walk historic streets, climb rocky cliffs, eat some of the best pizza and seafood on the East Coast, and maybe even spot a whale or two along the way.
Starting in NYC and ending in one of the most breathtaking national parks in the country, this road trip has everything.
So grab your bags, fill up the tank, and let’s hit the road!
1. New York City
New York City needs no introduction—towering skyscrapers, nonstop energy, and enough pizza spots to keep you eating for weeks.
This is where our epic road trip kicks off, so grab a coffee and let’s get moving!
2. New Haven, CT
New Haven, Connecticut, sits on the northern shore of the Long Island Sound and is best known as the home of Yale University, established in 1701.
It’s packed with history, stunning architecture, and way too many smart people.
But let’s be real—the real reason to stop here is the pizza, and if you haven’t tried a New Haven-style apizza (yes, that’s how they say it), you’re seriously missing out.
Frank Pepe’s and Sally’s are the legends, serving up coal-fired, charred-crust perfection, with the white clam pizza at Pepe’s being the ultimate must-try.
You can also take a stroll around the Yale campus, pop into the free Yale University Art Gallery, or walk along the waterfront at Lighthouse Point Park for some fresh ocean air.
3. Mystic, CT
Next up is Mystic, a charming seaside town that feels straight out of a nautical daydream—think historic ships and all the fresh seafood you can handle.
The star here is the Mystic Seaport Museum, where you can step aboard massive 19th-century sailing ships and see what life was like before GPS and autopilot did all the work.
Downtown Mystic is packed with cute shops, waterfront views, and the famous Mystic Pizza—yes, the one from the Julia Roberts movie, and yes, you absolutely need a slice.
Before you hit the road again, swing by Olde Mistick Village, a cool little shopping area designed to look like a colonial village, because why not throw in a little time travel with your road trip?
4. Newport, RI
Welcome to Newport, Rhode Island—where you can explore Gilded Age mansions, and rocky coastal cliffs.
The must-do here is the Cliff Walk, a 3.5-mile trail that winds between jaw-dropping ocean views on one side and ridiculously over-the-top mansions on the other.
Seriously, these places make Gatsby’s house look modest!
If you’re into history, take a tour of The Breakers, the grandest of them all, built by the Vanderbilts as their “summer cottage” (because apparently, 70-room palaces were just casual vacation homes back then).
Before you go, grab a lobsta roll at Flo’s Clam Shack or sip an iced coffee from a local café while strolling the harbor, watching yachts that cost more than most houses.
Just a note: Flo’s Clam Shack takes a winter break and reopens in March—be sure to check online before heading over!
5. Salem, MA
Salem, Massachusetts, brings a whole new vibe to the trip—think eerie history, witch trials, and enough spooky energy to make even the biggest skeptic raise an eyebrow.
The Salem Witch Museum is the go-to spot for diving into the infamous 1692 trials, complete with dramatic exhibits and life-size figures that make history feel way too real.
But Salem isn’t just about witches—you can also explore The House of the Seven Gables, a 17th-century mansion made famous by Nathaniel Hawthorne’s novel, or stroll Derby Wharf for some classic New England harbor views.
Before you leave, pop into a witchy boutique for a fun (or cursed?) souvenir, or grab a freshly baked treat from a local bakery to snack on as you hit the road.
6. Portsmouth, NH
Portsmouth, New Hampshire, feels like old-school New England—think cobblestone streets, historic houses, and waterfront views straight out of a postcard.
Start with a wander through Market Square, where cute indie shops, bookshops, and cozy cafés make it way too easy to lose track of time (no complaints there).
History buffs will love Strawbery Banke Museum, an outdoor history museum with preserved colonial homes and costumed guides who make the 1600s feel surprisingly relatable.
Please note: the historic house season runs from April through October, with special events and programs offered throughout the year.
Before you go, grab a bowl of seafood chowder at River House or kick back with a craft beer at one of the town’s many breweries—because nothing says road trip like a perfect pint by the water.
7. Portland, ME
Portland, Maine, is all about lighthouses, lobster rolls, and a seriously good food scene that punches way above its weight for a small city.
Start at the iconic Portland Head Light in Cape Elizabeth—it’s the oldest lighthouse in Maine, and the views of the rocky coastline are pure postcard perfection.
Back in town, the Old Port district is packed with brick-lined streets, cool boutiques, and enough seafood joints to keep you debating the best lobster roll in town (hint: Eventide Oyster Co. is a strong contender).
If you need a break from all the eating, hop on a ferry to the Casco Bay Islands for a quick island escape.
8. Boothbay Harbor, ME
Boothbay Harbor is the kind of place where time slows down, thanks to its scenic harbor, classic fishing boats, and fresh ocean air.
Hop on a boat tour to spot puffins, seals, or even a passing whale, or take a stroll across the historic Footbridge for the best panoramic views of the harbor.
If you’re craving more nature, the Coastal Maine Botanical Gardens is a must, with giant sculptures hidden among the flowers and walking trails that make you feel like you’ve stepped into a storybook.
Just a heads-up: The garden normally closes over winter and usually reopens for its regular season from May through October.
Before you leave, grab a lobster roll (because, let’s be honest, there’s no such thing as too many in Maine) and soak in the small-town charm.
9. Camden, ME
Camden, Maine, is where the mountains meet the sea—literally—giving you jaw-dropping views whether you’re out on the water or hiking above it.
For the best lookout, head up to Camden Hills State Park and hike (or drive) to the top of Mount Battie, where you’ll get a postcard-perfect view of the harbor, sailboats, and endless blue ocean.
Back in town, Camden’s waterfront is packed with charming shops, cozy cafés, and seafood restaurants that will make you want to stay forever (try the lobster stew at The Waterfront Restaurant).
If you’re up for an adventure, hop on a windjammer cruise for an old-school sailing experience, complete with stunning coastline views, and that “wow, I never want to leave” feeling.
10. Penobscot Narrows Bridge & Observatory, ME
Just when you thought Maine couldn’t get any more scenic, the Penobscot Narrows Bridge & Observatory shows up with some of the best panoramic views in the entire state.
This isn’t just any bridge—it’s home to the tallest public bridge observatory in the world, soaring 420 feet above the Penobscot River with a lookout that lets you see for miles.
On a clear day, you can spot the Camden Hills, Cadillac Mountain, and a whole lot of rugged Maine coastline.
While you’re here, check out nearby Fort Knox, a massive granite fort from the 1800s that’s fun to explore and surprisingly eerie with its dark tunnels and towering stone walls.
Just be aware that the Penobscot Narrows Bridge & Observatory and Fort Knox normally close for the winter season and usually reopen in May, so plan accordingly.
11. Acadia National Park, ME
And finally, the grand finale—Acadia National Park, where rocky cliffs, pine-covered mountains, and crashing waves create one of the most stunning landscapes on the East Coast.
Start your day by driving up Cadillac Mountain, the highest point on the U.S. Atlantic coast, where you can catch a sunrise so epic it feels like nature is showing off just for you.
From there, hit the Park Loop Road for jaw-dropping coastal views, hike the thrilling Beehive Trail if you’re up for some heart-pounding iron rungs, or relax with a picnic at Jordan Pond.
Before you wrap up this epic road trip, take a walk along Sand Beach, breathe in that salty ocean air, and soak in the wild beauty of Acadia—because trust me, you’re going to want to remember this place forever.
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