This trip from Philadelphia to Maine has everything—big city energy, quiet coastal escapes, and some of the best food you’ll ever eat (yes, there will be lobster).
You’ll hike to insane vistas, explore hidden beaches, and wander through streets packed with history, all while stopping at some of the East Coast’s coolest spots.
So gas up the car, grab your co-pilot, and get ready—because this is the ultimate road trip you’ll be talking about for years.
1. Philadelphia, PA
Philadelphia is a city where America’s story began, home to iconic landmarks like the Liberty Bell and Independence Hall.
Located in southeastern Pennsylvania, it’s also known for its cheesesteaks, die-hard sports fans, and the iconic Rocky Steps at the Philadelphia Museum of Art.
South Street is the go-to spot for funky shops and some seriously cool street art, while Reading Terminal Market has over 80 food vendors that are sure to make you drool.
And if you love quirky stuff, don’t miss the Mütter Museum—it’s filled with medical oddities like creepy skeletons and even pieces of Albert Einstein’s brain.
2. New York City, NY
New York City is nonstop energy, with towering skyscrapers, honking taxis, and enough neon lights in Times Square to make your head spin.
It’s the city of Broadway shows, dollar slice pizza, and famous landmarks—hello, Empire State Building, Central Park, and the Statue of Liberty.
Want the best views?
Head up to the Top of the Rock for a perfect skyline shot, or take the Staten Island Ferry for a free front-row look at Lady Liberty.
For something weird and wonderful, check out the tiny Mmuseumm in Lower Manhattan.
It’s tucked inside a freight elevator and filled with bizarre objects from around the world.
3. Kent Falls State Park
Kent Falls State Park is a place you won’t forget, with a waterfall that drops 250 feet down a rocky hillside in the middle of Connecticut’s rolling countryside.
You can reach the base via a short, ADA-accessible paved path, or tackle the steep trail that lets you hike up alongside the falls with misty viewpoint stops.
It’s especially stunning in the fall, when the trees explode into reds, oranges, and yellows!
And if you packed snacks, there’s a big grassy picnic area right by the water—great for kicking back and relaxing.
4. Newport, RI
Newport, Rhode Island, has ocean views, salty breezes, and jaw-dropping mansions that look like they belong in a Gatsby novel.
The famous Cliff Walk gives you the best of both worlds.
It’s a scenic path with stunning coastal views on one side and a peek at Gilded Age mansions on the other.
If you’re into history, touring The Breakers (AKA the Vanderbilt family’s gold and marble decorated “summer cottage”) is a must.
When you’re ready for seafood, hit up Bowen’s Wharf for fresh-off-the-boat lobster rolls, clam chowder, and unforgettable waterfront views.
5. Cape Cod National Seashore
Cape Cod National Seashore is 40 miles of wild, sandy perfection, with rolling dunes, windswept beaches, and beautiful lighthouses.
You can hike through pine forests, bike along the scenic Cape Cod Rail Trail, or just stretch out on the sand at the top-ranking Coast Guard Beach.
You might spot seals bobbing in the waves, or even a great white shark fin in the distance.
And for the ultimate sunset, Race Point Beach in Provincetown is the spot, where the sky turns pink and the waves glow gold as the sun dips into the Atlantic.
6. Boston, MA
Boston is where old meets new, with cobblestone streets and colonial buildings standing next to shiny skyscrapers and packed sports bars.
History is everywhere here.
Walk the Freedom Trail to see Paul Revere’s house, the site of the Boston Massacre, and don’t forget to visit the historic Old State House.
If you’re a baseball fan (or just want to experience the city’s obsession with the Red Sox), catching a game at Fenway Park is basically a rite of passage.
And when you get hungry, Quincy Market is the place to go, with everything from lobster rolls to giant bowls of clam chowder.
7. Odiorne Point State Park
Odiorne Point State Park is a little gem on the New Hampshire coast, where you’ll find tide pools, beaches, and hidden WWII bunkers.
At low tide, you can hop between the rocks and find tiny crabs, sea stars, and hidden anemones, or wander along the shore with wide-stretch views of the Atlantic.
The park is also home to the Seacoast Science Center, where you can check out touch tanks, learn about the area’s marine life, and even see a massive whale skeleton.
If you’re into history, keep an eye out for the old military bunkers that were built during World War II and still stand as eerie reminders of the past.
8. Portland, ME
Portland is an incredible mix of salty sea air, historic brick buildings, and some of the best seafood you’ll ever eat.
The Old Port district is the heart of it all, with cobblestone streets, cute little shops, and waterfront restaurants serving up fresh lobster rolls.
For the best views, head to Portland Head Light—a gorgeous lighthouse perched on dramatic cliffs, just a short drive from downtown.
With a booming craft beer scene, Portland offers everything from flights at Allagash Brewing to unique blends at small-batch spots scattered around town.
9. Boothbay Harbor, ME
Boothbay Harbor is the kind of charming, nautical town that makes you want to quit your job and become a lighthouse keeper.
The harbor is packed with sailboats, fishing vessels, and waterfront spots where you can crack into fresh lobster while watching the boats bob in the water.
If you’re up for an adventure, hop on a puffin cruise to see these tiny, ‘tuxedo-wearing’ seabirds up close, or take a kayak out to explore the rocky coastline.
For a peaceful escape, the Coastal Maine Botanical Gardens is filled with sculptures, fairy houses, and walking trails that wind through colorful flower beds and forests.
(Coastal Maine Botanical Gardens normally closes in October and usually reopens in May.)
10. Camden Hills State Park
Camden Hills State Park is where Maine’s rugged coastline meets epic mountain views, and the payoff for even a short hike is ridiculously stunning.
The must-do here is the trek (or drive) up Mount Battie, where you’ll get a sweeping view of Camden’s harbor, speckled with sailboats and backed by rolling green hills.
If you’re feeling extra adventurous, the trail up Mount Megunticook is a bit more challenging but rewards you with even higher views and far fewer people.
When you’re done conquering the trails, downtown Camden is just a few minutes away where you can grab blueberry muffins or a cup of chowder by the water.
11. Acadia National Park
Acadia National Park is pure Maine wilderness at its best, with craggy cliffs, pine-covered mountains, and waves crashing against the rocky shore.
Start your day with the sunrise at Cadillac Mountain, where you’ll be the first in the U.S. to see daylight at certain times of the year.
From there, you can bike along the park’s historic carriage roads, hike the cliff-hugging Beehive Trail, or find a quiet spot along Jordan Pond to take in the scenery.
If you’re craving a classic Maine treat, don’t skip the popovers at Jordan Pond House—light, buttery, and best enjoyed with jam and a view of the Bubbles mountains.
(Jordan Pond House normally closes in late October and usually reopens mid-May.)
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