If you’re looking for a road trip that’s packed with beauty, history, and ocean views around every corner, this one’s for you.
It starts in a big city full of cobblestone streets and famous landmarks, then winds past spooky towns, salty harbors, and super lovely lighthouses.
You’ll even stop for fresh lobster, stroll through tiny downtowns, hike to epic views, and maybe even catch the first sunrise in the country.
Every stop has its own personality, and by the end, you’ll wonder why you didn’t take this trip sooner.
1. Boston, Massachusetts
Boston is a historic city packed with famous spots like Fenway Park, the Freedom Trail, and the Boston Tea Party Ships & Museum.
You’ll also find cobblestone streets in Beacon Hill, amazing clam chowder at Quincy Market, and lively waterfront areas to explore.
Fun fact: Many of the events that led to the American Revolution happened in Boston, so if you’re into history, this place is loaded with it.
2. Salem, Massachusetts
Just 35 minutes from Boston, Salem feels like a whole different world with its spooky, witchy reputation.
It’s best known for the 1692 Salem Witch Trials, and you can still visit the Salem Witch Museum, the Witch House, and old cemeteries that tell its eerie story.
That’s why October is peak season here, with crowds, costumes, and nonstop Halloween fun all month long.
But if you’re not into ghosts and broomsticks, there’s still a pretty harbor, cool indie shops on Essex Street, and seriously delicious seafood at spots like Turner’s.
3. Portsmouth, New Hampshire
Cross the state line into New Hampshire and you’ll hit Portsmouth, a small seacoast town with big charm.
It’s got brick sidewalks, 17th-century homes, and cute cafes tucked between galleries and bookstores in the Market Square area.
You can also tour historic homes at the Strawbery Banke Museum or hop on a harbor cruise to see old lighthouses from the water.
Food is a big draw here too, with local favorites like The Friendly Toast and Row 34 serving up everything from lobster rolls to tasty brunch.
4. Kennebunkport, Maine
Next stop is Kennebunkport, Maine, a postcard-perfect coastal town straight out of a summer movie.
Dock Square is the heart of it all, packed with jewelry shops, art galleries, and local boutiques where you can easily spend an afternoon wandering.
If you’re after scenic views, watch lobster boats come and go from the harbor or head to Goose Rocks Beach for soft sand and calm waves.
Cool fact: This is where the Bush family has their famous summer compound, so don’t be surprised if the area feels a little presidential.
5. Portland, Maine
Only 35 minutes up the coast is Portland, Maine’s largest city, known for its artsy vibe, bold flavors, and a working waterfront still buzzing with lobster boats.
Head straight to the Old Port, where cobblestone streets, salty sea air, and top-tier food set the tone, from Standard Baking Co. to Central Provisions.
From there, you can check out local art at the Portland Museum of Art, hop on a ferry to Peaks Island, or grab skyline shots from the Portland Observatory.
It’s the kind of place where you can eat like a champ, explore all day, and still catch a dreamy sunset over Casco Bay.
(The Portland Observatory is open seasonally, with tours typically running from late May through mid-October.)
6. Pemaquid Point Lighthouse, Maine
From Portland, take the scenic drive up to Pemaquid Point Lighthouse, one of Maine’s most iconic photo spots.
It’s perched on craggy, crazy-cool striped rocks with waves crashing below and sweeping ocean views that are straight-up stunning.
You can even climb to the top before spending time in the tiny museum inside the keeper’s house.
It’s peaceful, windswept, and a must-stop for that classic Maine lighthouse moment.
7. Camden, Maine
Up next is Camden, a dreamy harbor town where the mountains meet the sea.
The highlight here is Camden Hills State Park, where a short but steep hike up Mount Battie delivers unreal views across Penobscot Bay.
Down in town, you’ll find sailboats bobbing in the water, plenty of bookstores and bakeries, and places like Camden Deli known for great lobster rolls.
And if you visit in summer, windjammer cruises are a popular way to get out on the water, while fall brings next-level foliage.
8. Acadia National Park, Maine
End your road trip with a bang at Acadia National Park, one of the most jaw-dropping spots in all of New England.
If you’re feeling brave, hike the 1.4-mile Beehive Trail with iron rungs and steep drop-offs, or keep it easy on the 4.4-mile Ocean Path with nonstop coastal views.
Another must here is sunrise from Cadillac Mountain, one of the first places in the U.S. to see the sun come up and well worth the early wake-up.
Afterwards, you can pop into Bar Harbor right next door, which is full of cute shops, blueberry everything, and all the seafood you can eat.
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