New England Road Trip: A 7-Day Loop from Boston
Coast, mountains and small towns in one easy loop.
A 7-day New England road trip looping out of Boston — coastline, mountain roads and small towns, planned day by day with drive times and stops.
Freedom Trail
Boston's iconic historic walk hits the key Revolutionary War sites in a compact loop, perfect before hitting the road.
Union Oyster House
America's oldest continuously operating restaurant, a classic New England seafood send-off for lunch.
Portland Head Light
Maine's most photographed lighthouse sits on a dramatic rocky point overlooking Casco Bay.
Eventide Oyster Co.
Portland's celebrated oyster bar showcases the best of Maine's coastal seafood scene for dinner.
Overnight in Portland, Maine
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Portland, Maine · $$
Booking happens on the partner's site.
Camden Hills State Park
A short detour up Mount Battie rewards with sweeping views over Penobscot Bay, a classic mid-coast Maine stop.
Red's Eats
A legendary roadside lobster roll shack in Wiscasset, a rite of passage on the Maine coast.
Acadia National Park
Granite peaks meeting the Atlantic make this the crown jewel of the New England coast.
Overnight in Bar Harbor, Maine
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Bar Harbor, Maine · $$
Booking happens on the partner's site.
Cadillac Mountain
The highest point on the North Atlantic seaboard offers one of the first sunrises in the US and panoramic island views.
Jordan Pond Path
An easy, scenic loop trail around a glacial pond framed by the iconic 'Bubbles' peaks.
Jordan Pond House Restaurant
Famous for popovers with a view of the pond, a beloved Acadia tradition since the 1890s.
Overnight in Bar Harbor, Maine
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Bar Harbor, Maine · $$
Booking happens on the partner's site.
Moody's Diner
A Maine institution since 1927, a classic diner stop en route inland.
Kancamagus Highway
One of America's great scenic drives, winding through the White Mountain National Forest with waterfalls and overlooks.
Overnight in North Conway, New Hampshire
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North Conway, New Hampshire · $$
Booking happens on the partner's site.
Mt. Washington Auto Road
A drive to the summit of the Northeast's tallest peak delivers one of the most dramatic views in New England.
Diana's Baths
A gentle, family-friendly cascade walk through the White Mountain forest, easy to reach and beautiful.
Delaney's Hole In the Wall
A local favorite in North Conway for hearty New England comfort fare after a day outdoors.
Overnight in North Conway, New Hampshire
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North Conway, New Hampshire · $$
Booking happens on the partner's site.
Strawbery Banke Museum
A living history museum of restored colonial and early American homes in the heart of historic Portsmouth.
Waterfront Overlook
A charming tidal river walk through one of America's oldest port cities, rich with maritime history.
Row 34 | Portsmouth
A top-notch oyster and seafood spot capping off the coastal theme of the trip.
Overnight in Portsmouth, New Hampshire
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Portsmouth, New Hampshire · $$
Booking happens on the partner's site.
Public Garden
A peaceful green finale to the trip, right in the heart of the city where the journey began.
Neptune Oyster
A final indulgent New England seafood meal in Boston's historic North End before departure.
Make this trip your own
Plan your own road trip →This route was drafted with AI. Please double-check roads, opening hours and local conditions before you go.
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