New England Triangle: A 10-Day Road Trip Through Coastal Classics and Mountain Scenery

Day 4: Portland → Bar Harbor (Acadia region), Maine

Start the morning with one of New England’s most iconic coastal landmarks: Portland Head Light. Then return to Portland for a short walk through the Old Port area—brick architecture, boutiques, and a great café scene.

Continue north along the coast with an optional stop in Freeport, known for outlet shopping and the flagship presence of classic New England brands. We recommend planning lunch in a coastal village along the way—this is prime territory for lobster-focused dishes and waterfront dining.

Arrive in the Bar Harbor / Acadia region by early evening. Many of the best lodging options are just outside the town center, so if you’d like an evening stroll and dinner in Bar Harbor, plan to drive in and use municipal parking.

Night: Bar Harbor / Acadia area, 4-star superior coastal hotel or boutique inn (preferred network). We prioritize walkability or easy access to the harbor area whenever possible.

Day 5: Bar Harbor → Acadia National Park

Today is dedicated to Acadia National Park—one of the most scenic coastal parks in the U.S. Exploring by vehicle is straightforward, with a classic loop-style drive linking major viewpoints, short walks, and panoramic overlooks across Mount Desert Island.

We recommend pacing the day with a mix of scenic stops and one or two short trails. Depending on season and local access rules, we can also advise on sunrise/sunset viewpoints and the best times to avoid peak traffic.

In the afternoon, consider a boat experience from Bar Harbor—options range from sightseeing cruises to nature-focused outings, and in some seasons, experiences tied to local maritime traditions.

Free evening back in Bar Harbor.

Night: Bar Harbor / Acadia area, 4-star superior coastal hotel or boutique inn (preferred network).

Day 6: Bar Harbor → White Mountains (New Hampshire)

Leave the Maine coast behind and travel inland to New Hampshire’s high-country landscapes. This is a longer drive day, but the destination shift is worth it—moving from rocky shoreline to mountain scenery.

Upon arrival in the White Mountains, you can focus on the Mount Washington region. Mount Washington is famous for its dramatic conditions and rapidly changing weather, so we recommend dressing in layers and keeping plans flexible.

Depending on season and your comfort level, there are several ways to experience the summit area, including a historic rail-style ascent, guided options, or driving a private mountain road when conditions allow.

Driving guide (approx.): ~4.5–5 hours (traffic dependent)

Night: White Mountains region, best-available upscale mountain resort or lodge (preferred network).
This is a smaller market—here we focus on the strongest combination of comfort, services, and setting.
 

Day 7: White Mountains → Montpelier → Stowe → Burlington (Vermont)

Today you’ll enter Vermont, where the scenery softens into classic countryside landscapes and mountain-town charm.

Begin with a brief stop in Montpelier, one of the smallest state capitals in the country—pleasant for a short walk and a café break. Continue to Stowe, Vermont’s best-known mountain village, ideal for scenic drives, short hikes, and classic “New England countryside” atmosphere.

Optional add-ons here depend on your travel style: a gondola-style scenic ride (seasonal), a classic mountain toll road experience (seasonal), or simply a relaxed afternoon exploring Stowe’s village center.

Continue to Burlington, set on Lake Champlain, for an evening in a lively, walkable town known for shopping streets, dining, and lakeside ambiance.

Optional stop (sweet classic): the Ben & Jerry’s visitor experience in Waterbury, Vermont (time permitting).

Night: Burlington, Vermont, 4-star superior hotel (preferred network). Where available, we can prioritize a central location for easy evening walks and dining.

Day 8: Burlington → Salem → Boston, Massachusetts

Leaving Lake Champlain behind, travel south into Massachusetts for a cultural stop in Salem—best known for its 1692 witch trials history and walkable historic streets. Depending on your interests, you can visit a museum experience, browse small shops, and enjoy a relaxed lunch before continuing to Boston.

Arrive in Boston in the afternoon and enjoy a first panoramic introduction to the city. A great “first taste” is a stroll through Boston Common and the elegant streets of Beacon Hill—ideal for early evening atmosphere and dinner.

Night: Boston, 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.
We recommend a central location to maximize walkability and minimize the need for driving/parking.

Day 9: Boston

Today is dedicated to Boston’s historic and cultural core. Follow the Freedom Trail at a comfortable pace, choosing the highlights that match your interests—Revolutionary-era landmarks, historic churches, iconic markets, and waterfront atmosphere.

Later, cross into Cambridge for time around Harvard and MIT—two of the most recognized universities in the U.S.—and enjoy the neighborhood energy, bookstores, and cafés.

Optional seasonal add-on: a whale-watching excursion (best scheduled in the morning if you choose to do it).

Night: Boston, 4-star superior hotel (preferred network), with an optional upgrade to 5-star luxury.

Day 10: Boston → New York City (End of services)

Enjoy a free morning for a final walk, shopping, or a relaxed breakfast. Then depart for New York City.

Driving guide (approx.): ~4.5–5 hours (traffic dependent)

Arrive in New York in the evening, return the vehicle, and conclude services.

End of services.

Customization note: This itinerary can be tailored as a round trip (start/end in Boston) or as an open-jaw route (start in New York and end in Boston, or the reverse), depending on flight plans and travel style.

OPTIONAL ACTIVITIES