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New England Fall Foliage Road Trip
Routes › North America › United States
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New England Fall Foliage Road Trip

schedule9 daysplan for pin_drop7stops directions_car~1 360 kmon the road flight_landBoston (BOS)fly into

This New England fall foliage road trip is perfect for those who love a mix of nature, history, and good food. Starting in Boston, you can explore the Freedom Trail before heading to Portland for some fresh seafood. Bar Harbor offers stunning views of Acadia National Park, while North Conway invites you to unwind in the mountains.

The rhythm of the trip is relaxed, with two nights in North Conway allowing you to take your time. Stowe’s charming streets and Lenox’s cultural spots add to the experience before you loop back to Boston. It’s a great way to enjoy the changing leaves and the local flavors at a leisurely pace.

Boston
Day 1–2

Boston

1 night · Travel guide
Walk the Freedom Trail, enjoy dinner in the North End
Things to do
Nearby: Freedom Trail
Portland
Day 2–3

Portland

1 night · Travel guide
Explore the Old Port, visit Portsmouth for lunch and sights
Things to do
Nearby: Old Port · Portsmouth
Bar Harbor
Day 3–4

Bar Harbor

1 night · Travel guide
Hike in Acadia National Park, sunset at Cadillac Mountain
Things to do
Nearby: Acadia National Park · Cadillac Mountain
North Conway
Day 4–6

North Conway

2 nights · Travel guide
Explore the White Mountains, drive the Kancamagus Highway
Hiking or leaf-peeping in the White Mountains
Things to do
Nearby: White Mountains · Kancamagus Highway
Stowe
Day 6–7

Stowe

1 night · Travel guide
Visit Stowe Village, enjoy local cider tasting
Things to do
Nearby: Stowe Village
Lenox
Day 7–8

Lenox

1 night · Travel guide
Explore the Berkshires, enjoy a nice dinner in Lenox
Things to do
Nearby: Berkshires
Boston
Day 8–9

Boston

1 night · Travel guide
Relax and enjoy a final day in Boston before departure
Things to do
Make this trip yours →

from ~$1,834 p.p. · a rough estimate for flights and stays; you pick the real ones

The Kiomigo promise

Make this your route

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Change any stop, any stay, any day. Even mid-trip. Only your flights are fixed.

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No group bus. No fixed program. Stay longer where it is good, skip what is not.

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Tick off what you dream of, not what the world expects.

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9 days · 7 stops from ~$1,834 p.p. Make it yours →