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1
Middletown
2
Cape Neddick
3
Portland
4
Bar Harbor
5
North Conway
6
Kancamagus Highway
7
Portsmouth

6-Day Fall Foliage Road Trip from Wilmington to Philadelphia

1 days
7 cities
39 experiences
6 hotels
7 transports
Download
Wilmington
Middletown
Oct 3 – 4
Cape Neddick
Oct 4 – 4
Portland
Oct 4 – 4
Bar Harbor
Oct 4 – 7
North Conway
Oct 7 – 7
Kancamagus Highway
Oct 7 – 7
Portsmouth
Oct 7 – 15
Philadelphia
Day 1
Oct 3 – 4
Middletown

Hey! Your trip kicks off in Middletown, Rhode Island, a charming spot just minutes from Newport's famous mansions. This leg is perfect for soaking in the stunning coastal fall foliage and enjoying a relaxing walk along the Cliff Walk, offering breathtaking ocean views paired with vibrant autumn colors. It's a great way to start your journey with a blend of historic charm and natural beauty before heading up to Maine.

Stay
Day 1
Oct 3 – 4
1 night

Sonesta Select Newport Middletown

7.6
Good1,010 reviews
Itinerary
Day 1
Oct 3 – 4
Day 1•Oct 3•2 Experiences

Arrival in Middletown and Relaxing Evening

Day 2•Oct 4•3 Experiences

Gilded Age Mansion Tour and Departure

Day 2
Oct 4 – 4
Cape Neddick

On October 4th, enjoy a scenic stop in Cape Neddick, Maine, a charming coastal town known for its stunning fall foliage and the iconic Nubble Lighthouse. This picturesque spot offers a perfect blend of natural beauty and quaint New England charm, ideal for a relaxing walk and photo opportunities. It's a great way to break up your drive from Middletown to Portland while soaking in some of the region's best autumn colors.

Stay
Day 2
Oct 4 – 4
Add a stay for Cape Neddick
Day 2
Oct 4 – 4
Portland

On October 4th, enjoy a stop in Portland, Maine, a vibrant coastal city known for its charming Old Port district, excellent seafood, and scenic waterfront. This leg offers a perfect blend of urban exploration and fall foliage views, with opportunities to stroll through historic streets, visit local shops, and savor fresh lobster rolls. Portland serves as a delightful midpoint between Cape Neddick and Bar Harbor, making it an ideal spot to relax and soak in the autumn colors before heading to Acadia National Park.

Stay
Day 2
Oct 4 – 4
Add a stay for Portland
Days 2-5
Oct 4 – 7
Bar Harbor

Your stay in Bar Harbor from October 4th to 7th places you right in the heart of Acadia National Park, a must-see for fall foliage enthusiasts. Enjoy scenic drives, hiking trails, and the breathtaking views from Cadillac Mountain, the first place to see sunrise in the U.S. This leg offers a perfect blend of nature, outdoor activities, and charming small-town vibes to maximize your autumn experience.

Stay
Days 2-5
Oct 4 – 7
3 nights

Days Inn Bar Harbor

Breakfast included
7.4
Good1,009 reviews
Itinerary
Days 2-5
Oct 4 – 7
Day 2•Oct 4••4 Experiences

Arrival and Settling into Bar Harbor

Day 3•Oct 5••6 Experiences

Acadia National Park and Summit Views

Day 4•Oct 6••5 Experiences

Bar Harbor Village and Coastal Charm

Day 5•Oct 7•Weather icon22°C•2 Experiences

Departure from Bar Harbor

Day 5
Oct 7 – 7
North Conway

On October 7th, enjoy a day in North Conway, a charming village nestled in the White Mountains. This destination offers stunning fall foliage views, quaint shops, and local dining. It's the perfect spot to relax and soak in the vibrant autumn colors before heading out on the scenic drive along the Kancamagus Highway the next day.

Stay
Day 5
Oct 7 – 7
Add a stay for North Conway
Day 5
Oct 7 – 7
Kancamagus Highway

On October 7th, enjoy a scenic drive along the iconic Kancamagus Highway, renowned for its breathtaking fall foliage views. This route offers numerous opportunities for short hikes, photo stops, and immersing yourself in New Hampshire's vibrant autumn colors. It's a perfect day to experience the heart of New England's fall beauty before heading to Portsmouth.

Stay
Day 5
Oct 7 – 7
Add a stay for Kancamagus Highway
Days 5-13
Oct 7 – 15
Portsmouth

Your stay in Portsmouth, New Hampshire, from October 7th to 15th offers a perfect blend of charming coastal town vibes and stunning fall foliage. Explore the historic downtown area with its walkable streets, local shops, and excellent dining options. Portsmouth also serves as a great base for a scenic drive along the Kancamagus Highway, ensuring you maximize your fall colors before heading back to Philadelphia.

Stay
Days 5-13
Oct 7 – 15
8 nights
Add a stay for Portsmouth
Itinerary
Days 5-13
Oct 7 – 15
Day 5•Oct 7•1 Experience

Arrival in Portsmouth

Day 6•Oct 8•4 Experiences

Historic Portsmouth Exploration and Ghost Tour

Day 7•Oct 9•2 Experiences

Biking the Coast

Day 8•Oct 10•1 Experience

Nature and Greenway Trails

Day 9•Oct 11•2 Experiences

Shopping in Kittery

Day 10•Oct 12•2 Experiences

Park Strolls and Local Flavors

Day 11•Oct 13•2 Experiences

Coastal Landmarks

Day 12•Oct 14•2 Experiences

Historic Mansions

Day 13•Oct 15•1 Experience

Departure

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This itinerary was created with Layla, the free AI trip planner.