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1
Bangor
2
Bar Harbor
3
Portland
4
North Conway
5
Salem
6
Boston
7
Newport
8
Mystic
9
Poughkeepsie
10
Philadelphia
11
Wilmington
12
Washington

14-Day Northeastern Fall Road Trip

14 days
12 cities
104 experiences
12 hotels
12 transports
Download
Bangor
Oct 15 – 15
Bar Harbor
Oct 15 – 17
Portland
Oct 17 – 17
North Conway
Oct 17 – 18
Salem
Oct 18 – 19
Boston
Oct 19 – 21
Newport
Oct 21 – 22
Mystic
Oct 22 – 23
Poughkeepsie
Oct 23 – 25
Philadelphia
Oct 25 – 27
Wilmington
Oct 27 – 27
Washington
Oct 27 – 29
Day 1
Oct 15 – 15
Bangor

Starting your fall road trip at Bangor International Airport places you right at the gateway to Maine's stunning natural beauty and vibrant autumn colors. Bangor offers a charming small-town atmosphere with easy access to the scenic wonders of the region, making it a perfect launch point for your journey. Enjoy the crisp fall air and the picturesque landscapes as you begin your adventure.

Car Rental
Oct 15
Kia Soul

Kia Soul

Compact • Automatic • 4-5 Door
Stay
Day 1
Oct 15 – 15
Add a stay for Bangor
Days 1-3
Oct 15 – 17
Bar Harbor

Hi! Your fall road trip kicks off beautifully in Bar Harbor, Maine, where you and your husband can immerse yourselves in the stunning fall foliage and charming coastal vibes. Explore Acadia National Park's scenic trails and enjoy cozy moments in this quintessential New England town. It's the perfect start to your 17-day adventure!

Stay
Days 1-3
Oct 15 – 17
2 nights

Bar Harbor Manor

Deluxe Room, 2 Queen Beds, Non Smoking
9.6
Wonderful1,003 reviews
Located directly in the West Street Historic District
Itinerary
Days 1-3
Oct 15 – 17
Day 1•Oct 15•Weather icon15°C•4 Experiences

Arrival in Bar Harbor and Evening Ghost Tour

Day 2•Oct 16•Weather icon9°C•5 Experiences

Exploring Acadia National Park and Scenic Coastal Views

Day 3•Oct 17•Weather icon13°C•3 Experiences

Morning in Bar Harbor and Departure to Portland

Day 3
Oct 17 – 17
Portland

Your trip begins in Portland, Maine, a charming coastal city known for its vibrant arts scene and delicious seafood. Explore the historic Old Port district, enjoy stunning views of Casco Bay, and savor fresh lobster rolls. Portland is the perfect starting point for your fall road trip, offering a blend of coastal beauty and New England charm.

Stay
Day 3
Oct 17 – 17
Add a stay for Portland
Day 3
Oct 17 – 18
North Conway

Your journey through North Conway, New Hampshire, offers a perfect blend of breathtaking fall foliage and charming New England village vibes. Explore the scenic mountain views and enjoy cozy moments in local cafes, making it an ideal stop for a romantic getaway with your husband. This leg sets the tone for your 17-day fall road trip with unforgettable natural beauty and peaceful relaxation.

Stay
Day 3
Oct 17 – 18
1 night

Kearsarge Inn

9.8
Wonderful1,001 reviews
Located just 5 minutes from historic Conway Scenic Railway
Itinerary
Day 3
Oct 17 – 18
Day 3•Oct 17•4 Experiences

Scenic Arrival and White Mountain Exploration in North Conway

Day 4•Oct 18•4 Experiences

Morning in North Conway and Departure to Salem

Day 4
Oct 18 – 19
Salem

Explore the charming and historic town of Salem, Massachusetts, known for its rich colonial history and famous witch trials. In mid-October, Salem comes alive with festive fall events and spooky Halloween celebrations, making it a perfect stop on your fall road trip. Enjoy walking through the quaint streets, visiting museums, and soaking in the autumn atmosphere before heading to Boston.

Stay
Day 4
Oct 18 – 19
1 night

Silsbee's by Daniels House

Family SuiteBreakfast included
9.6
Wonderful90 reviews
Located in the heart of the historic district, steps from Salem Common
Itinerary
Day 4
Oct 18 – 19
Day 4•Oct 18•Weather icon18°C•7 Experiences

Exploring Salem's Witch Trial History and Historic Charm

Day 5•Oct 19•Weather icon22°C•5 Experiences

Coastal Heritage and Art in Salem

Days 5-7
Oct 19 – 21
Boston

Your trip includes a stop in Boston, Massachusetts, where you can immerse yourself in the city's rich history and vibrant fall atmosphere. Explore iconic landmarks like the Freedom Trail, enjoy the colorful autumn foliage in Boston Common, and savor delicious seafood by the harbor. This leg perfectly blends historical exploration with the beauty of fall in New England, making it a memorable part of your road trip.

Stay
Days 5-7
Oct 19 – 21
2 nights

The Dagny Boston

Superior Room, 2 Queen Beds
9.6
Wonderful7,448 reviews
Centrally located near the Freedom Trail and Faneuil Hall
Itinerary
Days 5-7
Oct 19 – 21
Day 5•Oct 19•Weather icon21°C•5 Experiences

Historic Boston Exploration and Freedom Trail Walk

Day 6•Oct 20•Weather icon20°C•7 Experiences

Tea Party History and Waterfront Stroll

Day 7•Oct 21•Weather icon20°C•5 Experiences

Beacon Hill Charm and Departure

Day 7
Oct 21 – 22
Newport

On your way to Mystic, Connecticut, make sure to stop in Newport, Rhode Island, a charming coastal city known for its stunning Gilded Age mansions and vibrant waterfront. Enjoy a scenic stroll along the Cliff Walk and savor fresh seafood while taking in the picturesque harbor views. Newport's rich history and beautiful fall scenery make it a perfect highlight of your northeastern road trip.

Stay
Day 7
Oct 21 – 22
1 night

Mill Street Inn

Studio Suite, 1 King BedBreakfast included
9.8
Wonderful1,000 reviews
Steps away from historic Thames Street and Bowen's Wharf
Itinerary
Day 7
Oct 21 – 22
Day 7•Oct 21•Weather icon13°C•4 Experiences

Scenic Cliff Walk and Historic Newport Trolley Tour

Day 8•Oct 22•Weather icon10°C•4 Experiences

Vanderbilt Mansions and Coastal Drives in Newport

Day 8
Oct 22 – 23
Mystic

On your way to Poughkeepsie, make a stop in Mystic, Connecticut, to enjoy its charming coastal vibe and rich maritime history. Explore the Mystic Seaport Museum and savor fresh seafood while soaking in the fall colors. This leg offers a perfect blend of scenic beauty and historical exploration for you and your husband.

Stay
Day 8
Oct 22 – 23
1 night

The Taber Inne & Suites

Deluxe Room, 1 Queen BedBreakfast included
9.6
Wonderful1,002 reviews
Historic property with classic New England charm
Itinerary
Day 8
Oct 22 – 23
Day 8•Oct 22•5 Experiences

Maritime History and Coastal Charm in Mystic

Day 9•Oct 23•3 Experiences

Charming Village Stroll and Departure

Days 9-11
Oct 23 – 25
Poughkeepsie

Your trip includes a stop in Poughkeepsie, New York, where you can enjoy the beautiful fall scenery along the Hudson River. This charming city offers a perfect blend of nature and history, with highlights like the Walkway Over the Hudson, a breathtaking pedestrian bridge with panoramic views. It's an ideal spot to relax and take in the vibrant autumn colors before continuing your journey.

Stay
Days 9-11
Oct 23 – 25
2 nights

Homewood Suites by Hilton Poughkeepsie

Breakfast included
9.6
Wonderful1,001 reviews
Full kitchens with stovetops and refrigerators for longer stays
Itinerary
Days 9-11
Oct 23 – 25
Day 9•Oct 23•1 Experience

Arrival and Evening Stroll in Poughkeepsie

Day 10•Oct 24•4 Experiences

Exploring FDR History and Culinary Delights

Day 11•Oct 25•1 Experience

Departure to Philadelphia

Days 11-13
Oct 25 – 27
Philadelphia

Your trip includes a visit to Philadelphia, Pennsylvania, where you can explore iconic historical landmarks such as the Liberty Bell and Independence Hall. This leg offers a perfect blend of rich American history and vibrant city life, making it an essential stop on your northeastern road trip. Enjoy the charming fall atmosphere as you walk through the streets steeped in revolutionary heritage.

Stay
Days 11-13
Oct 25 – 27
2 nights

Penn's View Hotel

Standard Room, 1 Queen Bed with Juliet Balcony - Penn's Landing Bridge View
9.4
Wonderful1,272 reviews
Located steps from Independence National Historical Park
Itinerary
Days 11-13
Oct 25 – 27
Day 11•Oct 25•Weather icon16°C•3 Experiences

Arrival in Philadelphia and Evening Exploration

Day 12•Oct 26•Weather icon16°C•5 Experiences

Historic Philadelphia Walking Tour and Landmarks

Day 13•Oct 27•Weather icon15°C•4 Experiences

Revolutionary History and Departure

Day 13
Oct 27 – 27
Wilmington

On your way from Bangor to Washington, D.C., make a memorable stop in Wilmington, Delaware. This charming city offers a perfect blend of history and scenic beauty, ideal for a relaxing break during your fall road trip. Enjoy the vibrant autumn colors and explore local landmarks before continuing your journey to the nation's capital.

Stay
Day 13
Oct 27 – 27
Add a stay for Wilmington
Days 13-15
Oct 27 – 29
Washington

Explore the heart of American history in Washington, D.C., where you and your husband can visit iconic landmarks like the Lincoln Memorial, the Washington Monument, and the White House. Mid-October is perfect for enjoying the crisp fall air and vibrant autumn colors while walking through the National Mall and other historic sites. This leg of your road trip offers a rich blend of culture, history, and scenic beauty, making it a memorable highlight of your journey.

Stay
Days 13-15
Oct 27 – 29
2 nights

The Mayflower Hotel, Autograph Collection

Room, 1 King Bed
8.8
Very Good1,003 reviews
Historic landmark hotel listed on National Register of Historic Places
Itinerary
Days 13-15
Oct 27 – 29
Day 13•Oct 27•Weather icon17°C•8 Experiences

Arrival and Exploring the National Mall Monuments

Day 14•Oct 28•Weather icon14°C•7 Experiences

Capitol Hill and Iconic DC Landmarks

Day 15•Oct 29•Weather icon15°C•6 Experiences

Tidal Basin Memorials and Departure

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