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Boston

Newport

Mystic

Stowe

North Conway

Portland

Kennebunkport

11-Day New England Fall Road Trip

11 days

7 cities

65 experiences

7 hotels

6 transports

Download

Boston

Sep 28 – 30

Newport

30 Sep – 1 Oct

Mystic

Oct 1 – 2

Stowe

Oct 2 – 4

North Conway

Oct 4 – 6

Portland

Oct 6 – 7

Kennebunkport

Oct 7 – 8

Boston

Days 1-3

Sep 28 – 30

Boston

Hey! Your trip kicks off in Boston, Massachusetts, where history meets vibrant city life. Explore the iconic Freedom Trail, enjoy the charming waterfront, and savor world-class seafood. This leg perfectly blends historic landmarks, coastal charm, and urban energy to set the tone for your New England adventure.

Car Rental

Sep 28

Toyota Corolla

Compact • Automatic • 2/4 Door

Stay

Days 1-3

Sep 28 – 30

2 nights

Clarendon Square

Deluxe Room, 1 Queen Bed, Private Bathroom

9.2

Wonderful256 reviews

Victorian-style boutique guesthouse in the historic South End

Itinerary

Days 1-3

Sep 28 – 30

Day 1•Sep 28•

18°C•5 Experiences

Historic Boston Charm and Beacon Hill Stroll

Day 2•Sep 29•

27°C•5 Experiences

Culture and Sunset Sails in Boston

Day 3•Sep 30•

24°C•3 Experiences

Boston Skyline Views and Departure

Day 3

30 Sep – 1 Oct

Newport

Experience the charm of Newport, Rhode Island, with its stunning coastal views and historic mansions. Enjoy romantic walks along the Cliff Walk and savor fresh seafood at waterfront restaurants. This leg offers a perfect blend of classic New England elegance and breathtaking ocean scenery for a memorable getaway.

Stay

Day 3

30 Sep – 1 Oct

1 night

The Chanler at Cliff Walk

Federal

9.8

Wonderful303 reviews

Located directly on the historic Cliff Walk trail

Itinerary

Day 3

30 Sep – 1 Oct

Day 3•Sep 30•

23°C•5 Experiences

Gilded Age Mansions and Sunset Sails in Newport

Day 4•Oct 1••5 Experiences

Coastal Elegance and Ocean Views Before Heading South

Day 4

Oct 1 – 2

Mystic

On your journey through Mystic, Connecticut, immerse yourselves in the charm of this historic coastal town known for its quaint maritime village atmosphere and picturesque waterfront views. Enjoy romantic strolls along the Mystic River, explore the famous Mystic Seaport Museum, and savor fresh seafood at cozy local eateries. This leg perfectly blends classic New England charm with relaxing coastal vibes, setting a lovely tone for your trip.

Stay

Day 4

Oct 1 – 2

1 night

Eileen of Mystic

Suite 4: The White RoomBreakfast included

10.0

Wonderful71 reviews

Charming bed & breakfast setting matches the requested style

Itinerary

Day 4

Oct 1 – 2

Day 4•Oct 1•5 Experiences

Maritime History and Coastal Charm in Mystic

Day 5•Oct 2•3 Experiences

Morning Stroll and Departure to Vermont

Days 5-7

Oct 2 – 4

Stowe

Experience the charm of Stowe, Vermont, nestled in the heart of the Green Mountains. Enjoy breathtaking mountain scenery, cozy up in romantic boutique inns, and explore classic New England villages with your loved one. This leg promises a perfect blend of nature, comfort, and quintessential autumn vibes for your trip.

Stay

Days 5-7

Oct 2 – 4

2 nights

Green Mountain Inn

9.6

Wonderful1,003 reviews

Historic charm in heart of Stowe village

Itinerary

Days 5-7

Oct 2 – 4

Day 5•Oct 2•

17°C•2 Experiences

Arrival in Stowe and Cozy Evening Dinner

Day 6•Oct 3••4 Experiences

Scenic Paths and Local Flavors in Stowe

Day 7•Oct 4••2 Experiences

Mountain Views and Departure to New Hampshire

Days 7-9

Oct 4 – 6

North Conway

Experience the charm of North Conway, New Hampshire, nestled in the heart of the White Mountains. Enjoy breathtaking mountain scenery, explore classic New England villages, and indulge in cozy evenings at romantic boutique inns. This leg of your trip promises a perfect blend of nature and quaint small-town charm, ideal for a memorable autumn escape.

Stay

Days 7-9

Oct 4 – 6

2 nights

The White Mountain Hotel & Resort

Breakfast included

9.2

Wonderful1,005 reviews

Full-service spa offering massages and body treatments

Itinerary

Days 7-9

Oct 4 – 6

Day 7•Oct 4•2 Experiences

Arrival and Scenic Kancamagus Highway Drive

Day 8•Oct 5•2 Experiences

White Mountain Exploration and Nature Walks

Day 9•Oct 6•3 Experiences

Morning Shopping and Departure to Portland

Day 9

Oct 6 – 7

Portland

Experience the charm of Portland, Maine, with its vibrant arts scene, historic Old Port district, and renowned seafood cuisine. Enjoy scenic coastal views and explore boutique shops and galleries that capture the essence of New England. This leg offers a perfect blend of culture, culinary delights, and picturesque harbor views.

Stay

Day 9

Oct 6 – 7

1 night

The Weldon Hotel

Standard Suite, 1 Queen Bed

9.8

Wonderful118 reviews

4.5-star luxury rating fits your comfort requirements

Itinerary

Day 9

Oct 6 – 7

Day 9•Oct 6•

1°C•5 Experiences

Coastal Views and Casco Bay Cruises

Day 10•Oct 7••4 Experiences

Exploring Historic Portland and Victorian Elegance

Day 10

Oct 7 – 8

Kennebunkport

Kennebunkport, Maine, is a charming coastal town known for its quaint seaside village atmosphere, beautiful beaches, and historic architecture. It's the perfect spot to enjoy romantic coastal drives and savor fresh seafood, especially lobster. This destination offers a cozy and picturesque setting that fits perfectly with your New England autumn escape.