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Louisville

Lexington

Cleveland

Aurora

Burlington

Kennebunk

Boston

11-Day Fall Foliage Road Trip from Kansas City to New England

11 days

7 cities

48 experiences

5 hotels

7 transports

Download

Kansas City

Louisville

Sep 27 – 28

Lexington

Sep 28 – 29

Cleveland

Sep 29 – 30

Aurora

30 Sep – 1 Oct

Burlington

Oct 1 – 3

Kennebunk

Oct 3 – 5

Boston

Oct 5 – 7

Kansas City

Day 1

Sep 27 – 28

Louisville

Hi! Your stop in Louisville, Kentucky, is a fantastic chance to explore the heart of bourbon country with visits to the iconic Buffalo Trace and Woodford Reserve distilleries. Plus, you can enjoy a tour of a beautiful retired thoroughbred horse farm, perfectly blending your interests in local culture and equestrian heritage. Don't miss the chance to dine on fine local cuisine and soak in the unique charm of Louisville before heading to Lexington!

Stay

Day 1

Sep 27 – 28

1 night

The Brown Hotel

Luxury Room, 1 King Bed, Non Smoking

9.4

Wonderful1,308 reviews

Itinerary

Day 1

Sep 27 – 28

Day 1•Sep 27•3 Experiences

Arrival in Louisville and Relaxing Evening

Day 2•Sep 28•3 Experiences

Exploring Louisville History Before Departing for Lexington

Day 2

Sep 28 – 29

Lexington

Experience the charm of Lexington, Kentucky, with a visit to a retired thoroughbred horse farm tour, immersing yourself in the heart of horse country. Enjoy the unique ambiance of the Manchester Hotel and savor fine local cuisine in the city known for its rich equestrian heritage. This leg offers a perfect blend of relaxation and cultural exploration before heading to Cleveland.

Stay

Day 2

Sep 28 – 29

1 night

The Manchester

Room (The Quad)

9.6

Wonderful1,421 reviews

Itinerary

Day 2

Sep 28 – 29

Day 2•Sep 28•4 Experiences

Bourbon and Bluegrass Horse Farms

Day 3•Sep 29•2 Experiences

Historic Estate and Departure

Day 3

Sep 29 – 30

Cleveland

On your stop in Cleveland, Ohio, enjoy a comfortable stay at the Hyatt Regency Cleveland at The Arcade, a unique and historic hotel. Explore the vibrant local dining scene with fine cuisine options for dinner. This leg offers a perfect blend of relaxation and urban charm as you prepare for your journey to Aurora, New York.

Stay

Day 3

Sep 29 – 30

1 night

Hyatt Regency Cleveland At The Arcade

Room, 2 Double Beds

9.0

Very Good1,302 reviews

Itinerary

Day 3

Sep 29 – 30

Day 3•Sep 29•

27°C•3 Experiences

Arrival in Cleveland and Fine Dining at The Arcade

Day 4•Sep 30•

28°C•1 Experience

Morning Departure to Aurora

Day 4

30 Sep – 1 Oct

Aurora

Your stay at the Inns of Aurora Resort & Spa offers a perfect blend of relaxation and local charm. Explore the quaint village of Aurora, known for its beautiful lakeside views and unique artisan shops. Don't miss the chance to enjoy fine dining experiences and the serene ambiance of this historic area, making it a delightful stop on your fall foliage journey.

Stay

Day 4

30 Sep – 1 Oct

1 night

Inns of Aurora Resort & Spa

Standard Room, 1 Queen Bed (Wallcourt Hall Deluxe Queen)

9.8

Wonderful483 reviews

Itinerary

Day 4

30 Sep – 1 Oct

Day 4•Sep 30•2 Experiences

Arrival in Aurora and Culinary Evening

Day 5•Oct 1•2 Experiences

Morning in Aurora and Departure to Vermont

Days 5-7

Oct 1 – 3

Burlington

Experience the charm of Burlington, Vermont, from October 1 to October 3, 2026, where you can enjoy the vibrant fall foliage along scenic blue highways and indulge in fine local cuisine. Stay at the luxurious Essex Resort and Spa, perfectly situated for exploring the area's natural beauty and cultural attractions. Don't miss the sunset cruise on Lake Champlain, offering breathtaking views that capture the essence of Vermont's autumn.

Stay

Days 5-7

Oct 1 – 3

2 nights

The Essex Resort & Spa

Culinary Double Queen

9.0

Very Good1,010 reviews

Itinerary

Days 5-7

Oct 1 – 3

Day 5•Oct 1•2 Experiences

Arrival and Relaxation in Burlington

Day 6•Oct 2•5 Experiences

Exploring Burlington and Lake Champlain Sunset

Day 7•Oct 3•2 Experiences

Departure for Maine

Days 7-9

Oct 3 – 5

Kennebunk

Experience the charm of Kennebunk, Maine, from October 3 to 5, 2026, with a stay at the cozy and inviting Inn at English Meadows. Enjoy the scenic coastal views and explore the quaint town known for its unique shops and fine dining options. This leg of your trip offers a perfect blend of relaxation and local culture, making it an ideal stop before heading to Boston.

Stay

Days 7-9

Oct 3 – 5

2 nights

Add a stay for Kennebunk

Itinerary

Days 7-9

Oct 3 – 5

Day 7•Oct 3•3 Experiences

Arrival in Kennebunk and Coastal Evening Views

Day 8•Oct 4•3 Experiences

Kennebunkport History and Iconic Coastal Views

Day 9•Oct 5•3 Experiences

Coastal Morning and Departure to Boston

Days 9-11

Oct 5 – 7

Boston

Your visit to Boston from October 5 to 7 offers a wonderful opportunity to explore the city's rich history and vibrant culture. Enjoy visiting relatives and savoring the local fine cuisine, making your stay both meaningful and delicious. Boston's charming neighborhoods and historic sites provide a perfect conclusion to your fall foliage road trip before your flight home.