Fall Foliage Rail Holiday • View Itinerary
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Portland, Oregon
Boston, USA
Paul Revere Statue, Boston
Autumn in Boston Public Garden
California Zephyr
Portland Head Lighthouse in Maine

Fall Foliage By Rail

6 day Rail Holiday – from £1155

With flights from £1705

This fall foliage excursion through New England is the perfect way to spend 6 days during this colourful season.

Highlights:
  • Explore historic Boston along this iconic trail
  • Visit the USA’s oldest park for a tranquil escape
  • Witness the stunning colors of autumn
  • Experience both land and sea on a unique expedition
  • Enjoy the vibrant nightlife in Portland

Your Itinerary

Expand All

This itinerary is customisable. Just let us know if you would like to add extra nights, activities or destinations.

Boston, USA

Day 1 – Welcome to Boston

Welcome to the Boston! This historic coastal city is full of sights you won’t want to…

Welcome to the Boston! This historic coastal city is full of sights you won’t want to miss. Begin to explore ‘Beantown’ today on your hop on, hop off sightseeing tour of the city. Visit historic sites, like Paul Revere’s House, the Boston Common, and the Old State House. Take a leisurely stroll through the gorgeous Public Garden and enjoy a swan boat ride. You’ll also have the chance to see Boston’s modern marvels, including Copley Square and the Boston Christian Science Centres magnificent reflecting pool.

    Sheraton Boston or similar

Boston, USA
Paul Revere Statue, Boston

Day 2 – Boston

Relive history with a journey back in time to the Revolutionary War era as you follow…

Relive history with a journey back in time to the Revolutionary War era as you follow the route of Paul Revere as he warned the countryside with his infamous cry of ‘the British are coming!’ Travel along the famous Battle Road Trail and see the homes of renowned literary greats, like Hawthorne, Alcott, and Emerson in the charming town of Concord. Stand on Lexington Green, where Captain Jonathan Parker and 77 Minutemen fiercely stood their ground against 700 Redcoats. Visit the Old North Bridge, where the ‘shot heard round the world’ was fired. Hang out in Harvard Yard and stroll through Cambridge Common, where George Washington took control of the Continental Army. Drive along ‘Tory Row’ past the home of Henry Wadsworth Longfellow. Today is a history lover’s dream come true!  

    Sheraton Boston or similar

Paul Revere Statue, Boston
Autumn in Boston Public Garden

Day 3 – Boston

Take a ride through a region awash in stunning seasonal colours. Sit back and relax as…

Take a ride through a region awash in stunning seasonal colours. Sit back and relax as you travel past quiet ponds, ancient farms, weathered roadside taverns, and sturdy colonial churches, all of which are surrounded by the glorious red, orange, and yellow hues. Your pleasant afternoon of leaf peeping will be capped off with a stop at a native orchard for apples and cider. Tonight enjoy dinner at one of Boston’s most iconic restaurants! 

    Sheraton Boston or similar

    Dinner
Autumn in Boston Public Garden
California Zephyr

Day 4 – Boston to Portland

Wake up this morning and travel on your own to Boston’s North Station, where you will…

Wake up this morning and travel on your own to Boston’s North Station, where you will board Amtrak for a ride on the north to Portland! The pubs, shops, and restaurants of downtown Portland are always buzzing with tourists, locals, and fishermen alike, creating a convivial atmosphere where everyone is welcome. Portland’s vibrant performing arts scene, amazing cuisine, and eclectic group of shops are all part of why locals call this city ‘New England’s Best Kept Secret’. There’s so much to do here—from food and wine festivals to trolley tours and art gallery exhibits.

    Westin Portland Harbour view or similar

California Zephyr
Portland Head Lighthouse in Maine

Day 5 – Portland

Explore Portland today on a tour of this classic New England city. Sit back and relax…

Explore Portland today on a tour of this classic New England city. Sit back and relax as your guide regales you with tales of Portland’s diverse history. When stopping along the way you will get to visit the childhood home of Henry Wadsworth Longfellow, the Victoria Mansion, and the busy Old Port. The tour will also stop at the many lighthouses that pepper Portland’s shores, particularly the Portland Head Light, Maine’s oldest lighthouse. Don’t forget to bring a camera!

    Westin Portland Harbour view or similar

Portland Head Lighthouse in Maine
Portland, Oregon

Day 6 – Farewell from Portland

Say a fond farewell to New England today as you depart to your next destination or…

Say a fond farewell to New England today as you depart to your next destination or head to the airport for your flight home.

Portland, Oregon

Your Itinerary

This itinerary is customisable. Just let us know if you would like to add extra nights, activities or destinations.

Day 1

|

Welcome to Boston

Welcome to the Boston! This historic coastal city is full of sights you won’t want to miss. Begin to explore ‘Beantown’ today on your hop on, hop off sightseeing tour of the city. Visit historic sites, like Paul Revere’s House, the Boston Common, and the Old State House. Take a leisurely stroll through the gorgeous Public Garden and enjoy a swan boat ride. You’ll also have the chance to see Boston’s modern marvels, including Copley Square and the Boston Christian Science Centres magnificent reflecting pool.

    Sheraton Boston or similar

Boston, USA

Day 2

|

Boston

Relive history with a journey back in time to the Revolutionary War era as you follow the route of Paul Revere as he warned the countryside with his infamous cry of ‘the British are coming!’ Travel along the famous Battle Road Trail and see the homes of renowned literary greats, like Hawthorne, Alcott, and Emerson in the charming town of Concord. Stand on Lexington Green, where Captain Jonathan Parker and 77 Minutemen fiercely stood their ground against 700 Redcoats. Visit the Old North Bridge, where the ‘shot heard round the world’ was fired. Hang out in Harvard Yard and stroll through Cambridge Common, where George Washington took control of the Continental Army. Drive along ‘Tory Row’ past the home of Henry Wadsworth Longfellow. Today is a history lover’s dream come true!  

    Sheraton Boston or similar

Paul Revere Statue, Boston

Day 3

|

Boston

Take a ride through a region awash in stunning seasonal colours. Sit back and relax as you travel past quiet ponds, ancient farms, weathered roadside taverns, and sturdy colonial churches, all of which are surrounded by the glorious red, orange, and yellow hues. Your pleasant afternoon of leaf peeping will be capped off with a stop at a native orchard for apples and cider. Tonight enjoy dinner at one of Boston’s most iconic restaurants! 

    Sheraton Boston or similar

    Dinner
Autumn in Boston Public Garden

Day 4

|

Boston to Portland

Wake up this morning and travel on your own to Boston’s North Station, where you will board Amtrak for a ride on the north to Portland! The pubs, shops, and restaurants of downtown Portland are always buzzing with tourists, locals, and fishermen alike, creating a convivial atmosphere where everyone is welcome. Portland’s vibrant performing arts scene, amazing cuisine, and eclectic group of shops are all part of why locals call this city ‘New England’s Best Kept Secret’. There’s so much to do here—from food and wine festivals to trolley tours and art gallery exhibits.

    Westin Portland Harbour view or similar

California Zephyr

Day 5

|

Portland

Explore Portland today on a tour of this classic New England city. Sit back and relax as your guide regales you with tales of Portland’s diverse history. When stopping along the way you will get to visit the childhood home of Henry Wadsworth Longfellow, the Victoria Mansion, and the busy Old Port. The tour will also stop at the many lighthouses that pepper Portland’s shores, particularly the Portland Head Light, Maine’s oldest lighthouse. Don’t forget to bring a camera!

    Westin Portland Harbour view or similar

Portland Head Lighthouse in Maine

Day 6

|

Farewell from Portland

Say a fond farewell to New England today as you depart to your next destination or head to the airport for your flight home.

Portland, Oregon

This Rail Holiday Includes

5 nights hotel accommodation
Comfortable travel by rail journey
Excursions and activities as detailed in the itinerary

Flights & More

With FREEDOM, you can book your Fall Foliage By Rail rail holiday and flights together, as an ATOL protected package. Our Travel Experts can find the best priced Economy, Premium or Business Class flights for you.

Next Step

Please get in touch with our America Experts to start planning your holiday. You’ll have a single point of contact from your first enquiry through booking.

Fall Foliage By Rail

6 day Rail Holiday – from £1155

With flights from £1705

Prices are per person, based on two people sharing a double or twin room and include meals where shown. Hotel and room facilities vary and may be subject to additional fees. Some hotels require payment of local city taxes on arrival. Amtrak travel is for Coach Accommodations unless otherwise stated. Upgrades to Roomette or Bedroom accommodations on board Amtrak are available. Call Freedom Destinations for departure dates and availability Seasonal variations may apply.

Map

Fall Foliage By Rail Map