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Great Rail Journeys · Escorted tour

New England in the Fall

Ten-day New England autumn loop from Boston through White Mountains to Portland

Illustration of New England in the Fall

Great Rail Journeys operates this 10-day escorted tour to New England in autumn, departing London Heathrow and spending days in Boston, the White Mountains, and Portland, Maine. A UK Tour Manager accompanies the group throughout. The itinerary balances guided city exploration with scenic rail journeys: Day 1 arrives in Boston; Day 2 covers a guided walking tour of the Freedom Trail and historic landmarks. Day 3 combines a cruise to Salem with a coach journey to North Conway. Days 4 and 5 feature two heritage railways: the Mount Washington Cog Railway (the world's first, opened 1869) climbing to the summit, and the North Conway Scenic Railroad's Mountaineer train running through Crawford Notch. Days 6 through 8 move to Portland, Maine, with a lake cruise, trolley museum visit, and lighthouse tour. Day 9 returns to Boston by Amtrak Downeaster before an overnight flight home. The tour is suited to first-time rail travellers and history enthusiasts seeking guided comfort and dramatic autumn scenery.

What to know before you look closer

  • Single supplement is GBP 1,500 (from GBP 5,099 total), significantly higher than half the double price; couples receive better value.
  • Group size capped at 30 travellers; the tour is escorted but not intimate.
  • Only two dinners are included; most other meals require independent arrangement or payment.

Day by day

  1. Day 1overnight: Boston

    Arrival in Massachusetts' capital, Boston

    Your holiday begins at London Heathrow airport, meeting the Tour Manager and fellow travellers ahead of the flight to Boston. Arriving in the late afternoon, transferred to the downtown hotel in the theatre district. Boston is the capital of Massachusetts and New England's largest city, one of the oldest European settlements in the United States and played a key role in American independence. Dinner together this evening at a local restaurant.

    Meals: Dinner

  2. Day 2overnight: Boston

    Uncovering historic Boston

    A guided sightseeing tour of Boston reveals the Freedom Trail, Harvard University, Faneuil Hall, the Paul Revere House, USS Constitution, Copley Square and Beacon Hill. The rest of the day is free to explore further - options include the Museum of Fine Arts, Fenway Park, or Cheers bar. Evening at leisure.

    Meals: Breakfast

  3. Day 3overnight: North Conway

    Sailing to Salem and the White Mountains

    Leaving Boston after breakfast, board an hour-long cruise across Massachusetts Bay to historic Salem, renowned for the witch trials of 1692. Free time over lunch to explore Salem. Later, board a coach to travel into the White Mountains through New Hampshire's 'golden season' scenery to the mountain village of North Conway.

    Meals: Breakfast

  4. Day 4railovernight: North Conway

    Mount Washington Cog Railway and Kancamagus Highway

    After an early breakfast, transfer to Marshfield station to board the 10am Mount Washington Cog Railway. This bio-diesel service runs on the world's first cog railway (opened 1869), climbing to the summit of Mount Washington with an hour at the top for panoramic views. Return by coach via Woodstock (free time over lunch) and along the Kancamagus Scenic Highway with stops at waterfalls and covered bridges. Return to hotel mid-afternoon, remainder of day at leisure.

    Meals: Breakfast

  5. Day 5railovernight: North Conway

    A superb journey on the North Conway Scenic Railroad

    Travel aboard the iconic Mountaineer train on the Crawford Notch route of the North Conway Scenic Railroad in 1950s-era streamlined passenger cars. The route travels over the rugged terrain of Crawford Notch and alongside the Saco River Valley to Bartlett. Transferred back to hotel by coach in the afternoon. Free afternoon and evening in North Conway.

    Meals: Breakfast

  6. Day 6overnight: Portland

    Cruising Lake Winnipesaukee to Wolfeboro

    Check out after breakfast and travel by coach to Weirs Beach on Lake Winnipesaukee. Board the historic MS Mount Washington for a narrated cruise across New Hampshire's largest lake. Disembark in Wolfeboro with free time over lunch to explore the 'oldest summer resort in America'. Journey eastwards to Portland, Maine. Free evening to dine independently.

    Meals: Breakfast

  7. Day 7overnight: Portland

    Seashore Trolley Museum and Portland Head Lighthouse

    Head to the Seashore Trolley Museum near Kennebunkport - the oldest and largest electric tram museum in the world (established 1939). Enjoy a ride on one of the exhibits. Continue to Fort Williams Park to visit Portland Head Lighthouse (dating from 1791, Maine's oldest lighthouse). Free time to explore the museum or park. Return to Portland for an independent dinner.

    Meals: Breakfast

  8. Day 8railovernight: Portland

    Free day in Portland

    A free day to explore Portland as you wish. Options include the Maine Narrow Gauge Railroad and Museum, museums and art galleries in the Old Port district including the IM Pei-designed Museum of Art, craft beer taprooms (Allagash, Shipyard, Bissell Brothers). Final dinner together at a local restaurant this evening.

    Meals: Breakfast, Dinner

  9. Day 9railovernight: In flight

    Return to Boston on Amtrak's Downeaster

    Step aboard the Amtrak Downeaster to return to Boston by rail while luggage is carried by coach. Free time in Boston including Quincy Market, the Public Garden and Boston Common. After transferring to the airport by coach, board the overnight flight home.

    Meals: Breakfast

  10. Day 10

    Homeward bound

    Landing back in the UK this morning, your exploration of New England in the Fall comes to a conclusion and you are free to make your way home.

The moments this trip is built around

  • Day 4Ride the Mount Washington Cog Railway, the world's first cog railway opened in 1869, climbing by bio-diesel to the summit with an hour for panoramic views.
  • Day 5Travel the North Conway Scenic Railroad's Mountaineer train in restored 1950s-era streamlined passenger cars through Crawford Notch alongside the Saco River Valley.
  • Day 3Cruise across Massachusetts Bay to historic Salem to explore the town linked to the 1692 witch trials.
  • Day 6Board the MS Mount Washington for a narrated cruise across Lake Winnipesaukee, New Hampshire's largest lake, to Wolfeboro.

Included

  • Expertise of a UK Tour Manager from start to finish
  • 8 nights' 3 & 4-Star hotel accommodation
  • Coach Seat Class rail travel
  • All rail, cruise and coach travel throughout the tour
  • Return flights from London Heathrow and Boston
  • Breakfast each day
  • 2 dinners
  • All guided tours and excursions

Not included

  • Cancellation & Travel Insurance

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Questions travellers ask

Is the train travel included?
Yes. The price includes all rail travel: the Mount Washington Cog Railway, North Conway Scenic Railroad, and Amtrak Downeaster, plus all coach and cruise travel throughout the tour.
Is this an escorted or independent tour?
Escorted. Great Rail Journeys provides a UK Tour Manager from London Heathrow through to the return flight; all guided tours, rail journeys, and transfers are arranged.
Which trains are included?
The Mount Washington Cog Railway to the summit of Mount Washington, the North Conway Scenic Railroad's Mountaineer on the Crawford Notch route, and Amtrak's Downeaster from Portland back to Boston.
What hotels are included?
The Revere Hotel in Boston (2 nights), the North Conway Grand Hotel in North Conway (3 nights), and the Aloft Portland Downtown Waterfront in Portland (3 nights), all 3- or 4-star.
When does the tour run?
Departures run in September and October 2026 and 2027, to experience New England's autumn colours.
How much walking is involved?
A guided sightseeing tour of Boston includes walking the Freedom Trail and city landmarks; Salem is explored during free time; other days involve museum visits and waterfall stops but no strenuous hiking.

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