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Vacations By Rail has withdrawn this trip from sale. We keep the page for reference and comparison. The same itinerary is still sold by another operator, listed under Also sold by below.

Vacations By Rail · Escorted tour

New England in the Fall

Nine-day New England fall foliage tour from Boston to Portland by rail and boat

Illustration of New England in the Fall

Vacations By Rail's New England in the Fall is a 9-day escorted autumn tour from Boston to Portland, visiting Salem, North Conway, and Kennebunkport. A Tour Manager accompanies the group throughout. The itinerary balances guided city exploration with heritage railway experiences and scenic cruises. Days begin in Boston with a guided tour of the Freedom Trail and historic landmarks; the tour then moves to the White Mountains to ride the Mount Washington Cog Railway to the summit and the Conway Scenic Railroad through Crawford Notch in vintage streamlined cars. A narrated cruise across Lake Winnipesaukee and visits to the Seashore Trolley Museum and Kennebunkport round out the journey. The tour includes 8 nights in 3 and 4-star hotels, all rail and coach travel, daily breakfast, two dinners, and all escorted excursions. It suits history lovers, photographers seeking fall foliage, and travelers who prefer guided itineraries with included experiences.

What to know before you look closer

  • Only 2 dinners are included; most other meals are not covered
  • Flights and airport transfers are not included in the from-price
  • Day 8 is free time in Portland with suggestions but no escorted activities

Day by day

  1. Day 1overnight: Boston

    Arrival in Massachusetts' capital, Boston

    Check in to the downtown hotel in the theater district; group dinner in the evening.

    Meals: Dinner

  2. Day 2overnight: Boston

    Uncovering historic Boston

    Guided tour of the Freedom Trail, Harvard University, Faneuil Hall, the Paul Revere House, USS Constitution, Copley Square and Beacon Hill.

    Meals: Breakfast

  3. Day 3overnight: North Conway

    Sailing to Salem and the White Mountains

    Hour-long boat cruise across Massachusetts Bay to Salem, free time there, then coach into the White Mountains to North Conway.

    Meals: Breakfast

  4. Day 4railovernight: North Conway

    Mount Washington Cog Railroad and Kancamagus Highway

    10am Mount Washington Cog Railroad to the summit, then a scenic drive along the Kancamagus Highway with stops for waterfalls and covered bridges.

    Meals: Breakfast

  5. Day 5railovernight: North Conway

    A superb journey on the Conway Scenic Railroad

    Ride the Mountaineer train on the Conway Scenic Railroad's Crawford Notch route in 1950s-era streamlined cars.

    Meals: Breakfast

  6. Day 6overnight: Portland

    Cruising Lake Winnipesaukee to Wolfeboro

    Narrated cruise on the historic MS Mount Washington across Lake Winnipesaukee to Wolfeboro, then on to Portland, Maine.

    Meals: Breakfast

  7. Day 7overnight: Portland

    Seashore Trolley Museum and Kennebunkport

    Visit the Seashore Trolley Museum near Kennebunkport with a ride on a vintage tram, then free time in Kennebunkport.

    Meals: Breakfast

  8. Day 8railovernight: Portland

    Free day in Portland

    Free day in Portland, with suggestions including the Maine Narrow Gauge Railroad and Museum and the Old Port district; group dinner in the evening.

    Meals: Breakfast, Dinner

  9. Day 9

    Homeward bound

    Return to Boston by Amtrak (luggage carried by coach) to connect with onward travel home.

    Meals: Breakfast

The moments this trip is built around

  • Day 2Guided tour of Boston's Freedom Trail, Harvard University, Faneuil Hall, the Paul Revere House, USS Constitution, Copley Square, and Beacon Hill
  • Day 4Mount Washington Cog Railway to the summit in bio-diesel trains, followed by a scenic drive along the Kancamagus Highway with stops for waterfalls and covered bridges
  • Day 5Ride the Mountaineer train on the Conway Scenic Railroad's Crawford Notch route in 1950s-era streamlined passenger cars through the White Mountains
  • Day 6Narrated cruise on the historic MS Mount Washington across Lake Winnipesaukee to Wolfeboro

Included

  • Expertise of a Tour Manager from start to finish
  • 8 nights' 3 & 4-Star hotel accommodation
  • All rail and coach travel throughout your tour
  • Coach Seat Class rail travel
  • Breakfast each day, 2 dinners
  • All tour excursions

Not included

  • Cancellation & Travel Insurance (not included but can be arranged)
  • Flights and Airport transfers not included

Also sold by

The same itinerary is listed by more than one company. Prices and inclusions can differ; compare before booking.

Questions travellers ask

Is all rail travel included?
Yes. The package includes Coach Seat Class rail travel on the Mount Washington Cog Railway, Conway Scenic Railroad, and the return Amtrak service to Boston. All rail, coach, and boat travel throughout the tour is covered.
Is this an escorted tour?
Yes. A Tour Manager travels with the group from start to finish.
Which trains do we ride?
The Mount Washington Cog Railway (bio-diesel trains from Marshfield station to the summit), the Conway Scenic Railroad's Mountaineer on the Crawford Notch route in 1950s streamlined cars, and Amtrak from Portland back to Boston on Day 9.
What hotels are included?
The Revere Hotel in Boston (2 nights), North Conway Grand Hotel (3 nights), and Aloft Portland Downtown Waterfront (3 nights). All are 3 or 4-star properties.
What meals are included?
Breakfast each day and two group dinners (one in Boston on Day 1, one in Portland on Day 8). Lunches are not included.
How much walking is involved?
The tour has a Mobility Rating 2, which includes guided walking tours of Boston, stairs in historic areas like Beacon Hill, and typical city walking in Salem, Kennebunkport, and Portland. Most excursions and train travel involve moderate activity.

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