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Vacations By Rail · Escorted tour

Fall Colors, Scenic Trains & Martha's Vineyard

Ten-day New England fall foliage tour from Boston with scenic trains and Martha's Vineyard

Illustration of Fall Colors, Scenic Trains & Martha's Vineyard

Vacations By Rail's ten-day Fall Colors, Scenic Trains & Martha's Vineyard is an escorted journey through five New England states, beginning in Boston and ending in Oak Bluffs on Martha's Vineyard. A Tour Manager accompanies the group throughout, coordinating all logistics, guided excursions, meals, and travel. The itinerary moves by motorcoach, scenic train, river cruiser, and ferry, with stops in Portland, Maine; Plymouth, New Hampshire; Sturbridge and Mystic, Connecticut; and Martha's Vineyard. You ride the Conway Scenic Railroad through Crawford Notch with views of Mount Washington, take a narrated cruise across Lake Winnipesaukee, visit the Mystic Seaport Museum and Old Sturbridge Village living-history museum, and enjoy a five-course dinner aboard the Cape Cod Central Railroad as it crosses the Cape Cod Canal. The tour traces New England's maritime and colonial heritage, moving through autumn foliage along the Kancamagus Highway and coastal towns. Nine nights in three- and four-star hotels, daily breakfast, and five additional meals are included. This trip suits first-time rail travellers seeking guided comfort and history enthusiasts wanting to explore the region's museums and landmarks.

What to know before you look closer

  • Flights and airport transfers are not included; transfers to Boston South Station or Logan Airport are available for departures after 1:00 p.m. on the final day
  • The from-price of $3,499 USD applies to Standard Class rail; upgrades are available but unspecified in the operator's details
  • Day 1 features no guided activities; you arrive and make your own way to the hotel; an optional Old Town Trolley tour is payable locally

Day by day

  1. Day 1overnight: Boston, MA

    Arriving in New England in Boston

    Arrive in Boston and make your own way to the downtown Back Bay hotel. Free afternoon, with an optional Old Town Trolley tour (payable locally). Meet the Tour Manager and travel group this evening; dinner on your own.

  2. Day 2overnight: Portland, ME

    Sightseeing in Boston and on to Maine

    Guided city tour of Boston including the Freedom Trail (16 sites) and Quincy Market, then a motorcoach journey north to Portland, Maine, checking into a hotel on Casco Bay.

  3. Day 3overnight: Portland, ME

    A look at Maine's maritime history

    Travel to Bath, Maine, to visit the Maine Maritime Museum (over 21,000 artifacts, site of the historic Wyoming shipyard), then board a river cruiser on the Kennebec River passing the Bath Iron Works and Doubling Point Lighthouse. Return via Freeport with free time for lunch, then a lobster dinner at a local restaurant.

  4. Day 4railovernight: Plymouth, NH

    The Conway Scenic Railroad

    Drive to North Conway, New Hampshire, to ride the Conway Scenic Railroad toward Crawford Notch Station, with views of Crawford Notch and Mount Washington, then continue by motorcoach through Franconia Notch State Park to the hotel in Plymouth, NH.

  5. Day 5overnight: Plymouth, NH

    Cruising Lake Winnipesaukee

    Coach to Weirs Beach to board the MS Mount Washington for a narrated cruise across Lake Winnipesaukee to Wolfeboro, NH, then return to Plymouth via the Kancamagus Highway.

  6. Day 6overnight: Sturbridge, MA

    The scenic drive to Sturbridge

    Drive to Sturbridge, Massachusetts, stopping in Concord to tour the New Hampshire State Capitol Building, then a traditional New England dinner at an 18th-century farmhouse restaurant set on 600 acres.

  7. Day 7overnight: Mystic, CT

    Stepping back in time at Old Sturbridge Village

    Tour Old Sturbridge Village, a living-history museum with gardens, farms and heritage-breed animals, followed by lunch at a historic inn, then travel to Mystic, Connecticut, with free time to explore.

  8. Day 8railovernight: Hyannis, MA

    Mystic Seaport and the Cape Cod Central Railroad's Dinner Train

    Visit Mystic Seaport, a maritime museum founded in 1929, then travel to Hyannis, MA, on Cape Cod for a two-night stay. Evening excursion aboard the Cape Cod Central Railroad's Dinner Train through cranberry bogs and marshes, with a five-course dinner crossing the Cape Cod Canal Railroad bridge to Buzzard's Bay.

  9. Day 9overnight: Hyannis, MA

    An island adventure to Martha's Vineyard

    Ferry from Woods Hole aboard the M/V Island Home to Martha's Vineyard for a guided driving tour, with time for shopping and dining in Edgartown and a visit to the Victorian gingerbread cottages of Oak Bluffs, returning to Hyannis by ferry in the late afternoon.

  10. Day 10

    Tour conclusion

    Check out of the hotel and transfer by coach back to Boston, with included transfers to Boston's South Station or Logan Airport accommodating trains and flights departing after 1:00 p.m.

The moments this trip is built around

  • Day 4Ride the Conway Scenic Railroad toward Crawford Notch Station with views of Crawford Notch and Mount Washington
  • Day 5Board the MS Mount Washington for a narrated cruise across Lake Winnipesaukee to Wolfeboro, returning via the Kancamagus Highway
  • Day 8Evening excursion aboard the Cape Cod Central Railroad Dinner Train through cranberry bogs and marshes, crossing the Cape Cod Canal Railroad bridge with a five-course dinner
  • Day 9Ferry to Martha's Vineyard for a guided tour including the Victorian gingerbread cottages of Oak Bluffs and shopping in Edgartown

Included

  • Expertise of a Tour Manager from start to finish
  • 9 nights' hotel accommodation
  • Standard Class rail travel on local rail networks
  • All rail and coach travel throughout the tour
  • Breakfast each day, 2 lunches, 3 dinners
  • All guided tours and excursions

Not included

  • Cancellation & Travel Insurance
  • Flights and Airport transfers

Questions travellers ask

Is train travel included?
Yes. The package includes standard-class rail travel on the Conway Scenic Railroad and the Cape Cod Central Railroad Dinner Train, plus all motorcoach and boat transfers. Rail and coach travel throughout the tour is covered.
Is this an escorted tour?
Yes. Vacations By Rail provides a Tour Manager from start to finish. All guided tours, excursions, and transfers are arranged; you do not travel independently.
What meals are included?
Breakfast each day, two lunches, and three dinners. The Cape Cod Central Dinner Train includes a five-course dinner. Day 1 dinner is on your own.
Which two scenic trains are featured?
The Conway Scenic Railroad toward Crawford Notch Station in New Hampshire, and the Cape Cod Central Railroad Dinner Train departing Hyannis through cranberry bogs and marshes.
How much walking and physical activity is involved?
Rated Mobility Level 2. The tour includes city walking tours, museum visits, and typical travel logistics such as luggage handling and boarding buses and trains, but no hiking or high-altitude activity.
When does this tour run?
The itinerary is designed for fall foliage season. Specific departure dates are not listed in the operator's information; confirm with Vacations By Rail for availability.

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