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Fall Colors, Scenic Trains & Martha's Vineyard

Boston's Public Gardens Gay Head Cliffs, Martha's Vineyard Mystic Seaport Road along the Mountains Crawford Depot Doubling Point Lighthouse Nubble Lighthouse

Surround yourself with a kaleidoscope of autumn colors on this scenic tour of the Eastern seaboard.

10 days    $2,895

About the Tour

Whether it is the charm of yesteryear, fall scenes or iconic towns you seek, there is plenty to experience on this New England journey. Your round-trip expedition begins in Boston, where you have time to see the sites both on your own and with a guided sightseeing tour. Venturing out of the city, enjoy an unforgettable ride aboard the Cape Cod Central Railroad’s Elegant Dinner Train and sightseeing through the famed destination of Martha’s Vineyard. Spend a full day immersed in the maritime history of the region at Mystic Seaport and take in the autumn splendor of Massachusetts aboard the Essex Steam Train and the Becky Thatcher Riverboat. History comes to life once more at Old Sturbridge Village. Take another look at the fall hues from Lake Winnipesaukee, soak in the scenes from the famous Kancamagus Scenic Byway and take in the red, yellow and orange brilliance from the Conway Scenic Railroad. The tour concludes in Maine, where we enjoy one last scenic cruise, a tour of a marine museum and a traditional lobster dinner. Autumn on the East Coast has never been more memorable.


  • Three scenic rail excursions Conway Scenic Railroad, Cape Cod Central Railroad and Essex Steam Train
  • Hotel accommodations for 9 nights
  • 13 meals, including a lobster dinner
  • Boston city tour, including the Freedom Trail
  • Martha’s Vineyard tour, including the quaint village of Edgartown
  • Mystic Seaport Museum
  • Cruise on the Becky Thatcher Riverboat
  • Sturbridge Village
  • Lake Winnipesaukee cruise
  • America’s top fall foliage drive, the Kancamagus Highway
  • Maine Maritime Museum and Kennebec River cruise
  • Transportation by deluxe motorcoach
  • Services of a professional tour manager
  • Baggage handling
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Call to Book 1-877-929-7245

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  • Day 1 – Boston

    Arrive in Boston today, check in to your hotel and take the remainder of the day to explore the city on your own. You may wish to take an Old Town Trolley tour to get acquainted with the city and see all its most impressive sights. Meet your tour manager at the hotel for a brief meeting before heading out to dinner at your choice of local restaurants. Overnight Boston, MA.

  • Day 2 – Boston City Tour/Cape Cod Central Railroad

    This morning, learn about Boston's rich history on a guided city tour including the Freedom Trail. Your sightseeing ends at Quincy Market, where there is time for lunch on your own. This afternoon, board your motorcoach for the journey to Hyannis, where we board the Cape Cod Central Railroad for an evening dinner train excursion. Enjoy your meal as the train crosses the famous Cape Cod Canal railroad bridge into the historic village of Buzzard's Bay. Overnight Hyannis, MA. (B, D)

  • Day 3 – Martha’s Vineyard

    Today's excursion takes us aboard the M/V Island Home, a passenger and vehicle ferry which crosses from the mainland of Cape Cod to the Island retreat community of Martha's Vineyard. Once on the island, enjoy tales of its fishing and whaling past, shopping and dining opportunities in the charming town of Edgartown and a visit to the colorful Victorian gingerbread cottages of Oak Bluffs. Later, we return by ferry to Woods Hole, MA, and on to Hyannis. Overnight Hyannis, MA. (B)

  • Day 4 – Mystic Seaport Museum

    Marvel at the fiery colors of fall as we travel inland this morning bound for Mystic, CT. Our destination is Mystic Seaport, a maritime museum that was founded in 1929 and tells the nautical history of the Eastern Seaboard through fascinating exhibits and immersive experiences. Learn about different types of boats, lighthouses, art and whaling in the museum; step back in time at Seaport Village, a recreated 19th-century village with authentic buildings from the 1800s and storytellers, craftsmen and historians dressed in period attire; step aboard America’s last remaining whaling ship, the Charles W. Morgan; set out onto the water aboard a historic ship; and discover how sailors from years past used the stars to navigate the seas in the Planetarium. Overnight Mystic, CT. (B)

  • Day 5 – Essex Steam Train and Becky Thatcher Riverboat

    New England’s autumn landscape is presented from both the rails and the water today. We travel by motorcoach to the Essex Train Station, a historic building that dates to 1892. Our steam train awaits, and we set off through the scenic Connecticut River Valley for a 12-mile journey. The route is fully narrated and provides a majestic look at the changing foliage. The train takes us to Deep River Landing, where we embark on the next phase of our adventure aboard the Becky Thatcher Riverboat to see the Connecticut River’s most beautiful autumn features. We stop for lunch before boarding our motorcoach for a scenic drive north into Massachusetts. Take some time to settle into your room or to begin your explorations as we arrive in Sturbridge, then reconvene with your fellow travelers for a traditional New England dinner at the Salem Cross Inn, an 18th-century farmhouse surrounded by 600 acres of unspoiled scenery. Overnight Sturbridge, MA. (B, L, D)

  • Day 6 – Sturbridge Village

    The charm of years long past awaits at Old Sturbridge Village today. With heritage gardens, farms and even heritage breeds of pigs, sheep and cows onsite, this attraction provides an in-depth look at rural life in the 1800s. During your time at Old Sturbridge, you have a chance to walk through the historic buildings in the village, to see the beautifully restored main house and to explore more than 50,000 period artifacts that were made or used by New Englanders. Further, on-site demonstrations, presentations and employees in full colonial dress make for a fully immersive experience. Following our time at the village, our beautiful route through the colors of the East continues as we drive to the edge of White Mountain National Forest. Overnight Plymouth, NH. (B)

  • Day 7 – Lake Winnipesaukee Cruise

    We travel to Weirs Beach this morning to board the MS Mount Washington for a cruise on Lake Winnipesaukee. Step off the vessel and into the charming village of Wolfeboro, NH, for lunch on your own and to browse the quaint shops. The remainder of the day is at your leisure. Overnight Plymouth, NH. (B)

  • Day 8 – Conway Scenic Railroad

    Keep your camera within reach this morning as we travel through Franconia North State Park, located in the heart of the White Mountains, via the Kancamagus Scenic Byway. This highway is renowned as one of the best fall foliage viewing areas in America and offers stunning views of colorful trees, soaring mountain peaks, the Swift River, Rocky Gorge and more. We continue to North Conway for lunch on own and time to explore the fabulous little boutiques. The train depot in North Conway is now a National Historic Landmark that contains a museum and roundhouse. Board the Conway Scenic Railroad for an old-fashioned railroading experience on historic rail routes in vintage passenger cars to Bartlett. The day’s travels conclude in Portland, ME, where the remainder of your day is at leisure. Overnight Portland, ME. (B)

  • Day 9 – Bath, ME/Maine Maritime Museum/Kennebec River Cruise

    Admire the scenic beauty of Maine's coast in the autumn this morning as we travel through quaint seaside villages en route to Bath, Maine. Our sightseeing begins at the Maine Maritime Museum, located on the original site where large four-, five- and six-masted wooden ships were built, including the world's largest wooden ship, the Wyoming. The museum features over 21,000 artifacts and crafts to explore during our visit. A real gem of the Maritime Museum is the Lobstering and the Maine Coast exhibit. We learn lobster biology and ecology, discover different types of boats and engines and marvel over modern trapping and processing methodology.

    From the museum, we step aboard a river cruiser for an up-close look at the Kennebec River and the sites along it. The first landmark we pass is the Bath Iron Works, a place where impressive vessels have been built for more than 400 years and where modern Navy ships are still built today. A retired Bath Iron Works employee joins us on board to discuss his experience as a shipbuilder. As we continue down the Kennebec, we pass the 1898 Doubling Point Lighthouse and the Kennebec River Range Light Station before returning to the museum. Enjoy lunch and shopping on your own and take the time to explore some of the beautifully restored 19th-century homes of Bath before we return to Portland. The afternoon is yours to enjoy in the Old Wharf District. This evening is highlighted by a lobster dinner at a local restaurant. Overnight Portland, ME. (B, D)

  • Day 10 – Tour Conclusion

    Your fall foliage vacation concludes this morning. A group transfer to Boston South Amtrak Station or Boston Logan Airport will accommodate trains and planes departing after 1:00 pm. (B)


Hotels include the Boston Park Plaza, Fairfield Inn & Suites (Hyannis)*, Hampton Inn & Suites (Mystic), Comfort Inn & Suites (Sturbridge), Fairfield Inn & Suites (Plymouth), and Hyatt Place Old Port (Portland).

Conway Scenic Railway - Notch Train
Set out on tracks laid nearly 150 years ago aboard the Conway Scenic Railway’s Notch Train. This diesel electric locomotive journeys through New Hampshire’s rugged wilderness on its round-trip journey to and from North Conway Station, passing dramatic cliffs, stunning mountains and cascading waterways.

Essex Steam Train
Making a 12-mile round-trip journey, the Essex Steam Train offers a glimpse at rural New England life. The vintage locomotive sets off from Essex Station and pulls its coaches deep into the heart of the Connecticut River Valley. Along the way, passengers will see the charming towns of Deep River and Chester and get a look at the unspoiled beauty of Selden Neck State Park. In all, this journey takes approximately 1 hour.

Cape Cod Central Railroad - Cape Cod Dinner Train
Journey through salt marshes and sand dunes on the Cape Cod Railway’s Cape Cod Dinner Train. This 3-hour journey begins and ends at Hyannis Railroad Station and sets out along the Cape Cod Bay for an unforgettable ride. Passengers will be treated to vistas that can only be seen from the railway as they dine on a freshly prepared 5-course meal. Dinner Train requires a specific dress code that will be  provided in final travel documents.

Hotel accommodations are based on availability, substitutes will be similar in quality.

* The September 23 and September 30 departures will stay at the Cape Codder Hyannis

+ Vacations By Rail can supply connecting rail from your closest Amtrak Station.

It is your responsibility to check and fulfill the passport, visa, health and immigration requirements applicable to your itinerary. We do not accept any responsibility if you cannot travel, or incur any other loss because you have not complied with any passport, visa, immigration requirements or health formalities. You agree to reimburse us in relation to any fines or other losses which we incur as a result of your failure to comply with any passport, visa, immigration requirements or health formalities.


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Prices are land-only, per person based on double occupancy. Prices are correct at the time of this web page going live; however are subject to confirmation at time of booking. Hotels & Accommodations are subject to change based on availability.
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