New England - Rails & Trails
October 4, 2026 - 9 Days
Experience the charm of autumn in New England on this scenic 9-day journey through Massachusetts, Vermont, New Hampshire, and Maine. Begin with two nights in historic Boston, including a city tour and a visit to the JFK Presidential Library. Discover Vermont’s small-town beauty with stops at Billings Farm, the Shelburne Museum, and Ben & Jerry’s. Ride the iconic Mount Washington Cog Railway and take in sweeping views from the Kancamagus Highway. Cap it off with a lobster farewell dinner in coastal Portland, Maine after a relaxing Casco Bay Cruise. This tour blends vibrant fall foliage, local flavor, and iconic New England experiences in one unforgettable trip.
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2 Rail Journeys
Granite State Scenic Railway
Mt. Washington Cog Rail
Boston City Tour
Faneuil Hall Marketplace & Quincy Market
JFK Presidential Library & Museum
Billings Farm & Museum
Woodstock, VT
North Conway, NH
Maple Sugar Farm
Ben & Jerry's Factory
Shelburne Museum
Kancamagus Highway
Portland, Maine
Casco Bay Cruise
Morse Libby House
Cold Hollow Cider Mill
Portland Head Lighthouse
Lobster Farewell Dinner
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Shuttle to and from MSP airport
MSP Roundtrip Airfare
8 Nights Hotel Accommodations
11 Meals: 8 Breakfasts - 3 Dinners
Hotel Transfers
Professional Tour Director
Sightseeing per itinerary
Admissions per itinerary
Baggage handling at all Hotels
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Day 1: Depart MSP - Arrive in Boston
Upon arrival in Boston meet your Tour Director and transfer to your Boston Area hotel for a two-night stay. Enjoy the evening at leisure in this historic city filled with amazing restaurants.
Day 2: Boston Sightseeing
Today enjoy a Boston City Tour featuring Boston Commons, the Old State House, the Old North church from where Paul Revere got the signal to start his famous ride, the Old South Meeting House, Beacon Hill and Old Ironsides. Visit the Faneuil Hall Marketplace, located in downtown Boston near the waterfront and originally gifted to the city in 1742. Enjoy lunch and shopping in this area which also features Quincy Market, added to the complex due to Boston's growth in 1826. Later visit the John F. Kennedy Presidential Library & Museum, which is dedicated to the memory of our nation's thirty-fifth president. Located on Boston's waterfront, the Library & Museum is set on a 10-acre park landscaped to be reminiscent of President Kennedy's beloved Cape Cod. Tonight enjoy a Welcome Dinner.
Day 3: Boston - Burlington
After breakfast travel to the scenic town of Woodstock, often referred to as America's Prettiest Town with its colonial architecture and New England charm. Visit the Billings Farm & Museum, a modern working dairy farm and history museum of Vermont life in the 1890's. This afternoon pass through quaint villages and mountain scenery before arriving in Burlington for a two-night stay in the famous and historic Vermont mountain town.
Day 4: Vermont Sightseeing
Visit the Shelburne Museum, located in Vermont's scenic Lake Champlain Valley & one of the nation's finest, most diverse and unconventional museums of art and Americana. Later visit Cold Hollow Cider Mill, one of the largest apple cider mills in New England and known for cold-pressed cider. Also visit the home of Ben & Jerry's Ice Cream, founded in 1978 in a renovated gas station. Enjoy a brief factory tour and a scoop of one of the creative flavors. Late afternoon return to your hotel for an evening at your own pace.
Day 5: Maple Sugar Farm - Granite State Scenic Railroad - White Mountains
This morning visit a Maple Sugar Farm to sample some authentic Vermont Maple sweets and learn about the sugaring process. Later board the Granite State Scenic Railway in Lincoln formerly known as the Hobo Railroad. The picturesque 80-minute experience rides along the banks of Pemigewasset River and through the woods on a historic rail system that dates back to the late 1800s. Continue to your hotel for a two-night stay in the beautiful White Mountains and enjoy dinner with your fellow travelers.
Day 6: Mt. Washington Cog Rail - North Conway
This morning board the historic Mount Washington Cog Railway. Enjoy breathtaking vistas during the three-hour rail experience aboard the world's first (1869) mountain climbing Cog Railway to the top of the highest peak in the Northeast, Mount Washington. Then travel to the small town of North Conway for some leisure & shopping time. Continue to one of New England's most popular scenic drives, the Kancamagus Highway. The drive offers spectacular views of rushing rivers, covered bridges and mountain scenery. Enjoy the evening at leisure.
Day 7: White Mountains - Portland
After breakfast board your motorcoach and enjoy the scenery as you travel from the mountains to the coast. Arrive in Portland. Maine's largest city that sits on a peninsula jutting out into beautiful island-filled Casco Bay. Visit the Victoria Mansion, also known as the Morse Libby House, the nation's premier showpiece of Victorian architecture. Arrive at your hotel for a two-night stay in Portland.
Day 8: Portland
Today enjoy a scenic Casco Bay Cruise past lovely Victorian cottages on the shorelines of Little & Great Diamond Island. Then enjoy some leisure time for shopping and lunch on your own in Old Port, Portland's historic waterfront. Later visit the Portland Head Lighthouse & Museum in Cape Elizabeth, one of America's oldest and most photographed lighthouses. Tonight enjoy a Lobster Farewell Dinner with your fellow travelers. Lobster is a favorite dish of New Englanders in the summer and fall.
Day 9: Portland - Boston - Arrive in MSP
Travel to Boston & fly home with wonderful new memories of your New England Experiences. -
2 Night in Boston Area
2 Nights in White Mountains Area, NH
2 Nights in Burlington, VT
2 Nights in Portland, ME
*On some dates alternative hotels may be used
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With Booking Discount: $4575 pp double
Regular Rate: $4675 pp double
Single Supplement: $1400