Travel with the Chamber: New England Rails & Trails

October 7–15, 2026 | 9 Days

Tour Highlights

• Granite State Scenic Railway
• Mount Washington Cog Railway
• Boston city tour and JFK Presidential Library
• Vermont countryside and Ben & Jerry’s Factory
• White Mountains and Kancamagus Highway
• Portland, Maine and Casco Bay cruise
• Lobster farewell dinner

What’s Included

• Roundtrip airfare from FAT
• 8 nights hotel accommodations
• 11 meals
• Professional Tour Director
• Guided sightseeing and rail experiences

Tour Details

• Activity Level: Moderate
• Pricing starts at $4,775 per person, double occupancy

Full Itinerary

Day 1 – Arrive Boston

Upon arrival in Boston, meet your Tour Director and transfer to your Boston-area hotel. Tonight enjoy a Welcome Dinner.

Day 2 – Boston – North Conway

This morning enjoy a Boston City Tour featuring Boston Common, 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 leisure time to grab a bite to eat, wander, people-watch, and shop.

Later leave Boston and travel into New Hampshire’s scenic White Mountains, arriving in the picturesque North Conway area for a two-night stay.

Day 3 – Conway Scenic Railroad and Mt. Washington Cog Railway

This morning board the Conway Scenic Railroad for a nostalgic ride through the scenic Mount Washington Valley countryside aboard restored historic railcars powered by diesel and electric locomotives.

Next travel to board the historic Mount Washington Cog Railway. Enjoy breathtaking vistas during your three-hour rail experience aboard the world’s first (1869) mountain-climbing cog railway to the summit of Mount Washington, the highest peak in the Northeast. Later enjoy the evening at your own pace.

Day 4 – North Conway – Burlington

This morning motorcoach along one of New England’s most popular scenic drives, the Kancamagus Highway. The drive connects North Conway with Lincoln and offers spectacular views of rushing rivers and covered bridges.

Continue to Quechee Gorge, Vermont’s “Little Grand Canyon.” Later arrive in the scenic town of Woodstock to visit the Billings Farm and Museum, a modern working dairy farm and museum of Vermont life in the 1890s.

This afternoon pass through quaint villages and mountain scenery before arriving in Burlington for a two-night stay in this historic Vermont mountain town.

Day 5 – Vermont Sightseeing

Visit the Shelburne Museum, located in Vermont’s scenic Lake Champlain Valley and one of the nation’s finest and 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, known for its 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 or two of their creative flavors.

Late afternoon return to your hotel for an evening at leisure.

Day 6 – Burlington – Portland, Maine

This morning visit a Maple Sugar Farm to sample authentic Vermont maple sweets and learn about the sugaring process.

Later relax and enjoy spectacular New England scenery en route to the Maine coast. Arrive in scenic Portland, Maine for a two-night stay. Portland is Maine’s largest city and sits on a peninsula jutting out into island-filled Casco Bay.

Day 7 – Portland

Today enjoy a scenic Casco Bay Cruise past lovely Victorian cottages along the shores of Little and Great Diamond Islands.

Then enjoy leisure time in Old Port, Portland’s historic waterfront district. Later visit the Portland Head Lighthouse and Museum in Cape Elizabeth, one of America’s oldest and most photographed lighthouses.

Tonight enjoy a Lobster Farewell Dinner with your fellow travelers.

Day 8 – Portland – Boston – Flight Home

Travel to Boston and fly home with wonderful memories of your New England experiences.

Land-only rates do not include hotel transfers. Roundtrip air package includes hotel transfers.