2027 New England Fall Colors by Rail

Arrive in Portland and get settled at the hotel. The hotel has a shuttle available from the airport and railway station to the hotel.

In the evening, get acquainted with our Trains Magazine special guest as well your fellow tour guests, while we will enjoy a private sunset harbor cruise with drinks, followed by our welcome dinner back on land.

First we’ll make our way to the world’s oldest and largest museum of mass transit vehicles, the Seashore Trolley Museum. While the main focus of the collection is trolley cars, it also includes rapid transit trains, inter-urban cars, trolley buses, and motor buses.

After a drive to New Hampshire in the late afternoon, we’ll enjoy a private car excursion on the famous Turkey Dinner Train which journeys around beautiful Lake Winnipesaukee. After dinner, we’ll settle into the Lake Opechee Resort for a 3-night stay.

Today’s adventure features an exclusive Conway Scenic Railroad excursion in private cars, offering a truly memorable rail experience. We’ll begin with the charming Valley Train Excursion, followed by the Mountaineer, which winds through the breathtaking Crawford Notch—a dramatic mountain pass that showcases the rugged beauty of New Hampshire’s White Mountains.

We begin the day with a thrilling journey on the world’s first cog railway, traveling by bus to the base of Mount Washington, New Hampshire’s highest peak at 6,288 feet. After a meet-and-greet with the steam crew, we’ll ascend the mountain, enjoying panoramic vistas and the breathtaking beauty of the White Mountains.

As the sun begins to set, the adventure continues aboard the Cafe Lafayette Dinner Train, where a delightful dinner awaits, combining scenic splendor with a truly memorable dining experience.

We’ll begin our day with a visit to the Wiscasset, Waterville & Farmington Railway, a faithful recreation of the rural 2-foot gauge line that originally operated from 1894 to 1933 and was lovingly revived beginning in 1989. Guests will enjoy an exclusive steam charter, complete with thrilling photo run-bys and a fascinating shop tour, offering a behind-the-scenes glimpse into the art of historic railroading.

Next, we’ll continue to the Boothbay Rail Village, a charming destination for rail enthusiasts and casual visitors alike. Here, guests can explore an extensive collection of restored vintage railcars, learn about Maine’s rail history through engaging exhibits, and marvel at the intricate model railroad layout.

The day concludes with a classic lobster bake on-site, where guests can savor freshly prepared coastal cuisine while soaking in the relaxed and scenic atmosphere of the village.

Today we’ll journey to Mount Desert Island for an unforgettable guided tour of Acadia National Park, one of the crown jewels of the Maine coast.

Before exploring the park, guests will have free time to wander the historic streets of Bar Harbor, a charming and lively town filled with boutiques, galleries, and scenic waterfront views, and enjoy lunch on their own at one of its inviting restaurants.

We’ll begin the day with an exclusive private train charter and shop tour on the Belfast & Moosehead Railway, winding through untamed forests and sparkling lakes for a truly immersive Maine rail experience.

In the afternoon, we’ll return to Portland for our final train adventure—a steam charter with the Maine Narrow Gauge Railway, offering one last opportunity to experience the charm and nostalgia of historic rail travel.

After the charter, we’ll transfer to our Portland hotel, where a farewell dinner awaits to celebrate the journey’s highlights and our final night in Maine, providing the perfect conclusion to an unforgettable rail adventure.

Breakfast will be provided at the hotel and shuttles will be available for guests to transfer to the airport and Amtrak station at their leisure. Until next time, intrepid travelers!